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Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of thoughtfully curated living space designed for the most discerning buyer. From the moment you step inside, you're greeted by soaring ceilings, sun-filled interiors, and beautifully appointed living spaces that seamlessly blend everyday comfort with grand-scale entertaining. Every detail has been carefully considered, creating an atmosphere of refined luxury throughout. The home's versatile floor plan features five spacious bedrooms, including a desirable first-floor guest suite with a full bath—perfect for extended family, overnight guests, or a private executive home office. The spectacular primary suite is a private sanctuary unlike any other, offering a spacious bedroom retreat, expansive custom walk-in closets, and luxurious his-and-her spa-inspired bathrooms, providing the ultimate in comfort, privacy, and everyday indulgence. Designed for effortless indoor-outdoor living, the resort-style backyard is an entertainer's dream. Spend summer days relaxing beside the stunning in-ground pool and spa or host unforgettable gatherings beneath the covered patio, complete with built-in heaters, integrated speakers, and a fully equipped outdoor kitchen—allowing you to enjoy every season in style. The expansive walk-out lower level offers endless possibilities, whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, or additional living quarters. Its exceptional scale provides the flexibility to accommodate every lifestyle. Perfectly positioned in one of the area's most desirable neighborhoods, this remarkable estate is just minutes from Armonk's vibrant downtown, Metro-North, award-winning schools, fine dining, boutique shopping, parks, and convenient access to New York City.

5 Beds ⋅ 6 Baths ⋅ 1023249 MLS

Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of thoughtfully curated living space designed for the most discerning buyer. From the moment you step inside, you're greeted by soaring ceilings, sun-filled interiors, and beautifully appointed living spaces that seamlessly blend everyday comfort with grand-scale entertaining. Every detail has been carefully considered, creating an atmosphere of refined luxury throughout. The home's versatile floor plan features five spacious bedrooms, including a desirable first-floor guest suite with a full bath—perfect for extended family, overnight guests, or a private executive home office. The spectacular primary suite is a private sanctuary unlike any other, offering a spacious bedroom retreat, expansive custom walk-in closets, and luxurious his-and-her spa-inspired bathrooms, providing the ultimate in comfort, privacy, and everyday indulgence. Designed for effortless indoor-outdoor living, the resort-style backyard is an entertainer's dream. Spend summer days relaxing beside the stunning in-ground pool and spa or host unforgettable gatherings beneath the covered patio, complete with built-in heaters, integrated speakers, and a fully equipped outdoor kitchen—allowing you to enjoy every season in style. The expansive walk-out lower level offers endless possibilities, whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, or additional living quarters. Its exceptional scale provides the flexibility to accommodate every lifestyle. Perfectly positioned in one of the area's most desirable neighborhoods, this remarkable estate is just minutes from Armonk's vibrant downtown, Metro-North, award-winning schools, fine dining, boutique shopping, parks, and convenient access to New York City.

15 Heritage Drive, Pleasantville

$2,350,000

Welcome to this meticulously maintained Colonial home in the heart of Pleasantville, offering modern, youthful style and the warmth of a true community. The light-filled interior is move-in ready, with four generous bedrooms, three full baths, and a convenient powder room designed for everyday living and effortless entertaining. The fully finished lower level expands the home’s footprint with a spacious recreation room, dedicated workout space, and a full bath—perfect for guests, movie nights, or unwinding after a long day. Step outside to your own private retreat, where an expansive deck and sparkling pool area create the ultimate setting for summer gatherings and quiet weekends. Set in a neighborhood where Halloween is a tradition not to be missed. This home also falls within the highly regarded Byram Hills School District. A rare opportunity to own a turnkey home in one of Westchester’s most sought-after communities.

4 Beds ⋅ 4 Baths ⋅ 987097 MLS

Welcome to this meticulously maintained Colonial home in the heart of Pleasantville, offering modern, youthful style and the warmth of a true community. The light-filled interior is move-in ready, with four generous bedrooms, three full baths, and a convenient powder room designed for everyday living and effortless entertaining. The fully finished lower level expands the home’s footprint with a spacious recreation room, dedicated workout space, and a full bath—perfect for guests, movie nights, or unwinding after a long day. Step outside to your own private retreat, where an expansive deck and sparkling pool area create the ultimate setting for summer gatherings and quiet weekends. Set in a neighborhood where Halloween is a tradition not to be missed. This home also falls within the highly regarded Byram Hills School District. A rare opportunity to own a turnkey home in one of Westchester’s most sought-after communities.

25 Pheasant Run Road, Pleasantville

$2,105,000

TIMELESS APPEAL! This stunning Colonial is the perfect blend of traditional charm and modern functionality! The spacious two storied family room/ gas fireplace is ideal for everyday living and grand entertaining. Add a banquet sized dining room…perfect for memorable feasts makes hosting the holidays a joy. Tucked away, a formal living room for quiet moments. 2 car garage with entry convenient to kitchen..... Laundry room and a tastefully papered powder room. Bright Primary bedroom on first floor … his and her closets and luxurious bath. On the second floor there are two generous bedrooms with a Jack and Jill bath. Bonus room, high ceilings ( pool table negotiable)…great for kids private space. And in addition a third bedroom as well as another bath, walk in closet. Downstairs finds a full unfinished basement loads of storage, great potential depending on your imagination and needs. Access door to driveway.. To top it all off there is a private rear yard, a 2 car garage and two patio areas for summer relaxation. This home was built by the current, original owner with “ uncompromising quality”. A rare opportunity to own a custom built home in a neighborhood of premier residences “THE ESTATES”…..an exclusive enclave!

4 Beds ⋅ 4 Baths ⋅ 958358 MLS

TIMELESS APPEAL! This stunning Colonial is the perfect blend of traditional charm and modern functionality! The spacious two storied family room/ gas fireplace is ideal for everyday living and grand entertaining. Add a banquet sized dining room…perfect for memorable feasts makes hosting the holidays a joy. Tucked away, a formal living room for quiet moments. 2 car garage with entry convenient to kitchen..... Laundry room and a tastefully papered powder room. Bright Primary bedroom on first floor … his and her closets and luxurious bath. On the second floor there are two generous bedrooms with a Jack and Jill bath. Bonus room, high ceilings ( pool table negotiable)…great for kids private space. And in addition a third bedroom as well as another bath, walk in closet. Downstairs finds a full unfinished basement loads of storage, great potential depending on your imagination and needs. Access door to driveway.. To top it all off there is a private rear yard, a 2 car garage and two patio areas for summer relaxation. This home was built by the current, original owner with “ uncompromising quality”. A rare opportunity to own a custom built home in a neighborhood of premier residences “THE ESTATES”…..an exclusive enclave!

14 Pond Hollow Court, Pleasantville

$2,005,000

Welcome to 301 Bear Ridge Road, where classic charm, modern luxury, and an extraordinary setting come together to create a truly special place to call home. From its timeless exterior architecture to its beautifully renovated interior, this exceptional residence seamlessly blends the warmth and character of a 1940s home with the comfort and functionality today’s buyers desire. Step inside to a gracious living room featuring rich wood floors, elegant crown molding, custom built-ins, and a cozy wood-burning fireplace—an inviting space for both quiet evenings and lively gatherings. The sun-drenched sunroom offers a cheerful retreat, perfect for playtime, reading, or simply enjoying the natural light. A formal dining room provides the ideal backdrop for holidays, celebrations, and memorable dinners. At the heart of the home, the renovated chef’s kitchen impresses with an oversized island and flows effortlessly into the spacious family room. A wall of windows, custom built-ins, and direct access to the deck create an open, airy atmosphere designed for everyday living and entertaining alike. Let the fun begin. The main level also offers a flexible first-floor bedroom featuring a custom Murphy bed—ideal for overnight guests, a private home office, or multigenerational living—just steps from a full bathroom. Thoughtfully designed for real life, the entry from the two-car garage includes a pantry and convenient drop zone, keeping backpacks, shoes, and essentials neatly organized. Upstairs, the second floor offers room to roam with five bedrooms and three full bathrooms. The expansive primary suite is a true retreat, featuring multiple closets, a spa-like bath with double sinks, a step-in steam shower, and walls of windows overlooking the breathtaking property. Enjoy a bedroom with a full bath, three additional bedrooms, full sized laundry with shelving and a full bath that completes the second floor. The lower level adds yet another dimension of living space, complete with a dedicated fitness room—perfect for weightlifters who can workout any time of day. Outdoors, the property is nothing short of spectacular, offering a lifestyle that engages all the senses. Enjoy the sight of snowy egrets, blue herons, and other wildlife as they visit the pond, and the gentle chatter of birds among the surrounding trees. Watch fish leap from the pond or turtles bask along the shore. Fish from the rowboat in warm weather and play pond hockey in the winter. Take advantage of your private putting green, built-in pool, and multiple outdoor spaces designed for relaxation and entertaining—from lounging poolside with a good book to hosting friends on the patio or two-tiered deck with the gas grill fired up. Rarely does a home offer this perfect balance of beauty, comfort, and serenity. The moment you arrive at 301 Bear Ridge Road and experience all it has to offer, you’ll know—you’re home.

5 Beds ⋅ 4 Baths ⋅ 987380 MLS

Welcome to 301 Bear Ridge Road, where classic charm, modern luxury, and an extraordinary setting come together to create a truly special place to call home. From its timeless exterior architecture to its beautifully renovated interior, this exceptional residence seamlessly blends the warmth and character of a 1940s home with the comfort and functionality today’s buyers desire. Step inside to a gracious living room featuring rich wood floors, elegant crown molding, custom built-ins, and a cozy wood-burning fireplace—an inviting space for both quiet evenings and lively gatherings. The sun-drenched sunroom offers a cheerful retreat, perfect for playtime, reading, or simply enjoying the natural light. A formal dining room provides the ideal backdrop for holidays, celebrations, and memorable dinners. At the heart of the home, the renovated chef’s kitchen impresses with an oversized island and flows effortlessly into the spacious family room. A wall of windows, custom built-ins, and direct access to the deck create an open, airy atmosphere designed for everyday living and entertaining alike. Let the fun begin. The main level also offers a flexible first-floor bedroom featuring a custom Murphy bed—ideal for overnight guests, a private home office, or multigenerational living—just steps from a full bathroom. Thoughtfully designed for real life, the entry from the two-car garage includes a pantry and convenient drop zone, keeping backpacks, shoes, and essentials neatly organized. Upstairs, the second floor offers room to roam with five bedrooms and three full bathrooms. The expansive primary suite is a true retreat, featuring multiple closets, a spa-like bath with double sinks, a step-in steam shower, and walls of windows overlooking the breathtaking property. Enjoy a bedroom with a full bath, three additional bedrooms, full sized laundry with shelving and a full bath that completes the second floor. The lower level adds yet another dimension of living space, complete with a dedicated fitness room—perfect for weightlifters who can workout any time of day. Outdoors, the property is nothing short of spectacular, offering a lifestyle that engages all the senses. Enjoy the sight of snowy egrets, blue herons, and other wildlife as they visit the pond, and the gentle chatter of birds among the surrounding trees. Watch fish leap from the pond or turtles bask along the shore. Fish from the rowboat in warm weather and play pond hockey in the winter. Take advantage of your private putting green, built-in pool, and multiple outdoor spaces designed for relaxation and entertaining—from lounging poolside with a good book to hosting friends on the patio or two-tiered deck with the gas grill fired up. Rarely does a home offer this perfect balance of beauty, comfort, and serenity. The moment you arrive at 301 Bear Ridge Road and experience all it has to offer, you’ll know—you’re home.

301 Bear Ridge Road, Pleasantville

$2,000,000

Set on over an acre of private, bucolic property, this spacious mid-century modern inspired home offers the perfect blend of stylish design and warm, inviting living spaces. Soaring ceilings, natural materials, and an open floor plan create an airy, light-filled atmosphere. Thoughtfully updated throughout, the home features a renovated kitchen and updated bathrooms, along with four bedrooms and three full baths across 3,400 square feet of living space. The finished lower level offers tremendous versatility with a large playroom, family room, office, full bath, and the fourth bedroom. Outside, enjoy the expansive usable yard and peaceful natural setting that make this a truly special place to call home. All this, and add the Pleasantville community - restaurants, culture and hometown vibe! A winning combination.

4 Beds ⋅ 3 Baths ⋅ 997716 MLS

Set on over an acre of private, bucolic property, this spacious mid-century modern inspired home offers the perfect blend of stylish design and warm, inviting living spaces. Soaring ceilings, natural materials, and an open floor plan create an airy, light-filled atmosphere. Thoughtfully updated throughout, the home features a renovated kitchen and updated bathrooms, along with four bedrooms and three full baths across 3,400 square feet of living space. The finished lower level offers tremendous versatility with a large playroom, family room, office, full bath, and the fourth bedroom. Outside, enjoy the expansive usable yard and peaceful natural setting that make this a truly special place to call home. All this, and add the Pleasantville community - restaurants, culture and hometown vibe! A winning combination.

3 Banks Hill Road, Pleasantville

$1,815,000

This beautifully updated and renovated mid-century contemporary home is set on a quiet street and on over an acre of private property, with a choice of either Byram Hills (Armonk) or Chappaqua schools. Move-in ready, energy-efficient, and meticulously renovated and maintained, 153 Deerfield Lane North is a true gem. This sun-filled home offers over 3,500 sq. ft. of living space, including four bedrooms, a bonus room, and an additional finished lower level with a separate entrance, 2 car attached garage. The main level features a dramatic vaulted-ceiling living room with a fireplace, an open dining area leading to a wrap-around porch, and a modern kitchen with stainless steel appliances, walk-in pantry, and custom cabinetry. The oversized primary suite includes a luxurious en-suite bath with radiant heat and a cedar walk-in closet. Two additional bedrooms and a hall bath with radiant heat complete the main level. A separate bonus room with its own entrance is perfect for a home office, guest suite, or au pair. The walk-out finished lower level (1,102 sq. ft., included in total sq. footage) offers a large open area ideal for a family room, recreation space, plus a bedroom and a full bathroom, well suited for multi-generational living or a private workspace. Every detail has been thoughtfully updated for comfort, efficiency, and modern living: new roof, Andersen 400 Series windows, Fujitsu Airstage ductless air-conditioning and heat pump system, custom kitchen with stainless steel appliances, and bathrooms finished with upcycled natural stone and Kohler/Toto fixtures. Smart home systems include EERO Wi-Fi, Wyze cameras, automated lighting, and energy monitoring, smart-zoned comfort throughout. Additional highlights include a two-car garage with EV charging ports, cedar closets, a whirlpool tub, European-style radiators, and more. Set on two tax lots totaling 1.1 acres, this home offers privacy and convenience, close to train, schools, and Chappaqua town amenities. Buyers have a choice between Byram Hills and Chappaqua schools. Current taxes correspond to the Chappaqua school district and do not include STAR savings. Buyers should verify all information with the Town of Mount Pleasant. Possible pool site. Request a list of updates and special features.

4 Beds ⋅ 3 Baths ⋅ 926384 MLS

This beautifully updated and renovated mid-century contemporary home is set on a quiet street and on over an acre of private property, with a choice of either Byram Hills (Armonk) or Chappaqua schools. Move-in ready, energy-efficient, and meticulously renovated and maintained, 153 Deerfield Lane North is a true gem. This sun-filled home offers over 3,500 sq. ft. of living space, including four bedrooms, a bonus room, and an additional finished lower level with a separate entrance, 2 car attached garage. The main level features a dramatic vaulted-ceiling living room with a fireplace, an open dining area leading to a wrap-around porch, and a modern kitchen with stainless steel appliances, walk-in pantry, and custom cabinetry. The oversized primary suite includes a luxurious en-suite bath with radiant heat and a cedar walk-in closet. Two additional bedrooms and a hall bath with radiant heat complete the main level. A separate bonus room with its own entrance is perfect for a home office, guest suite, or au pair. The walk-out finished lower level (1,102 sq. ft., included in total sq. footage) offers a large open area ideal for a family room, recreation space, plus a bedroom and a full bathroom, well suited for multi-generational living or a private workspace. Every detail has been thoughtfully updated for comfort, efficiency, and modern living: new roof, Andersen 400 Series windows, Fujitsu Airstage ductless air-conditioning and heat pump system, custom kitchen with stainless steel appliances, and bathrooms finished with upcycled natural stone and Kohler/Toto fixtures. Smart home systems include EERO Wi-Fi, Wyze cameras, automated lighting, and energy monitoring, smart-zoned comfort throughout. Additional highlights include a two-car garage with EV charging ports, cedar closets, a whirlpool tub, European-style radiators, and more. Set on two tax lots totaling 1.1 acres, this home offers privacy and convenience, close to train, schools, and Chappaqua town amenities. Buyers have a choice between Byram Hills and Chappaqua schools. Current taxes correspond to the Chappaqua school district and do not include STAR savings. Buyers should verify all information with the Town of Mount Pleasant. Possible pool site. Request a list of updates and special features.

153 Deerfield Lane N, Pleasantville

$1,750,000

Welcome to a truly special and rare opportunity located within the Briarcliff school district with Mt. Pleasant taxes. Nestled on a picturesque cul-de-sac in a sought-after part of the district, this beautifully updated 4 BR, 2.5 bath colonial offers the perfect blend of timeless charm, thoughtful design, and exceptional outdoor living. Set on a stunning, professionally landscaped property, this move-in ready home has been extensively renovated and meticulously maintained, with major updates beginning in 2019. The chef's kitchen is outfitted with luxury Wolf and Sub-Zero appliances, blending high-end performance with timeless design. Step outside to a backyard that's been completely transformed into a true retreat. A full grading renovation created a flattened, usable backyard, anchored by an expansive, oversized Cambridge paver patio built for outdoor living. The custom built-in outdoor kitchen comes complete with a gas line connection, while an integrated outdoor Sonos sound system and outdoor TV make this space ideal for everything from quiet evenings to lively gatherings. Offering luxurious indoor and outdoor living in one of Westchester's most desirable communities, this exceptional home presents a rare opportunity to simply move in and enjoy. Just minutes from hiking and biking trails and nearby center of Briarcliff Village. Easy commute to NYC on the Metro North Harlem Line. You do not want to miss this one.

4 Beds ⋅ 3 Baths ⋅ 1013231 MLS

Welcome to a truly special and rare opportunity located within the Briarcliff school district with Mt. Pleasant taxes. Nestled on a picturesque cul-de-sac in a sought-after part of the district, this beautifully updated 4 BR, 2.5 bath colonial offers the perfect blend of timeless charm, thoughtful design, and exceptional outdoor living. Set on a stunning, professionally landscaped property, this move-in ready home has been extensively renovated and meticulously maintained, with major updates beginning in 2019. The chef's kitchen is outfitted with luxury Wolf and Sub-Zero appliances, blending high-end performance with timeless design. Step outside to a backyard that's been completely transformed into a true retreat. A full grading renovation created a flattened, usable backyard, anchored by an expansive, oversized Cambridge paver patio built for outdoor living. The custom built-in outdoor kitchen comes complete with a gas line connection, while an integrated outdoor Sonos sound system and outdoor TV make this space ideal for everything from quiet evenings to lively gatherings. Offering luxurious indoor and outdoor living in one of Westchester's most desirable communities, this exceptional home presents a rare opportunity to simply move in and enjoy. Just minutes from hiking and biking trails and nearby center of Briarcliff Village. Easy commute to NYC on the Metro North Harlem Line. You do not want to miss this one.

14 Briarwood Lane, Pleasantville

$1,700,000

Beautifully updated and exuding timeless elegance, this classic Colonial in the Village of Pleasantville blends historic charm with a relaxed, modern sensibility. A gracious wraparound porch sets the tone—welcoming, unhurried, and distinctly at home in its surroundings. Inside, the flow feels natural from the moment you enter. Sunlight moves easily through the living spaces, creating an environment that adapts effortlessly to the day—morning coffee in the kitchen, afternoons that spill outdoors, evenings gathered with friends. The kitchen, equipped with Sub-Zero and Wolf appliances, anchors it all, connecting seamlessly to both living areas and the backyard for an intuitive and easy indoor-outdoor lifestyle. Upstairs, the primary bedroom suite offers a quiet retreat, complete with a gas fireplace and stunning bath with a soaking tub and separate shower. Three additional generous bedrooms and a full hall bath complete the second floor, while the third level adds two more bedrooms, a full bath, and flexible space ready to become whatever the day calls for—workspace, studio, or guest retreat. Life here naturally extends into the Village. Start your Saturday at the farmers market, enjoy the afternoon exploring Rockefeller Preserve or relax at the Village pool before spending the evening at the Jacob Burns Film Center. Dinner, cafes, shops, and the train are all minutes away, making it just as easy to head into the city as it is to stay close to home. This is Pleasantville living—connected, accessible, and effortlessly part of your everyday.

6 Beds ⋅ 4 Baths ⋅ 990334 MLS

Beautifully updated and exuding timeless elegance, this classic Colonial in the Village of Pleasantville blends historic charm with a relaxed, modern sensibility. A gracious wraparound porch sets the tone—welcoming, unhurried, and distinctly at home in its surroundings. Inside, the flow feels natural from the moment you enter. Sunlight moves easily through the living spaces, creating an environment that adapts effortlessly to the day—morning coffee in the kitchen, afternoons that spill outdoors, evenings gathered with friends. The kitchen, equipped with Sub-Zero and Wolf appliances, anchors it all, connecting seamlessly to both living areas and the backyard for an intuitive and easy indoor-outdoor lifestyle. Upstairs, the primary bedroom suite offers a quiet retreat, complete with a gas fireplace and stunning bath with a soaking tub and separate shower. Three additional generous bedrooms and a full hall bath complete the second floor, while the third level adds two more bedrooms, a full bath, and flexible space ready to become whatever the day calls for—workspace, studio, or guest retreat. Life here naturally extends into the Village. Start your Saturday at the farmers market, enjoy the afternoon exploring Rockefeller Preserve or relax at the Village pool before spending the evening at the Jacob Burns Film Center. Dinner, cafes, shops, and the train are all minutes away, making it just as easy to head into the city as it is to stay close to home. This is Pleasantville living—connected, accessible, and effortlessly part of your everyday.

247 Broadway, Pleasantville

$1,602,000

Welcome to Pleasantville! Tucked at the end of a picturesque cul-de-sac, this move-in ready home offers exceptional privacy, abundant natural light, and modern comfort throughout. With 4 bedrooms, a dedicated home office, and 3 full baths, it’s thoughtfully designed for today’s lifestyle. The sun-filled main level features an expansive living room with oversized picture windows and a beautifully updated eat-in kitchen with rich cherry wood cabinetry. The kitchen flows seamlessly into an open dining area—perfect for everyday living and entertaining—while a separate formal dining room offers flexible use as an additional sitting area or den. Step outside to a deck and large patio overlooking a private backyard, ideal for effortless indoor-outdoor living. A half-flight down from the kitchen leads to a versatile bonus level with an additional bedroom, office space, large laundry room, utility room, and a well-placed mudroom for everyday convenience. Upstairs, the generous primary suite includes a Juliette balcony, walk-in closet, two additional closets, and a private en-suite bath. Two additional bedrooms and a full hall bath complete this level. The expansive lower level offers even more flexible living space, featuring a recreation room with sliding doors that open to a paver patio. Set on beautifully landscaped, park-like grounds with mature plantings, this home combines tranquility with convenience. Just minutes from downtown Pleasantville and the Chappaqua train station, it offers easy access to shopping, and dining and more.

4 Beds ⋅ 3 Baths ⋅ 990519 MLS

Welcome to Pleasantville! Tucked at the end of a picturesque cul-de-sac, this move-in ready home offers exceptional privacy, abundant natural light, and modern comfort throughout. With 4 bedrooms, a dedicated home office, and 3 full baths, it’s thoughtfully designed for today’s lifestyle. The sun-filled main level features an expansive living room with oversized picture windows and a beautifully updated eat-in kitchen with rich cherry wood cabinetry. The kitchen flows seamlessly into an open dining area—perfect for everyday living and entertaining—while a separate formal dining room offers flexible use as an additional sitting area or den. Step outside to a deck and large patio overlooking a private backyard, ideal for effortless indoor-outdoor living. A half-flight down from the kitchen leads to a versatile bonus level with an additional bedroom, office space, large laundry room, utility room, and a well-placed mudroom for everyday convenience. Upstairs, the generous primary suite includes a Juliette balcony, walk-in closet, two additional closets, and a private en-suite bath. Two additional bedrooms and a full hall bath complete this level. The expansive lower level offers even more flexible living space, featuring a recreation room with sliding doors that open to a paver patio. Set on beautifully landscaped, park-like grounds with mature plantings, this home combines tranquility with convenience. Just minutes from downtown Pleasantville and the Chappaqua train station, it offers easy access to shopping, and dining and more.

74 Dogwood Lane, Pleasantville

$1,580,017

Come home to this stylishly updated cedar shake colonial with a great open layout. Located on a beautiful and flat lot at the end of a quiet private road within the Byram Hills School District, this home blends country charm with effortless convenience. Gracious entry leads to an open main level featuring a living room with woodburning fireplace, dining room, spacious eat-in kitchen opens to the great room, perfect for everyday living and entertaining alike. Upstairs, a private primary suite with en-suite bath, and large WIC is joined by two additional bedrooms and an updated full bath. A separate office or Bonus room offers flexibility. Additional 547sq ft in basement(laundry and storage) Outdoors you will find a new slate patio for BBQ's and lounging, lush lawns, plenty of play spaces and blooming perennials. All just minutes from trains, towns of Armonk, Pleasantville and Chappaqua and one of the district's easiest commutes.

3 Beds ⋅ 3 Baths ⋅ 1001078 MLS

Come home to this stylishly updated cedar shake colonial with a great open layout. Located on a beautiful and flat lot at the end of a quiet private road within the Byram Hills School District, this home blends country charm with effortless convenience. Gracious entry leads to an open main level featuring a living room with woodburning fireplace, dining room, spacious eat-in kitchen opens to the great room, perfect for everyday living and entertaining alike. Upstairs, a private primary suite with en-suite bath, and large WIC is joined by two additional bedrooms and an updated full bath. A separate office or Bonus room offers flexibility. Additional 547sq ft in basement(laundry and storage) Outdoors you will find a new slate patio for BBQ's and lounging, lush lawns, plenty of play spaces and blooming perennials. All just minutes from trains, towns of Armonk, Pleasantville and Chappaqua and one of the district's easiest commutes.

17 Woodbrook Road, Pleasantville

$1,550,000

Welcome to 20 Robbins Road—perfectly set on a quiet cul-de-sac on a half-acre with a fenced in backyard in one of Westchester’s most desirable communities. Step inside to an inviting living and dining area where oversized windows and a cathedral ceiling with skylight fill the space with natural light. A cut-stone fireplace, recessed lighting, and oak floors create a warm, stylish setting for everyday living and entertaining. At the heart of the home, the spacious chef’s dream eat-in kitchen impresses with cherry wood cabinetry, quartz countertops, skylight, slate tile floors, and premium stainless appliances including a six-burner Viking range, GE Monogram refrigerator, wine cooler and Bosch dishwasher. Sliding doors open to an attractive Trex deck overlooking the serene rear property—perfect for summer dining and weekend gatherings. The main level is completed with three bedrooms, including an oversized primary suite, and an updated hall bath. The primary suite offers a generous walk-in closet with pocket door, ceiling fan, custom cabinetry, a wall of windows for abundant light, and a window seat with additional storage, plus a gorgeous updated en-suite bath. Downstairs, enjoy a spacious recreation/TV room with beadboard trim and sliders to the backyard. A paver walkway leads to a patio designed for effortless outdoor entertainment. A second family room/TV space features built-in custom cabinetry and vinyl floating flooring. The lower level also includes an office/bedroom, laundry area, and an updated bath—ideal for guests, work-from-home, or multi-generational flexibility. Just minutes from vibrant downtown Pleasantville—dining, the Jacob Burns Film Center, schools, library, shopping, farmers market, and community pool—with easy access to the Metro-North train station, Saw Mill River Parkway, and Sprain Brook Parkway.

4 Beds ⋅ 3 Baths ⋅ 981861 MLS

Welcome to 20 Robbins Road—perfectly set on a quiet cul-de-sac on a half-acre with a fenced in backyard in one of Westchester’s most desirable communities. Step inside to an inviting living and dining area where oversized windows and a cathedral ceiling with skylight fill the space with natural light. A cut-stone fireplace, recessed lighting, and oak floors create a warm, stylish setting for everyday living and entertaining. At the heart of the home, the spacious chef’s dream eat-in kitchen impresses with cherry wood cabinetry, quartz countertops, skylight, slate tile floors, and premium stainless appliances including a six-burner Viking range, GE Monogram refrigerator, wine cooler and Bosch dishwasher. Sliding doors open to an attractive Trex deck overlooking the serene rear property—perfect for summer dining and weekend gatherings. The main level is completed with three bedrooms, including an oversized primary suite, and an updated hall bath. The primary suite offers a generous walk-in closet with pocket door, ceiling fan, custom cabinetry, a wall of windows for abundant light, and a window seat with additional storage, plus a gorgeous updated en-suite bath. Downstairs, enjoy a spacious recreation/TV room with beadboard trim and sliders to the backyard. A paver walkway leads to a patio designed for effortless outdoor entertainment. A second family room/TV space features built-in custom cabinetry and vinyl floating flooring. The lower level also includes an office/bedroom, laundry area, and an updated bath—ideal for guests, work-from-home, or multi-generational flexibility. Just minutes from vibrant downtown Pleasantville—dining, the Jacob Burns Film Center, schools, library, shopping, farmers market, and community pool—with easy access to the Metro-North train station, Saw Mill River Parkway, and Sprain Brook Parkway.

20 Robbins Road, Pleasantville

$1,531,000

Don’t miss this rare opportunity to own a beautifully updated, spacious Colonial with rocking chair front porch in the heart of one of Pleasantville's most sought-after neighborhoods—Grove Street. A true classic with timeless charm, this home offers front-row views of Pleasantville's many traditions in an unbeatable location. Leave the car behind—this prime location is just a short stroll to the train, award winning schools, parks, restaurants, and the popular Saturday Farmer’s Market. Step inside to an inviting entry foyer that opens to a formal dining room and a cozy living room (both of which can be interchangably used) featuring a stone fireplace—perfect for entertaining or relaxing with family and friends. The oversized eat-in chef’s kitchen is a standout, with granite countertops, a center island, radiant heated floors, and stainless steel appliances. The second floor features three generously sized bedrooms, a full bathroom, and a versatile bonus room with laundry—ideal for playroom, home gym, office, or den. Retreat to your private third-floor primary suite, an oversized sanctuary with a flexible layout, walk-in dressing room closet, and a full bath. Additional features include fully owned solar panels, gleaming hardwood floors, elegant crown molding, ample storage throughout, a level backyard with patio, one-car garage (a rare find in the Pleasantville village), and a full walk-out basement offering excellent potential for future expansion. This is the central neighborhood lifestyle you’ve been waiting for!

4 Beds ⋅ 3 Baths ⋅ 921039 MLS

Don’t miss this rare opportunity to own a beautifully updated, spacious Colonial with rocking chair front porch in the heart of one of Pleasantville's most sought-after neighborhoods—Grove Street. A true classic with timeless charm, this home offers front-row views of Pleasantville's many traditions in an unbeatable location. Leave the car behind—this prime location is just a short stroll to the train, award winning schools, parks, restaurants, and the popular Saturday Farmer’s Market. Step inside to an inviting entry foyer that opens to a formal dining room and a cozy living room (both of which can be interchangably used) featuring a stone fireplace—perfect for entertaining or relaxing with family and friends. The oversized eat-in chef’s kitchen is a standout, with granite countertops, a center island, radiant heated floors, and stainless steel appliances. The second floor features three generously sized bedrooms, a full bathroom, and a versatile bonus room with laundry—ideal for playroom, home gym, office, or den. Retreat to your private third-floor primary suite, an oversized sanctuary with a flexible layout, walk-in dressing room closet, and a full bath. Additional features include fully owned solar panels, gleaming hardwood floors, elegant crown molding, ample storage throughout, a level backyard with patio, one-car garage (a rare find in the Pleasantville village), and a full walk-out basement offering excellent potential for future expansion. This is the central neighborhood lifestyle you’ve been waiting for!

30 Grove Street, Pleasantville

$1,500,000

Welcome to Pleasantville! A high-end chef’s kitchen blends professional-grade functionality with luxury design — it’s the dream space for serious home cooks, entertainers, or anyone who wants a kitchen that rivals a restaurant setup in both performance and beauty. Timeless Elegance Meets Modern Comfort in This Spectacular Center Hall Colonial This impeccably maintained Center Hall Colonial seamlessly blends classic architecture with luxurious modern updates. Featuring 4 generously sized bedrooms, this home offers space, comfort, and refined style throughout. Step into the updated chef’s kitchen, beautifully appointed with quartz countertops, a Wolf stove, Sub-Zero refrigerator, stainless steel appliances, and a cozy wood-burning fireplace that adds warmth and character. The main level flows effortlessly through a series of elegant spaces, including a formal living room, formal dining room, bonus den, and an enormous family room — ideal for both everyday living and entertaining. Upstairs, the primary suite is a private retreat with two spacious walk-in closets, a home office, and a recently updated en-suite bathroom featuring a luxurious shower and breathtaking mountain views. Three additional bedrooms provide ample closet space and abundant natural light. An upstairs laundry room adds everyday convenience. Outside, enjoy serene outdoor living in the lushly landscaped backyard, complete with mature plantings, a lanai, and a fully equipped outdoor kitchen—perfect for summer evenings and alfresco dining. Additional highlights include: Epoxy-finished garage floors Garage loft with extensive storage Numerous thoughtful upgrades throughout This exceptional home offers the perfect balance of timeless elegance, modern amenities, and high-quality craftsmanship. Truly a must-see!

4 Beds ⋅ 3 Baths ⋅ 912796 MLS

Welcome to Pleasantville! A high-end chef’s kitchen blends professional-grade functionality with luxury design — it’s the dream space for serious home cooks, entertainers, or anyone who wants a kitchen that rivals a restaurant setup in both performance and beauty. Timeless Elegance Meets Modern Comfort in This Spectacular Center Hall Colonial This impeccably maintained Center Hall Colonial seamlessly blends classic architecture with luxurious modern updates. Featuring 4 generously sized bedrooms, this home offers space, comfort, and refined style throughout. Step into the updated chef’s kitchen, beautifully appointed with quartz countertops, a Wolf stove, Sub-Zero refrigerator, stainless steel appliances, and a cozy wood-burning fireplace that adds warmth and character. The main level flows effortlessly through a series of elegant spaces, including a formal living room, formal dining room, bonus den, and an enormous family room — ideal for both everyday living and entertaining. Upstairs, the primary suite is a private retreat with two spacious walk-in closets, a home office, and a recently updated en-suite bathroom featuring a luxurious shower and breathtaking mountain views. Three additional bedrooms provide ample closet space and abundant natural light. An upstairs laundry room adds everyday convenience. Outside, enjoy serene outdoor living in the lushly landscaped backyard, complete with mature plantings, a lanai, and a fully equipped outdoor kitchen—perfect for summer evenings and alfresco dining. Additional highlights include: Epoxy-finished garage floors Garage loft with extensive storage Numerous thoughtful upgrades throughout This exceptional home offers the perfect balance of timeless elegance, modern amenities, and high-quality craftsmanship. Truly a must-see!

68 Mountain Road, Pleasantville

$1,475,000

The One You’ve Been Waiting For Has Arrived At the end of a quiet cul de sac in Pleasantville Country Club, one of Westchester County’s most sought after communities, lies a residence that feels less like a townhome and more like a private retreat. Here, luxury meets convenience and melts seamlessly into daily life, creating a rhythm that feels both elevated and effortless. A First Floor Primary Suite Designed for Serenity Imagine waking to sunlight filtering through walls of windows in your first floor primary suite. You linger a moment longer, the soft breeze drifting in through the sliding doors, carrying with it the quiet hush of the morning. A spa like bath awaits with marble tile underfoot, a soaking tub that invites long evenings with a book, and a walk in shower to refresh and restore. Dual walk in closets and custom vanities ensure everything has its place, leaving your mornings as calm as they are beautiful. An Open Concept Main Level That Celebrates Light and Connection Downstairs, hardwood floors glow in the morning light as you move toward the sun filled kitchen. This spacious, updated kitchen offers the perfect spot to enjoy your morning coffee while taking in views of the golf course greens through expansive windows as the day begins. Later, friends gather in the living room, laughter spilling across a space anchored by the warm glow of a fireplace. As the day fades, you step outside to your 40 foot deck, a coveted feature at Pleasantville Country Club, where cotton candy sunsets stretch across the horizon. The grill sizzles, glasses clink, and it feels as if the evening were designed just for you. Upstairs Comfort and Versatile Living Spaces Upstairs, the rhythm changes. A guest suite offers privacy and comfort, while a sunlit loft with a Palladian window invites quiet afternoons, a cup of tea in hand, a novel you’ve been meaning to finish, and the warm glow of the afternoon sun across your shoulders. A Walk Out Lower Level with Endless Possibilities The finished lower level is where imagination takes shape. A second fireplace sets the mood for movie nights or game day gatherings. Two bonus rooms transform easily into a home office, gym, studio, or guest quarters. Sliding doors open to a private fenced yard, a rare find in Pleasantville Country Club, offering your own peaceful escape into nature. A Lifestyle Beyond Compare Life here is as easy as it is extraordinary. Weekends drift by poolside with meals delivered from the seasonal club restaurant, or evenings spent celebrating under starlit skies. Pickleball and tennis courts are a short stroll away, and the pro shop has everything you need to refine your swing before heading to the golf course. From fitness center mornings to golf course afternoons and restaurant evenings, the pace is yours to choose. When you crave a change of scenery, Pleasantville Village awaits just beyond the gates with Saturday mornings at the Farmers Market, a screening at the Jacob Burns Film Center, dinner at your favorite local spot, and when the city calls, the Metro North train whisks you to Manhattan in under an hour. This isn’t just a home. It’s a story of mornings bathed in sunlight, evenings filled with laughter, and a lifestyle that feels like it was written just for you.

2 Beds ⋅ 4 Baths ⋅ 919097 MLS

The One You’ve Been Waiting For Has Arrived At the end of a quiet cul de sac in Pleasantville Country Club, one of Westchester County’s most sought after communities, lies a residence that feels less like a townhome and more like a private retreat. Here, luxury meets convenience and melts seamlessly into daily life, creating a rhythm that feels both elevated and effortless. A First Floor Primary Suite Designed for Serenity Imagine waking to sunlight filtering through walls of windows in your first floor primary suite. You linger a moment longer, the soft breeze drifting in through the sliding doors, carrying with it the quiet hush of the morning. A spa like bath awaits with marble tile underfoot, a soaking tub that invites long evenings with a book, and a walk in shower to refresh and restore. Dual walk in closets and custom vanities ensure everything has its place, leaving your mornings as calm as they are beautiful. An Open Concept Main Level That Celebrates Light and Connection Downstairs, hardwood floors glow in the morning light as you move toward the sun filled kitchen. This spacious, updated kitchen offers the perfect spot to enjoy your morning coffee while taking in views of the golf course greens through expansive windows as the day begins. Later, friends gather in the living room, laughter spilling across a space anchored by the warm glow of a fireplace. As the day fades, you step outside to your 40 foot deck, a coveted feature at Pleasantville Country Club, where cotton candy sunsets stretch across the horizon. The grill sizzles, glasses clink, and it feels as if the evening were designed just for you. Upstairs Comfort and Versatile Living Spaces Upstairs, the rhythm changes. A guest suite offers privacy and comfort, while a sunlit loft with a Palladian window invites quiet afternoons, a cup of tea in hand, a novel you’ve been meaning to finish, and the warm glow of the afternoon sun across your shoulders. A Walk Out Lower Level with Endless Possibilities The finished lower level is where imagination takes shape. A second fireplace sets the mood for movie nights or game day gatherings. Two bonus rooms transform easily into a home office, gym, studio, or guest quarters. Sliding doors open to a private fenced yard, a rare find in Pleasantville Country Club, offering your own peaceful escape into nature. A Lifestyle Beyond Compare Life here is as easy as it is extraordinary. Weekends drift by poolside with meals delivered from the seasonal club restaurant, or evenings spent celebrating under starlit skies. Pickleball and tennis courts are a short stroll away, and the pro shop has everything you need to refine your swing before heading to the golf course. From fitness center mornings to golf course afternoons and restaurant evenings, the pace is yours to choose. When you crave a change of scenery, Pleasantville Village awaits just beyond the gates with Saturday mornings at the Farmers Market, a screening at the Jacob Burns Film Center, dinner at your favorite local spot, and when the city calls, the Metro North train whisks you to Manhattan in under an hour. This isn’t just a home. It’s a story of mornings bathed in sunlight, evenings filled with laughter, and a lifestyle that feels like it was written just for you.

26 Club Court, Pleasantville

$1,450,000

Enjoy carefree living in this exquisite private townhome located in the highly desirable Enclave in Pleasantville. Meticulously upgraded with luxurious finishes, the primary suite is conveniently situated on the main level for those looking for one-level living. Natural light floods the home through a two-story entryway, flanked by a formal dining room and a den featuring built-in shelves and a wine cooler. The chef's kitchen, with its expansive quartz island and high-end stainless steel appliances, flows into the great room, complete with vaulted coffered ceilings, a gas fireplace. The primary suite provides a serene retreat with its ensuite bathroom and extended walk-in closet. Upstairs, you'll find two generous bedrooms, a spacious full bathroom, and a versatile loft space that overlooks the living area below. The 1,000+ SF finished walk-out lower level adds even more value, with a full bathroom, a bright office/guest room, a recreation room, a gym alcove, and ample storage areas that offer potential for future expansion. Situated between Pleasantville and Chappaqua, you'll be close to a variety of local attractions, including weekly Farmer’s Markets, the Jacob Burns Film Center, unique dining spots, and charming boutiques. Just minutes from train stations and highways, this elegant maintenance-free home provides easy access to all the conveniences you need.

3 Beds ⋅ 4 Baths ⋅ 826855 MLS

Enjoy carefree living in this exquisite private townhome located in the highly desirable Enclave in Pleasantville. Meticulously upgraded with luxurious finishes, the primary suite is conveniently situated on the main level for those looking for one-level living. Natural light floods the home through a two-story entryway, flanked by a formal dining room and a den featuring built-in shelves and a wine cooler. The chef's kitchen, with its expansive quartz island and high-end stainless steel appliances, flows into the great room, complete with vaulted coffered ceilings, a gas fireplace. The primary suite provides a serene retreat with its ensuite bathroom and extended walk-in closet. Upstairs, you'll find two generous bedrooms, a spacious full bathroom, and a versatile loft space that overlooks the living area below. The 1,000+ SF finished walk-out lower level adds even more value, with a full bathroom, a bright office/guest room, a recreation room, a gym alcove, and ample storage areas that offer potential for future expansion. Situated between Pleasantville and Chappaqua, you'll be close to a variety of local attractions, including weekly Farmer’s Markets, the Jacob Burns Film Center, unique dining spots, and charming boutiques. Just minutes from train stations and highways, this elegant maintenance-free home provides easy access to all the conveniences you need.

46 Dennis Lane, Pleasantville

$1,445,000

Welcome to a half acre of heaven. You will fall in love with the incredible landscaping and gardening that has entertained garden club members. The glorious interior is light and bright with lots of windows strategically placed for viewing the beautiful outdoors. Plus, there is additional recessed lighting. The main level consists of a gracious entry foyer and guest closet, along with a powder room. Additionally, on this level, there is the large living room with an easy gas fire plae and door to a lanai style wrap around trex deck. There is also the dining room and an eat-in-kitchen with all the accoutrements and stainless steel appliances. plus a door to the back deck and oversized patio. The second level is a short and artful staircase to the second level. Here you will find the large primary suite with beautiful bathroom and several customized closets. There are two other bedrooms on this level and a full bathroom. Enjoy the comfort of radiant floor heating in both the kitchen and primary bathroom. You will spend a lot of time on the lower level, which has a large muti-purpose room with plenty of space for an exercise area, an entertainment area, and a possible office area. You will also find a bedroom, a full bath, the laundry room, garage access, and doors to the huge back patio where you can relax--a hot tub and firepit are there for you and come with the house! The house is situated between Chappaqua and Pleasantville and provides easy access to both downtown areas, recreation, trains and highways. This is a move-in ready home you will always remember.

4 Beds ⋅ 4 Baths ⋅ 969776 MLS

Welcome to a half acre of heaven. You will fall in love with the incredible landscaping and gardening that has entertained garden club members. The glorious interior is light and bright with lots of windows strategically placed for viewing the beautiful outdoors. Plus, there is additional recessed lighting. The main level consists of a gracious entry foyer and guest closet, along with a powder room. Additionally, on this level, there is the large living room with an easy gas fire plae and door to a lanai style wrap around trex deck. There is also the dining room and an eat-in-kitchen with all the accoutrements and stainless steel appliances. plus a door to the back deck and oversized patio. The second level is a short and artful staircase to the second level. Here you will find the large primary suite with beautiful bathroom and several customized closets. There are two other bedrooms on this level and a full bathroom. Enjoy the comfort of radiant floor heating in both the kitchen and primary bathroom. You will spend a lot of time on the lower level, which has a large muti-purpose room with plenty of space for an exercise area, an entertainment area, and a possible office area. You will also find a bedroom, a full bath, the laundry room, garage access, and doors to the huge back patio where you can relax--a hot tub and firepit are there for you and come with the house! The house is situated between Chappaqua and Pleasantville and provides easy access to both downtown areas, recreation, trains and highways. This is a move-in ready home you will always remember.

31 Pierce Drive, Pleasantville

$1,410,000

Welcome to this beautifully designed END + CORNER UNIT townhome offering 2 spacious bedrooms, plus 2 extra rooms, with flexible options for guest rooms, additional bedrooms, or a home office. Perfectly situated just across from the Clubhouse, pool, restaurant, and pro shop, this home puts world-class amenities right at your doorstep. With two attached garages and a spacious open layout, comfort and convenience are effortlessly combined. Step inside to find gleaming wood floors and sun-drenched interiors, with expansive windows framing breathtaking green forest views. The open floor plan is ideal for entertaining, highlighted by a luxurious dine-in kitchen that inspires memorable meals and gatherings. The inviting living room features a cozy fireplace and opens to a private deck, the perfect spot to unwind and enjoy serene surroundings. Upstairs, the generously sized primary suite offers a peaceful retreat with a spa-like bathroom, including a soaking tub, stand-alone shower, and elegant tilework. Two additional rooms share a full bath and are complemented by generous closet and attic storage. The oversized lower level expands the home’s versatility, ideal for a media room, home gym, or private office. A second fireplace, full bath, and glass doors to another deck complete this exceptional space. Enjoy a truly maintenance-free lifestyle with HOA benefits that include golf membership, access to tennis and pickleball courts, clubhouse use, snow removal, and exterior maintenance. Located in the sought-after Pleasantville School District, this home is just minutes from the charming village of Pleasantville, the Jacob Burns Theater, the weekly Farmers’ Market, and more. The middle and high schools are nearby, with a convenient path that leads directly from the unit to the school track. Embrace the perfect balance of luxury, flexibility, and community living at Pleasantville Country Club. Some Property Updates: Hot Water Tank: January 2024, A/C System: August 2022, Garage Door & Roof: 2024.

2 Beds ⋅ 4 Baths ⋅ 891163 MLS

Welcome to this beautifully designed END + CORNER UNIT townhome offering 2 spacious bedrooms, plus 2 extra rooms, with flexible options for guest rooms, additional bedrooms, or a home office. Perfectly situated just across from the Clubhouse, pool, restaurant, and pro shop, this home puts world-class amenities right at your doorstep. With two attached garages and a spacious open layout, comfort and convenience are effortlessly combined. Step inside to find gleaming wood floors and sun-drenched interiors, with expansive windows framing breathtaking green forest views. The open floor plan is ideal for entertaining, highlighted by a luxurious dine-in kitchen that inspires memorable meals and gatherings. The inviting living room features a cozy fireplace and opens to a private deck, the perfect spot to unwind and enjoy serene surroundings. Upstairs, the generously sized primary suite offers a peaceful retreat with a spa-like bathroom, including a soaking tub, stand-alone shower, and elegant tilework. Two additional rooms share a full bath and are complemented by generous closet and attic storage. The oversized lower level expands the home’s versatility, ideal for a media room, home gym, or private office. A second fireplace, full bath, and glass doors to another deck complete this exceptional space. Enjoy a truly maintenance-free lifestyle with HOA benefits that include golf membership, access to tennis and pickleball courts, clubhouse use, snow removal, and exterior maintenance. Located in the sought-after Pleasantville School District, this home is just minutes from the charming village of Pleasantville, the Jacob Burns Theater, the weekly Farmers’ Market, and more. The middle and high schools are nearby, with a convenient path that leads directly from the unit to the school track. Embrace the perfect balance of luxury, flexibility, and community living at Pleasantville Country Club. Some Property Updates: Hot Water Tank: January 2024, A/C System: August 2022, Garage Door & Roof: 2024.

5 Country Club Lane, Pleasantville

$1,400,000

Welcome to 55 Greenmeadow Road - a one-of-a-kind private retreat just steps from the heart of Pleasantville. Set on an expansive 1-acre lot, this four-bedroom, three-bath home offers newly renovated finishes, exceptional outdoor space, privacy, and one of the only private pools in the village. This beautifully updated Cape Cod home features a brand-new skylit chef’s kitchen, thoughtfully designed and built in 2025. The space includes high-quality custom cabinetry, new stainless steel appliances, sophisticated subway tile, and quartzite countertops. Bay windows fill the dining and living rooms with natural light and charm, complemented by a fireplace with a reclaimed wood mantel, custom built-in bookshelves, and brand new wide-plank oak floors throughout. Step through the storybook Dutch door into a spectacular three-season room overlooking the pool—a perfect setting for morning coffee, al fresco dining, or breezy summer night entertaining. The expansive first-floor primary suite includes a spa-like en-suite bath with radiant heated floors and a six-head electronic shower system. A large second bedroom (currently used as an office) also features an updated full bath with heated floors. Upstairs are two generously sized bedrooms and an updated hall bath, along with a cedar closet and a large attic offering ample storage or potential for future expansion. Enjoy your own private resort with a fabulous 40x20 heated saltwater pool, complete with a diving board and hot tub. Located just minutes from Pleasantville’s shops, restaurants, and train, this is an opportunity you don’t want to miss.

4 Beds ⋅ 3 Baths ⋅ 954814 MLS

Welcome to 55 Greenmeadow Road - a one-of-a-kind private retreat just steps from the heart of Pleasantville. Set on an expansive 1-acre lot, this four-bedroom, three-bath home offers newly renovated finishes, exceptional outdoor space, privacy, and one of the only private pools in the village. This beautifully updated Cape Cod home features a brand-new skylit chef’s kitchen, thoughtfully designed and built in 2025. The space includes high-quality custom cabinetry, new stainless steel appliances, sophisticated subway tile, and quartzite countertops. Bay windows fill the dining and living rooms with natural light and charm, complemented by a fireplace with a reclaimed wood mantel, custom built-in bookshelves, and brand new wide-plank oak floors throughout. Step through the storybook Dutch door into a spectacular three-season room overlooking the pool—a perfect setting for morning coffee, al fresco dining, or breezy summer night entertaining. The expansive first-floor primary suite includes a spa-like en-suite bath with radiant heated floors and a six-head electronic shower system. A large second bedroom (currently used as an office) also features an updated full bath with heated floors. Upstairs are two generously sized bedrooms and an updated hall bath, along with a cedar closet and a large attic offering ample storage or potential for future expansion. Enjoy your own private resort with a fabulous 40x20 heated saltwater pool, complete with a diving board and hot tub. Located just minutes from Pleasantville’s shops, restaurants, and train, this is an opportunity you don’t want to miss.

55 Greenmeadow Road, Pleasantville

$1,375,000

Experience the pinnacle of sophisticated, maintenance-free living in this stunning end-unit townhouse at The Enclave. Built in 2019 by renowned builder Toll Brothers, this impeccably maintained 3-bedroom, 2.5-bath home enjoys premier southern exposure, filling the interior with natural light throughout the day. The open-concept main level is designed for modern living and effortless entertaining, featuring a gourmet chef’s kitchen with premium Wolf stainless steel appliances, durable Silestone countertops, and a massive center island with seating for six. Seven-inch white oak hardwood floors flow throughout this level , complemented by a cozy gas fireplace in the oversized living area, while 2 butler’s pantries with a built-in wine refrigerator and coffee bar seamlessly serve the formal dining and living spaces. Upstairs, the primary suite is a true retreat, showcasing dramatic tray ceilings, two custom walk-in closet with built-ins, and a spa-like ensuite finished in elegant white Carrara marble with double vanities and an oversized shower. Two additional light-filled bedrooms, a pristine full bath, and a dedicated laundry room complete the second level. The versatile lower level offers flexible bonus space, including a mudroom and a dedicated gym area—ideal for a home office or playroom. Step outside to a private, professionally landscaped paver patio framed by lush arborvitae, boxwoods, and white roses, perfect for relaxing or entertaining. An attached two-car garage with extra storage adds convenience. Ideally located in the charming Village of Pleasantville, this home is just minutes from Farmer's Market, boutique shopping, dining, the Jacob Burns Film Center, and Metro-North for an easy Manhattan commute. Enjoy the ease of a true “lock-and-leave” lifestyle with landscaping and snow removal included in the HOA.

3 Beds ⋅ 3 Baths ⋅ 970356 MLS

Experience the pinnacle of sophisticated, maintenance-free living in this stunning end-unit townhouse at The Enclave. Built in 2019 by renowned builder Toll Brothers, this impeccably maintained 3-bedroom, 2.5-bath home enjoys premier southern exposure, filling the interior with natural light throughout the day. The open-concept main level is designed for modern living and effortless entertaining, featuring a gourmet chef’s kitchen with premium Wolf stainless steel appliances, durable Silestone countertops, and a massive center island with seating for six. Seven-inch white oak hardwood floors flow throughout this level , complemented by a cozy gas fireplace in the oversized living area, while 2 butler’s pantries with a built-in wine refrigerator and coffee bar seamlessly serve the formal dining and living spaces. Upstairs, the primary suite is a true retreat, showcasing dramatic tray ceilings, two custom walk-in closet with built-ins, and a spa-like ensuite finished in elegant white Carrara marble with double vanities and an oversized shower. Two additional light-filled bedrooms, a pristine full bath, and a dedicated laundry room complete the second level. The versatile lower level offers flexible bonus space, including a mudroom and a dedicated gym area—ideal for a home office or playroom. Step outside to a private, professionally landscaped paver patio framed by lush arborvitae, boxwoods, and white roses, perfect for relaxing or entertaining. An attached two-car garage with extra storage adds convenience. Ideally located in the charming Village of Pleasantville, this home is just minutes from Farmer's Market, boutique shopping, dining, the Jacob Burns Film Center, and Metro-North for an easy Manhattan commute. Enjoy the ease of a true “lock-and-leave” lifestyle with landscaping and snow removal included in the HOA.

57 Dennis Lane, Pleasantville

$1,370,000

Welcome to this spacious contemporary home featuring three bedrooms and three baths, perfectly situated on a half-acre lot on a desirable cul-de-sac. Inside you'll find a bright dining room and an eat-in kitchen with a separate laundry room for added convenience. The kitchen enjoys easy outdoor access to a double deck, which is perfect for outdoor entertaining and offers a front-row seat to spectacular sunsets in a peaceful setting. The living room features vaulted ceilings and one of two wood-burning fireplaces, creating a warm and inviting space for both everyday living and entertaining. The home includes a generous primary bedroom suite with a tastefully renovated full bathroom next to two additional bedrooms that share a hall bath with a tub. The finished lower level features a spacious casual living room with a second wood burning fireplace, wet bar and built-ins, plus additional rooms for a home gym, private remote office, or recreation space as well as a renovated third full bath. All of these areas have walkout sliders to the expansive patio. A 2-car garage and a driveway that easily fits six cars completes the property. This home is located just minutes from the Pleasantville pool and the scenic trails and open space of Nannahagan Park, which is perfect for outdoor recreation and relaxation. It is also minutes from the vibrant downtown Pleasantville Village scene, offering numerous dining options, the Jacob Burns Film Center, the train station, and Saturday's Farmers Market. This home perfectly blends privacy, comfort, and convenience.

3 Beds ⋅ 3 Baths ⋅ 969726 MLS

Welcome to this spacious contemporary home featuring three bedrooms and three baths, perfectly situated on a half-acre lot on a desirable cul-de-sac. Inside you'll find a bright dining room and an eat-in kitchen with a separate laundry room for added convenience. The kitchen enjoys easy outdoor access to a double deck, which is perfect for outdoor entertaining and offers a front-row seat to spectacular sunsets in a peaceful setting. The living room features vaulted ceilings and one of two wood-burning fireplaces, creating a warm and inviting space for both everyday living and entertaining. The home includes a generous primary bedroom suite with a tastefully renovated full bathroom next to two additional bedrooms that share a hall bath with a tub. The finished lower level features a spacious casual living room with a second wood burning fireplace, wet bar and built-ins, plus additional rooms for a home gym, private remote office, or recreation space as well as a renovated third full bath. All of these areas have walkout sliders to the expansive patio. A 2-car garage and a driveway that easily fits six cars completes the property. This home is located just minutes from the Pleasantville pool and the scenic trails and open space of Nannahagan Park, which is perfect for outdoor recreation and relaxation. It is also minutes from the vibrant downtown Pleasantville Village scene, offering numerous dining options, the Jacob Burns Film Center, the train station, and Saturday's Farmers Market. This home perfectly blends privacy, comfort, and convenience.

80 Ridgeview Drive, Pleasantville

$1,370,000

Set privately in the highly sought-after Enclave neighborhood, this beautiful end unit offers the perfect blend of luxury, space, and convenience. Exceptionally upgraded and meticulously maintained, this home is truly move-in ready. Step inside to discover an open and inviting floor plan featuring a light-filled great room with vaulted ceilings, a gas fireplace, and sliding doors that open to a spacious deck—ideal for relaxing or entertaining. The chef’s kitchen is equipped with stainless steel appliances, a central island with seating, and elegant finishes. The dining room impresses with a dramatic two-story ceiling and a view of the turned staircase. A versatile living room/den offers flexible use for work or leisure. The first-floor primary suite provides effortless living with a spa-like ensuite bath and ample walk in closets. Upstairs, a generous loft space overlooks the main level and leads to two large bedrooms that share a well-appointed full bath with double vanities and large closets. The expansive walk-out lower level, with high ceilings, presents endless possibilities for further living space. Additional highlights include a two-car garage with a sleek epoxy floor, driveway parking, and a prime location alongside lovely plantings and green space. Perfectly positioned between the charming downtowns of Pleasantville and Chappaqua, The Enclave offers residents an unbeatable lifestyle close to shopping, dining, schools, and transportation. Truly a pleasure to call home.

3 Beds ⋅ 3 Baths ⋅ 896216 MLS

Set privately in the highly sought-after Enclave neighborhood, this beautiful end unit offers the perfect blend of luxury, space, and convenience. Exceptionally upgraded and meticulously maintained, this home is truly move-in ready. Step inside to discover an open and inviting floor plan featuring a light-filled great room with vaulted ceilings, a gas fireplace, and sliding doors that open to a spacious deck—ideal for relaxing or entertaining. The chef’s kitchen is equipped with stainless steel appliances, a central island with seating, and elegant finishes. The dining room impresses with a dramatic two-story ceiling and a view of the turned staircase. A versatile living room/den offers flexible use for work or leisure. The first-floor primary suite provides effortless living with a spa-like ensuite bath and ample walk in closets. Upstairs, a generous loft space overlooks the main level and leads to two large bedrooms that share a well-appointed full bath with double vanities and large closets. The expansive walk-out lower level, with high ceilings, presents endless possibilities for further living space. Additional highlights include a two-car garage with a sleek epoxy floor, driveway parking, and a prime location alongside lovely plantings and green space. Perfectly positioned between the charming downtowns of Pleasantville and Chappaqua, The Enclave offers residents an unbeatable lifestyle close to shopping, dining, schools, and transportation. Truly a pleasure to call home.

54 Dennis Lane, Pleasantville

$1,351,000

Nestled on a quiet cul-de-sac, this elegant Colonial blends timeless design with modern comfort. A grand two-story entry leads to formal living and dining rooms with hardwood floors, crown molding, and classic details. Gather in the living room to enjoy the wood burning fireplace with marble surround on a cold winter’s night. The chef’s kitchen features granite counters, stainless steel appliances, a mahogany-topped island with wine rack, a cozy coffee bar with second sink, and a spacious sunlit eating are. The kitchen is open to the family room boasting built-ins and sliding glass doors to a private bluestone patio - perfect for entertaining. Upstairs, the primary suite offers a walk-in closet and spa-like bath with Jacuzzi tub and tiled shower. Two additional bedrooms, a hall bath and conveniently located laundry room complete the second level. The walk-up attic and finished lower level provide ample storage. This low maintenance home with generator hook-up is surrounded by mature landscaping and bordering Graham Hills Park. This peaceful retreat is just minutes from all that Pleasantville has to offer.

3 Beds ⋅ 3 Baths ⋅ 915167 MLS

Nestled on a quiet cul-de-sac, this elegant Colonial blends timeless design with modern comfort. A grand two-story entry leads to formal living and dining rooms with hardwood floors, crown molding, and classic details. Gather in the living room to enjoy the wood burning fireplace with marble surround on a cold winter’s night. The chef’s kitchen features granite counters, stainless steel appliances, a mahogany-topped island with wine rack, a cozy coffee bar with second sink, and a spacious sunlit eating are. The kitchen is open to the family room boasting built-ins and sliding glass doors to a private bluestone patio - perfect for entertaining. Upstairs, the primary suite offers a walk-in closet and spa-like bath with Jacuzzi tub and tiled shower. Two additional bedrooms, a hall bath and conveniently located laundry room complete the second level. The walk-up attic and finished lower level provide ample storage. This low maintenance home with generator hook-up is surrounded by mature landscaping and bordering Graham Hills Park. This peaceful retreat is just minutes from all that Pleasantville has to offer.

200 Central Avenue, Pleasantville

$1,330,000

Modern convenience meets the tranquility of nature in this mid-century inspired retreat. Set on 1.04 acres, this 3,160 SF contemporary home blends privacy, clean lines, and seamless indoor-outdoor living. Expansive Marvin windows, vaulted ceilings with skylights, exposed beams, and a sunken living room connect every space to the outdoors. Multiple decks invite you to read, bird watch, or simply soak in the serene landscape. The chef’s kitchen with granite waterfall island, mahogany counters, stainless Thermador appliances, and double ovens flows to the dining room and large slate patio overlooking meadows, rock walls, and mature trees. Hardwood floors, mahogany siding and a wood-burning stove add warmth and character. Upstairs offers three bedrooms including a primary suite with private bath and balcony, plus a large bonus room, laundry, and a full walk-up attic with potential for expansion. Lush pollinator gardens, lower lawn, and versatile outbuildings - garden sheds, and storage - enhance a sustainable lifestyle. Additional highlights include an ADT alarm/fire system, generator hook-up, plenty of storage and a two-car garage. Minutes from town, highways, and a 30-minute train to Grand Central, this property offers modern living in harmony with nature.

3 Beds ⋅ 3 Baths ⋅ 903108 MLS

Modern convenience meets the tranquility of nature in this mid-century inspired retreat. Set on 1.04 acres, this 3,160 SF contemporary home blends privacy, clean lines, and seamless indoor-outdoor living. Expansive Marvin windows, vaulted ceilings with skylights, exposed beams, and a sunken living room connect every space to the outdoors. Multiple decks invite you to read, bird watch, or simply soak in the serene landscape. The chef’s kitchen with granite waterfall island, mahogany counters, stainless Thermador appliances, and double ovens flows to the dining room and large slate patio overlooking meadows, rock walls, and mature trees. Hardwood floors, mahogany siding and a wood-burning stove add warmth and character. Upstairs offers three bedrooms including a primary suite with private bath and balcony, plus a large bonus room, laundry, and a full walk-up attic with potential for expansion. Lush pollinator gardens, lower lawn, and versatile outbuildings - garden sheds, and storage - enhance a sustainable lifestyle. Additional highlights include an ADT alarm/fire system, generator hook-up, plenty of storage and a two-car garage. Minutes from town, highways, and a 30-minute train to Grand Central, this property offers modern living in harmony with nature.

2 Cecilia Lane, Pleasantville

$1,325,000

Stunning four-bedroom Village Victorian in the heart of Pleasantville, rich with late 1800s character and timeless architectural detail. This exceptional home showcases exquisite original features including ornate crown molding, soaring 10-foot ceilings, bay windows, hardwood floors, and a beautifully crafted wood banister spanning all three levels. The first floor offers a gracious and welcoming layout with a spacious foyer, living room, dining room, den, powder room, and an eat-in kitchen with direct access to an expansive back deck overlooking a private fenced in backyard, perfect for indoor-outdoor living and entertaining. Upstairs, the second-floor features four bedrooms and two full baths. The third floor presents a versatile open space with endless possibilities—ideal for a home office, recreation room, private primary suite, or additional bedrooms. A covered front wrap around porch enhances the home’s undeniable charm, creating the perfect setting for morning coffee or relaxed summer evenings. Set on over half an acre of flat, level property, the grounds offer ample space for outdoor living enhancements. With exceptional curb appeal and an unbeatable location close to schools, Metro-North, the Jacob Burns Film Center, farmers market, and village shops, this home is a rare offering. First time on the market in over 30 years, truly a swoon-worthy opportunity not to be missed.

4 Beds ⋅ 3 Baths ⋅ 1001347 MLS

Stunning four-bedroom Village Victorian in the heart of Pleasantville, rich with late 1800s character and timeless architectural detail. This exceptional home showcases exquisite original features including ornate crown molding, soaring 10-foot ceilings, bay windows, hardwood floors, and a beautifully crafted wood banister spanning all three levels. The first floor offers a gracious and welcoming layout with a spacious foyer, living room, dining room, den, powder room, and an eat-in kitchen with direct access to an expansive back deck overlooking a private fenced in backyard, perfect for indoor-outdoor living and entertaining. Upstairs, the second-floor features four bedrooms and two full baths. The third floor presents a versatile open space with endless possibilities—ideal for a home office, recreation room, private primary suite, or additional bedrooms. A covered front wrap around porch enhances the home’s undeniable charm, creating the perfect setting for morning coffee or relaxed summer evenings. Set on over half an acre of flat, level property, the grounds offer ample space for outdoor living enhancements. With exceptional curb appeal and an unbeatable location close to schools, Metro-North, the Jacob Burns Film Center, farmers market, and village shops, this home is a rare offering. First time on the market in over 30 years, truly a swoon-worthy opportunity not to be missed.

280 Bedford Road, Pleasantville

$1,325,000

Welcome to 302 Washington Avenue, a beautifully crafted 5-bedroom, 4-bathroom Colonial located in one of Pleasantville’s most sought-after neighborhoods. This newly constructed home combines timeless design with modern amenities, all within walking distance to Metro North, local shops, restaurants, and scenic parks—perfect for those seeking convenience without compromising on luxury. Step inside to discover a thoughtfully designed open floor plan, ideal for entertaining yet offering distinct spaces for privacy and productivity, including dedicated areas perfect for working from home. Every detail of this home reflects superior craftsmanship, from the high-end Anderson windows to the custom finishes and modern fixtures. The heart of the home is a spacious, contemporary kitchen designed to make hosting effortless, whether you're throwing a dinner party or enjoying a quiet meal. Outfitted with energy-efficient appliances, ample cabinetry, and a generous island, the kitchen seamlessly connects to the dining and living areas for a cohesive, welcoming atmosphere. Additional highlights include a fully wired Internet/Wi-Fi system for reliable connectivity throughout the home, a state-of-the-art fire sprinkler system, and an oversized one-car garage offering extra storage space. The landscaped yard provides a serene outdoor retreat, ready for summer barbecues or peaceful evenings. With its blend of elegance, functionality, and unbeatable location, 302 Washington Avenue is more than just a house—it’s the perfect place to call home. Property currently has temporary tenants and photos are from previous listing

5 Beds ⋅ 4 Baths ⋅ 990378 MLS

Welcome to 302 Washington Avenue, a beautifully crafted 5-bedroom, 4-bathroom Colonial located in one of Pleasantville’s most sought-after neighborhoods. This newly constructed home combines timeless design with modern amenities, all within walking distance to Metro North, local shops, restaurants, and scenic parks—perfect for those seeking convenience without compromising on luxury. Step inside to discover a thoughtfully designed open floor plan, ideal for entertaining yet offering distinct spaces for privacy and productivity, including dedicated areas perfect for working from home. Every detail of this home reflects superior craftsmanship, from the high-end Anderson windows to the custom finishes and modern fixtures. The heart of the home is a spacious, contemporary kitchen designed to make hosting effortless, whether you're throwing a dinner party or enjoying a quiet meal. Outfitted with energy-efficient appliances, ample cabinetry, and a generous island, the kitchen seamlessly connects to the dining and living areas for a cohesive, welcoming atmosphere. Additional highlights include a fully wired Internet/Wi-Fi system for reliable connectivity throughout the home, a state-of-the-art fire sprinkler system, and an oversized one-car garage offering extra storage space. The landscaped yard provides a serene outdoor retreat, ready for summer barbecues or peaceful evenings. With its blend of elegance, functionality, and unbeatable location, 302 Washington Avenue is more than just a house—it’s the perfect place to call home. Property currently has temporary tenants and photos are from previous listing

302 Washington Avenue, Pleasantville

$1,321,000

Step into this beautifully and thoughtfully, fully renovated 3-bedroom, 3-full bathroom home featuring brand-new Hickory floors, energy-certified heating and cooling systems and appliances, and all-new Marvin windows and doors—all designed for everyday comfort and peace of mind. The stunning new kitchen with quartz countertops and ample storage flows effortlessly to a Trex deck, with direct access from both the kitchen and living room, perfect for entertaining or relaxing. Closets throughout feature flexible custom systems, and the lower-level walkout opens to a covered patio and backyard. Outside, enjoy low-maintenance HardiePlank siding and a covered front porch with a gorgeous mahogany ceiling—charming details that invite you home. With a fabulous connection to town, this home sits one block away from Roselle Park, and is walkable to the Metro-North train station, Pleasantville's acclaimed restaurants, shops, the Jacob Burns Film Center, and Saturday's Farmers Market. 11 Roselle offers the rare combination of energy-efficient, fully updated living with true turnkey convenience. A gem all around. See it for yourself—this home is ready for you to move in and enjoy!

3 Beds ⋅ 3 Baths ⋅ 954609 MLS

Step into this beautifully and thoughtfully, fully renovated 3-bedroom, 3-full bathroom home featuring brand-new Hickory floors, energy-certified heating and cooling systems and appliances, and all-new Marvin windows and doors—all designed for everyday comfort and peace of mind. The stunning new kitchen with quartz countertops and ample storage flows effortlessly to a Trex deck, with direct access from both the kitchen and living room, perfect for entertaining or relaxing. Closets throughout feature flexible custom systems, and the lower-level walkout opens to a covered patio and backyard. Outside, enjoy low-maintenance HardiePlank siding and a covered front porch with a gorgeous mahogany ceiling—charming details that invite you home. With a fabulous connection to town, this home sits one block away from Roselle Park, and is walkable to the Metro-North train station, Pleasantville's acclaimed restaurants, shops, the Jacob Burns Film Center, and Saturday's Farmers Market. 11 Roselle offers the rare combination of energy-efficient, fully updated living with true turnkey convenience. A gem all around. See it for yourself—this home is ready for you to move in and enjoy!

11 Roselle Avenue, Pleasantville

$1,300,501

Set far back from the street on a quiet residential street, this home sits on .94 beautifully landscaped, irrigated acres with charming stone walls. It also backs onto Pocantico Lake County Park for additional privacy and a country feel. Yet so close to the Briarcliff, Pleasantville and Tarrytown Village centers. Pleasantville PO with Briarcliff schools, and both Town of Mount Pleasant and Village Of Briarcliff Manor amenities available. Updated inside and out, including 3 full updated bathrooms and hardwood floors on main level plus six panel, solid wood colonial interior doors. New front doors & AZAK columns on front porch (2026). New Driveway (2026)--please pull in and out directly (do not turn around in driveway while it is still curing) . Young boiler (2016), well pump (2018), hot water heater (2025), and above ground oil tank (2012) and young AC compressor. 50-year roof installed 2014. Recessed lights throughout. Pack your bags and move right in!

4 Beds ⋅ 3 Baths ⋅ 978011 MLS

Set far back from the street on a quiet residential street, this home sits on .94 beautifully landscaped, irrigated acres with charming stone walls. It also backs onto Pocantico Lake County Park for additional privacy and a country feel. Yet so close to the Briarcliff, Pleasantville and Tarrytown Village centers. Pleasantville PO with Briarcliff schools, and both Town of Mount Pleasant and Village Of Briarcliff Manor amenities available. Updated inside and out, including 3 full updated bathrooms and hardwood floors on main level plus six panel, solid wood colonial interior doors. New front doors & AZAK columns on front porch (2026). New Driveway (2026)--please pull in and out directly (do not turn around in driveway while it is still curing) . Young boiler (2016), well pump (2018), hot water heater (2025), and above ground oil tank (2012) and young AC compressor. 50-year roof installed 2014. Recessed lights throughout. Pack your bags and move right in!

46 Bacon Hill Road, Pleasantville

$1,285,000

AO, contracts out. 9/15. This custom-built Contemporary Colonial offers the best of modern luxury, elegant amenities with attention to detail all in this private park like setting at the end of a cul-de sac. This lovely home is impeccably maintained and shows pride of ownership with an expansive yet intimate environment for comfortable family living, and great flow for entertaining. As you enter you will notice tiled entry hall, gleaming hardwood flooring, powder room, updated kitchen (2016) with custom built walnut cabinets, stainless steel appliances, granite counters, and large pantry. Additionally, there is an eat-in area with sliders to a 2-tier deck-great for family gatherings. Inviting family room offers soaring cathedral ceilings, 2 skylights with a focus on the gas fireplace and brick facade floor to ceiling. Enjoy holidays in the spacious formal dining room and well portioned living room with a large picture window. On the second level you will find a primary bedroom with high ceilings, 3 closets, and jacuzzi bath, separate shower, cathedral ceilings and skylight. There are 3 additional bedrooms, (one bedroom used as an office with built in desk), and hall bath. The basement offers recreation room, utilities, and washer/dryer, and a door out to yard. There are many upgrades including AC compressors, and 1 air handler-2 years old, kitchen (2016), hot water tank, roof and skylights 2013, hall bath and primary bath-2008, 1/2 bath-2016, windows in primary bedroom, and slider in eat-in area. Peaceful setting, but yet close to train, bus, major highways, restaurants, Jacob burns film center, bike trails and adjacent to Graham Hills Park. A must see!

4 Beds ⋅ 3 Baths ⋅ 904706 MLS

AO, contracts out. 9/15. This custom-built Contemporary Colonial offers the best of modern luxury, elegant amenities with attention to detail all in this private park like setting at the end of a cul-de sac. This lovely home is impeccably maintained and shows pride of ownership with an expansive yet intimate environment for comfortable family living, and great flow for entertaining. As you enter you will notice tiled entry hall, gleaming hardwood flooring, powder room, updated kitchen (2016) with custom built walnut cabinets, stainless steel appliances, granite counters, and large pantry. Additionally, there is an eat-in area with sliders to a 2-tier deck-great for family gatherings. Inviting family room offers soaring cathedral ceilings, 2 skylights with a focus on the gas fireplace and brick facade floor to ceiling. Enjoy holidays in the spacious formal dining room and well portioned living room with a large picture window. On the second level you will find a primary bedroom with high ceilings, 3 closets, and jacuzzi bath, separate shower, cathedral ceilings and skylight. There are 3 additional bedrooms, (one bedroom used as an office with built in desk), and hall bath. The basement offers recreation room, utilities, and washer/dryer, and a door out to yard. There are many upgrades including AC compressors, and 1 air handler-2 years old, kitchen (2016), hot water tank, roof and skylights 2013, hall bath and primary bath-2008, 1/2 bath-2016, windows in primary bedroom, and slider in eat-in area. Peaceful setting, but yet close to train, bus, major highways, restaurants, Jacob burns film center, bike trails and adjacent to Graham Hills Park. A must see!

61 Walnut Street, Pleasantville

$1,275,000

Welcome to 88 Ridgeview Road, a place where quiet mornings, effortless entertaining, and the charm of Pleasantville come together in perfect harmony. Tucked away at the end of a coveted cul-de-sac and set on over an acre of beautifully landscaped property, this exceptional Colonial offers the rare combination of privacy, space, and convenience in one of Westchester County's most sought-after communities. As you arrive, there is an immediate sense of serenity. Mature trees frame the property, lush lawns stretch across the landscape, and the peaceful setting feels worlds away while remaining just minutes from the vibrant Village of Pleasantville, Metro-North, award-winning schools, restaurants, and local shops. Step inside and discover a home designed for both comfortable everyday living and memorable gatherings. Sunlight fills the spacious interior, creating warm and inviting spaces throughout. The heart of the home is the stunning family room, where dramatic beamed ceilings, a beautiful fireplace, and French doors create an atmosphere that is both elegant and welcoming. Open the doors and seamlessly extend your living space outdoors to the oversized deck, a true retreat overlooking tranquil landscaping and complete privacy. Whether hosting summer barbecues, enjoying morning coffee, or unwinding beneath the stars, this outdoor space was made to be enjoyed. The thoughtfully designed first-floor layout offers remarkable flexibility and convenience, including a desirable first-floor primary suite, providing comfortable one-level living when desired. A dedicated home office creates the perfect environment for remote work, creative pursuits, or quiet study. For those who love to cook and entertain, the expansive eat-in kitchen is sure to impress. Featuring a premium Thermador gas range, Bosch dishwasher, abundant cabinetry, and generous prep space, the kitchen flows naturally into the surrounding living and dining areas, making it easy to stay connected with family and guests. From holiday celebrations to casual weeknight dinners, this home was designed for bringing people together. Adding warmth and character are two fireplaces, including one in the elegant dining room and another in the stunning family room, creating inviting spaces to gather throughout the seasons. Upstairs, three generously sized bedrooms provide comfortable accommodations for family and guests. A beautifully appointed full bathroom serves the second level, offering both functionality and convenience while maintaining the home's timeless appeal. The lower level adds tremendous value and versatility with a walk-out basement featuring abundant storage, a dedicated workshop area, and endless possibilities for hobbies, recreation, fitness, or future expansion. What truly sets 88 Ridgeview Road apart is its ability to offer the best of Pleasantville living. Here, you'll enjoy the privacy of an acre-plus setting while remaining close to everything that makes Pleasantville so special—its charming downtown, beloved farmers market, community events, parks, dining, and easy commute to New York City. Homes offering this combination of location, privacy, first-floor primary living, entertaining space, and over an acre of property rarely become available. Whether you're searching for a peaceful retreat, a place to host family and friends, or the opportunity to establish roots in one of Westchester's most desirable communities, 88 Ridgeview Road delivers an extraordinary lifestyle opportunity. This is more than a home. It's where summer evenings linger on the deck, holiday gatherings fill the rooms with laughter, and everyday moments become lasting memories.

4 Beds ⋅ 2 Baths ⋅ 978272 MLS

Welcome to 88 Ridgeview Road, a place where quiet mornings, effortless entertaining, and the charm of Pleasantville come together in perfect harmony. Tucked away at the end of a coveted cul-de-sac and set on over an acre of beautifully landscaped property, this exceptional Colonial offers the rare combination of privacy, space, and convenience in one of Westchester County's most sought-after communities. As you arrive, there is an immediate sense of serenity. Mature trees frame the property, lush lawns stretch across the landscape, and the peaceful setting feels worlds away while remaining just minutes from the vibrant Village of Pleasantville, Metro-North, award-winning schools, restaurants, and local shops. Step inside and discover a home designed for both comfortable everyday living and memorable gatherings. Sunlight fills the spacious interior, creating warm and inviting spaces throughout. The heart of the home is the stunning family room, where dramatic beamed ceilings, a beautiful fireplace, and French doors create an atmosphere that is both elegant and welcoming. Open the doors and seamlessly extend your living space outdoors to the oversized deck, a true retreat overlooking tranquil landscaping and complete privacy. Whether hosting summer barbecues, enjoying morning coffee, or unwinding beneath the stars, this outdoor space was made to be enjoyed. The thoughtfully designed first-floor layout offers remarkable flexibility and convenience, including a desirable first-floor primary suite, providing comfortable one-level living when desired. A dedicated home office creates the perfect environment for remote work, creative pursuits, or quiet study. For those who love to cook and entertain, the expansive eat-in kitchen is sure to impress. Featuring a premium Thermador gas range, Bosch dishwasher, abundant cabinetry, and generous prep space, the kitchen flows naturally into the surrounding living and dining areas, making it easy to stay connected with family and guests. From holiday celebrations to casual weeknight dinners, this home was designed for bringing people together. Adding warmth and character are two fireplaces, including one in the elegant dining room and another in the stunning family room, creating inviting spaces to gather throughout the seasons. Upstairs, three generously sized bedrooms provide comfortable accommodations for family and guests. A beautifully appointed full bathroom serves the second level, offering both functionality and convenience while maintaining the home's timeless appeal. The lower level adds tremendous value and versatility with a walk-out basement featuring abundant storage, a dedicated workshop area, and endless possibilities for hobbies, recreation, fitness, or future expansion. What truly sets 88 Ridgeview Road apart is its ability to offer the best of Pleasantville living. Here, you'll enjoy the privacy of an acre-plus setting while remaining close to everything that makes Pleasantville so special—its charming downtown, beloved farmers market, community events, parks, dining, and easy commute to New York City. Homes offering this combination of location, privacy, first-floor primary living, entertaining space, and over an acre of property rarely become available. Whether you're searching for a peaceful retreat, a place to host family and friends, or the opportunity to establish roots in one of Westchester's most desirable communities, 88 Ridgeview Road delivers an extraordinary lifestyle opportunity. This is more than a home. It's where summer evenings linger on the deck, holiday gatherings fill the rooms with laughter, and everyday moments become lasting memories.

88 Ridgeview Drive, Pleasantville

$1,275,000

Looking to immerse yourself in the vibrant Pleasantville community? Don’t miss this rare opportunity to own a beautifully updated village home just steps from the award-winning Bedford Road Elementary School. This charming, light-filled residence offers 3 spacious bedrooms and 2.5 bathrooms, with thoughtful updates, abundant storage, and flexible living spaces throughout. The eat-in kitchen and formal dining room flow seamlessly for everyday meals or effortless entertaining, while the formal living room and sun-drenched family room with cathedral ceilings create inviting spaces for relaxation and gathering. A versatile den/library is ideal for a home office, gym, or playroom. The fully finished basement, featuring a Murphy bed and full bathroom, is perfect for additional 4th bedroom or a cozy media lounge as it creates an an easily accessible suite. Endless potential for rec room or additonal suite awaits in the full walkup attic. Outside, enjoy garage and driveway parking plus a large, versatile backyard—perfect for outdoor play, summer barbecues, and quiet evenings under the stars. The school playground is just moments away for added convenience. Recent upgrades include brand new hot water heater and generator with hookup.

3 Beds ⋅ 3 Baths ⋅ 992599 MLS

Looking to immerse yourself in the vibrant Pleasantville community? Don’t miss this rare opportunity to own a beautifully updated village home just steps from the award-winning Bedford Road Elementary School. This charming, light-filled residence offers 3 spacious bedrooms and 2.5 bathrooms, with thoughtful updates, abundant storage, and flexible living spaces throughout. The eat-in kitchen and formal dining room flow seamlessly for everyday meals or effortless entertaining, while the formal living room and sun-drenched family room with cathedral ceilings create inviting spaces for relaxation and gathering. A versatile den/library is ideal for a home office, gym, or playroom. The fully finished basement, featuring a Murphy bed and full bathroom, is perfect for additional 4th bedroom or a cozy media lounge as it creates an an easily accessible suite. Endless potential for rec room or additonal suite awaits in the full walkup attic. Outside, enjoy garage and driveway parking plus a large, versatile backyard—perfect for outdoor play, summer barbecues, and quiet evenings under the stars. The school playground is just moments away for added convenience. Recent upgrades include brand new hot water heater and generator with hookup.

10 Grandview Avenue, Pleasantville

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