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Welcome to your move-in ready lakefront retreat! Set in a picturesque park-like setting directly on Bear Ridge Lake, this beautifully improved home offers year-round enjoyment with fishing and rowing in the summer and ice-skating in the winter. Officially a 4-bedroom, it lives more like a 5-bedroom, providing plenty of space and flexibility. Recent updates over the past two years (new boiler, new AC, updated bathrooms and kitchen, open floor plan, …) bring this home up to today’s lifestyle standards with modern comfort and efficiency. The property is further enhanced by a lush perennial garden, freshly cleaned up and ready for seasons of color, to be enjoyed from the deck. The walk-out lower level, with its own entrance, offers a family/recreation room, fourth bedroom, and a flexible office or guest room —perfect for a mother-in-law suite, remote work or guest space. Enjoying award-winning Pleasantville schools, and low Mount Pleasant Taxes, the house is just minutes away from local attractions, such as a weekly farmer's market, Jacob Burns Film center, unique dining spots and charming stores, as well as highways and the Metro-North train station. Whether your passion is gardening, kayaking, fishing , or simply relaxing by the water, this property delivers a lifestyle of relaxation and recreation with easy access to all the conveniences you need.

4 Beds ⋅ 3 Baths ⋅ 914372 MLS

Welcome to your move-in ready lakefront retreat! Set in a picturesque park-like setting directly on Bear Ridge Lake, this beautifully improved home offers year-round enjoyment with fishing and rowing in the summer and ice-skating in the winter. Officially a 4-bedroom, it lives more like a 5-bedroom, providing plenty of space and flexibility. Recent updates over the past two years (new boiler, new AC, updated bathrooms and kitchen, open floor plan, …) bring this home up to today’s lifestyle standards with modern comfort and efficiency. The property is further enhanced by a lush perennial garden, freshly cleaned up and ready for seasons of color, to be enjoyed from the deck. The walk-out lower level, with its own entrance, offers a family/recreation room, fourth bedroom, and a flexible office or guest room —perfect for a mother-in-law suite, remote work or guest space. Enjoying award-winning Pleasantville schools, and low Mount Pleasant Taxes, the house is just minutes away from local attractions, such as a weekly farmer's market, Jacob Burns Film center, unique dining spots and charming stores, as well as highways and the Metro-North train station. Whether your passion is gardening, kayaking, fishing , or simply relaxing by the water, this property delivers a lifestyle of relaxation and recreation with easy access to all the conveniences you need.

174 Lake Shore Drive, Pleasantville

$1,255,000

Move right into this beautifully updated Colonial and start enjoying life in one of Pleasantville’s most convenient locations—Just a 1/2 mile from the Metro-North train station, Pleasantville’s acclaimed restaurants, shops, the Jacob Burns Film Center, and Saturday’s Farmers Market. Inside, the home feels bright, easy, and welcoming from the moment you step in. Gleaming hardwood floors and custom details set the tone, while the living room flows naturally into the dining room with built-ins and a cozy window seat—perfect for everyday living or hosting friends. The updated kitchen brings it all together with a center island, wine fridge, and an open connection to the family room with a gas fireplace. Sliding doors lead right out to a Trex deck and level, fenced-in yard—great for barbecues, play, or just unwinding. Upstairs, the primary suite is a true retreat with a walk-in closet, private bath, lots of natural light, and a tray ceiling. Three additional bedrooms with custom closets share a full hall bath and complete the second floor. Downstairs, the finished lower level adds approximately 800 sq. ft. of finished storage space with access to the one-car garage. With a full-house generator and thoughtful upgrades throughout, everything is ready for you to move in and enjoy from day one. This turnkey gem is not to be missed.

4 Beds ⋅ 3 Baths ⋅ 986312 MLS

Move right into this beautifully updated Colonial and start enjoying life in one of Pleasantville’s most convenient locations—Just a 1/2 mile from the Metro-North train station, Pleasantville’s acclaimed restaurants, shops, the Jacob Burns Film Center, and Saturday’s Farmers Market. Inside, the home feels bright, easy, and welcoming from the moment you step in. Gleaming hardwood floors and custom details set the tone, while the living room flows naturally into the dining room with built-ins and a cozy window seat—perfect for everyday living or hosting friends. The updated kitchen brings it all together with a center island, wine fridge, and an open connection to the family room with a gas fireplace. Sliding doors lead right out to a Trex deck and level, fenced-in yard—great for barbecues, play, or just unwinding. Upstairs, the primary suite is a true retreat with a walk-in closet, private bath, lots of natural light, and a tray ceiling. Three additional bedrooms with custom closets share a full hall bath and complete the second floor. Downstairs, the finished lower level adds approximately 800 sq. ft. of finished storage space with access to the one-car garage. With a full-house generator and thoughtful upgrades throughout, everything is ready for you to move in and enjoy from day one. This turnkey gem is not to be missed.

228 Sarles Lane, Pleasantville

$1,249,000

Don’t miss the chance to create your perfect home! This modern young colonial, is currently under construction by an experienced builder, offers a unique opportunity to tailor the design to your preferences. There is still time to customize! Currently under construction, frame, windows, siding, and plumbing is completed. Built with high-quality materials, including Andersen 400 Series windows and white Hardiplank siding, spray foam insulation, this home perfectly combines style, durability, and comfort. The spacious first-floor features living and dining rooms, a powder room, a pantry, and an open-concept chef’s kitchen with a large island. The kitchen seamlessly connects to the family room, which opens to the backyard for indoor-outdoor living. The second floor offers a primary bedroom with an en-suite bath, two additional bedrooms, a large hall bathroom with a double vanity and tub, and a laundry room. The finished basement, approximately 600 square feet, adds valuable living space and is included in the total square footage. Situated on an 80’ x 155’ lot, the property includes a detached 1-car garage with storage and a private backyard. Utilities: municipal water, sewer, propane, electric. This home will be delivered move-in ready with appliances included. With design customization options available, you can make this house uniquely yours. In close proximity to Jacob Burns Film Center, charming restaurants, shops, and the train station, ensuring both convenience and a vibrant lifestyle. Pleasantville school district. STAR tax savings (if eligible) is $1,720. Photos are from completed projects at 64 and 68 Sky Top. Please, do not walk the property without a confirmed appointment.

3 Beds ⋅ 3 Baths ⋅ 809054 MLS

Don’t miss the chance to create your perfect home! This modern young colonial, is currently under construction by an experienced builder, offers a unique opportunity to tailor the design to your preferences. There is still time to customize! Currently under construction, frame, windows, siding, and plumbing is completed. Built with high-quality materials, including Andersen 400 Series windows and white Hardiplank siding, spray foam insulation, this home perfectly combines style, durability, and comfort. The spacious first-floor features living and dining rooms, a powder room, a pantry, and an open-concept chef’s kitchen with a large island. The kitchen seamlessly connects to the family room, which opens to the backyard for indoor-outdoor living. The second floor offers a primary bedroom with an en-suite bath, two additional bedrooms, a large hall bathroom with a double vanity and tub, and a laundry room. The finished basement, approximately 600 square feet, adds valuable living space and is included in the total square footage. Situated on an 80’ x 155’ lot, the property includes a detached 1-car garage with storage and a private backyard. Utilities: municipal water, sewer, propane, electric. This home will be delivered move-in ready with appliances included. With design customization options available, you can make this house uniquely yours. In close proximity to Jacob Burns Film Center, charming restaurants, shops, and the train station, ensuring both convenience and a vibrant lifestyle. Pleasantville school district. STAR tax savings (if eligible) is $1,720. Photos are from completed projects at 64 and 68 Sky Top. Please, do not walk the property without a confirmed appointment.

133 Lake Shore Drive, Pleasantville

$1,237,500

Don’t walk—run to this rare 3,500 square foot end-unit townhome in The Enclave, Pleasantville. Perfectly situated on one of the community’s most desirable lots, it offers a private oversized backyard, expansive deck, and patio. Inside, the light-filled open layout showcases a Chef’s kitchen with stainless steel appliances, a walk-in pantry, hardwood floors, custom millwork, and plantation shutters. The finished walk-out lower level provides a flex space, full bath, and additional guest room or office for versatile living. Enjoy walkability at its finest with easy pedestrian access to both the Pleasantville and Chappaqua train stations, award-winning farmers markets, restaurants, shops, and more—all while enjoying the ease of maintenance-free living. Pleasantville residency includes train parking, pool, and recreation. Wired for an electric car charger and featuring Bose in-ceiling speakers on the main level, this home is truly move-in ready with thoughtful design and convenience at every turn.

3 Beds ⋅ 4 Baths ⋅ 907199 MLS

Don’t walk—run to this rare 3,500 square foot end-unit townhome in The Enclave, Pleasantville. Perfectly situated on one of the community’s most desirable lots, it offers a private oversized backyard, expansive deck, and patio. Inside, the light-filled open layout showcases a Chef’s kitchen with stainless steel appliances, a walk-in pantry, hardwood floors, custom millwork, and plantation shutters. The finished walk-out lower level provides a flex space, full bath, and additional guest room or office for versatile living. Enjoy walkability at its finest with easy pedestrian access to both the Pleasantville and Chappaqua train stations, award-winning farmers markets, restaurants, shops, and more—all while enjoying the ease of maintenance-free living. Pleasantville residency includes train parking, pool, and recreation. Wired for an electric car charger and featuring Bose in-ceiling speakers on the main level, this home is truly move-in ready with thoughtful design and convenience at every turn.

30 Dennis Lane, Pleasantville

$1,225,000

Welcome to Pleasantville Country Club, the golf community where luxury meets convenience in this pristine unit with walls of windows and an expansive sunny golf course view. perfectly sited on a cul-de-sac, this home offers a newly renovated (2025) spectacular open sparkling white designer kitchen with top-of-the line appliances and cabinetry, a breakfast bar and pantry storage, and gleaming quartzite counters.. The seamless transition into the great room where there is ample room for seating and conversation and a generously sized dining area, with recessed lighting and new hardwood floors, and a newly renovated custom fireplace surround makes for easy living. The low maintenance Trex deck with glorious golf course views rimmed by towering trees has an eclectic awning and is the perfect spot for plein air entertaining and respite. The new powder room and direct main floor garage access complete the first floor. The King size primary bedroom suite offers dual walk-in closets and a gracious size spa style en-suite full bath. There is an additional bedroom and hall bath. The lower level family room with glass sliders to a patio and wood burning stove (with gas line for future connection) offers ample space for recreation, media and exercise area and an also has an additional office/sleeping alcove, full bathroom with steam shower , laundry room (with laundry shoot from bedroom level) and storage/mechanical room . There is 3 zone HVAC. The HOA includes golf membership (9 hole course), tennis/pickleball, clubhouse, snow plowing/gardening and exterior maintenance. The complex is well managed, financially sound and impeccably maintained and is close to shops, market, restaurants and commuter train and offers the highly rated Pleasantville school district.

2 Beds ⋅ 4 Baths ⋅ 936234 MLS

Welcome to Pleasantville Country Club, the golf community where luxury meets convenience in this pristine unit with walls of windows and an expansive sunny golf course view. perfectly sited on a cul-de-sac, this home offers a newly renovated (2025) spectacular open sparkling white designer kitchen with top-of-the line appliances and cabinetry, a breakfast bar and pantry storage, and gleaming quartzite counters.. The seamless transition into the great room where there is ample room for seating and conversation and a generously sized dining area, with recessed lighting and new hardwood floors, and a newly renovated custom fireplace surround makes for easy living. The low maintenance Trex deck with glorious golf course views rimmed by towering trees has an eclectic awning and is the perfect spot for plein air entertaining and respite. The new powder room and direct main floor garage access complete the first floor. The King size primary bedroom suite offers dual walk-in closets and a gracious size spa style en-suite full bath. There is an additional bedroom and hall bath. The lower level family room with glass sliders to a patio and wood burning stove (with gas line for future connection) offers ample space for recreation, media and exercise area and an also has an additional office/sleeping alcove, full bathroom with steam shower , laundry room (with laundry shoot from bedroom level) and storage/mechanical room . There is 3 zone HVAC. The HOA includes golf membership (9 hole course), tennis/pickleball, clubhouse, snow plowing/gardening and exterior maintenance. The complex is well managed, financially sound and impeccably maintained and is close to shops, market, restaurants and commuter train and offers the highly rated Pleasantville school district.

19 Club Court, Pleasantville

$1,205,000

Well-maintained split-level home on a quiet cul-de-sac in Pleasantville with Armonk schools (Byram Hills School District). Carefully cared for over the years, this 3-bedroom home features hardwood floors throughout and a kitchen with updated appliances, along with private, usable outdoor space. The main level includes a living room, dining area, and kitchen with access to a deck and backyard. The upper level offers a primary suite with its own bath, plus two additional bedrooms and a hall bath. The lower level has a family room and access to the attached two-car garage. A solid home with great bones, offering an excellent opportunity to update, expand, or customize to your needs. Convenient to the North White Plains train station and major roadways.

3 Beds ⋅ 2 Baths ⋅ 992949 MLS

Well-maintained split-level home on a quiet cul-de-sac in Pleasantville with Armonk schools (Byram Hills School District). Carefully cared for over the years, this 3-bedroom home features hardwood floors throughout and a kitchen with updated appliances, along with private, usable outdoor space. The main level includes a living room, dining area, and kitchen with access to a deck and backyard. The upper level offers a primary suite with its own bath, plus two additional bedrooms and a hall bath. The lower level has a family room and access to the attached two-car garage. A solid home with great bones, offering an excellent opportunity to update, expand, or customize to your needs. Convenient to the North White Plains train station and major roadways.

29 Maplewood Way, Pleasantville

$1,200,000

Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living. Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living room stretches the full width of the home and is bathed in natural light from eastern, southern, and western exposures. A wood-burning fireplace serves as a warm focal point, while a wall of windows showcases picturesque views of mature trees, a tranquil pond, and abundant wildlife. The formal dining room is perfectly suited for both holiday entertaining and intimate gatherings. The spacious eat-in kitchen, complete with two pantries, provides direct access to an expansive deck—ideal for outdoor dining—and the attached two-car garage. A convenient powder room completes the main level. Upstairs, you’ll find a gracious primary suite, three additional bedrooms, and a beautifully renovated full hall bath. The lower level offers remarkable versatility, featuring a welcoming family room with a fireplace, as well as a workshop, laundry area, ample storage space and more. Wood floors, crown molding, central air-conditioning and an oversized two car garage are just some of the special features you will enjoy. The grounds are truly extraordinary, highlighted by exquisite stonework, garden beds, and meticulously maintained landscaping. The backyard invites out door fun, recreation and relaxation, while serene water views create a breathtaking natural backdrop. This stately home boarders scenic Opperman's Pond, where all-season activities from fishing and birdwatching to ice skating - can be enjoyed. This exceptional property is more than a home—it will be your sanctuary offering comfort, beauty, and memories.

4 Beds ⋅ 3 Baths ⋅ 1013140 MLS

Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living. Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living room stretches the full width of the home and is bathed in natural light from eastern, southern, and western exposures. A wood-burning fireplace serves as a warm focal point, while a wall of windows showcases picturesque views of mature trees, a tranquil pond, and abundant wildlife. The formal dining room is perfectly suited for both holiday entertaining and intimate gatherings. The spacious eat-in kitchen, complete with two pantries, provides direct access to an expansive deck—ideal for outdoor dining—and the attached two-car garage. A convenient powder room completes the main level. Upstairs, you’ll find a gracious primary suite, three additional bedrooms, and a beautifully renovated full hall bath. The lower level offers remarkable versatility, featuring a welcoming family room with a fireplace, as well as a workshop, laundry area, ample storage space and more. Wood floors, crown molding, central air-conditioning and an oversized two car garage are just some of the special features you will enjoy. The grounds are truly extraordinary, highlighted by exquisite stonework, garden beds, and meticulously maintained landscaping. The backyard invites out door fun, recreation and relaxation, while serene water views create a breathtaking natural backdrop. This stately home boarders scenic Opperman's Pond, where all-season activities from fishing and birdwatching to ice skating - can be enjoyed. This exceptional property is more than a home—it will be your sanctuary offering comfort, beauty, and memories.

1 Woodland Drive, Pleasantville

$1,200,000

"HAYS HILL HAVEN" - Tucked at the end of a quiet cul-de-sac in the heart of one of Westchester's most beloved and vibrant villages, 7 Hays Hill Road is the kind of home that feels instantly comforting the moment you arrive. Framed by mature trees, thoughtful landscaping and glowing natural light throughout, this fully renovated striking Colonial offers a rare balance of timeless charm and modern ease - where every space has been carefully designed for the rhythm of everyday living while still feeling elevated, calm and effortlessly stylish. Located just moments from the center of Pleasantville, 1.1 miles from the train station, seconds to town favorite Craft Pizza and only about 45 minutes from Manhattan, the home places you in the middle of one of Westchester's most dynamic communities, known for its bustling farmers markets, acclaimed restaurants, independent cafes, Jacob Burns Film Center, Metro-North access, boutique shops, parks and highly regarded schools. It is a village with real energy and character - where weekends are spent walking downtown for coffee, dinner with friends, outdoor concerts, or evening strolls through tree-lined streets. Inside, the home unfolds with over 2,000 square feet of beautifully updated living space, renovated extensively in 2016 and then updated in years since, with a level of care and intentionality that makes it feel completely turn-key. The atmosphere throughout is warm, bright and soothing, with oversized windows pouring sunlight into nearly every room and an open-concept layout that creates an effortless flow between spaces. The kitchen serves as the heart of the home - beautifully appointed with granite countertops, a farmhouse sink, stainless steel appliances and a generous center island perfect for gathering, cooking, or entertaining. Just beyond, the dining area opens directly to the expansive bluestone patio through sliding glass doors, creating a seamless indoor-outdoor connection ideal for summer dinners, morning coffee, or weekend barbecues with family and friends. One of the home's standout spaces is the dramatic 500-square-foot family room addition, where soaring cathedral ceilings create a retreat unlike anything typically found in a home of this size. The space feels equally suited for cozy movie nights, entertaining guests, or simply relaxing. The expansive living room, anchored by a classic wood-burning fireplace and bathed in warm natural light, offers a beautifully inviting setting for everything from intimate evenings by the fire to lively gatherings, bringing a sense of warmth and calm to the home. A custom-built mudroom and stylish powder room add both functionality and polish to the main level, while new recessed lighting, updated fixtures, newer windows and doors, hardwood flooring and refined finishes throughout reinforce the home's move-in-ready appeal. Upstairs, the home continues to impress with a serene primary suite, updated bathroom and two additional bedrooms that feel both inviting and tranquil. A redesigned staircase and elegant handrail subtly elevate the architecture of the home while adding warmth and sophistication to the interiors. The fully finished lower level offers incredible flexibility - perfect for a home office, gym, media room, or play space - along with ample storage and laundry. Outside, the backyard has been thoughtfully transformed into a private extension of the home itself. Tiered stone walls, curated landscaping and a dedicated play area create both beauty and function, while the expansive bluestone patio offers the perfect backdrop for entertaining under the stars or enjoying peaceful evenings surrounded by nature. With its incredible village location, turn-key condition, abundant natural light and calming atmosphere throughout, 7 Hays Hill Road is more than simply a home - it is an opportunity to step into the very best of Pleasantville living.

3 Beds ⋅ 3 Baths ⋅ 998533 MLS

"HAYS HILL HAVEN" - Tucked at the end of a quiet cul-de-sac in the heart of one of Westchester's most beloved and vibrant villages, 7 Hays Hill Road is the kind of home that feels instantly comforting the moment you arrive. Framed by mature trees, thoughtful landscaping and glowing natural light throughout, this fully renovated striking Colonial offers a rare balance of timeless charm and modern ease - where every space has been carefully designed for the rhythm of everyday living while still feeling elevated, calm and effortlessly stylish. Located just moments from the center of Pleasantville, 1.1 miles from the train station, seconds to town favorite Craft Pizza and only about 45 minutes from Manhattan, the home places you in the middle of one of Westchester's most dynamic communities, known for its bustling farmers markets, acclaimed restaurants, independent cafes, Jacob Burns Film Center, Metro-North access, boutique shops, parks and highly regarded schools. It is a village with real energy and character - where weekends are spent walking downtown for coffee, dinner with friends, outdoor concerts, or evening strolls through tree-lined streets. Inside, the home unfolds with over 2,000 square feet of beautifully updated living space, renovated extensively in 2016 and then updated in years since, with a level of care and intentionality that makes it feel completely turn-key. The atmosphere throughout is warm, bright and soothing, with oversized windows pouring sunlight into nearly every room and an open-concept layout that creates an effortless flow between spaces. The kitchen serves as the heart of the home - beautifully appointed with granite countertops, a farmhouse sink, stainless steel appliances and a generous center island perfect for gathering, cooking, or entertaining. Just beyond, the dining area opens directly to the expansive bluestone patio through sliding glass doors, creating a seamless indoor-outdoor connection ideal for summer dinners, morning coffee, or weekend barbecues with family and friends. One of the home's standout spaces is the dramatic 500-square-foot family room addition, where soaring cathedral ceilings create a retreat unlike anything typically found in a home of this size. The space feels equally suited for cozy movie nights, entertaining guests, or simply relaxing. The expansive living room, anchored by a classic wood-burning fireplace and bathed in warm natural light, offers a beautifully inviting setting for everything from intimate evenings by the fire to lively gatherings, bringing a sense of warmth and calm to the home. A custom-built mudroom and stylish powder room add both functionality and polish to the main level, while new recessed lighting, updated fixtures, newer windows and doors, hardwood flooring and refined finishes throughout reinforce the home's move-in-ready appeal. Upstairs, the home continues to impress with a serene primary suite, updated bathroom and two additional bedrooms that feel both inviting and tranquil. A redesigned staircase and elegant handrail subtly elevate the architecture of the home while adding warmth and sophistication to the interiors. The fully finished lower level offers incredible flexibility - perfect for a home office, gym, media room, or play space - along with ample storage and laundry. Outside, the backyard has been thoughtfully transformed into a private extension of the home itself. Tiered stone walls, curated landscaping and a dedicated play area create both beauty and function, while the expansive bluestone patio offers the perfect backdrop for entertaining under the stars or enjoying peaceful evenings surrounded by nature. With its incredible village location, turn-key condition, abundant natural light and calming atmosphere throughout, 7 Hays Hill Road is more than simply a home - it is an opportunity to step into the very best of Pleasantville living.

7 Hays Hill Road, Pleasantville

$1,200,000

Welcome to 300 Washington Ave! Rebuilt in 2020, this refined 4-bedroom, 4-bath Colonial offers thoughtfully designed living spaces and exceptional flexibility in one of Westchesters most desirable residential settings. The main level showcases a seamless open layout anchored by a beautifully appointed kitchen with a generous center island, quartz countertops and backsplash, stainless steel appliances, and gas cooking. Sliding doors lead to the rear deck, creating a seamless connection between indoor and outdoor living. A versatile first-floor bedroom or playroom/home office, full bath, and laundry complete the main level. Upstairs, the primary suite is a private retreat featuring a balcony overlooking the yard, a spa-like bath with a double vanity, and ample closet space. Two additional bedrooms and a full hall bath complete the second floor. The finished lower level adds substantial living flexibility with a full bathroom, kitchenette/wet bar, and multiple areas well-suited for recreation, fitness, guests, or extended living, complemented by a separate entrance. Outdoor spaces include a welcoming front porch, rear deck and patio, and a spacious, private yard. The home features town water and sewer, central air, forced-air heating with natural gas, and an owned solar system (not leased) that helps offset electric usage. All major systems were updated during the 2020 rebuild. Ideally located just moments from Pleasantville’s vibrant village center, the Jacob Burns Film Center, shops, dining, parks, and Metro-North, this home offers a rare blend of comfort, efficiency, and the walkable village lifestyle Pleasantville is known for.

4 Beds ⋅ 4 Baths ⋅ 956443 MLS

Welcome to 300 Washington Ave! Rebuilt in 2020, this refined 4-bedroom, 4-bath Colonial offers thoughtfully designed living spaces and exceptional flexibility in one of Westchesters most desirable residential settings. The main level showcases a seamless open layout anchored by a beautifully appointed kitchen with a generous center island, quartz countertops and backsplash, stainless steel appliances, and gas cooking. Sliding doors lead to the rear deck, creating a seamless connection between indoor and outdoor living. A versatile first-floor bedroom or playroom/home office, full bath, and laundry complete the main level. Upstairs, the primary suite is a private retreat featuring a balcony overlooking the yard, a spa-like bath with a double vanity, and ample closet space. Two additional bedrooms and a full hall bath complete the second floor. The finished lower level adds substantial living flexibility with a full bathroom, kitchenette/wet bar, and multiple areas well-suited for recreation, fitness, guests, or extended living, complemented by a separate entrance. Outdoor spaces include a welcoming front porch, rear deck and patio, and a spacious, private yard. The home features town water and sewer, central air, forced-air heating with natural gas, and an owned solar system (not leased) that helps offset electric usage. All major systems were updated during the 2020 rebuild. Ideally located just moments from Pleasantville’s vibrant village center, the Jacob Burns Film Center, shops, dining, parks, and Metro-North, this home offers a rare blend of comfort, efficiency, and the walkable village lifestyle Pleasantville is known for.

300 Washington Avenue, Pleasantville

$1,170,000

Welcome to a rare offering where timeless elegance meets refined suburban living. Nestled on an expansive half-acre corner lot within the coveted Schuhmann Park enclave, this tri-level home is more than a property. This distinguished split-level residence unfolds across 2,142 square feet of thoughtfully curated living space, where every level reveals a new layer of comfort and character. Step through the welcoming foyer and into a home defined by cathedral ceilings and oversized windows, where natural light dances across rich hardwood floors, creating an atmosphere that feels both expansive and intimate. At the heart of the home lies a beautifully appointed eat-in kitchen, enhanced by stainless steel appliances and a renovation that blends modern functionality with timeless appeal. The residence offers three bedrooms and three bathrooms, including a flexible first-floor bedroom ideal for guests or a private office suite. Enjoy outdoor living with a deck, patio, and partially fenced backyard. Positioned just moments from train access, parks, schools, and boutique shopping, this home delivers the rare balance of suburban tranquility with effortless connectivity. Pleasantville is known for its charm, community, and accessibility making this home not just desirable, but deeply livable.

3 Beds ⋅ 3 Baths ⋅ 980979 MLS

Welcome to a rare offering where timeless elegance meets refined suburban living. Nestled on an expansive half-acre corner lot within the coveted Schuhmann Park enclave, this tri-level home is more than a property. This distinguished split-level residence unfolds across 2,142 square feet of thoughtfully curated living space, where every level reveals a new layer of comfort and character. Step through the welcoming foyer and into a home defined by cathedral ceilings and oversized windows, where natural light dances across rich hardwood floors, creating an atmosphere that feels both expansive and intimate. At the heart of the home lies a beautifully appointed eat-in kitchen, enhanced by stainless steel appliances and a renovation that blends modern functionality with timeless appeal. The residence offers three bedrooms and three bathrooms, including a flexible first-floor bedroom ideal for guests or a private office suite. Enjoy outdoor living with a deck, patio, and partially fenced backyard. Positioned just moments from train access, parks, schools, and boutique shopping, this home delivers the rare balance of suburban tranquility with effortless connectivity. Pleasantville is known for its charm, community, and accessibility making this home not just desirable, but deeply livable.

1 Anne Place, Pleasantville

$1,147,080

Lovely modern Ranch on a cul-de-sac that offers 3+ bedrooms and 3 baths. A covered screened in back deck, where you can view nature and beautiful surroundings, with plenty of privacy. The first floor has very good circular motion, with open access to the living room, kitchen and dining room. Square footage does not include the lower level. With easy living on the main level and fabulous space on the lower level, this home will go quickly. The lower level includes a Murphy bed, within the library, and a summer kitchen in the recreational room. The Office is presently being used as an exercise room. Access to the lower level from both the inside and outside. Walk-out to a fabulous patio area perfect for entertaining. Updates include siding, front door, gutters. Windows and roof were replaced in 2016. Walking distance to Chappaqua train station and very close to the Pleasantville village, which has restaurants, trains, and shops for you to enjoy. Taxes do not reflect the basic star exemption of $1406.60

3 Beds ⋅ 3 Baths ⋅ 1011711 MLS

Lovely modern Ranch on a cul-de-sac that offers 3+ bedrooms and 3 baths. A covered screened in back deck, where you can view nature and beautiful surroundings, with plenty of privacy. The first floor has very good circular motion, with open access to the living room, kitchen and dining room. Square footage does not include the lower level. With easy living on the main level and fabulous space on the lower level, this home will go quickly. The lower level includes a Murphy bed, within the library, and a summer kitchen in the recreational room. The Office is presently being used as an exercise room. Access to the lower level from both the inside and outside. Walk-out to a fabulous patio area perfect for entertaining. Updates include siding, front door, gutters. Windows and roof were replaced in 2016. Walking distance to Chappaqua train station and very close to the Pleasantville village, which has restaurants, trains, and shops for you to enjoy. Taxes do not reflect the basic star exemption of $1406.60

28 Summit Place, Pleasantville

$1,125,000

Fantastic opportunity in the heart of Pleasantville. This beautifully updated two-family Colonial offers flexibility for investors, owner-occupants, or multi-generational living. The lower unit features a renovated kitchen, expansive living and dining areas, two bedrooms, one full bath, a separate office/mudroom space, and its own laundry room. The upper unit offers three bedrooms (one currently used as a dining room), an additional office-sized room, spacious living area, and one full bath. Set on a flat .20-acre lot, the property includes a private backyard with a storage shed and ample off-street parking with four dedicated spaces. Ideally located within walking distance to downtown Pleasantville, the train station with approximately a 55-minute commute to Grand Central Terminal, the farmers market, local dining, and the Jacob Burns Film Center. Convenient access to the Saw Mill River Parkway for an easy commute.

5 Beds ⋅ 2 Baths ⋅ 996207 MLS

Fantastic opportunity in the heart of Pleasantville. This beautifully updated two-family Colonial offers flexibility for investors, owner-occupants, or multi-generational living. The lower unit features a renovated kitchen, expansive living and dining areas, two bedrooms, one full bath, a separate office/mudroom space, and its own laundry room. The upper unit offers three bedrooms (one currently used as a dining room), an additional office-sized room, spacious living area, and one full bath. Set on a flat .20-acre lot, the property includes a private backyard with a storage shed and ample off-street parking with four dedicated spaces. Ideally located within walking distance to downtown Pleasantville, the train station with approximately a 55-minute commute to Grand Central Terminal, the farmers market, local dining, and the Jacob Burns Film Center. Convenient access to the Saw Mill River Parkway for an easy commute.

17 Grant Street, Pleasantville

$1,115,000

Historic 1830's home, original Pleasantville School Building located on a small private road in the heart of Pleasantville. Just a short walk to all this beautiful town has to offer. Beautiful features such as a wrap around porch, cozy family room with a fire place, large eat in kitchen and a private primary bedroom, will have you wanting to move right in and make this house your home. All of this perfectly situated on a double lot. You wont want to miss this one!

4 Beds ⋅ 2 Baths ⋅ 905435 MLS

Historic 1830's home, original Pleasantville School Building located on a small private road in the heart of Pleasantville. Just a short walk to all this beautiful town has to offer. Beautiful features such as a wrap around porch, cozy family room with a fire place, large eat in kitchen and a private primary bedroom, will have you wanting to move right in and make this house your home. All of this perfectly situated on a double lot. You wont want to miss this one!

15 Old School Lane, Pleasantville

$1,110,000

Perfect location, perfect layout and perfect opportunity! Positioned in the sought-after walkable village of Pleasantville, this colonial offers more than a home—it offers a lifestyle. Just steps from the train to NYC, award-winning schools, and local parks, Saturday Farmers market, and restaurants, this 4 bedroom home offers a wonderful balance of convenience, community, and connectivity. The main level blends both a living room and family room centered around a wood-burning fireplace. A spacious kitchen stands ready for any cook, equipped with a prepping island, stainless steel appliances, slate-style tile flooring, and a charming garden window ideal for growing fresh herbs. Glass sliders extend the space outdoors, opening to a fenced backyard with a patio and tiered flower gardens—perfect for entertaining or relaxing. Convenience continues with a laundry room just off the kitchen, while the formal dining room provides ample space for hosting dinner parties. Hardwood floors flow through much of the main floor, adding warmth and continuity. A turned staircase leads you upstairs to the serene primary suite, complete with a spa-like bath featuring a jetted tub, dual quartz-topped vanities, and an oversized shower. Secondary bedrooms offer generous closet space, making the upper level as practical as it is comfortable. An unfinished basement presents many storage options and comes roughed in for a future bath, and direct access to the garage. Additional features enhancing the home include a whole-house generator, solar panels, and efficient heating. Easy access to major highways, restaurants, a playground, a Saturday farmers market, Metro North Trains to NYC and community happenings all within walking distance, this home is more than a place to call home —it’s a place to belong.

4 Beds ⋅ 3 Baths ⋅ 911035 MLS

Perfect location, perfect layout and perfect opportunity! Positioned in the sought-after walkable village of Pleasantville, this colonial offers more than a home—it offers a lifestyle. Just steps from the train to NYC, award-winning schools, and local parks, Saturday Farmers market, and restaurants, this 4 bedroom home offers a wonderful balance of convenience, community, and connectivity. The main level blends both a living room and family room centered around a wood-burning fireplace. A spacious kitchen stands ready for any cook, equipped with a prepping island, stainless steel appliances, slate-style tile flooring, and a charming garden window ideal for growing fresh herbs. Glass sliders extend the space outdoors, opening to a fenced backyard with a patio and tiered flower gardens—perfect for entertaining or relaxing. Convenience continues with a laundry room just off the kitchen, while the formal dining room provides ample space for hosting dinner parties. Hardwood floors flow through much of the main floor, adding warmth and continuity. A turned staircase leads you upstairs to the serene primary suite, complete with a spa-like bath featuring a jetted tub, dual quartz-topped vanities, and an oversized shower. Secondary bedrooms offer generous closet space, making the upper level as practical as it is comfortable. An unfinished basement presents many storage options and comes roughed in for a future bath, and direct access to the garage. Additional features enhancing the home include a whole-house generator, solar panels, and efficient heating. Easy access to major highways, restaurants, a playground, a Saturday farmers market, Metro North Trains to NYC and community happenings all within walking distance, this home is more than a place to call home —it’s a place to belong.

76 Sarles Lane, Pleasantville

$1,100,000

**Back on Market - Buyer’s Financing Fell Through! ** This is your chance to own the lowest-priced home in The Enclave at Pleasantville, one of the area’s most sought-after communities. With other residences selling at significantly higher price points, this property offers exceptional value and tremendous upside potential - especially with the opportunity to finish the basement and instantly add equity, living space, and your own personal touch. This 3-bedroom, 2.5-bath residence features spacious living areas, modern finishes, and abundant natural light and the builder upgrade of an expanded kitchen - perfect for cooking, entertaining, and everyday living. It is fully move-in ready while still allowing room for customization to fit your lifestyle. Enjoy all the benefits of this desirable community, from its convenient location to its welcoming atmosphere, at a price point that combines comfort, creativity, and investment potential. Just minutes from the heart of Pleasantville, this location offers easy access to a charming array of shops, restaurants, and attractions - including the renowned Jacob Burns Film Center and the popular local farmers market. You're also only 10 minutes from Chappaqua Crossing, where you'll find Whole Foods, Lifetime Fitness, additional shopping, and a variety of dining options - all conveniently within reach. Close proximity to NYC Don’t miss this rare opportunity - schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 875336 MLS

**Back on Market - Buyer’s Financing Fell Through! ** This is your chance to own the lowest-priced home in The Enclave at Pleasantville, one of the area’s most sought-after communities. With other residences selling at significantly higher price points, this property offers exceptional value and tremendous upside potential - especially with the opportunity to finish the basement and instantly add equity, living space, and your own personal touch. This 3-bedroom, 2.5-bath residence features spacious living areas, modern finishes, and abundant natural light and the builder upgrade of an expanded kitchen - perfect for cooking, entertaining, and everyday living. It is fully move-in ready while still allowing room for customization to fit your lifestyle. Enjoy all the benefits of this desirable community, from its convenient location to its welcoming atmosphere, at a price point that combines comfort, creativity, and investment potential. Just minutes from the heart of Pleasantville, this location offers easy access to a charming array of shops, restaurants, and attractions - including the renowned Jacob Burns Film Center and the popular local farmers market. You're also only 10 minutes from Chappaqua Crossing, where you'll find Whole Foods, Lifetime Fitness, additional shopping, and a variety of dining options - all conveniently within reach. Close proximity to NYC Don’t miss this rare opportunity - schedule your private showing today!

20 Dennis Lane, Pleasantville

$999,000

Welcome to 294 Bedford Road - this enchanting antique home, built in 1902, is nestled in the heart of Pleasantville. With a prime in-town location just half a mile from the train station, you’ll enjoy the perfect blend of historic charm and modern convenience. This 5-bedroom gem boasts a classic front porch that invites you to sit back and relax while sipping your morning coffee. The spacious interiors are brimming with character, offering endless possibilities for transformation. Whether you're looking to restore its original glory or put your own creative spin on it, this home is a renovator's dream scenario! Set on a generous 15,200 sq ft lot, there is potential to subdivide into two building lots with the appropriate variances. Located in an R-2A zoning district, the property presents an exciting opportunity for conversion into an income-generating two-family home. Both options have been preliminarily verified with the village; while not guaranteed, it is likely that approval could be obtained with the proper permits and variances. There is an additional full bathroom installed on the third floor, work was done without obtaining permits. The property is being sold “as-is”. Don’t miss out on this rare opportunity to own a piece of Pleasantville's history, where you can personalize a stunning residence and explore the opportunity for income potential. Seize this chance to make it your own!

5 Beds ⋅ 2 Baths ⋅ 980732 MLS

Welcome to 294 Bedford Road - this enchanting antique home, built in 1902, is nestled in the heart of Pleasantville. With a prime in-town location just half a mile from the train station, you’ll enjoy the perfect blend of historic charm and modern convenience. This 5-bedroom gem boasts a classic front porch that invites you to sit back and relax while sipping your morning coffee. The spacious interiors are brimming with character, offering endless possibilities for transformation. Whether you're looking to restore its original glory or put your own creative spin on it, this home is a renovator's dream scenario! Set on a generous 15,200 sq ft lot, there is potential to subdivide into two building lots with the appropriate variances. Located in an R-2A zoning district, the property presents an exciting opportunity for conversion into an income-generating two-family home. Both options have been preliminarily verified with the village; while not guaranteed, it is likely that approval could be obtained with the proper permits and variances. There is an additional full bathroom installed on the third floor, work was done without obtaining permits. The property is being sold “as-is”. Don’t miss out on this rare opportunity to own a piece of Pleasantville's history, where you can personalize a stunning residence and explore the opportunity for income potential. Seize this chance to make it your own!

294 Bedford Road, Pleasantville

$999,000

Tucked away on one of Pleasantville Village’s most picturesque, tree lined streets, where the setting feels as though it has been lifted straight from the pages of a storybook, 47 Brookfield offers a truly rare and special opportunity. Perfectly positioned on a quiet cul de sac, this is the kind of place where children play freely, neighbors stroll by with a friendly wave, and life slows down just enough to savor it. For decades, this charming 1930s home has been lovingly maintained and thoughtfully cared for by generations of dentists, serving as both a professional space and a residence. Today, it stands ready for its next chapter. The first floor, currently configured as a dental office complete with a welcoming waiting area and 2 bathrooms, offers a seamless footprint for transformation. Upstairs, a cozy one bedroom apartment provides a glimpse into what this home can become, a warm and inviting single-family residence filled with character and charm. Original details, including a nostalgic milk box, serve as a gentle nod to the home’s rich history. This is where vision meets opportunity. With a two-car garage and a layout that lends itself beautifully to reimagination, 47 Brookfield is the perfect canvas for anyone looking to create something truly their own. You can always renovate a home, tailor it to your taste, expand and enhance, but you can never recreate a location like this. In real estate, location is everything, and this one is simply irreplaceable. Imagine mornings walking to the train, grabbing coffee from your favorite local coffee shop, weekends spent at the farmers market, and evenings dining in the vibrant village just moments from your door. Nice stroll to all Pleasantville schools. Here, convenience and charm live hand in hand. And somehow, here, it really does feel like the sun shines a little brighter and the grass grows a little greener. 47 Brookfield is more than a home. It is a story waiting to be written

1 Beds ⋅ 3 Baths ⋅ 985054 MLS

Tucked away on one of Pleasantville Village’s most picturesque, tree lined streets, where the setting feels as though it has been lifted straight from the pages of a storybook, 47 Brookfield offers a truly rare and special opportunity. Perfectly positioned on a quiet cul de sac, this is the kind of place where children play freely, neighbors stroll by with a friendly wave, and life slows down just enough to savor it. For decades, this charming 1930s home has been lovingly maintained and thoughtfully cared for by generations of dentists, serving as both a professional space and a residence. Today, it stands ready for its next chapter. The first floor, currently configured as a dental office complete with a welcoming waiting area and 2 bathrooms, offers a seamless footprint for transformation. Upstairs, a cozy one bedroom apartment provides a glimpse into what this home can become, a warm and inviting single-family residence filled with character and charm. Original details, including a nostalgic milk box, serve as a gentle nod to the home’s rich history. This is where vision meets opportunity. With a two-car garage and a layout that lends itself beautifully to reimagination, 47 Brookfield is the perfect canvas for anyone looking to create something truly their own. You can always renovate a home, tailor it to your taste, expand and enhance, but you can never recreate a location like this. In real estate, location is everything, and this one is simply irreplaceable. Imagine mornings walking to the train, grabbing coffee from your favorite local coffee shop, weekends spent at the farmers market, and evenings dining in the vibrant village just moments from your door. Nice stroll to all Pleasantville schools. Here, convenience and charm live hand in hand. And somehow, here, it really does feel like the sun shines a little brighter and the grass grows a little greener. 47 Brookfield is more than a home. It is a story waiting to be written

47 Brookfield Place, Pleasantville

$999,000

Location, location, location! Welcome to the heart of Pleasantville, NY, where walkability, convenience, and lifestyle come together. Just steps from the Metro-North train, village shops, restaurants, schools, and the Jacob Burns Film Center, this versatile property offers an exceptional opportunity for both investors and those seeking a multi-generational living solution. This sun-filled home features three floors with flexible floor plans, each offering one to two bedrooms, eat-in kitchens, full baths, and comfortable living areas, and is ideal for rental income, extended family, or owner-occupied living with added flexibility. Highlights include wood floors, abundant natural light, generous storage, and a generous flat, usable and deep backyard...perfect for outdoor enjoyment. A charming covered front porch, ample parking, and a separate oversized barn provide rare bonus space for additional storage, parking, or creative use. The basement includes laundry, utilities, and extra storage. Commuters will love the easy access to major highways and public transportation, making this a truly turnkey Pleasantville lifestyle opportunity. Don’t miss this chance to own a property that combines prime village living, investment potential, and everyday convenience in one of Westchester’s most desirable communities.

3 Beds ⋅ 3 Baths ⋅ 935576 MLS

Location, location, location! Welcome to the heart of Pleasantville, NY, where walkability, convenience, and lifestyle come together. Just steps from the Metro-North train, village shops, restaurants, schools, and the Jacob Burns Film Center, this versatile property offers an exceptional opportunity for both investors and those seeking a multi-generational living solution. This sun-filled home features three floors with flexible floor plans, each offering one to two bedrooms, eat-in kitchens, full baths, and comfortable living areas, and is ideal for rental income, extended family, or owner-occupied living with added flexibility. Highlights include wood floors, abundant natural light, generous storage, and a generous flat, usable and deep backyard...perfect for outdoor enjoyment. A charming covered front porch, ample parking, and a separate oversized barn provide rare bonus space for additional storage, parking, or creative use. The basement includes laundry, utilities, and extra storage. Commuters will love the easy access to major highways and public transportation, making this a truly turnkey Pleasantville lifestyle opportunity. Don’t miss this chance to own a property that combines prime village living, investment potential, and everyday convenience in one of Westchester’s most desirable communities.

161 Washington Avenue, Pleasantville

$999,000

Welcome to this beautifully updated home that blends classic charm with modern convenience in the heart of Pleasantville, NY. Just a short stroll from the Village’s vibrant shops, cozy cafes and acclaimed restaurants, this 3-bedroom, 2-bathroom Colonial offers an ideal mix of comfort, character, and location. The main level features a formal dining room, inviting living room, and an updated eat-in kitchen with direct access to the back deck. Upstairs, you'll find three sun-drenched bedrooms and a full shared bathroom. With abundant natural light from morning through evening, each room feels bright and welcoming. Thoughtful upgrades include a brand-new roof and gutters, fresh interior and exterior paint, and beautifully refinished hardwood floors in several rooms, making this home truly move-in ready. The fully finished lower level offers flexible living space—perfect for a recreation room, home office, or gym—and includes a second full bathroom plus direct access to the backyard for seamless indoor-outdoor living. All of this, just minutes from the Metro-North station for an easy commute to NYC, and ideally located to truly take advantage of all the town offers. Don’t miss the opportunity to make this turnkey home your own.

3 Beds ⋅ 2 Baths ⋅ 897937 MLS

Welcome to this beautifully updated home that blends classic charm with modern convenience in the heart of Pleasantville, NY. Just a short stroll from the Village’s vibrant shops, cozy cafes and acclaimed restaurants, this 3-bedroom, 2-bathroom Colonial offers an ideal mix of comfort, character, and location. The main level features a formal dining room, inviting living room, and an updated eat-in kitchen with direct access to the back deck. Upstairs, you'll find three sun-drenched bedrooms and a full shared bathroom. With abundant natural light from morning through evening, each room feels bright and welcoming. Thoughtful upgrades include a brand-new roof and gutters, fresh interior and exterior paint, and beautifully refinished hardwood floors in several rooms, making this home truly move-in ready. The fully finished lower level offers flexible living space—perfect for a recreation room, home office, or gym—and includes a second full bathroom plus direct access to the backyard for seamless indoor-outdoor living. All of this, just minutes from the Metro-North station for an easy commute to NYC, and ideally located to truly take advantage of all the town offers. Don’t miss the opportunity to make this turnkey home your own.

250 Washington Avenue, Pleasantville

$999,000

Nestled in a peaceful and private setting on two lots totaling 0.81 acres, this enchanting 1927 French Normandy Tudor home blends timeless charm and modern comfort, including central air. Rich in character, the home showcases original architectural details such as beamed ceilings, classic casement Tudor windows, arched doorways, and a distinctive Belgian tile roof. A gracious tiled entry leads you to a spacious step-down formal living room with a brick fireplace, oversized windows and French doors opening to the family room. The formal dining room flows effortlessly into a bright, updated kitchen adorned with granite countertops, tile back splash, Mexican terra cotta tile florr, and a sunny dining area. A thoughtfully designed hallway with a laundry closet and breakfast counter is open to the step-down family room, which boasts wood floors, beamed ceiling and a sliding glass door that opens to a tranquil side blue stone patio. Upstairs, the primary suite includes a walk-in shower and wood floors, while three additional bedrooms offer ample space and character. The lower level includes a recreation room with a fireplace, utility space, and direct access to the side yard oasis complete with a lighted waterfall and Koi pond. Surrounded by mature trees and lush plantings, this home is a rare retreat just moments from local amenities.

4 Beds ⋅ 4 Baths ⋅ 888973 MLS

Nestled in a peaceful and private setting on two lots totaling 0.81 acres, this enchanting 1927 French Normandy Tudor home blends timeless charm and modern comfort, including central air. Rich in character, the home showcases original architectural details such as beamed ceilings, classic casement Tudor windows, arched doorways, and a distinctive Belgian tile roof. A gracious tiled entry leads you to a spacious step-down formal living room with a brick fireplace, oversized windows and French doors opening to the family room. The formal dining room flows effortlessly into a bright, updated kitchen adorned with granite countertops, tile back splash, Mexican terra cotta tile florr, and a sunny dining area. A thoughtfully designed hallway with a laundry closet and breakfast counter is open to the step-down family room, which boasts wood floors, beamed ceiling and a sliding glass door that opens to a tranquil side blue stone patio. Upstairs, the primary suite includes a walk-in shower and wood floors, while three additional bedrooms offer ample space and character. The lower level includes a recreation room with a fireplace, utility space, and direct access to the side yard oasis complete with a lighted waterfall and Koi pond. Surrounded by mature trees and lush plantings, this home is a rare retreat just moments from local amenities.

60 Cedar Avenue, Pleasantville

$997,500

Welcome to Pleasantville Country Club where luxury meets ease and every day feels like a retreat. Perfectly positioned just steps from the tennis and pickleball courts, this sun-drenched townhome places you in the heart of one of Westchester’s most coveted lifestyle communities. Whether you’re a player, a spectator, or simply someone who enjoys the hum of an active, close-knit neighborhood, this is where you’ll feel instantly at home. Step inside to discover light cascading through walls of glass, illuminating the airy, open-concept living and dining areas. The kitchen, thoughtfully positioned to capture the morning sun, offers the perfect spot for coffee at the breakfast table as the day unfolds. Seamlessly connected to the living and dining spaces, the main level opens to an expansive deck, an entertainer’s dream where summer barbecues stretch into starlit evenings and lazy Sunday brunches overlook golfers teeing off in the distance. Upstairs, the primary suite serves as a serene sanctuary, featuring a spa-inspired bath with soaking tub, separate glass-enclosed shower, and generous walk-in closets. A secondary bedroom and hall bath provide comfort and privacy for family or guests, all bathed in gentle natural light. The lower level extends the home’s lifestyle versatility with space ideal for game nights, a fitness studio, or festive gatherings, complete with a full bath and sliding doors that open to a secluded patio. Picture mornings spent reading among hydrangeas or quiet evenings unwinding beneath a canopy of twilight. Life here is as effortless as it is exceptional. Weekends drift by poolside, meals arrive from the seasonal restaurant, and celebrations unfold under endless summer skies. The pickleball and tennis courts are just a stroll away, the pro shop stands ready to outfit your next round, and the fitness center beckons for early workouts before a leisurely afternoon on the golf course. When you crave a change of scenery, the charm of Pleasantville Village awaits just beyond the gates. Saturday mornings at the Farmers Market, evening screenings at the Jacob Burns Film Center, dinner at your favorite local restaurant, and when the city calls, an easy train ride delivers you to Manhattan in under an hour. Here, every detail is designed for comfort, connection, and the simple joy of everyday living, a rare offering where resort-style amenities and village convenience meet in perfect harmony.

2 Beds ⋅ 4 Baths ⋅ 927829 MLS

Welcome to Pleasantville Country Club where luxury meets ease and every day feels like a retreat. Perfectly positioned just steps from the tennis and pickleball courts, this sun-drenched townhome places you in the heart of one of Westchester’s most coveted lifestyle communities. Whether you’re a player, a spectator, or simply someone who enjoys the hum of an active, close-knit neighborhood, this is where you’ll feel instantly at home. Step inside to discover light cascading through walls of glass, illuminating the airy, open-concept living and dining areas. The kitchen, thoughtfully positioned to capture the morning sun, offers the perfect spot for coffee at the breakfast table as the day unfolds. Seamlessly connected to the living and dining spaces, the main level opens to an expansive deck, an entertainer’s dream where summer barbecues stretch into starlit evenings and lazy Sunday brunches overlook golfers teeing off in the distance. Upstairs, the primary suite serves as a serene sanctuary, featuring a spa-inspired bath with soaking tub, separate glass-enclosed shower, and generous walk-in closets. A secondary bedroom and hall bath provide comfort and privacy for family or guests, all bathed in gentle natural light. The lower level extends the home’s lifestyle versatility with space ideal for game nights, a fitness studio, or festive gatherings, complete with a full bath and sliding doors that open to a secluded patio. Picture mornings spent reading among hydrangeas or quiet evenings unwinding beneath a canopy of twilight. Life here is as effortless as it is exceptional. Weekends drift by poolside, meals arrive from the seasonal restaurant, and celebrations unfold under endless summer skies. The pickleball and tennis courts are just a stroll away, the pro shop stands ready to outfit your next round, and the fitness center beckons for early workouts before a leisurely afternoon on the golf course. When you crave a change of scenery, the charm of Pleasantville Village awaits just beyond the gates. Saturday mornings at the Farmers Market, evening screenings at the Jacob Burns Film Center, dinner at your favorite local restaurant, and when the city calls, an easy train ride delivers you to Manhattan in under an hour. Here, every detail is designed for comfort, connection, and the simple joy of everyday living, a rare offering where resort-style amenities and village convenience meet in perfect harmony.

4 Rockledge Lane, Pleasantville

$988,800

Welcome to your slice of Pleasantville—where small-town charm meets everyday convenience. This 3-bedroom, 1.5-bath Craftsman-style home offers warmth, character, and a lifestyle that’s hard to resist. Start your mornings on the classic front porch, then head to the local Saturday farmers market just a short stroll away for fresh produce and friendly faces. Inside, the vintage kitchen features marble countertops, a farmhouse sink and cozy touches that make it feel like home from day one. The fenced-in backyard and patio are perfect for weekend gatherings or quiet evenings under the stars. Need to commute or explore? The Pleasantville train station is within walking distance, offering easy access to the city while keeping you grounded in a peaceful, walkable neighborhood. With shops, parks, and community events all within reach, this home is more than a place to live—it’s a place to call home.

3 Beds ⋅ 2 Baths ⋅ 897921 MLS

Welcome to your slice of Pleasantville—where small-town charm meets everyday convenience. This 3-bedroom, 1.5-bath Craftsman-style home offers warmth, character, and a lifestyle that’s hard to resist. Start your mornings on the classic front porch, then head to the local Saturday farmers market just a short stroll away for fresh produce and friendly faces. Inside, the vintage kitchen features marble countertops, a farmhouse sink and cozy touches that make it feel like home from day one. The fenced-in backyard and patio are perfect for weekend gatherings or quiet evenings under the stars. Need to commute or explore? The Pleasantville train station is within walking distance, offering easy access to the city while keeping you grounded in a peaceful, walkable neighborhood. With shops, parks, and community events all within reach, this home is more than a place to live—it’s a place to call home.

55 Sarles Lane, Pleasantville

$980,000

Excellent investment or owner-occupant opportunity in the heart of Pleasantville! This well-maintained multi-family property features three apartments, including one 3-bedroom unit and two 2-bedroom units—ideal for generating steady rental income. Each unit offers 1 full bathroom, a functional layout, and great natural light throughout. The 2-bedroom apartments located on the second and third floors are currently tenant-occupied, while the 3-bedroom apartment on the first floor is vacant—perfect for owner occupancy or additional rental potential. The property includes two parking spaces in the driveway, one garage space, and plenty of public street parking available. The property is being sold As-is. Ideally located approximately 0.5 miles (about a 10-minute walk) from the Pleasantville train station, with easy access to local shops, restaurants, and everyday amenities. Enjoy a private backyard garden, offering outdoor space for relaxation or tenant use. Property is being sold as-is.

7 Beds ⋅ 3 Baths ⋅ 985279 MLS

Excellent investment or owner-occupant opportunity in the heart of Pleasantville! This well-maintained multi-family property features three apartments, including one 3-bedroom unit and two 2-bedroom units—ideal for generating steady rental income. Each unit offers 1 full bathroom, a functional layout, and great natural light throughout. The 2-bedroom apartments located on the second and third floors are currently tenant-occupied, while the 3-bedroom apartment on the first floor is vacant—perfect for owner occupancy or additional rental potential. The property includes two parking spaces in the driveway, one garage space, and plenty of public street parking available. The property is being sold As-is. Ideally located approximately 0.5 miles (about a 10-minute walk) from the Pleasantville train station, with easy access to local shops, restaurants, and everyday amenities. Enjoy a private backyard garden, offering outdoor space for relaxation or tenant use. Property is being sold as-is.

33 Hopper Street, Pleasantville

$980,000

Highly sought-after Bear Ridge Lake, neighborhood. This special location offers ice skating in the winter, kayaking and fishing in the summer. Perhaps, the first home built in the area. Charming curb appeal. From the front bluestone walkway to the neatly arranged plantings, trimmed bushes and landscaping. This majestically improved Colonial features a primary bedroom on the first floor, formal dining room with brick fireplace, updated kitchen, expanded living room that walks out to a sunroom and level backyard for seasonal enjoyment. Second level has three additional bedrooms with one that could be used as a second primary bedroom. Basement features ample storage, laundry, and garage. Just a few minutes to top rated Pleasantville Schools, town, Metro North Railroad, and parkway. The town is walkable with restaurants, shops, and Jacob Burns Film Center. Don’t miss the opportunity to own this home! Star, discount $1,406.00

4 Beds ⋅ 3 Baths ⋅ 935919 MLS

Highly sought-after Bear Ridge Lake, neighborhood. This special location offers ice skating in the winter, kayaking and fishing in the summer. Perhaps, the first home built in the area. Charming curb appeal. From the front bluestone walkway to the neatly arranged plantings, trimmed bushes and landscaping. This majestically improved Colonial features a primary bedroom on the first floor, formal dining room with brick fireplace, updated kitchen, expanded living room that walks out to a sunroom and level backyard for seasonal enjoyment. Second level has three additional bedrooms with one that could be used as a second primary bedroom. Basement features ample storage, laundry, and garage. Just a few minutes to top rated Pleasantville Schools, town, Metro North Railroad, and parkway. The town is walkable with restaurants, shops, and Jacob Burns Film Center. Don’t miss the opportunity to own this home! Star, discount $1,406.00

155 Lake Shore Drive, Pleasantville

$980,000

Charming and stylish Colonial offers a perfect blend of modern updates and classic appeal. The home features a stunning two-story entry and a soaring cathedral ceiling in the Living Room, creating an open and airy atmosphere. Custom windows fill the space with natural light, highlighting the wood flooring throughout. The spacious Kitchen and cozy Dining area with doors to the yard make this home ideal for everyday living and entertaining. The second-floor laundry provides added convenience, while the Master Bedroom boasts two separate vanity areas and whirlpool, offering a spa like retreat. The additional two Bedrooms offer loads of elbow room with ample closet space. A large unfinished basement with outside access provides for plentiful storage or potential for future finished space. The residence is surrounded by beautifully landscaped grounds, providing a serene outdoor setting. Located on a dead end street near downtown Pleasantville, residents enjoy easy access to shops, restaurants, parks, and transportation, including train service to NYC. Experience comfort, style, and versatility in this special home.

3 Beds ⋅ 3 Baths ⋅ 932239 MLS

Charming and stylish Colonial offers a perfect blend of modern updates and classic appeal. The home features a stunning two-story entry and a soaring cathedral ceiling in the Living Room, creating an open and airy atmosphere. Custom windows fill the space with natural light, highlighting the wood flooring throughout. The spacious Kitchen and cozy Dining area with doors to the yard make this home ideal for everyday living and entertaining. The second-floor laundry provides added convenience, while the Master Bedroom boasts two separate vanity areas and whirlpool, offering a spa like retreat. The additional two Bedrooms offer loads of elbow room with ample closet space. A large unfinished basement with outside access provides for plentiful storage or potential for future finished space. The residence is surrounded by beautifully landscaped grounds, providing a serene outdoor setting. Located on a dead end street near downtown Pleasantville, residents enjoy easy access to shops, restaurants, parks, and transportation, including train service to NYC. Experience comfort, style, and versatility in this special home.

18 Park Street, Pleasantville

$975,000

Welcome to 119 Manville Road — a beautifully maintained 4-bedroom, 2-bath split level on a peaceful dead-end street in Pleasantville, freshly painted throughout and ready to welcome its new owners. The updated kitchen features quartz countertops and stainless steel appliances, while hardwood and carpeted floors run seamlessly through the home. Central A/C, an included washer/dryer, and a 1-car garage complete the package, with added convenience of municipal sewer and water. Within walking distance of Pleasantville's highly regarded schools and a short distance to shops, dining, parks, the library, and major commuter routes. A turnkey opportunity you won't want to miss.

4 Beds ⋅ 2 Baths ⋅ 999905 MLS

Welcome to 119 Manville Road — a beautifully maintained 4-bedroom, 2-bath split level on a peaceful dead-end street in Pleasantville, freshly painted throughout and ready to welcome its new owners. The updated kitchen features quartz countertops and stainless steel appliances, while hardwood and carpeted floors run seamlessly through the home. Central A/C, an included washer/dryer, and a 1-car garage complete the package, with added convenience of municipal sewer and water. Within walking distance of Pleasantville's highly regarded schools and a short distance to shops, dining, parks, the library, and major commuter routes. A turnkey opportunity you won't want to miss.

119 Manville Road, Pleasantville

$975,000

Nestled in a highly sought-after neighborhood near Pleasantville and Chappaqua, this well maintained single-story ranch blends comfort, style, and convenience. A welcoming covered entry with decorative columns sets the tone for the warmth you’ll find inside. Step into a thoughtfully renovated interior featuring a tastefully updated kitchen and refreshed bathrooms that combine timeless design with everyday practicality. An attached garage with a spacious driveway offers easy parking, while the manicured front landscaping—with neatly trimmed shrubs, decorative mulch beds, and foundation plantings—adds charming curb appeal. The property is framed by mature trees that provide shade and privacy for the spacious rear deck, perfect for outdoor dining, entertaining or simply relaxing. This move-in-ready property presents an excellent opportunity in a prime location. Schedule your visit today. Taxes split between Town of Mt Pleasant and Village of Pleasantville 2 TAX LOTS (.24 & .09 in size) = 1/3 of an acre Estimated Taxes Total: 20,821.57 before STAR Updates: Roof is 4 years new. AC/Heat Pump 2025, Fridge 2025, washer and Dryer 2024, Dishwasher 2024, Oil Tank 2025, deck 2020. Entire home painted 2022

3 Beds ⋅ 2 Baths ⋅ 915524 MLS

Nestled in a highly sought-after neighborhood near Pleasantville and Chappaqua, this well maintained single-story ranch blends comfort, style, and convenience. A welcoming covered entry with decorative columns sets the tone for the warmth you’ll find inside. Step into a thoughtfully renovated interior featuring a tastefully updated kitchen and refreshed bathrooms that combine timeless design with everyday practicality. An attached garage with a spacious driveway offers easy parking, while the manicured front landscaping—with neatly trimmed shrubs, decorative mulch beds, and foundation plantings—adds charming curb appeal. The property is framed by mature trees that provide shade and privacy for the spacious rear deck, perfect for outdoor dining, entertaining or simply relaxing. This move-in-ready property presents an excellent opportunity in a prime location. Schedule your visit today. Taxes split between Town of Mt Pleasant and Village of Pleasantville 2 TAX LOTS (.24 & .09 in size) = 1/3 of an acre Estimated Taxes Total: 20,821.57 before STAR Updates: Roof is 4 years new. AC/Heat Pump 2025, Fridge 2025, washer and Dryer 2024, Dishwasher 2024, Oil Tank 2025, deck 2020. Entire home painted 2022

88 Oak Ridge Road, Pleasantville

$970,000

Welcome to 60 Pleasant Avenue, a beautifully renovated home in the heart of Pleasantville. Thoughtfully updated in 2020, this property blends modern finishes with everyday functionality, offering a truly move-in ready experience. Inside, you’ll find updated systems, stylish design elements, and a smart, efficient layout that maximizes every inch of space. Designed with practical living in mind, the home offers abundant storage throughout, creating a place that feels both organized and comfortable. Located just moments from the vibrant village center, enjoy easy access to local shops, dining, parks, and a 5 min walk to the Metro North for a seamless commute. The surrounding neighborhood offers a strong sense of community with everything Pleasantville is known for right at your fingertips. Turnkey homes with this level of thoughtful design and location are hard to find. This is your opportunity to step into a fully updated home without the time, cost, and uncertainty of renovations.

4 Beds ⋅ 3 Baths ⋅ 987907 MLS

Welcome to 60 Pleasant Avenue, a beautifully renovated home in the heart of Pleasantville. Thoughtfully updated in 2020, this property blends modern finishes with everyday functionality, offering a truly move-in ready experience. Inside, you’ll find updated systems, stylish design elements, and a smart, efficient layout that maximizes every inch of space. Designed with practical living in mind, the home offers abundant storage throughout, creating a place that feels both organized and comfortable. Located just moments from the vibrant village center, enjoy easy access to local shops, dining, parks, and a 5 min walk to the Metro North for a seamless commute. The surrounding neighborhood offers a strong sense of community with everything Pleasantville is known for right at your fingertips. Turnkey homes with this level of thoughtful design and location are hard to find. This is your opportunity to step into a fully updated home without the time, cost, and uncertainty of renovations.

60 Pleasant Avenue, Pleasantville

$960,555

Welcome to this beautifully maintained Colonial, ideally located just moments from the vibrant village of Pleasantville. This prime location offers seamless access to town life—enjoy weekend strolls to the acclaimed Farmer’s Market, top-rated dining, boutique shopping, and cultural attractions. Commuting is simple and stress-free with the Metro-North train station just a short walk away. Inside, you'll find light-filled, open-concept living and dining spaces that create a warm and inviting atmosphere, perfect for both everyday living and entertaining. The main floor includes a convenient powder room for guests. Upstairs, the spacious primary bedroom features an en suite bath, while a second comfortable bedroom and a full hall bathroom complete the upper level. Throughout the home, timeless built-ins add charm, character, and smart storage. Recent updates include a new roof and a newly built back deck with easy access from the main level. The deck leads directly to a fenced-in backyard, ideal for play, pets, or outdoor gatherings. The home also includes an EV charger, offering convenient at-home electric vehicle charging along with a generator hookup to ensure peace of mind during power outages. The lower level provides direct backyard access and features a versatile recreation space along with a quiet office area, perfect for remote work or study. This move-in ready home blends classic charm with modern updates, making it a perfect match for those looking to enjoy their new place from day one.

2 Beds ⋅ 3 Baths ⋅ 925399 MLS

Welcome to this beautifully maintained Colonial, ideally located just moments from the vibrant village of Pleasantville. This prime location offers seamless access to town life—enjoy weekend strolls to the acclaimed Farmer’s Market, top-rated dining, boutique shopping, and cultural attractions. Commuting is simple and stress-free with the Metro-North train station just a short walk away. Inside, you'll find light-filled, open-concept living and dining spaces that create a warm and inviting atmosphere, perfect for both everyday living and entertaining. The main floor includes a convenient powder room for guests. Upstairs, the spacious primary bedroom features an en suite bath, while a second comfortable bedroom and a full hall bathroom complete the upper level. Throughout the home, timeless built-ins add charm, character, and smart storage. Recent updates include a new roof and a newly built back deck with easy access from the main level. The deck leads directly to a fenced-in backyard, ideal for play, pets, or outdoor gatherings. The home also includes an EV charger, offering convenient at-home electric vehicle charging along with a generator hookup to ensure peace of mind during power outages. The lower level provides direct backyard access and features a versatile recreation space along with a quiet office area, perfect for remote work or study. This move-in ready home blends classic charm with modern updates, making it a perfect match for those looking to enjoy their new place from day one.

159 Sarles Lane, Pleasantville

$950,000

Welcome home to 37 Orchard Street, a timeless Colonial nestled in the heart of the Village of Pleasantville. Ideally located just steps from everything this beloved community has to offer, you'll enjoy award-winning schools, the acclaimed Jacob Burns Film Center, the Pleasantville Farmers Market, charming shops, restaurants, cafes, and the Metro-North train station. Built in 1910, this special home has been lovingly cared for by only its fourth owners, a testament to the warmth and memories it has provided for generations. Rich in character and filled with original charm, the home offers a spacious living room, formal dining room with a charming bump-out reading nook, a family room, powder room, and kitchen on the main level. Upstairs, you'll find three comfortable bedrooms and a full bath, all filled with natural light and classic architectural details. A detached two-car garage provides ample parking and storage. This home presents an incredible opportunity for the next owner to restore, renovate, and make it their own. Whether you're looking to preserve its historic charm or reimagine it with today's modern finishes, the possibilities are truly endless. Homes with this location, character, and potential rarely come to market. Perhaps the most cherished feature is the expansive wraparound front porch—a place where countless mornings began with a cup of coffee, afternoons were spent reading a favorite book, and even rainy days became something to savor. It is an extension of the home itself, inviting you to slow down and enjoy village life. A home with history and heart. A Colonial with endless potential, ready for its next steward to write the next chapter.

3 Beds ⋅ 2 Baths ⋅ 1008828 MLS

Welcome home to 37 Orchard Street, a timeless Colonial nestled in the heart of the Village of Pleasantville. Ideally located just steps from everything this beloved community has to offer, you'll enjoy award-winning schools, the acclaimed Jacob Burns Film Center, the Pleasantville Farmers Market, charming shops, restaurants, cafes, and the Metro-North train station. Built in 1910, this special home has been lovingly cared for by only its fourth owners, a testament to the warmth and memories it has provided for generations. Rich in character and filled with original charm, the home offers a spacious living room, formal dining room with a charming bump-out reading nook, a family room, powder room, and kitchen on the main level. Upstairs, you'll find three comfortable bedrooms and a full bath, all filled with natural light and classic architectural details. A detached two-car garage provides ample parking and storage. This home presents an incredible opportunity for the next owner to restore, renovate, and make it their own. Whether you're looking to preserve its historic charm or reimagine it with today's modern finishes, the possibilities are truly endless. Homes with this location, character, and potential rarely come to market. Perhaps the most cherished feature is the expansive wraparound front porch—a place where countless mornings began with a cup of coffee, afternoons were spent reading a favorite book, and even rainy days became something to savor. It is an extension of the home itself, inviting you to slow down and enjoy village life. A home with history and heart. A Colonial with endless potential, ready for its next steward to write the next chapter.

37 Orchard Street, Pleasantville

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