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335 Croton Dam Road, Ossining
$3,725,000
10 Beds ⋅ 6 Baths ⋅ 999615 MLS
Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing sophistication or convenience, this is the ultimate retreat. From the moment you arrive, the estate feels transported from another era. A winding cobblestone driveway crafted from salvaged historic Bronx street stones loops through rolling lawns, curated gardens, and towering trees before revealing the magnificent manor overlooking its own private 3-acre pond. The original boathouse sits at the water’s edge, while a heated pool, tennis court, Japanese garden, orchard, vegetable and berry gardens, greenhouse, and heated pottery studio create a lifestyle reminiscent of a private European country estate. The nearly 9,000-square-foot residence is rich with warmth, grandeur, and unforgettable architectural detail. The awe-inspiring Great Room is nothing short of spectacular, anchored by a massive stone fireplace, soaring 40-foot oak-beamed ceilings, and dramatic walls of glass opening to sweeping pond views. Every room tells a story, from the stately oak-paneled library and elegant entertaining spaces to intimate sitting rooms, hidden carved staircases, and beautifully preserved plaster walls that showcase the home’s old-world craftsmanship. Designed for luxurious multi-generational living and grand entertaining alike, the estate features 10 bedrooms spread across thoughtfully designed wings, including guest accommodations and private caretaker quarters. The newly renovated primary suite rivals a five-star hotel, complete with its own fireplace, lounge/office with kitchenette, spa-like bath, dressing room, and tranquil views over the grounds. Nearly every fireplace throughout the home is operational, bringing warmth and romance to every season. Three separate tax lots, including an additional lot near the guest house, add a level of rarity and long-term value seldom found in estates of this caliber. Modern upgrades quietly support the property’s timeless elegance, including heated garages, multiple propane generators, upgraded well systems, mixed central air, and extensive utility and storage spaces. Private, historic, and impossibly romantic, this is more than a home. It is a destination, a lifestyle, and a once-in-a-generation opportunity to own one of the Hudson Valley’s most magical estates, all within easy reach of New York City.

335 Croton Dam Road, Ossining

41 Croton Dam Road, Ossining
$1,775,000
4 Beds ⋅ 3 Baths ⋅ 954268 MLS
Experience refined new construction living at 41 Croton Dam Road, a thoughtfully designed 2026-built single-family residence set on 1.38 acres with Hudson River views. Offering 3,550 square feet of elegant living space, this 4-bedroom, 2.5-bath home blends architectural sophistication with modern functionality. The main level features 10-foot ceilings, dramatic 8-foot front entry doors, custom crown molding throughout, and wide-plank 7-inch white oak hardwood floors. The chef’s kitchen is equipped with GE Monogram appliances, under-cabinet lighting, and premium finishes designed for both everyday living and entertaining. The upper level offers 9-foot ceilings and a spacious primary suite complete with a custom closet system. The lower level is built with 10-foot foundation walls, structural steel beams eliminating lally columns, and rough plumbing for a future full bathroom, providing exceptional flexibility and expansion potential. Outdoor living is enhanced by a rear patio, creating a seamless extension of the home’s interior space, ideal for entertaining, relaxation, and enjoying the surrounding natural setting. Additional highlights include a multi-zone irrigation system servicing both lawn and plantings. A rare combination of new construction, craftsmanship, and setting with Hudson River views serving as the home’s defining feature.

41 Croton Dam Road, Ossining

1306 Grants Lane, Ossining
$1,625,000
2 Beds ⋅ 2 Baths ⋅ 1023302 MLS
Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes. Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles of organic architecture, where walls of glass, natural materials, and thoughtful siting dissolve the boundaries between indoors and out. Built from Philippine mahogany, stone, slate, and glass, every detail was carefully considered to create harmony with the surrounding landscape. The result is a 2 bedroom 2 bathroom home that feels remarkably current nearly seventy years later. Inside, soaring glass walls frame the changing seasons while a dramatic stone fireplace anchors the main living space. Original built-ins, slate floors, rich mahogany, and a signature wraparound deck celebrate Henken's vision, while the thoughtfully updated kitchen and recent improvements allow the home to function beautifully for modern living. Designed using passive solar principles decades before sustainability became mainstream, the home captures the low winter sun for natural warmth while deep roof overhangs provide cooling shade throughout the summer additionally geothermal heating, solar, and other thoughtful updates bring modern all-electric comfort to the home. Complementing the main residence is a beautifully reimagined 1,200 square foot studio that expands the property's possibilities. Completely renovated, the space now offers a bedroom, full bath, living area, kitchenette, and a stunning spa-inspired sauna suite finished with terrazzo tile, warm Aspen wood, and premium contemporary materials throughout. Whether used as a guest retreat, artist's studio, wellness space, home office, or income-producing guest accommodation, it offers the same thoughtful design and craftsmanship found in the main home. Recent improvements, including a newly constructed carport, estate-style gravel driveway, high-performance siding, Energy Star windows, updated insulation, and new mechanical connections to the studio, ensure the property is ready for years of effortless enjoyment. The setting is every bit as extraordinary as the architecture. Wander your own seventeen-acre landscape, listen to the year-round stream, or spend the afternoon exploring nearby Teatown Lake Reservation. Just beyond, you'll find some of the Hudson Valley's most celebrated destinations, including Blue Hill at Stone Barns and The Farmer & The Fish. Nearby towns of Ridgefield, Pound Ridge, Katonah and Bedford, offer exceptional dining, galleries, farmers markets, and hiking. Metro-North provides easy access to New York City, making this an extraordinary full-time residence or one of the region's most remarkable weekend escapes. Architecturally significant homes of this caliber rarely become available. This is more than a residence—it's an opportunity to own a living piece of mid-century design history, thoughtfully preserved for the next generation.

1306 Grants Lane, Ossining

120 Spring Valley Road, Ossining
$1,500,000
11 Beds ⋅ 9 Baths ⋅ 1008123 MLS
Rare multi-residence property offering exceptional flexibility, income potential, and a picturesque setting on beautifully landscaped grounds with scenic views of a shared pond. Nestled among mature trees and expansive lawns, this unique offering features three separate residential structures situated on one parcel, creating an outstanding opportunity for investors, owner-occupants, multi-generational living arrangements, or those seeking additional rental income. The centerpiece of the property is a stately Center Hall Colonial featuring 4 bedrooms, 4 bathrooms, a finished walkout lower level with recreation room and summer kitchen, and a wraparound porch and patio overlooking the tranquil pond. Enjoy peaceful water views, fishing, canoeing, and the natural beauty of this remarkable setting right from your backyard. A second building offers two residential units. The lower level is configured as a 1-bedroom, 1-bathroom apartment with patio access and pond views. The upper level has been taken down to the studs and presents a value-add opportunity to complete a spacious 2-bedroom, 1-bathroom unit to your specifications. The third building is a two-family residence featuring a spacious 4-bedroom, 2.5-bathroom main unit with porch, plus an additional 1-bedroom, 1-bathroom apartment. Additional highlights include a detached garage, parking for 10+ vehicles, extensive stonework, mature landscaping, and a truly park-like setting surrounding the shared pond. A rare opportunity to own a versatile property with multiple income streams and exceptional outdoor amenities in a highly desirable setting.

120 Spring Valley Road, Ossining

352 Croton Dam Road, Ossining
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 995572 MLS
Set privately on a beautifully landscaped property, this exceptional colonial at 352 Croton Dam Road offers the perfect blend of timeless design, modern updates, and everyday comfort. A grand two-story entry welcomes you into sun-filled interiors featuring hardwood floors, oversized windows, and thoughtfully designed living spaces throughout. The stunning renovated chef’s kitchen is the centerpiece of the home, complete with custom cabinetry, expansive granite countertops, premium stainless steel appliances, designer lighting, and a large center island ideal for gathering and entertaining. The adjoining family room with fireplace creates a warm and inviting atmosphere, while formal living and dining rooms provide elegant spaces for hosting. A versatile first-floor office/playroom with French doors offers flexibility for today’s lifestyle needs. Upstairs, the luxurious primary suite features an expansive bedroom, spa-like bath, and generous closet space. Spacious secondary bedrooms and beautifully updated baths complete the upper level. Outside, enjoy sweeping lawns, mature trees, and a peaceful private setting perfect for outdoor entertaining, play, or simply relaxing in nature. This move-in ready home combines classic colonial charm with sophisticated modern updates, all conveniently located near parks, schools, shopping, dining, and major commuting routes. A rare opportunity to own a turnkey home with space, style, and privacy in one of Westchester’s most desirable settings.

352 Croton Dam Road, Ossining

14 Wyche Way, Ossining
$1,345,000
4 Beds ⋅ 3 Baths ⋅ 995878 MLS
Beautifully updated center hall Colonial, set on a private and professionally landscaped almost one-acre property on a quiet cul-de-sac in one of Ossining’s most desirable neighborhoods. This move-in ready home blends classic architecture with modern upgrades and a highly functional layout designed for today’s lifestyle. The centerpiece of the home is the newly installed Leicht kitchen, featuring sleek European cabinetry, premium appliances, contemporary finishes, and abundant workspace and storage. The kitchen opens seamlessly to the home’s main living areas, creating an ideal flow for both everyday living and entertaining. Sun-filled interiors include spacious formal living and dining rooms, a welcoming family room with fireplace, and generously sized bedrooms with ample closet space. The primary suite offers a private retreat with an en-suite bath and peaceful views of the surrounding property. Large windows throughout the home bring in natural light and enhance the bright, airy feel of the interiors. Additional features include an unfinished basement offering excellent storage or future expansion potential, as well as a spacious 3-car garage. The expansive level backyard provides exceptional outdoor space for entertaining, recreation, gardening, or future enhancements. Mature trees and established landscaping create a private and tranquil setting while still being conveniently located near shopping, dining, parks, schools, and close to both the Saw Mill and Taconic State Parkways, as well as two Metro-North train stations for an easy commute to Manhattan.

14 Wyche Way, Ossining

1821 Spring Valley Road, Ossining
$1,275,000
3 Beds ⋅ 4 Baths ⋅ 1015078 MLS
Wisteria & Wood: A Craftsman Masterpiece in the Heart of Teatown Tucked into nearly an acre of lush, private landscape in Croton-on-Hudson's most coveted enclave, this custom-built Craftsman residence is where architectural intention meets natural serenity. From the moment you arrive — welcomed by a wisteria-draped pergola and a stunning Belgian block driveway and courtyard — it's clear this home was designed with both beauty and purpose in mind. Inside, the open floor plan unfolds with the effortless flow that today's lifestyle demands. Walls of windows flood the rooms with natural light, while rich hardwood floors, recessed lighting, and an abundance of storage on every level create a home that feels both elevated and completely livable. The wood-burning fireplace anchors the living space with warmth and character, and a stunning wall of built-in bookcases adds depth and personality. Just off the living room, a den offers the perfect balance of connection and privacy — ideal as a reading room, media space, or quiet retreat. The chef's kitchen is appointed with top-of-the-line stainless steel appliances and opens seamlessly to both the dining room and living area — a layout made for entertaining and everyday connection alike. Step outside to the back deck and discover a deeply private outdoor retreat, where nature sets the stage for al fresco dining, morning coffee, or simply doing nothing at all. The spacious primary suite offers a true escape with a generous walk-in closet and a spa bath. Two additional bedrooms feature soaring beamed ceilings and large closets, sharing a full hall bath. The entry level delivers exceptional function with a large mudroom with custom coat cubbies, plus a beautifully finished flex space — ideal as a home office, studio, or guest suite — with a brand new ensuite modern bath. Three bedrooms. with the flexibility to live like 4, and three and a half baths. Craftsmanship in every corner. And then there's the setting. Spectacular rock outcroppings and ancient boulders punctuate the grounds with dramatic natural character, while towering mature trees — including a graceful dogwood and a statuesque magnolia — frame the yard in seasonal beauty. Walk to Teatown Lake Reservation for hiking and birding, or be in Croton village, the Hudson River waterfront, and the Metro-North station in just ten minutes — where a 48-minute express carries you directly into New York City. All within the award-winning Croton-Harmon School District. This is not just a home. It is a way of living.

1821 Spring Valley Road, Ossining

28 Barnes Road, Ossining
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 965266 MLS
Introducing ROCKDALE c. 1830 — a one-of-a-kind, captivating 5-bedroom historic Colonial farmhouse and barn set on 1.32 bucolic acres. The perfect full-time residence or weekend retreat for those who seek charm, originality, and significance. Proudly listed on the New Castle Historic Registry, this quintessential landmark is rich in history and character. Beautifully situated on a quiet country road, the gated entry is framed by a white picket fence and stately stone walls. A long gravel driveway lined with Belgian blocks opens to a picturesque setting with mature plantings, perennial gardens, and a newly expanded bluestone patio with fire-pit and stone wall seating overlooking the back lawn. Inside, the home’s antique character has been beautifully preserved and maintained, blending elegance and comfort. Original pine floors, wood beams, exposed brick, three wood-burning fireplaces, high ceilings, and original built-ins reflect the home’s rich history, while floor-to-ceiling windows fill the interiors with natural light. True to the home’s period, the interior layout connects the rooms in an ideal way for both entertaining and privacy. The recently updated farmhouse kitchen features new cabinetry, countertops, and stainless-steel appliances, complemented by a wood ceiling with original exposed beams and a large double window. The formal dining room with three built-in cabinets, gracious bay window, and butler's pantry is ideal for entertaining. An inviting and spacious living room and a family room/library with reading nook both feature built-in bookcases, fireplaces, and floor-to-ceiling windows. A full bath, laundry room, attached pantry, back hall/mudroom, and wide front porch complete the main level. The second level can be accessed by the main staircase or a quaint back hall staircase leading to a mezzanine level with two bedrooms — one equally suited for and currently used as an office. This space transitions seamlessly to the main hall leading to three additional bedrooms and two well-appointed full baths. A detached barn offers tremendous potential for guest quarters, a creative space, home office, gym, or garage — making this property as versatile as it is distinctive. The spacious backyard abuts farmland, creating a peaceful and scenic setting. Conveniently located near the North County Trailway, major parkways, rail lines, shopping, and Gedney Park, this home provides the benefit of New Castle taxes along with access to Chappaqua recreation and train station parking – a rare and exceptional opportunity to enjoy the best of both communities. ROCKDALE is for the discerning buyer who values a one-of-a-kind home with easy access to NYC.

28 Barnes Road, Ossining

6 Maria Lane, Ossining
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 1000282 MLS
Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich espresso cabinetry, quartz countertops, stainless steel appliances, a stylish tile backsplash, recessed lighting, and a large center island with seating. The open flow connects seamlessly to the dining room and main living areas, creating an inviting atmosphere for gatherings large and small. The spacious primary suite includes a private en-suite bath, while two additional bedrooms and a full bath round out the first floor. The finished lower level offers exceptional versatility with a separate entrance, additional family room, a full bath, another bedroom and a bonus room flexible for a home office, gym, or crafts. Enjoy the beautifully usable outdoor space complete with a patio and above-ground pool, perfect for relaxing or entertaining. Additional features include generous storage, an attached garage, and a convenient location close to shopping, parks, schools, and major commuter routes. A rare opportunity with endless possibilities for today’s lifestyle.

6 Maria Lane, Ossining

200 Route 9A, Ossining
$1,099,900
5 Beds ⋅ 4 Baths ⋅ 906409 MLS
Exceptional residence featuring a fully legal accessory apartment, offering rare flexibility for multigenerational living, extended family, guests, or private professional space. The thoughtfully designed additional living area includes its own entrance, kitchen, bath, and living quarters, creating a comfortable and private environment while maintaining the character of a single-family home. Approximately 900 sq ft of finished lower-level space enhances the home’s functionality beyond the main living area reported in municipal records. Tucked away at the end of a semi-private road in a peaceful neighborhood, this property combines privacy, versatility, and elegant design. The main residence features 3 bedrooms, hardwood floors throughout the living areas, spacious living and dining rooms, and a dramatic vaulted fireplace that serves as a warm and inviting centerpiece. The chef’s kitchen boasts a Wolf range with built-in grille, double oven, and Sub-Zero freezer—ideal for both everyday living and entertaining. Step outside to the expansive Ipe Brazilian walnut deck with a large overhead awning for seasonal indoor/outdoor comfort. The resort-style backyard is a private oasis with a heated pool, Caldera spa, and lush landscaping—perfect for relaxing or entertaining. A 3-car garage with a workshop area provides ample space for vehicles, storage, and hobbies. Central air conditioning ensures year-round comfort. Located just 5 minutes from the Croton-Harmon Metro-North Station with a 40-minute express ride to NYC, this home offers the ideal balance of luxury, convenience, and tranquility in one of Ossining’s most desirable hidden neighborhoods.

200 Route 9A, Ossining

119 Edgewood Road, Ossining
$1,041,000
4 Beds ⋅ 3 Baths ⋅ 990966 MLS
Vacation at Home! Gracious 4 bedroom, 2 1/2 bathroom, covered front porch colonial home with a gorgeous in-ground heated pool, located in a non-through street, residential neighborhood in the Town of New Castle section of Ossining. Set far back from the road, this one-acre lot offers a private backyard featuring a huge paver patio, a sprawling lawn and tree-lined backyard, including a Japanese Zen garden, plus the separately fenced pool area. Hardwood floors throughout. Updated kitchen (6 seat breakfast bar, granite counters & stainless steel appliances) and updated bathrooms, windows & central air, plus meticulous maintenance makes for easy living. Propane heats the pool and is for the gas range & dryer, and can be hooked up to the outdoor BBQ too! Nothing to do but pack your bags (don't forget to include a swim suit) and move right in. The 805 SF basement is not included in the SF, but offers great potential. Extra refrigerator in basement included. See special features sheet for additional highlights. Floor plans and PCDS attached as well.

119 Edgewood Road, Ossining

10 Stone Avenue, Ossining
$980,000
4 Beds ⋅ 2 Baths ⋅ 988793 MLS
Wonderful opportunity to own this updated 2 family home set on a beautiful .38 level acre property with a magnificent inground pool, fenced in area, and exceptional outdoor entertaining space. The main level features a spacious 3 bedroom layout with an updated kitchen showcasing quartz countertops, tiled backsplash, center island, and stainless appliances. The inviting living room includes an electric fireplace, creating a warm and modern atmosphere. The full bath has a whirlpool tub. Indoor/Outdoor living is highlighted with a fabulous three-season sun room, accessed directly from the main level, then out to the stone patio, inground swimming pool, fire pit, and expansive backyard designed for entertaining and relaxation. The newly painted exterior and many updates throughout make this move-in ready multi-family property a rare find. The lower level with own private entrance offers a 1 bedroom apartment with additional den, ideal for extended family, rental income, guests, or home office use. Central Air in both apartments. Conveniently located close to shopping, dining, and public transportation, this versatile property offers comfort, functionality, and income-producing potential. Perfect for owner occupants, multi-generational living or investors!

10 Stone Avenue, Ossining

3 Birch Court, Ossining
$955,000
3 Beds ⋅ 3 Baths ⋅ 986851 MLS
Set on a quiet cul-de-sac with seasonal river views and unforgettable sunsets, this beautifully maintained Colonial offers the perfect balance of style, comfort, and everyday ease. Built in 2004 and gently lived in, the home is filled with natural light, highlighted by high ceilings, generous proportions, and a seamless, inviting flow. The main level features formal living and dining rooms, a powder room, and a bright, functional kitchen that opens to a cozy den with fireplace and sliding glass doors to the deck; perfect for relaxed indoor-outdoor living. A convenient laundry/mudroom connects directly to the two-car garage. Upstairs, the spacious primary suite serves as a private retreat with a spa-like bath, including a jetted tub and separate shower. Two additional large bedrooms, a full hall bath, and a flexible bonus space, ideal for a home office or creative use, complete the second level. The walk-out lower level offers high ceilings, generous storage, sliding doors to the backyard, and plumbing already in place for a future bathroom; ready to be finished to suit your needs. Recent updates include a new driveway, new boiler and hot water heater, new dishwasher, and updated central air. Ideally located near Metro-North, parks, shopping, and everyday conveniences, this move-in ready home delivers space, flexibility, and a setting that truly stands out.

3 Birch Court, Ossining

5 Gualtiere Lane, Ossining
$945,000
4 Beds ⋅ 3 Baths ⋅ 1026827 MLS
Welcome to this beautiful 4 bedroom, 2 full bath, 1 half bath home offering stunning water views and views of the Hudson River and Mario M. Cuomo bridge. Thoughtfully designed with spacious living areas and inviting outdoor spaces, this home combines comfort, charm, and an exceptional setting. Step inside through the impressive two story foyer, where soaring ceilings create a bright and welcoming first impression. The home's spacious layout provides plenty of room for everyday living, entertaining, and working from home. Enjoy peaceful mornings or relaxing evenings on the expansive front porch while taking in the scenic views. The large rear yard offers abundant outdoor space for gatherings, gardening, recreation, or simply enjoying the privacy and natural surroundings. Additional features include an attached garage, generous living space, and an ideal location in Ossining. Conveniently located just minutes from the Ossining Metro-North Station,

5 Gualtiere Lane, Ossining

1 Thornton Hill, Ossining
$940,000
3 Beds ⋅ 4 Baths ⋅ 1004287 MLS
PRICED TO SELL! THIS ONE WON'T LAST!!! Discover this beautifully maintained home in Hawkes Crossing, offering a comfortable layout and low-maintenance lifestyle. The home features 3 spacious bedrooms, 2.5 bathrooms, and an additional room that can be used as a 4th bedroom, home office, or flex space. The main level includes a formal dining room, an open kitchen, and a flowing floor plan that makes everyday living and entertaining easy. Cathedral ceilings add to the home's spacious feel, while walk-in closets provide plenty of storage. Additional features include a two-car garage, backyard fire pit, sprinkler system, and a finished basement with approximately 680 square feet of additional living space. The lower level also includes a separate 430-square-foot storage room with potential for a home gym, recreation room, media room, or additional finished space. This area was expanded through excavation work completed during foundation and basement improvements, creating additional headroom and allowing for enhanced structural support. The monthly maintenance fee of $218 includes landscaping and snow removal, making homeownership even more convenient. Located in a desirable neighborhood and move-in ready, this home offers space, flexibility, and value. Don't miss this opportunity to make it your own.

1 Thornton Hill, Ossining

12 Riverview Court, Ossining
$935,000
4 Beds ⋅ 3 Baths ⋅ 1019889 MLS
Welcome to one of Ossining's most captivating homes, where breathtaking panoramic Hudson River views take center stage. Perfectly positioned on a quiet cul-de-sac in the sought-after Sparta neighborhood, this beautifully updated 4-bedroom, 2.5-bath residence offers an exceptional blend of style, comfort, and unforgettable scenery. From the moment you enter, you're greeted by abundant natural light and spectacular water views from nearly every level. The thoughtfully renovated kitchen flows seamlessly into the main living and dining spaces, while hardwood floors, two fireplaces, and oversized windows create a warm yet sophisticated atmosphere. Wake up to stunning river vistas from the bedrooms, then unwind each evening as the sun sets over the Hudson from your expansive wraparound patio. Designed for both entertaining and everyday living, the outdoor space features a private backyard with a stone fire pit—perfect for gathering with family and friends while enjoying the ever-changing beauty of the river. Located just moments from Sparta Park, the Ossining waterfront, restaurants, shopping, and the Scarborough Metro-North station, this home offers the perfect balance of tranquility and convenience. If you've been searching for a home with truly spectacular water views, timeless charm, and an unbeatable location, this is an opportunity you won't want to miss.

12 Riverview Court, Ossining

44 Beach Road, Ossining
$925,000
3 Beds ⋅ 3 Baths ⋅ 1022746 MLS
This charming renovated farmhouse offers 3,000 sq ft of living space and is nestled at the very end of a quiet cul-de-sac providing exceptional privacy and adjacent to protected parklands with scenic walking trails, and the Hudson River. The home features a newly added first floor primary suite complete with a tray ceiling, recessed lighting, oversized walk-in closet, and an adjoining home office all on its own HVAC system, creating the perfect private retreat. The custom kitchen offers granite countertops, custom cabinetry, GE appliances, and a sunny breakfast alcove. The kitchen flows seamlessly into the formal dining room and inviting living room with a wood-burning fireplace and access to the charming covered front porch. The separate and spacious family room on the south side of the home is filled with natural light from a wall of windows with access through sliding glass doors to the patio and fully fenced rear yard. Upstairs you will find two generously sized bedrooms and a versatile bonus room, ideal as a fourth bedroom, home office, laundry room or den. Additional features include a large detached two-car garage with expansive storage, newly installed generator, alarm system with video cameras, multiple laundry hook-ups including a second washer & dryer in the basement. There is also a cover front porch, and two patio areas around the property. Located just 1.5 miles from the Ossining train station! The location is truly exceptional. Situated at the entrance to the Crawbuckie Nature Preserve, this home offers immediate access to appx 20 acres of woodlands with walking trails winding through mature forest along the Hudson River. Enjoy scenic overlooks, observation platforms, and year-round hiking and nature just steps from your front door. This unique combination of character, modern updates, and an unparalleled natural setting makes this home a rare opportunity.

44 Beach Road, Ossining

8 Riverview Farm Road, Ossining
$900,000
3 Beds ⋅ 3 Baths ⋅ 1000674 MLS
Summer starts here! Nestled on a stunning park-like property surrounded by mature trees and lush landscaping, this beautifully maintained 3-bedroom, 3 full bathroom home offers the perfect blend of privacy, comfort, and timeless style. The sun-filled main level features an open-concept layout with gleaming hardwood floors, a spacious living room anchored by an oversized picture window overlooking the backyard, and a beautifully appointed chef's kitchen complete with custom cabinetry, granite countertops, stainless steel appliances, and a large center island with an induction cooktop. The adjoining dining area provides an ideal setting for both everyday living and entertaining, with direct access to the expansive stone patio and backyard. The primary suite offers a peaceful retreat, while two additional bedrooms and a well-appointed full bath provide flexibility for family, guests, or home office needs. The fully finished lower level significantly expands the living space and offers endless possibilities, featuring a large recreation area, a full bathroom, and a convenient wet bar, ideal for extended family, guests, hobbies, fitness, or work-from-home needs. Adding even more potential, the home includes a full unfinished attic offering abundant storage space and exciting possibilities for future expansion. Outside, enjoy the tranquil setting from the spacious patio overlooking the sprawling backyard, perfect for entertaining, gardening, play, or simply relaxing in nature.

8 Riverview Farm Road, Ossining

4 Cooper Drive, Ossining
$875,000
3 Beds ⋅ 3 Baths ⋅ 1021307 MLS
Enjoy easy living in this spacious, move-in-ready Raised Ranch featuring numerous updates and a functional floor plan. The bright kitchen offers abundant cabinetry, granite countertops, a breakfast bar, and stainless-steel appliances, while the adjacent dining area provides easy access to a two-tier deck, perfect for outdoor dining, entertaining, or just relaxing. Beautiful hardwood floors enhance the main level, while the lower-level family room features a brick fireplace, new flooring, a mini-split A/C system, and sliding glass doors leading to a large backyard with plenty of space for recreation, gardening, or play. Recent improvements include an updated heating system, newly installed A/C system, and beautifully renovated primary and hall bathrooms. An oversized two-car attached garage provides exceptional storage and everyday convenience. Ideally located close to transportation, shopping, restaurants, and everyday amenities, this well-maintained home offers the perfect combination of comfort, updates, and location.

4 Cooper Drive, Ossining

55 Hoags Cross Road, Ossining
$865,000
3 Beds ⋅ 2 Baths ⋅ 911023 MLS
Welcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. Privately set on a level acre and surrounded by trees and natural landscaping, this property offers a rare sense of quiet seclusion: your own peaceful retreat, just moments from town, commuting routes, and everyday conveniences. This beautifully maintained split-level ranch lives like a 4-bedroom and offers exceptional flexibility, effortless indoor-outdoor flow, and space to grow.  A welcoming entry foyer opens to a spacious family room with sliding doors leading to a stone patio, perfect for entertaining under the trees or enjoying quiet mornings immersed in nature. A full bath on this level adds convenience for guests. Upstairs, natural light fills the living room, where a fireplace creates a warm focal point. The space flows seamlessly into the dining room and kitchen, with hardwood floors throughout. Sliding doors off the dining room open to a deck overlooking the expansive, private grounds—an ideal setting for gatherings or simply taking in the peaceful surroundings. A generously sized flexible room just off the dining area can serve as a home office, guest suite, or additional bedroom. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. The upper level includes three well-proportioned bedrooms and a full hall bath. The lower level offers excellent storage, a laundry area, and an additional room with walkout—perfect for a gym, media space, or playroom. A detached two-car garage and the property’s wide, level lawn create a sense of openness while maintaining privacy—offering endless possibilities for outdoor living and recreation. Ideally located between Route 9A and the Taconic Parkway, with Metro-North access from Ossining or Croton-Harmon (approximately 45 minutes to Grand Central), and just minutes from Gedney Park, Teatown Lake Reservation, Hudson Hills Golf Course, scenic trails, restaurants, and shops. Located in the Ossining School District, whose high school participates in nationally recognized academic programs, including the Regeneron Science Talent Search.

55 Hoags Cross Road, Ossining

21 Hawkes Avenue, Ossining
$864,000
3 Beds ⋅ 3 Baths ⋅ 1010331 MLS
Offered for the first time ever, 21 Hawkes Avenue is a one of a kind contemporary residence in the Town of Ossining custom built by its current owner, an accomplished contractor, and designed by architect Jim Picone. Completed in 1983 and thoughtfully improved over the years, the home sits on a private, wooded 1.5-acre parcel originally acquired in 1980. A winding, tree-lined driveway leads to the residence, which is perfectly positioned atop a gentle rise overlooking beautifully maintained grounds. Defined by dramatic rooflines, soaring ceilings, expansive windows, and striking geometric forms, the home was designed to blur the line between indoors and out while embracing its natural surroundings. Surrounded by mature specimen trees, stone edged gardens, broad lawns, and woodland, the property offers exceptional privacy. A historic stone wall borders a gently flowing creek at the edge of the property, creating a peaceful setting rich with wildlife and seasonal beauty. Stone and timber steps lead to a covered entry and welcoming foyer. Inside, open concept living spaces feature exposed beam ceilings, stained softwood floors, and abundant natural light. A dramatic two-story dining area framed by towering trapezoidal windows serves as the heart of the home. The renovated kitchen features custom light green cabinetry, slate countertops sourced from a Vermont quarry, newer appliances, and a custom breakfast table and island inspired by George Nakashima. Glass doors connect the dining area to the wraparound deck, creating seamless indoor/outdoor living. A spacious living area provides the perfect setting for relaxing or entertaining. The main level also includes a full bath, private office or den with cathedral ceilings and built-ins, pantry, laundry room, and generous storage. A wood-burning stove adds warmth and ambiance during the winter months. The custom staircase rises to a light-filled second floor with vaulted ceilings and clerestory windows. The primary suite offers a renovated bath, ample closet space, and serene views of the surrounding landscape. Two additional bedrooms, each featuring signature trapezoidal windows, share a full bath. Above, a charming loft provides flexible space for play, storage, or a cozy retreat. The lower level includes a spacious one car garage with a 220V/40-amp outlet suitable for a Level II EV charger, ample storage space, as well as a workshop and utility room. A permitted accessory apartment, added in 2000, offers approximately 350 square feet with a private entrance, full kitchen, washer/dryer, radiant floor heat, cooling, and yard views. Ideal for rental income, guests, an au pair, in-laws, or a home office, it adds tremendous flexibility and value. Designed with energy efficiency in mind, the home's southern exposure provides passive solar warmth in winter. Solar panels were installed in 2023, and a whole-house automatic generator was added in 2024. Seven mini-split systems provide efficient heating and cooling throughout. Additional features include central vacuum, a monitored security system, and a woodshed stocked with a two-year supply of split hardwood. Despite its private, retreat-like setting, the home enjoys a convenient Ossining location near Route 9A, Route 134, shopping, schools, and everyday amenities. Croton-Harmon Metro-North Station is approximately ten minutes away, offering express service to Grand Central Terminal in roughly 40-45 minutes. Lovingly maintained by its original owners for more than four decades, 21 Hawkes Avenue presents a rare opportunity to own a thoughtfully designed home where architecture, craftsmanship, and nature exist in perfect harmony.

21 Hawkes Avenue, Ossining

1 Noel Drive, Ossining
$860,000
4 Beds ⋅ 3 Baths ⋅ 851466 MLS
Sprawling Cape Cod style home with first floor primary suite on a fabulous, private setting. Kitchen has stainless appliances and stone counters, formal dining room has large bay window looking out at the fenced-in property, and living room has high ceilings and a fireplace. Sun Room off the kitchen has 3 skylights and the covered patio off the kitchen overlooks the lush landscaping, backing up to Chilmark Park. There is also a first floor office and a large family room with fireplace and separate entrance. Three bedrooms on the second floor with full bath. Full walk out basement (863 sq ft not included in the square footage). Hardwood floors, crown molding, updated roof with solar panels, nest thermostat, and oversized garage. Close to park, schools, and shops. There are no audio recording devices inside this property. Additional Information: ParkingFeatures:2 Car Attached,

1 Noel Drive, Ossining

38 Terrace Avenue, Ossining
$855,000
8 Beds ⋅ 3 Baths ⋅ 939881 MLS
Welcome to a spacious, well-maintained multi-level home offering a rare blend of legal configuration and flexibility. Ideal for extended family living, owner-occupants seeking rental income, or buyers looking for long-term versatility. The legal lower level features three bedrooms, a full bathroom, direct interior access, and a separate entrance. The main level offers three additional bedrooms, a full bathroom, an eat-in kitchen, and a comfortable living room. The second-floor apartment includes two bedrooms, an eat-in kitchen, and a full bathroom, with walk-up access to a large unfinished attic—perfect for storage or future potential. The home has been updated within the last five years and will be delivered with a clean Certificate of Occupancy. A deep driveway running the full depth of the property provides ample off-street parking and added convenience. A thoughtfully laid-out property with strong utility, legal flexibility, and long-term value.

38 Terrace Avenue, Ossining

20 Highview Road, Ossining
$845,000
3 Beds ⋅ 2 Baths ⋅ 961773 MLS
Welcome to 20 Highview Road! Tucked away on a beautiful cul-de-sac in the desirable town of New Castle, this charming ranch offers a wonderful blend of comfort, functionality, and the opportunity to make it your own. Inside, you’ll find a bright, inviting layout featuring a spacious living room with a wood-burning fireplace, hardwood floors, and large windows that fill the space with natural light and warmth. The charming kitchen offers a practical design with ample cabinet storage and opens to the dining area, making everyday living and entertaining effortless. From there, step outside to a private patio overlooking a beautiful, level yard—perfect for relaxing, entertaining, or enjoying outdoor activities. Three first-floor bedrooms and two full bathrooms, including a primary bedroom with a full en-suite bath, complete the main level. Downstairs, the lower level offers a large, untapped flexible space with ample storage, a workshop area, and a dedicated laundry room. A pull-down attic provides additional storage. A one-car garage and spacious driveway make parking a breeze. With easy access to the Taconic State Parkway, Route 9A, and Metro-North Railroad, commuting to NYC is easy. Enjoy close proximity to Gedney Park, Teatown Lake Reservation, Hudson Hills Golf Course, scenic hiking trails, DeCicco & Sons, Tazza Cafe, and a variety of local restaurants and shops. With its desirable ranch layout and great potential, this home is an exceptional opportunity to enjoy the best of both Ossining and Chappaqua communities.

20 Highview Road, Ossining

78 Hudson Watch Drive, Ossining
$840,000
2 Beds ⋅ 4 Baths ⋅ 959221 MLS
Welcome to 78 Hudson Watch Drive, a stunning 2-bedroom, 3.5-bath tri-level townhouse offering an unparalleled luxury lifestyle. Experience breathtaking Hudson River views spanning all three floors of this meticulously maintained home. Step inside to a truly inviting space featuring a spacious sunken living room anchored by a cozy gas fireplace. The layout is wonderful for entertaining, leading into a dining room with a door that opens directly to a quiet deck—for al fresco dining with a view. The eat-in kitchen is the heart of the home with stainless steel appliances and granite counters. The first floor also includes an office and a powder room. The upper level features a primary suite complete with an ensuite bath with a steam shower, spa tub, and a large walk-in closet. Step out to your balcony and enjoy the mountains and river view. There is a lovely second bedroom, hall bath and a dedicated laundry area which complete this floor. The lower level has ample space for endless possibilities. It features a large family room with a kitchenette, a full bath and sliding glass doors to a covered patio. Enjoy year-round comfort with central air conditioning throughout the home. The community offers an in-ground pool and tennis court as well as lawn maintenance for the approximately 80 homes in Hudson Watch.

78 Hudson Watch Drive, Ossining

39 Washington Avenue, Ossining
$825,000
4 Beds ⋅ 2 Baths ⋅ 961718 MLS
Charming Victorian Colonial ideally located directly across from Nelson Park and just a short walk to schools, shops, and local amenities. This sun-filled home blends timeless character with thoughtful modern updates and offers a flexible layout that lives like a 4/5-bedroom home. Highlights include high ceilings, new thermopane windows, beautiful bay windows in the living room and bedrooms, and a coffered ceiling & wainscotting in the formal dining room, and updated baths. The renovated kitchen features white oak cabinetry, soapstone countertops, stainless steel appliances including a Smeg 5 burner gas range, a convenient breakfast bar, LED recessed lighting, and is perfect for everyday living and entertaining. A main-level laundry room with Bamboo floors & LG appliances, side mudroom porch to slate patio and fenced back yard, and easy-flow layout add to the home’s functionality. The main floor primary suite offers comfort and convenience with a renovated ensuite bath. Throughout the main floor you’ll find beautiful gleaming oak rifted and quartersawn hardwood floors with walnut borders. The home offers a seamless blend of vintage details and modern finishes. Major updates include seven new ductless heating and cooling units for great efficiency in all 4 seasons, new windows, and a new roof, and new steel column foundation supports. Additional features include a welcoming rocking chair front porch, slate patio, fenced flat front and backyard, regraded driveway, and stunning old-growth trees that enhance the home’s captivating curb appeal. Storage is abundant with a walk-up attic and full basement , and the updated second-floor hall bath adds to the home’s move-in-ready appeal.

39 Washington Avenue, Ossining

10 Pine Brook Road, Ossining
$810,000
3 Beds ⋅ 3 Baths ⋅ 935813 MLS
Nestled on a quiet cul-de-sac and set on a spacious, level yard, this immaculate, move-in-ready 3BR/3BA contemporary home offers bright, open living with soaring cathedral ceilings, skylights, and oversized windows throughout. The main level features gleaming hardwood floors, a sun-filled living and dining area, 3 bedrooms and an updated kitchen with granite countertops and Bosch and Samsung appliances. Sliding glass doors lead to a large deck, perfect for entertaining. The finished lower level includes a full bath, new Pergo flooring, a cozy brick fireplace, and walkout access to a private patio and beautifully landscaped yard. Additional highlights include central air, 3-zone gas heat, central vacuum, two-car garage, and abundant storage. Exceptional space, comfort, and location – do not miss it!

10 Pine Brook Road, Ossining

131 Spring Street, Ossining
$805,000
4 Beds ⋅ 2 Baths ⋅ 950694 MLS
Now offered at a compelling new price, 131 Spring Street is a restored brick two-family offering flexibility for owner-occupants or investors. Each unit features bright, connected layouts with updated kitchens and baths, balancing comfort, function, and privacy. The lower unit is configured for owner occupancy with potential to expand to a two-bedroom layout. A full standing-height attic provides additional space for future living area, workspace, or storage. Built with durable materials, including a brick exterior and ceramic tile roof, the home offers reduced long-term maintenance. Outdoor spaces include a front balcony and lower terrace, complemented by established perennial plantings. Ideally located in Ossining, less than a mile from the Metro-North Hudson Line, parks, schools, shops, and dining. Furnishings available as part of the sale. A versatile property with strong fundamentals and meaningful upside, now priced to create immediate opportunity.

131 Spring Street, Ossining

34 Piping Rock Drive, Ossining
$802,000
2 Beds ⋅ 3 Baths ⋅ 956227 MLS
34 Piping Rock is a stunning contemporary home that offers the perfect blend of style, functionality and comfort. Featuring 2 bedrooms but lives like 3 or more with stunning seasonal views of the Hudson River as well as a flexible floor plan ideal for a home office, den or guest space. The lower level which is completing above ground with its own private access and full bath offers endless possibilities. Truly "Move-In Ready", meticulously maintained with many recent upgrades to the roof, boiler, water heater and central AC mechanicals. Enjoy an open-concept living area, abundance of natural light and seamless indoor-outdoor flow- perfect for both everyday living and entertaining. The modern kitchen boasts stainless steel high-end appliances and quartz counters. A must-see property offering versatility, modern elegance and effortless living - this is contemporary living at its finest!

34 Piping Rock Drive, Ossining

86 Woods Brooke Terrace, Ossining
$800,000
2 Beds ⋅ 3 Baths ⋅ 1008140 MLS
Experience turnkey luxury in this beautifully renovated corner unit at The Woods, where every detail has been thoughtfully updated from top to bottom. The heart of the home is the custom high-end Bilotta kitchen, featuring a granite center island with seating, Bosch stainless steel appliances, induction cooktop, pantry, and under-cabinet lighting. The open-concept main level is ideal for both everyday living and entertaining, showcasing a custom fireplace, a sophisticated leathered quartzite bar, a private first-floor office, and a stylish powder room. Additional upgrades include updated electrical, baseboards, windows, recessed lighting, custom blinds, luxury vinyl flooring, and a redesigned balustrade. Upstairs, the spacious primary suite offers a true retreat with a luxurious spa-inspired bath featuring an oversized rainforest shower with marble seat and niche, dual quartzite vanity, and a custom walk-in closet illuminated by a skylight. The second level also includes an updated hall bath, a secondary bedroom with new carpeting, and an enclosed bonus room perfect for guests, a home office, or recreation space. Modern comforts continue with a Navien tankless boiler and hot water system providing efficient, unlimited hot water. Outdoors, relax on the private covered patio surrounded by beautifully landscaped specimen plantings, including Japanese maple and hydrangeas. A significant value-add: the $15,000 roof assessment has already been paid in full. Residents enjoy access to community amenities including a pool and tennis courts, offering a low-maintenance lifestyle in a desirable setting. There are no audio recording devices inside this property.

86 Woods Brooke Terrace, Ossining

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