Ossining School District Homes For Sale

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Explore homes in the diverse and innovative Ossining Union Free School District, renowned for its International Baccalaureate program and commitment to global education. This progressive district offers a comprehensive K-12 curriculum that fosters critical thinking, cultural understanding, and academic excellence.

Browse all MLS townhome listings within this dynamic riverside district, featuring a range of styles and prices to accommodate various preferences. Properties in Ossining often provide stunning Hudson River views and convenient access to the district's forward-thinking schools and Metro-North station.

Located just 30 miles from Manhattan, Ossining UFSD blends multicultural richness with scenic beauty. Experience cutting-edge educational programs, a strong sense of community, and attractive living options in these desirable Ossining School District homes.

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Latest Ossining School District Listings

$469,900
2 Beds ⋅ 2 Baths ⋅ 1049340 MLS
Welcome to this chic, beautifully renovated 2-bedroom, 2-bathroom condominium in Ossining's iconic 1820 schoolhouse conversion. Originally built as a schoolhouse and thoughtfully converted in 2007 into an intimate 12-unit condominium, this one-of-a-kind residence seamlessly blends a Soho-inspired aesthetic with the warmth, character and charm of the Hudson Valley. Step inside to a spacious, open-concept interior featuring soaring ceilings and a huge sun-filled living room. The elevated kitchen offers granite countertops and new stainless steel appliances (2025). The open-layout allows the kitchen, dining and living areas to flow effortlessly together, creating a sophisticated yet comfortable sense of space. The private bedroom area offers two beautiful bedrooms, including a large primary ensuite designed as a serene retreat. The primary bedroom is filled with natural light through large windows, complemented by automated window treatments for effortless comfort and privacy. A fews steps down lead to tastefully renovated primary bathroom, featuring a sophisticated, modern design complete with radiant heated floors. A walk-in custom organized closet completes this exceptional primary suite. The generously sized second bedroom is ideal for guests or a home office. Just beyond is the distinctive, updated second bathroom that adds another layer of style and sophistication to this home. The unit also comes with an assigned parking spot(#11) and private laundry. Fabulous location with easy access to the scenic Croton Aqueduct trail and all that Ossining has to offer. This vibrant, welcoming community has a cool vibe, with a Recreation Center offering something for everyone, from adult basketball to children's programs, as well as a stunning riverfront and close proximity to the Metro North Train station. Enjoy delicious local restaurants, an amazing famers market, lively street fairs, outdoor summer concerts and so much more-all adding to the energy that makes Ossining such a special place to call home.

88 Broadway Unit #2B, Ossining
$800,000
3 Beds ⋅ 3 Baths ⋅ 1048991 MLS
A rare convergence of land, privacy and proximity, 81 Glendale Road consists of 14.36 breathtaking acres in the Teatown area of New Castle, surrounded by some of Westchester County's most treasured protected landscapes. Set back from one of the area's most scenic roads, and nearly hidden from view (even in winter), the 3,990-square-foot residence is in the midst of a remarkable landscape of mature woodland, ponds and the streaming waters of Indian Brook. Built in 1870 and updated in the mid-1980s, the 3-bedroom, 2-and-one-half-bath home is connected to its setting. Approached by two driveways, the residence is introduced by a long covered front porch. Inside, well proportioned living and dining/family spaces follow a traditional arrangement, organized around a well-designed central kitchen that discreetly supports both everyday living and entertaining. Throughout the residence, carefully placed windows and french doors frame the surrounding woods, allowing the landscape to be part of the interior experience. The private quarters include 3 bedrooms, two full baths. A lower service level provides a mudroom, enclosed porch, media room, pantry, food-storage and preparation areas, lavatory and the home's mechanical systems. The land makes 81 Glendale Rd. truly exceptional. The properties private acres adjoins lands of Teatown Lake Reservation, and the protected, un-developable watershed property of the Ossining water supply. Teatown's 1,000-acre nature preserve and 15 mile long trail system is at the property's doorstep. Here, mornings can begin beside the brook, the woodland paths and the trails of Teatown without getting into a car. ~4 acres and the house are enclosed by a deer fence. Existing accessory structures include a garage, barn and storage buildings. These structures reflect their age and condition and an opportunity to reimagine the property's outbuildings and their uses, subject to applicable municipal requirements and approvals. For all its privacy, the property is exceptionally well connected. Millwood, Chappaqua, Ossining, Armonk, Pound Ridge, Katonah and Bedford are within easy reach, offering the restaurants, farmers markets, shops, galleries and outdoor experiences for which northern Westchester is well known. Celebrated regional destinations, including Blue Hill at Stone Barns and The Farmer & the Fish, are also nearby. Remarkably, the Croton-Harmon Metro-North station is approximately 3.3 miles and only ~8 minutes away, providing direct service to Grand Central Terminal in 46 minutes on express trains. The result is a rare combination: the privacy, acreage and natural surroundings of a true country property with New York City close at hand. 81 Glendale Road presents an opportunity to become steward of an extraordinary piece of the Teatown-area landscape, centered around a historic home that has occupied this setting since 1870, compelling as a full-time residence or as a weekend retreat within easy reach of Manhattan. Properties offering this combination of acreage, natural beauty, privacy and accessibility are seldom available in Westchester County. The property is being offered “as is” at an asking price substantially below what its underlying market value and opportunity represents, with the expectation that prospective purchasers will evaluate the property, its existing improvements and its considerable potential. The buyer will be the party that would make any changes found necessary. Additional information is available for discussion with qualified interested buyers. According to the parcel-history provided by the Town of New Castle for 81 Glendale Road, there are no open permits, and one Certificate of Occupancy, relating to the automobile shed. The residence dates to 1870 and predates the Town's current zoning framework. Prospective purchasers and their professional advisors should independently complete their own due diligence on current conditions and any contemplated future improvements.

81 Glendale Road, Ossining
$575,000
1 Beds ⋅ 2 Baths ⋅ 1049345 MLS
Welcome to The Brooke Club, an established residential community offering a wonderful combination of comfort, amenities, and convenience. Beautifully upgraded and thoughtfully maintained, this attached single-family home offers a flexible and distinctive floor plan complemented by a substantial list of meaningful improvements. On the main level, at the heart of the home, is a renovated chef's kitchen featuring quartz countertops, updated flooring, and a suite of Bosch appliances. Separate living and dining areas provide wonderful spaces for everyday living and entertaining as well as a fireplace. There is also a renovated full bathroom, separate laundry closet, pantry and direct access to the attached garage. The 2nd level offers an impressive primary suite providing a private retreat, complete with a beautifully renovated full bathroom and custom cedar-lined walk-in closet. The dramatic lofted mezzanine is multi-functional with cathedral ceilings adding architectural interest and valuable living space, plus a bonus room which can easily serve as a second bedroom. The home lives comfortably like a 2-bedroom, with excellent flexibility for guests, a home office or den. The private rear patio provides an inviting extension of the living space for outdoor dining, entertaining, or simply relaxing with park-like views and breathtaking seasonal sunsets. An attached garage plus 2 in driveway, offer the convenience of 3-car parking. Numerous upgrades and improvements have created a truly turn-key home designed to be enjoyed today and grown into for the long term, allowing its next owner to move in with confidence and make it their own for years to come. Residents of The Brooke Club enjoy updated community amenities, including an indoor pool complex and fitness center. Conveniently positioned near major parkway access and Metro-North, this location provides easy connections throughout Westchester, to New York City, and points north and south.

5-03 Brooke Club Drive, Ossining
$590,000
2 Beds ⋅ 3 Baths ⋅ 1039859 MLS
Love the NYC loft lifestyle, but not the NYC-sized floor plan—or price tag? Welcome to The Penthouse. Set within a reimagined historic 1820s schoolhouse, this dramatic tri-level penthouse loft delivers the attitude of a downtown loft with the space, light and breathing room Manhattan forgot to include. The result? Something seriously cool—and anything but ordinary. The Entertaining Level sets the tone with soaring volume, exposed brick elements, original wood beams, exposed copper piping, hardwood floors and distinctive low-set windows that help fill the space with natural light. An elevated kitchen with granite counters and stainless-steel appliances overlooks the expansive open-concept living and dining area, creating one incredible backdrop for entertaining or simply hanging out at home. A powder room completes the level. Then there’s The Loft—perched above and overlooking the entertaining space below. Skylights bring in even more natural light, while the open design gives you a completely different perspective on the architecture of The Penthouse. Home office, studio, lounge, reading retreat or creative escape—it’s the kind of flexible space that makes loft living so much fun. The Private Level changes gears completely. Two generously sized bedrooms each enjoy their own private en-suite bath. The oversized primary suite features a huge walk-in closet and spacious bath with double sinks and a jetted whirlpool tub. The second bedroom has its own beautifully refreshed en-suite bath with brand-new tile. In-unit laundry is conveniently tucked into this level as well. And here’s something you won’t see in the photos: some of the most impressive improvements in The Penthouse are hidden behind the finished walls. Extensive sound-control upgrades were incorporated into select walls and ceilings using additional framing and separation, ROCKWOOL mineral-wool insulation, spray foam and heavier 5/8-inch drywall. The primary-bedroom ceiling received its own extensive insulated assembly, all designed with acoustic comfort and reduced sound transmission in mind. Drenched in natural light? Absolutely. Drenched in noise? This renovation took that on from the inside out. And then there’s Ossining. Hudson River waterfront parks, marinas, downtown shops and cafes, the Old Croton Aqueduct Trail and Metro-North are all nearby—giving you the space and character of Hudson Valley living without giving up your connection to NYC. And when Manhattan calls? Metro-North express service can have you at Grand Central in under 50 minutes. Two assigned parking spaces and dedicated private storage round it all out—two more things Manhattan generally forgets to include. Historic character. Downtown attitude. Suburban breathing room. Three incredible levels. Serious sound-control improvements. This isn’t another suburban condo. This is The Penthouse—and that’s exactly the point.

88 Broadway Unit #PH4, Ossining
$349,900
1 Beds ⋅ 1 Baths ⋅ 1047960 MLS
Set among the mature landscaping and beautifully maintained grounds of Briarcliff Woods, this one-bedroom condo offers a peaceful setting for easy Hudson Valley living. The comfortable one-level layout features a spacious living room centered around a wood-burning fireplace, with sliding glass doors opening to a private balcony — a wonderful extension of the living space for relaxing outdoors. A dedicated dining area, separate kitchen, in-unit laundry, and excellent storage, including a generously sized walk-in closet, add everyday functionality, while the bedroom offers plenty of room to create a comfortable private retreat. One reserved parking space completes the package. Beyond the front door, Briarcliff Woods feels more like a landscaped retreat than a typical condo community, with a beautiful in-ground pool, tennis courts, clubhouse, an on-site superintendent, and well-cared-for grounds to enjoy throughout the seasons. Commuters will appreciate the convenient proximity to Croton-Harmon, with weekday jitney service from Briarcliff Woods to the station, express Metro-North service to Grand Central Terminal and Amtrak service to Penn Station, while the Ossining Metro-North station is also nearby. And when it’s time to stay closer to home, some of the best of the Hudson River Valley is just minutes away — waterfront parks, scenic walking and hiking trails, restaurants, shopping, seasonal events and the vibrant riverfront communities of Ossining and Croton-on-Hudson. It’s a wonderful combination of comfortable condo living, outdoor space, community amenities and easy access to everything that makes this corner of Westchester so appealing.

1 Briarcliff Drive S Unit #4, Ossining
$565,000
2 Beds ⋅ 3 Baths ⋅ 1025566 MLS
Make this spacious two-story, townhouse-style condominium your new home with beautiful Hudson River and Palisades views in Briarcliff Manor! This desirable Kemey's Cove condominium offers two bedrooms, two and a half baths, a versatile den, and views of the Hudson River from both levels. The main level opens to a living room and dining area, with a private terrace off the dining area overlooking the Hudson River, Palisades, and on clear days NYC skyline. A kitchen, powder room, and additional storage complete the first floor. Upstairs, the private bedrooms level features a generous primary bedroom with an updated en-suite bath and walk-in closet, a second bedroom, an updated full bath, and a large flexible den that can easily serve as a home office, guest room, or additional living space. A second balcony provides another opportunity to enjoy the Hudson River views, while in-unit laundry adds everyday convenience. Scarborough train station is .4 miles from Kemey's Cove along with shopping at the Arcadian Shopping center that includes Stop & Shop grocery store, CVS, Starbucks, delis and restaurants for incredible convenience. Only 1 of 6 units with sq footage of 1539! The home includes one assigned parking space, abundant guest parking, and dedicated basement storage. Kemeys Cove is a pet friendly community offering an array of amenities, including an outdoor pool, clubhouse, fitness center with showers and sauna, tennis and basketball courts, playground, dog parks, a community garden, grilling areas, and scenic outdoor spaces. Located conveniently close to the Scarborough Metro-North train station, shopping, dining, and that the surrounding Rivertowns have to offer. HOA fees include heat, hot water, landscaping, exterior maintenance, trash, and snow removal.

215 Kemeys Cove Unit #215, Briarcliff Manor
$1,149,000
1048659 MLS
Mixed-use investment opportunity in the heart of Ossining! This commercial property features a restaurant space plus two residential apartments, offering excellent income-producing potential for investors, owner-operators, or those looking to add value over time. The apartments and building require some updating and repairs, and the pricing reflects the current condition, making this a fantastic opportunity to renovate and maximize returns. Conveniently located near shops, restaurants, transportation, and all that Ossining has to offer, this property presents strong upside potential in a desirable and growing river town community. *SOME PHOTOS ARE VIRTUALLY STAGED*

185 Main Street, Ossining
$925,000
4 Beds ⋅ 3 Baths ⋅ 1047406 MLS
Exceptional value in a spectacular setting. Welcome to this beautifully renovated Dutch Colonial, an elegant blend of timeless architectural character, refined modern updates, and Hudson River views. Bathed in natural light and thoughtfully designed for both gracious living and entertaining, this exceptional home offers a rare combination of style, comfort, and an extraordinary setting. The beautifully renovated chef’s kitchen serves as the heart of the home, featuring crisp white cabinetry, quartz countertops, generous storage, and a seamless connection to the dining spaces. The inviting living room is anchored by a beautiful fireplace and enhanced by elegant French doors opening to a covered patio. Beyond, the expansive west-facing deck captures spectacular Hudson River vistas and provides an idyllic setting for outdoor entertaining, quiet relaxation, and magnificent sunsets. A private office or study, with sliding glass doors leading to the deck, offers an inspiring workspace surrounded by beautiful views. A beautifully renovated full bath completes the main level. Upstairs, the spacious primary suite is a serene retreat, featuring a generous walk-in dressing area and a luxurious, spa-inspired bath with a soaking tub, separate shower, and picturesque views. Three additional well-proportioned bedrooms and another beautifully updated full bath provide exceptional flexibility for family and guests. Additional amenities include a built-in speaker system throughout much of the home, an expansive yard, abundant parking, an oversized garage, and a full basement offering substantial storage and versatile possibilities for recreation, hobbies, etc... A rare opportunity at an attractive price, this beautifully renovated home pairs exceptional Hudson River views with sophisticated updates, generous living spaces, and an extraordinary setting.

27 Ryder Road, Ossining
$1,875,000
4 Beds ⋅ 4 Baths ⋅ 1036308 MLS
Welcome to 156 River Road, a fully renovated, turnkey Colonial in the "River Road" neighborhood of Briarcliff Manor with Breathtaking Hudson River Views. Set on a beautifully manicured acre in this quaint and highly desirable neighborhood, this fully renovated Colonial combines timeless character with modern comfort. From the moment you arrive, the home makes a striking first impression with exceptional curb appeal, mature landscaping, and an inviting setting. Inside, the thoughtfully renovated residence offers 4 bedrooms, 2 full baths, and 2 powder rooms, providing generous space for comfortable living and entertaining. The spectacular Hudson River views add an extraordinary backdrop to everyday life, while the expansive grounds offer privacy, beauty, and room to enjoy the outdoors. For commuters, the location is exceptional. The Scarborough Train Station is just a 1/2 mile away and those who appreciate the charm of Westchester's river communities, you can enjoy the ride along the Hudson River Line offering an approximately 40-minute ride directly to Grand Central Terminal. A rare opportunity to own a beautifully renovated Colonial in a picturesque riverfront setting, with convenience, character, and unforgettable views—all in the heart of charming Scarborough.

156 River Road, Briarcliff Manor
$895,000
2 Beds ⋅ 3 Baths ⋅ 1045247 MLS
There is something very special about Mystic Pointe, you feel it as soon as you enter through the gates. 33 Mystic Drive is a tri-level, end unit, Biscayne model home in the heart of Mystic, overlooking the Nature Trail. It offers a traditional layout with an eat-in kitchen, living and dining areas with sliding glass doors to one of the decks, a powder room, and access to the two-car garage all on the main level. The upper level has two generous bedrooms, two full baths, and a den/office room. The lower level is a wonderful all-around everything room, with sliding glass doors to the oversized deck, a generous walk-in storage closet, a laundry room, plus an additional storage room and utility room. One of the few homes with double decks for double entertaining! And Mystic Pointe has so much to offer: two pools, one adult and one for children; a clubhouse with a full kitchen and gym; a tennis/pickleball court; and a warm, welcoming community with weekly bridge nights, book club, and so much more. And since you don't have to mow the lawn, shovel the snow, or repair the exterior of your home, you will have plenty of time to enjoy it all.

33 Mystic Drive, Ossining
$610,000
3 Beds ⋅ 2 Baths ⋅ 1044920 MLS
GREAT INVESTMENT OPPORTUNITY — TREMENDOUS UPSIDE POTENTIAL! Calling all investors, contractors, and skilled DIYers! This property presents an excellent opportunity to build equity through renovation and improvements. With the right vision and workmanship, there is significant potential to transform this property into a beautiful home or profitable investment. Bring your tools, ideas, and contractor and take advantage of the opportunity to add substantial value. Whether you're looking to renovate and resell, create a rental property, or build sweat equity for yourself, this property offers plenty of possibilities. Priced with the work in mind and being sold as-is. Don't miss this chance to turn a diamond in the rough into a valuable investment! House is being sold "AS IS" please submit all written offers with proof of funds or pre-approval.

92 Linden Avenue, Ossining
$375,000
1 Beds ⋅ 2 Baths ⋅ 1044918 MLS
Discover an exceptional opportunity within the highly sought-after Liberty Knoll Town Home Community. Whether you are a first-time homebuyer seeking an entry into the Westchester market, a commuter desiring convenience with a walk to the Metro North Train Station or looking to downsize without compromising on quality and community, 3 Davids Lane presents a sophisticated, low-maintenance lifestyle. The main level boasts gleaming stainless-steel appliances in the kitchen updated powder room and built-in cabinetry with beverage center. The open layout extends to a private balcony which is perfect for al fresco dining or enjoying quiet moments. The upper level provides a tranquil retreat, featuring a generous sized bedroom with a large walk-in closet, a well-appointed updated full bathroom and a dedicated laundry area complete with washer and dryer. The home also has exceptional storage in the lower level. Residents enjoy access to an outdoor pool and well-equipped clubhouse. A children's playground and picnic facilities ensure endless outdoor enjoyment. The complex is proudly pet friendly. You're just moments away from the bustling Arcadian Shopping Center, home to essentials like Stop & Shop, CVS, various banks and popular eateries. 2 assigned parking spaces are directly in front of the home for easy access.

3 Davids Lane, Ossining
$699,500
4 Beds ⋅ 2 Baths ⋅ 1044513 MLS
Welcome to 9 Somerstown Road, nestled in a sought-after Ossining neighborhood with deep local history. This beautifully maintained home has had only two owners in its history, with the recent family here for over fifty years. The spacious layout offers four bedrooms and two full baths: three bedrooms upstairs, plus a fourth in the finished lower level, which doubles as a mother-daughter suite with a washer/dryer, its own living area with an added room for extra space, a functioning wood-burning stove set within a full brick wall, topped with a marble mantle, and just a kitchen away from full independence. Upstairs, beautiful cabinetry with a dishwasher anchors the updated kitchen, complemented by a formal dining room as well as a second dining space brightened by a built-in skylight with nearly floor-to-ceiling windows. Central air runs throughout the home, as well as hardwood floors. Generous closet space and abundant natural light create a bright, welcoming feel in every room. A full-length attic offers additional storage space. Recent updates include new gutters and a brand-new hot water tank. Outside a spacious backyard and patio are complemented by a gentle brook running along the edge of the property, very peaceful throughout the year. The driveway fits three cars comfortably. Location is a true highlight, with easy access to the Taconic State Parkway and Route 9A, plus an express Metro-North commute to Grand Central in about 45 minutes. Downtown Ossining's Main Street offers walkable restaurants, cafes and shops, along with Hudson River waterfront parks. The home falls within the Ossining School District. Within a short drive you can enjoy Teatown Lake Reservation, the New Croton Dam, Stone Barns Center for Food and Agriculture, and the Rockefeller State Park Preserve. After decades of cherished memories, 9 Somerstown Road awaits its new family.

9 Somerstown Road, Ossining
$799,999
3 Beds ⋅ 2 Baths ⋅ 1044028 MLS
Set back from the road and perched high on the hill, this move-in-ready 3-bedroom, 2-bath Raised Ranch offers privacy, scenic views, and a spacious 0.46-acre property with a large, level backyard. The bright and inviting main level features an open-concept living and dining area, an eat-in kitchen, and beautifully refinished hardwood floors throughout. Large windows provide abundant natural light, while the living space is enhanced by a newly added fireplace, creating a warm and welcoming focal point. The kitchen offers a great flow for everyday living and entertaining and includes a new refrigerator. Additional recent improvements include a new high-efficiency A/C heat pump system and a new hot water heater, providing added comfort and efficiency for the next owner. The primary bedroom offers private access to the full hall bathroom, with two additional bedrooms completing the main level. Downstairs, the large finished lower level provides flexible additional living space ideal for a family room, recreation room, home office, gym, or gaming/TV area. It also features a second full bathroom, laundry room, and direct access to the attached two-car garage. Enjoy indoor-outdoor living with dual access to the partially covered oversized deck overlooking the expansive backyard—offering plenty of room for a pool, gardens, play area, entertaining, or outdoor recreation. Conveniently located approximately five minutes from both the Ossining and Croton-Harmon Metro-North stations, providing express service to Manhattan, and close to restaurants, shopping, major thoroughfares, Teatown Lake Reservation, the Hudson River waterfront and marinas. Major updates, move-in-ready condition, refinished hardwood floors, a new fireplace, new A/C heat pump, new hot water heater, and new refrigerator make this home ready for its next owner to simply move in and enjoy.

6 Reeback Drive, Ossining
$350,000
1043333 MLS
Lot three is a beautiful 1.5 acre lot with level building site and part of a newly approved three-lot subdivision. Lots one and two are also available-all are approved for four bedrooms. Roughed in driveway leads up from the road to all three sites. Owner will also build to suit.

96 Somerstown Road, Ossining
$865,000
3 Beds ⋅ 2 Baths ⋅ 1033213 MLS
Modern, Lindal Cedar Home! If you are looking for a special, well-built home with privacy but also convenience, this is it! Open floor plan with 3 bedrooms, 2 baths, lots of windows, beamed ceilings, 2-car attached heated garage and rec room/office. Expansive flat yard has room for pool, if so desired. This 2.2-acre property is located just minutes to RR Station and under an hour commute to Manhattan. Also close to major highways and Teatown Preserve for nature hikes and wonderful summer camp for youngsters. Recent improvements are: new roof 2024, driveway, new Trex back deck, above ground oil tank October 2025, AC upgrade March 2025, exterior painted June 2024, interior painted July 2026, front walkway redone June 2026, remodeled bathrooms on the main floor and master bedroom suite. Also included are a fire sprinkler system, central vacuum, water filtration system. The house also has a transfer switch and wiring for a compatible portable generator for any power outages.

3 Little Lake Ridge, Ossining
$425,000
1 Beds ⋅ 2 Baths ⋅ 1041117 MLS
Welcome to LIBERTY KNOLL. . . This attractive 1 BEDROOM, 1.5 BATHS Tri-level townhouse is ready for its next owner! The Eat-in-Kitchen has ceramic tile flooring, a Frigidaire gas oven/range/microwave & dishwasher. The large Living Room leads to an inviting Deck that overlooks the rear yard. You'll find the Powder Room as well. The upper level showcases a generous size Bedroom that offers a walk-in closet and second closet. The clothes Washer/Dryer are located in the adjacent hall closet and next to the full Bathroom that offers a much appreciated double sink vanity. The Lower Level offers unfinished storage and potential living space at some point. Driveway parking along with an assigned space diagonally across the driveway is yours as well. Professionally maintained grounds, community pool, clubhouse and playground area amenities included. The Arcadian Shopping Center is across the way from the complex. And, the Scarborough Train Station is a stones throw (.6 miles) away providing timely access to GSC. Historic Sparta homes and Hudson River views are around the corner too.

17 Davids Lane, Ossining
$839,000
3 Beds ⋅ 3 Baths ⋅ 1038194 MLS
Welcome to 61 Ganung Drive, a spacious 3-bedroom, 3-bath home situated on .65 acres in the Town of Ossining. Offering privacy, versatility, and exceptional outdoor living, this property has so much to offer. Step inside to a welcoming sunken living room with skylights and a dining room featuring a wood-burning fireplace, filling the space with natural light while creating a warm and inviting atmosphere. The downstairs offers additional living space with its own private entrance, full bath, living room, office, and wood-burning stove, making it ideal for a variety of uses. A Certificate of Occupancy is currently in progress for a possible fourth bedroom on the lower level, offering even more flexibility and potential. Central air adds comfort throughout the warmer months. The backyard is where this home truly shines. Ryder Park borders the rear of the property, creating a wonderfully private setting with no homes directly behind you. The fenced-in yard is designed for entertaining and everyday enjoyment, featuring a heated above-ground pool, two decks, gazebo, basketball court, and plenty of space to relax and gatherings. A newer shed, approximately four years old, provides additional outdoor storage. A two-car garage, cobblestone-lined half-moon driveway, and ample parking add to the home’s convenience. Enjoy your own private retreat while remaining conveniently located just 2 miles from the train station. With its spacious property, incredible outdoor entertaining areas, privacy, flexible living space, and commuter-friendly location, 61 Ganung Drive is a home that truly needs to be experienced.

61 Ganung Drive, Ossining
$230,000
2 Beds ⋅ 1 Baths ⋅ 1036334 MLS
Welcome to this spacious and sun-filled two bedroom co-op in the beautiful Highland Terrace! Step into a welcoming foyer, currently arranged as a home office but easily adaptable as a dining area or flexible bonus space. The generously sized kitchen offers abundant cabinet storage and stainless-steel appliances. Just beyond, the bright and airy living room features large windows that fill the space with natural light. Down the hallway, you will find a spacious primary bedroom with ample closet space, along with a second bedroom that functions as a guest room, home office, or additional living space. The tiled bathroom is complete with a full bathtub. Outdoor enthusiasts will especially love the direct access to the historic Old Croton Aqueduct Trail from the property. This community is pet friendly, so your four-legged companion can enjoy the surroundings with you. Enjoy scenic and peaceful time in nature without having to get in the car. Return home and cool off in the beautiful swimming pool. Located less than two miles from the Ossining Metro-North station, this unit offers convenient access to transportation while keeping you close to the natural beauty and vibrant energy of the Hudson River area. Spacious, well located, and pet friendly, this co-op is an exciting opportunity you will not want to miss!

129-1 S Highland Avenue Unit #B3, Ossining
$550,000
1 Beds ⋅ 2 Baths ⋅ 1012405 MLS
Beautifully renovated one-bedroom townhouse with loft and attached garage in desirable Hudson Watch, tucked away on a cul-de-sac. This sun-filled home features hardwood floors, a stunning stone fireplace in the living room, and an open-concept floor plan perfect for modern living. The updated kitchen boasts white cabinetry, stainless steel appliances, quartz countertops, and recessed lighting, seamlessly flowing into the living and dining areas. Sliding doors lead to a private deck, ideal for relaxing or entertaining. Additional highlights include new central air conditioning and skylights (approximately 4 years old), bringing abundant natural light throughout. The spacious loft provides flexible additional living space, perfect for a home office, guest area, family room, or fitness space. Enjoy all that Hudson Watch has to offer, including a community pool and playground. Conveniently located close to the Croton-Harmon train station for an easy commute to NYC and just minutes from the Peekskill and Ossining waterfront with its restaurants, shops, and entertainment.

42 Hudson Watch Drive, Ossining
$202,500
1 Beds ⋅ 1 Baths ⋅ 1032192 MLS
Exciting 1-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. Walk to train, restaurants, stores, farmers' market, festivals, waterfront park, community recreation center, library, and more. Cats and dogs friendly (limit 2 per unit)! As an owner, you can obtain a parking permit for both the village and train station. This property is a part of "fair and affordable" housing. Per affordability restrictions under the HOME program, the potential new owner(s) income may not exceed 80% of the Westchester County area median income (As of August 1, 2025, those limits are: 1 person - $95,000, 2 persons - $108,600, 3 persons - $122,150, with maximum occupancy of the persons in the unit). Income limits are subject to change. MUST be occupied as a primary residence (no investors). The affordable sale price is $214,682 (your offer price may not exceed that amount). The Westchester County subsidy of $30,000 is available for this unit. It stays at the full amount for 20 years, then it terminates. ***AGENTS – MUST see confidential remarks and all MLS listing attachments for additional instructions***

135 Main Street Unit #201, Ossining
$229,222
2 Beds ⋅ 1 Baths ⋅ 1032252 MLS
Move right into this beautifully updated 2-bedroom unit featuring stylish finishes and modern upgrades throughout. New luxury waterproof vinyl flooring, new interior doors and hardware, and a renovated kitchen and bath create a fresh, contemporary feel. The updated kitchen boasts new cabinetry, butcher block countertops, a subway tile backsplash, and stainless steel appliances, including a built-in microwave and gas range. The open-concept living and dining area is filled with natural light and opens to a private balcony—perfect for relaxing and enjoying beautiful sunset views. The renovated bathroom features classic subway tile, a bathtub with a rainfall showerhead, and an updated vanity. Ceiling fans in both bedrooms and the living room provide added comfort, while the large picture window and generous closet space enhance the bright, spacious layout. Residents enjoy excellent amenities, including an outdoor pool, fitness center, on-site laundry, assigned parking, secure building entry with a security camera system, and an on-site superintendent for added convenience. Ideally located near parks, schools, the village, shopping, dining, and public transportation, this exceptionally well-maintained home offers comfort, style, and convenience in one desirable package. There are no audio recording devices inside this property.

119 S Highland Avenue Unit #5E, Ossining
$1,099,222
1034832 MLS
Exceptional opportunity to own a legal 6-unit multifamily property with stable, long-term tenants. All six units, 4-two bedroom units and 2-three bedroom units, are leased through September 2027, providing immediate, reliable rental income and a strong 7% cap rate. This well-maintained building is ideally situated in a convenient location directly across from Park School and within walking distance to shops, restaurants, the train station, and additional schools, making it an attractive location for tenants. The property's utility setup is designed to help minimize owner expenses. Tenants are responsible for their own gas and electric, while the landlord pays for water. The building features seven electric meters, six gas meters, and six individual water heaters. Street parking is readily available. Whether you're expanding your investment portfolio or seeking a turnkey income-producing property, this is a rare opportunity to acquire a well-maintained asset with dependable cash flow and long-term lease stability. There are no audio recording devices inside this property.

17 19 Edward Street, Ossining
$1,350,000
5 Beds ⋅ 4 Baths ⋅ 1034206 MLS
A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details, including wide-plank pine floors, original farm doors, hand-crafted millwork, and three fireplaces. Offering exceptional versatility, the estate is ideally suited as a private country retreat, equestrian property, or multi-generational residence. Set on over five picturesque acres, the grounds are a true sanctuary. Enjoy peaceful mornings on the multi-level stone patios surrounded by mature landscaping and native plantings, or gather with family and friends on the expansive covered front porch. Equestrian enthusiasts will appreciate the six-stall horse barn, multiple paddocks, and riding arena, while the heated 20' x 50' in-ground pool, complete with its own stone patio and custom-built pergola, provides the perfect setting for summer relaxation. Historic stone walls, crafted from stones found on the property, and impressive steps built from reclaimed West Point stone further showcase the estate's remarkable heritage. A gracious front porch welcomes you into the center hall. The main level features a living room with a wood-burning fireplace, an intimate reading room, formal dining room, eat-in kitchen with its own fireplace, powder room, family room, laundry room, and walk-in pantry. The second level features a spacious primary suite, three additional bedrooms, and a full bath highlighted by a timeless clawfoot tub. The approximately 1,200-square-foot finished walk-out lower level offers exceptional flexibility, featuring a spacious living and dining area with wide-plank flooring, a former tiled summer kitchen, two bedrooms with hardwood flooring—one with a fireplace—a storage/mechanical room, and multiple exterior entrances, creating an ideal space for extended family, guests, or a potential mother/daughter arrangement with the appropriate approvals. While this private estate feels like a world away, it is just minutes from the Village of Ossining, the scenic Hudson River waterfront, and an array of restaurants, shops, parks, hiking trails, and recreational activities that make the Hudson Valley such a sought-after destination. Located approximately 45 minutes from New York City, this extraordinary estate presents a rare opportunity to own an authentic piece of American history while enjoying the privacy, beauty, and lifestyle of a truly exceptional country property. Estates of this significance, craftsmanship, and versatility are exceedingly rare and simply cannot be replicated.

15 Inningwood Road, Ossining
$589,000
4 Beds ⋅ 2 Baths ⋅ 1031166 MLS
This 1800's Colonial offers a hidden backyard with in-ground pool/Formal and versatile living space is found throughout the home/A wide covered front porch, large living room and formal dining room, Eat-in-Kitchen along with full hall Bathroom compliment the main living level. There are two backyard access points from the Kitchen & Hallway too . . The Primary bedroom w/sitting room, is on the Upper level - along with three other Bedrooms & Hall Bathroom. . The finished Lower-level offers a Recreation Room w/built-in storage, Office Rm, Mud Rm and access into the unfinished Laundry Area. Gas hot/water heating system, Replacement windows, wide-plank floors, Stucco & Brick exterior siding, EV Charging station are amenities worth noting. The home had been utilized as a two-family years past. And while the zoning allows for it's current use, the floor-plan is flexible to suite your needs. Neighborhood shops, bus stop & Veterans Park are all close by and accessible via sidewalks. If commuting into NYC is needed, the Metro-North R. R. offers Express (45 mins) trips into GCS. Potential STAR savings of $1659/yr is not reflected in noted taxes.

41 Campwoods Road, Ossining
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