Westchester Homes with Ossining School district

Welcome to Westchester County, New York—a vibrant and diverse region that perfectly blends suburban charm with urban convenience. Nestled just north of New York City, Westchester is renowned for its picturesque landscapes, rich history, and thriving communities. With a wide array of recreational parks, cultural attractions, and top-notch dining options, it offers an exceptional quality of life for its residents.

One of the standout features of Westchester is its strong commitment to education, particularly within the Ossining School District. Families seeking a nurturing environment for their children will find Ossining's schools to be a cornerstone of the community. The district is dedicated to fostering academic excellence and personal growth, ensuring that students are well-prepared for their futures.

When it comes to real estate, the homes within the Ossining School District cater to a variety of lifestyles and budgets. Whether you’re looking for a charming historic home, a modern townhouse, or a spacious family residence, you’ll discover a multitude of options that reflect the area's unique character. Many properties boast stunning views of the Hudson River, lush gardens, and easy access to local amenities, making it an ideal place for families and professionals alike.

Living in Westchester means enjoying a perfect balance of tranquility and excitement. With convenient train access to Manhattan and a plethora of outdoor activities, including hiking and boating, you’ll find that this county truly has something for everyone. Come explore the welcoming neighborhoods of Westchester and discover your dream home in the Ossining School District today!

Newest Westchester Homes with Ossining School district

$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. 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

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.