Refine Search
Sort by
81 Glendale Road, Ossining
$800,000
3 Beds ⋅ 3 Baths ⋅ 1048991 MLS
A rare convergence of land, privacy and proximity to NYC, 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 heated porch, media room, pantry, clothes, washer and dryer, food-storage and preparation areas, lavatory, "slop" sink, and the home's mechanical systems. The land makes 81 Glendale Rd. truly exceptional. The properties 14.36 private acres adjoins the ~1,000 acres and ~15 miles of hiking trails and nature preserve of Teatown Lake Reservation, and the protected, un-developable watershed property of the Ossining water supply. Here, mornings can begin beside the brook, the woodland paths and the trails of Teatown without getting into a car. Approximately 4 acres and the house are enclosed by a high-quality black chainlink 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. The buyer will be the party that would make any improvements they find 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. As is customary and ordinary in the Westchester residential property market, prospective purchasers and their professional advisors will independently complete their own due diligence, and complete a home inspection prior to requesting a contract.

81 Glendale Road, Ossining

5-03 Brooke Club Drive, 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

88 Broadway Unit #PH4, 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

1 Briarcliff Drive S Unit #4, Ossining
$344,900
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

33 Mystic Drive, Ossining
$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

9 Somerstown Road, 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. I am told that road work in the area will be finished by the end of October 2026, and they are planning to bring in gas service to the area in the coming months. (Please verify independently). 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

6 Reeback Drive, 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

17 Davids Lane, 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

129-1 S Highland Avenue Unit #B3, 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

135 Main Street Unit #201, Ossining
$201,999
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

119 S Highland Avenue Unit #5E, 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

15 Inningwood Road, Ossining
$1,250,000
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

41 Campwoods 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

58 Quakerbridge Road, Ossining
$749,000
3 Beds ⋅ 3 Baths ⋅ 1023270 MLS
First Time on the Market in Over 35 Years! Welcome to 58 Quakerbridge Road, a spacious 3-bedroom, 2.5-bath home in one of Ossining's most convenient locations. Enjoy an easy commute with the nearby Metro-North station offering direct service to Grand Central, while being just minutes from Teatown Lake Reservation, the Old Croton Aqueduct Trail, parks, shopping, dining, and schools. Inside, you'll find a functional layout with generous living space, three bedrooms, study w/ half bath and plenty of room to make it your own. Outside, enjoy a large front yard, an oversized driveway with ample parking, a spacious deck, and an attached two-car garage. Major updates include a new HVAC system and new water heater. Owned by the same family since 1990 and offered for sale for the first time in over 35 years, this home combines space, location, and value in a rare opportunity. Taxes do not reflect STAR.

58 Quakerbridge Road, Ossining

97 Morningside Drive, Ossining
$799,999
4 Beds ⋅ 2 Baths ⋅ 1033351 MLS
Offered for the first time in over 60 years and a rare opportunity to own a piece of history! This historic mid-nineteenth century farmhouse sits on 1.3 private acres bordering the protected land of Ryder Park, ensuring permanent privacy and an undisturbed natural setting. This four bedroom, one and a half bathroom home has charm and character everywhere you look. Exposed beams, wood flooring, original wanescoting, barnwood, stonework, two fireplaces and more. The front porch is used as a three season room and is the perfect place to watch the birds and drink your morning coffee. Oversized two car garage can easily an double as a work shop. Recent upgrades in clue new roof (2021), Central AC on first floor (2023) and above ground oil tank (2025). All of this set on 1.3 acres with 3/4 acre zoning, offering future potential to split and create an additional building lot (buyer to verify with the town). The property features mature trees, historic stone walls and rolling hills surrounded by natural woodlands. Walk out your back door and onto the Ryder Park Walking Trail enjoy all of the features Ryder Park has to offer including baseball fields, tennis courts, summer camp, pavilion and more! Do not miss this unique opportunity to own a piece of history!

97 Morningside Drive, Ossining

34 Briarbrook Drive, Briarcliff Manor
$725,000
2 Beds ⋅ 3 Baths ⋅ 1030619 MLS
Welcome to effortless living in the highly desirable Scarborough Glen community. Beautifully updated and impeccably maintained, this move-in ready home offers the perfect combination of spacious living and a private natural setting. Step inside to discover hardwood floors throughout the main living areas, complemented by brand new carpeting in the bedrooms, loft, and finished lower level. The kitchen has been refreshed with brand new appliances, while a brand new roof and brand new skylights with remote-controlled shades provide both peace of mind and an abundance of natural light. The impressive primary suite is a true retreat, featuring soaring cathedral ceilings, a spacious walk-in closet, and an expansive loft that is perfect for a home office, reading nook, fitness area, or additional living space. The finished lower level offers exceptional flexibility for a recreation room, media room, home gym, or guest space. Sliding glass doors provide seamless access to a private stone patio, creating the perfect indoor-outdoor living space for relaxing, entertaining, or enjoying your morning coffee. Perfectly positioned within the community, the home enjoys one of Scarborough Glen's most desirable settings. Visitor parking is conveniently located directly across from the home, making it easy for family and friends to visit. Rather than looking into neighboring homes, your front view overlooks a tranquil brook and lush greenery, providing a rare sense of privacy and a peaceful natural backdrop. With extensive updates, a versatile floor plan, and a premium location, this exceptional home offers the comfort, convenience, and serene lifestyle that today's buyers have been searching for. Enjoy the ease of maintenance-free living while being just minutes from the village, shopping, restaurants, parks, and Metro-North for an easy commute to New York City.

34 Briarbrook Drive, Briarcliff Manor

61 Underhill Road, Ossining
$849,000
4 Beds ⋅ 3 Baths ⋅ 1023457 MLS
Welcome to 61 Underhill! Expanded in approximately 2008, this spacious home offers far more space than first meets the eye. The substantial rear addition nearly doubled the size of the home, creating a layout that blends the character of the original residence with a newer, expansive living area featuring generous room sizes and an open feel. While the original portion of the home is ready for updating, the addition provides comfortable living today, offering buyers the opportunity to modernize over time while building equity. The thoughtfully designed layout creates two distinct living areas within the home, offering exceptional flexibility for extended family, long-term guests or those simply looking for additional space and privacy. The full unfinished basement offers excellent ceiling height and abundant square footage, presenting outstanding potential for future finished living space, recreation, storage or a workshop. Outside, the terraced backyard features multiple levels, a storage shed and a charming playhouse, offering plenty of outdoor space to restore and personalize. Conveniently located near shopping, restaurants, parks and major commuting routes, this is an excellent opportunity for buyers with vision to unlock the full potential of a home with exceptional space and versatility.

61 Underhill Road, Ossining

20 Waller Avenue, Ossining
$899,000
4 Beds ⋅ 3 Baths ⋅ 1027151 MLS
Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless character with modern updates. The main level offers an updated kitchen with granite countertops, stainless steel appliances, a gas Viking stove, laundry, and access to a private backyard. The oversized primary bedroom features elegant arch and tray ceilings. The walk out basement includes a finished recreation room and plenty of storage. The second floor apartment features an updated kitchen, three bedrooms, two full bathrooms, and access to a finished attic with a wainscoted ceiling, providing excellent income potential or additional living space. Conveniently located just 0.5 miles from the Ossining train station and close to downtown restaurants, shops, the farmers market, parks, schools, and major highways. A fantastic opportunity for homeowners and investors alike!

20 Waller Avenue, Ossining

129-3 S Highland Avenue Unit #A2, Ossining
$150,000
1 Beds ⋅ 1 Baths ⋅ 1024369 MLS
Welcome to this beautifully maintained, pet-friendly 1-bedroom co-op in desirable Ossining, offering the perfect blend of comfort, convenience, and a rare private patio. A spacious foyer welcomes you inside and leads to a thoughtfully designed layout featuring an updated bathroom, a functional kitchen with ample cabinet space, and a generously sized bedroom. The expansive living and dining area provides an ideal setting for both everyday living and entertaining, with a private back door opening directly to your patio, creating a seamless indoor-outdoor lifestyle. Nestled within a well-maintained garden-style community, residents enjoy exceptional amenities including an in-ground swimming pool, basketball court, scenic walking trails, beautifully landscaped grounds, plentiful guest parking, and an assigned parking space conveniently located just steps from the building. Ideally situated just minutes from Metro-North, the Taconic State Parkway, shopping, dining, parks, and the vibrant Ossining waterfront, this home offers the perfect balance of tranquility and accessibility. Whether you're purchasing your first home, downsizing, or searching for a commuter-friendly residence with sought-after outdoor space, this move-in-ready opportunity is one you won't want to miss.

129-3 S Highland Avenue Unit #A2, Ossining

39 Secor Road, Ossining
$725,000
3 Beds ⋅ 2 Baths ⋅ 1021208 MLS
Welcome to 39 Secor Road. Being sold strictly as-is and as a buy one get one with 37 Secor Road ( offered @ $85K CASH ONLY). You cannot pass on this deal. Get this rare investment opportunity for this two bedroom over 1-bedroom multi- family home that offers street parking or with the purchase of municipal parking pass, tenants can park right behind the building in the municipal lot. This home boasts unobstructed windows of the Hudson River views from both units and the windows in the basement. Priced to be sold as a package with the adjoining Single-family home at 37 Secor road. These two homes are on one deed with two separate tax lots, but they are adjoined with ONE furnace and one oil tank. The single-family home is being sold for cash only while a buyer can obtain financing for the two-bedroom multi-family home. This is an amazing opportunity for a first time or veteran investor. Both units are being sold strictly AS IS but boast two new rooves. The unfinished basement extends the length of both homes. Street parking for the multi-family home, but there is a municipal lot located behind the homes. They are a short distance to the Ossining training station and down-town Ossining alike. Both homes have access to basements. Unfinished basements have windows and exterior access if a buyer would like

39 Secor Road, Ossining

28 Hamilton Avenue, Ossining
$1,350,000
6 Beds ⋅ 4 Baths ⋅ 1013182 MLS
Built in 1870 and lovingly restored by its current owners, this Queen Anne Victorian at 28 Hamilton Avenue sits in the heart of Historic Ossining. Both yards are planted with apple, cherry, Asian pear, pawpaw, hazelnut, raspberry, blueberry, and strawberry, along with a working vegetable garden — a rare thing to find alongside a home of this character. Approach through a deep front yard bursting with pollinators, wisteria draping the covered porches. The house keeps its greatest surprise for later — the breathtaking views of the Hudson River and the Palisades are revealed as you move deeper inside, unfolding room by room. Cross the double-door vestibule into a gracious foyer with soaring double-height ceilings, rich wainscoting, inlaid parquet floors, and a staircase anchored by an elaborately turned newel post — all presided over by the first of four hand-carved ceramic tile fireplaces. The main level was built for both formal entertaining and comfortable everyday living. Two spacious living rooms, each with its own ceramic tile fireplace, open into a sun-drenched den with a spectacular coffered wood ceiling, three walls of windows, and doors facing each other — one to the front porch, one to the rear. The formal dining room, with its own fireplace and a sweeping Hudson River School-inspired mural, connects to a well-appointed kitchen with an original farmhouse sink, a corner butler's pantry with intact original cabinetry, and discreet service stairs tucked behind. Throughout, the turret windows with their curved glass are a signature of the era, and of this street. Step out the back and the Hudson opens before you — wide, silver, and immediate — framed by a terraced garden and a covered rear porch made for long evenings. This is the river that stirred a generation of painters to invent an American landscape tradition, that carried commerce and dreams in equal measure, that poets and wanderers have stood before and felt genuinely small. It is your backyard now. Upstairs, four bedrooms include a primary suite of nearly 20 by 18 feet, wrapped in a turret bay, with a screened balcony, ensuite bath, and the kind of proportions that are simply not built anymore. The current owners have thoughtfully upgraded the electrical and insulation throughout the attic, creating a series of carefully considered spaces — a serene room for yoga, meditation, or quiet work, a jewel-like sitting room with leaded diamond windows, a full bath, and at the crown of it all, a lookout tower lined with curved bookshelves and wide-plank floors, from which this house has contemplated the mighty Hudson for 155 years. A ten minute walk brings you to Metro North and 45 minutes later, Grand Central. Historic downtown Ossining — its shops, restaurants, and the extraordinary Sing Sing Museum — is at your doorstep. A rare opportunity to live inside a piece of history, on the banks of one of the great rivers of the world.

28 Hamilton Avenue, Ossining

219 Spring Street, Ossining
$639,222
3 Beds ⋅ 1 Baths ⋅ 1011590 MLS
Welcome to this beautifully maintained vintage Colonial, ideally situated on a desirable corner lot in the heart of the village. Combining classic character with thoughtful updates, this spacious home offers comfortable living both inside and out. The first floor features hardwood floors, high ceilings, a bright eat-in kitchen, dining room, an inviting living room, and laundry off the kitchen. Upstairs, you'll find 3 generously sized bedrooms and a hall bath. A walk-up attic and expansive basement provide abundant storage and future possibilities. Outdoor living is equally impressive, with a fully fenced yard, expansive stone patio perfect for entertaining, front and rear porches, and an above-ground oil tank. A detached two-car garage and driveway offer off-street parking for up to four vehicles. Conveniently located within walking distance of schools, parks, village amenities, shops, restaurants, and public transportation, this home offers the perfect blend of historic charm, modern convenience, and exceptional outdoor space. Don’t miss this opportunity to enjoy village living at its best! There are no audio recording devices inside this property.

219 Spring Street, Ossining

54 Allapartus Road, Ossining
$1,079,000
4 Beds ⋅ 3 Baths ⋅ 1002953 MLS
Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping, dining, and everyday essentials. The Croton-Harmon Train Station is even closer, while convenient access to Route 9A and the Taconic State Parkway makes commuting throughout Westchester and beyond easily accessible. Thoughtfully redesigned and extensively reconstructed under architectural plans, the home features spacious light-filled living areas, a dramatic vaulted great room ceiling, and an architect-designed wall of glass that brings natural light and the surrounding landscape into the heart of the home. Multiple Marvin door systems were designed to create seamless indoor-outdoor flow and future deck integration. The home was designed with a similar footprint across both levels, resulting in an exceptionally large lower level that dramatically expands the usable space of the home and offers substantial flexibility for workshop space, storage, recreation, future finishing, home business use, gym space, or other expanded uses rarely found in the area. The kitchen and main living spaces were rebuilt from the foundation up during the 2008 reconstruction and create a true chef’s kitchen experience, featuring radiant heated flooring beneath large-format tile, custom-built cabinetry, an oversized 5’ x 7’ island, a large built-in KitchenAid refrigerator, KitchenAid dishwasher, and a Thermador professional oven. The kitchen was intentionally designed with exceptional spacing and flow for cooking, entertaining, and everyday living, creating an openness rarely found in homes of this style. A large high-ceiling lower level was also added during the reconstruction, offering excellent flexibility as a workshop, workspace, storage area, gym, hobby space, or potential future finished area. The lower level also includes a second laundry setup with an additional washer and dryer. The spacious primary suite addition includes a large ensuite bath with jacuzzi tub, oversized shower, and private water closet. A second primary-style bedroom offers its own ensuite bathroom with shower and direct access to the backyard, creating excellent flexibility for guests, extended family, multigenerational living, or private workspace use. A second primary bathroom was also fully renovated in 2025. The rare 4-car tandem garage configuration, expansive multi-driveway parking setup with space for approximately 20 vehicles, and oversized lower level create exceptional flexibility for car enthusiasts, collectors, hobbyists, workshop use, home business needs, or anyone seeking substantial additional storage and utility space rarely found in northern Westchester. Additional highlights include a central vacuum system with multiple in-wall outlets and kitchen kick-plate crumb sweeper, fireplace-ready buildout with propane option, generator-ready electrical infrastructure, alarm system, updated water systems, and numerous structural and mechanical improvements completed over the years. A unique opportunity to enjoy peaceful acreage, architectural character, exceptional utility space, commuter convenience, and a level of flexibility rarely found in one property.

54 Allapartus Road, Ossining

227 Cedar Lane, Ossining
$799,000
2 Beds ⋅ 2 Baths ⋅ 996003 MLS
A Rare 200-Year-Old Log Cabin Sanctuary with Subdivision/Expansion Potential! Step back in time without sacrificing an ounce of modern comfort in this enchanting, hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history, contemporary ease, and incredible future value with a potential buildable lot included. The interior showcases exceptional craftsmanship, featuring original wide-plank wood floors, a majestic stone fireplace, and a genuine Dutch door. The versatile layout includes two bedrooms plus an alcove and 1.5 baths highlighted by a hand-painted sink. A large, vintage-inspired country kitchen serves as the heart of the home, boasting a herringbone-patterned original brick floor, 1940s decor, and modern appliances including a dishwasher and washer-dryer. The exterior is a true nature lover's sanctuary, featuring a cedar shingle roof, a classic porch with Adirondack furniture, and a sophisticated bluestone slate patio. The expansive grounds are home to a picturesque pond and babbling brook that attract magnificent wildlife. While providing total seclusion, this property is remarkably accessible, located just five minutes from the Croton-on-Hudson train station and local supermarkets. Enjoy being minutes away from Hudson River dining, boating, and Teatown Lake Reservation, with an easy commute of less than one hour to New York City and a 50-minute drive to Thunder Ridge skiing. It is located in a Historic area near Old Croton Aqueduct and Senesqua Park. The community offers 17 parks, including a Westchester River Walk, hiking trails, views of the Hudson, and the Haverstraw-Ossining Ferry. Amenities include an indoor town pool, a Farmers Market, and local dining options. Community events include the Hudson River Music Festival and Teatown Annual Hudson River EagleFest.

227 Cedar Lane, Ossining

127-1 South Highland Avenue Unit #B3, Ossining
$230,000
2 Beds ⋅ 1 Baths ⋅ 987888 MLS
Spacious two bedroom light & airy updated END-unit in heart of town offers easy affordable living in a quiet, pet-friendly community. Common charges include taxes, heat, water, buildings/grounds and pool maintenance, insurance & parking. This low-maintenance one-level unit is located on the first floor. Features include an updated Kitchen with quartz countertops, white cabinetry, natural gas cooking stove; high-hat lighting and wiring for Verizon Fios/Spectrum/Cablevision. Multiple ceiling fans and windows in every room; multiple a/c units included. Corner location offers more windows and privacy than most and lets in more natural sunlight. Lovely landscaping, basketball/sports court, outdoor in-ground pool & common-use patios with BBQ set ups, along with well-maintained outdoor seating areas. Ossining's award-winning Schools are known for having the most Intel Science winners year after year along with great Robotics & STEM Programs. This is one of a very limited number of co-op complexes that is pet friendly (2 pet limit). Walk to the Arcadian Shopping Center's stores, banks and restaurants (i.e., McDonald's, Verizon, Starbucks, Capri Pizza, Valley Bank, Stop & Shop Supermarket +) all for your dining & shopping pleasure. If you work in the City, or want to head up north to Bear Mountain and beyond, Highland Terrace Co-ops has easy access to all main thoroughfares. You're only minutes from Metro-North's Hudson train line with less than an hour's commute to Manhattan. Nelson Park is just a block away. Scenic Aqueduct walking trails are nearby; and only seconds from riverfront options to fish or sail on the Hudson! Who needs anything more? Why not say "Welcome Home" to Unit #B3 today.

127-1 South Highland Avenue Unit #B3, Ossining

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.