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$124,900
1 Baths ⋅ 1031793 MLS
Welcome to The Parkview! This large studio at 117 South Highland Avenue lives like a one-bedroom, with a separate room comfortably fitting a full-size bed. The kitchen was fully renovated with stainless steel appliances, custom cabinetry, a large island, and quartz countertops. Oversized windows fill the space with natural light and frame wonderful Hudson River views year-round. The bathroom has also been remodeled, with a custom-built glass shower door, and hardwood floors run throughout. This unit comes with a guaranteed assigned parking spot. Building amenities include an in-ground pool, on-site fitness center, and a recently renovated lobby laundry room and main entrance. Located close to the train, shopping, and restaurants. Come see why Parkview residents love calling this home!

117 Highland Unit #4F, Ossining
$950,000
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
$425,000
2 Beds ⋅ 2 Baths ⋅ 1006040 MLS
This adorable Ossining Schools gem awaits new owners to provide personal touches and TLC. It boast a welcoming entry leading to living room with charming details including arched doorway, built in shelving, and fireplace. Bright airy dining/flex room, 1st floor half bath, eat in kitchen with breakfast nook/ dining area and sliding door to patio. Climb the stairs to enjoy two sunny bedrooms each with double closets, and large full skylit bath including laundry hook up. With so much to offer it’s hard to determine but the best detail of this home may be the expansive private yard ready to become the entertainment center for its new owners. Don't sleep on this amazingly convenient location…less than 1 mile to two train stations (Scarborough and Ossining), 35 min to NYC, walking distance to market, and Ossining village shops. Near to bus, schools and more! This might just be the best deal in town. Apx. $1500 STAR tax saving available. Make your appointment today.

42 Revolutionary Road, Ossining
$639,500
4 Beds ⋅ 2 Baths ⋅ 1021344 MLS
Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle. The private backyard offers a peaceful retreat with a patio ideal for outdoor dining, entertaining, or simply relaxing. Experience the best of Hudson Valley living with convenient access to the scenic Hudson River waterfront, parks, hiking and biking trails, local restaurants, shopping, and year-round community events. Whether you're commuting, exploring the outdoors, or enjoying the vibrant Rivertown lifestyle, this home offers the perfect balance of tranquility and convenience. Don't miss this opportunity to own a beautiful home in one of the Hudson Valley's most sought-after communities.

42 Pershing Avenue, Ossining
$160,000
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
$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
$1,750,000
9 Beds ⋅ 8 Baths ⋅ 1005133 MLS
Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining
$1,199,000
1002207 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
$2,995,000
5 Beds ⋅ 7 Baths ⋅ 986239 MLS
There are homes… and then there are places that feel quietly set apart from the world around them. Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally… like a secret meant only for those who understand what true luxury feels like. This is not just a home. This is a legacy estate. Set perfectly between the Hudson River and Sleepy Hollow Country Club, the location offers the rare balance today’s buyers search for privacy, proximity, and prestige. Minutes to Metro North, fine dining, boutique shopping, and everything that defines Westchester luxury living… yet once you arrive, the outside world seems to soften. There is a stillness here. You feel it walking the grounds, where mature trees frame rolling lawns and sunlight filters through in that unmistakable golden way. There is a rhythm to the property… the kind that invites long mornings on the porch, quiet afternoons by the pool, and evenings that stretch just a little longer than planned. And somewhere within it all… life quietly thrives. Bees drift from bloom to bloom, tending to the landscape in a way that feels both timeless and grounding… a subtle reminder that this estate is not just maintained, it is alive. Inside, the home unfolds with a level of craftsmanship and scale rarely seen today. Five ensuite bedrooms offer both privacy and comfort, anchored by a truly exceptional primary suite with its own fireplace, spa like bath, expansive dressing room, and a private sleeping porch… a nod to a more romantic era of living, where fresh air and slow mornings were part of everyday life. The kitchen is designed not just for cooking, but for gathering… a chef’s workspace complemented by a generous butler’s pantry, ideal for seamless entertaining. It flows effortlessly into a formal dining room that feels pulled from the pages of a design magazine, where hand printed Zuber wallpaper and a fireplace create a setting that is both refined and deeply inviting. Every room tells a story. A wood paneled office with its own fireplace opens to the front porch, offering a work from home experience that feels anything but ordinary. The living room, wrapped in double walls of French doors, blurs the line between indoors and out, filling the space with natural light throughout the day. Nearby, the sunroom becomes its own retreat… a place to pause, unwind, and simply take in the beauty of the property. Step outside, and the estate continues to reveal itself. A gunite pool set within manicured grounds. Multiple porches designed for every mood and moment. A historic Lord and Burnham greenhouse… a rare and remarkable feature that speaks to the property’s heritage. And a four plus car garage with a private apartment above, offering flexibility for guests, extended stays, or staff. This is Westchester luxury real estate at its finest, where historic architecture meets modern lifestyle, where privacy meets convenience, and where every detail has been thoughtfully considered. Because the truth is… You can always renovate a home. But you cannot recreate land like this. You cannot replicate this setting. And you cannot manufacture the feeling this property gives you the moment you arrive. 36 Revolutionary Road is not just being listed. It is being offered.

36 Revolutionary Road, Briarcliff Manor
$699,000
3 Beds ⋅ 2 Baths ⋅ 985026 MLS
This charming 3-bedroom, 2-bath home in the Village of Ossining, is a legal 2 family and is currently being used as a single family. Features include a small backyard, a detached 1-car garage, and a convenient location close to shops, transportation, and amenities.

32 Terrace Avenue, Ossining
$1,095,000
5 Beds ⋅ 3 Baths ⋅ 977120 MLS
This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed Main house layout features an expansive family room with wood-burning fireplace perfect for everyday gathering, first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room. The main floor features walls of windows showcasing the sylvan setting and a formal dining room that flows seamlessly into a spacious living room. The eat-in kitchen, complete with a charming breakfast nook, is easily accessible and well-suited for casual dining. This level also includes three additional bedrooms, including one with a private en-suite bath, two bedrooms share a well-appointed hall bath, and a laundry room. The Detached 3 car garage with guest quarters and guest patio with built-in wood grill and woodland views add to this retreat.

27 Allapartus Circle, Ossining
$825,000
3 Beds ⋅ 3 Baths ⋅ 888472 MLS
Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with possibility for in-law situation. The handsome house has cedar siding and lots of windows. Ground level has a 3 season porch, 2 rooms with kitchen, plus bath, utility room, laundry and potting room. From outside the beautiful stone steps lead to a large covered porch with entrance to a large room with stone fireplace and wood burning stove insert; there is also a large closet. Massive fireplace and center island are the focal points of the kitchen with terracotta tiling and walls of windows and door to a deck. 20'x24' Living room has a third fireplace and French doors to a slate patio and door to a second potting room that leads to a woodland path. Circular staircase leads to the private quarters; primary bedroom with spa bath including sauna and whirlpool tub. Second bedroom, hall bath and huge bonus room with fireplace and reading room/office/nursery. Please wear suitable shoes for walking the property. Amenities worth mentioning; cast iron baseboard radiators, hardwood floors, high ceilings and new oil burner. 7 mins drive to Croton Harmon RR Sta. Cash Purchase Only. Proof of Funds required before appt can be booked,

81 Glendale Road, 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.