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$599,000
3 Beds ⋅ 1 Baths ⋅ 1025170 MLS
This lovingly maintained, one level home offers the ideal location- so convenient to all and a beautiful level backyard....You will be impressed with the very private outdoor space ready for entertaining and warm weather enjoyment -a country neighborhood feel yet only 10 minutes to Metro North station- a 50 min express commute to Grand Central and 2-3 miles to Rt 9/ Taconic Parkway....A warm and welcoming ranch in the wonderful Rivertown of Ossining where comfort, charm, convenience and community come together....This cozy retreat offers spacious living and a dining area that seamlessly connects to the kitchen creating the perfect setting for everyday living and entertaining. Conveniently located first floor bedrooms provide added accessibility and ease. Step outside to a welcoming patio perfect for outdoor living, gardening or simply enjoying your own private oasis. Known for its rich history, vibrant downtown, beautiful river views and breathtaking sunsets, Ossining offers the charm of riverfront living with waterfront parks, scenic walking neighborhoods and vibrant dining and shopping. Nature lovers will appreciate nearby hiking trails, Teatown Nature Preserve, Veterans Park and the Ossining Farmers Market. If you you are looking for a move in condition home, tranquility, the ideal commuter location or a lifestyle that comes with Rivertown living, this home with gas heat/ cooking, town water & sewer could be just what you are looking for!

23 Gates Avenue, Ossining
$525,000
3 Beds ⋅ 2 Baths ⋅ 1024303 MLS
A true brick home in the Village of Ossining, offering beautiful sunset and river views, tremendous character, low taxes, and a location that’s hard to beat — just minutes to the train station, riverfront dining, and Teatown Nature Preserve. This 3-bedroom, 2-bath home features 1,240 sq ft across the main floors, plus a 340 sq ft walk-out lower level and a walk-up attic ideal for an artist loft, studio, or storage. Inside, original exposed beam ceilings and a striking stone-and-brick fireplace with a Jotul wood stove sets an unmistakable tone. Outside, enjoy a rare three-tiered outdoor living setup: a brick patio off the lower level, a large deck off the kitchen, and an upper balcony with year-round views of the Mario Cuomo Bridge and Croton Point Park — expanding to a full 180-degree Hudson River panorama in winter. The lower level includes a convenient kitchenette for guests or extended living. Classic brick architecture, arched window lintels, mature trees, a large rear yard, and a storage shed complete this home with genuine architectural soul.

33 Cedar Lane, Ossining
$507,000
2 Beds ⋅ 1 Baths ⋅ 1014067 MLS
Charming Cape Cod in Indian Village – Move-In Ready! A rare opportunity to own a home with a backyard sanctuary. Tucked away in the desirable Indian Village neighborhood, this recently remodeled and tastefully updated cape cod is turnkey and ready for its next owner. Offering the perfect blend of charm, comfort, and potential, this home presents the perfect starter home. An oversized deck overlooks your own private garden oasis perfect for entertaining, gardening, or simply relaxing in a peaceful setting surrounded by lush greenery, blooming flowers, and mature vegetation. Additional features include a full walkout basement offering ample storage and future expansion possibilities. With its thoughtful updates, inviting outdoor spaces, and endless potential, this home is ready to be enjoyed from day one.

53 Pleasantville Road, Ossining
$575,000
2 Beds ⋅ 3 Baths ⋅ 1010405 MLS
Tucked within the beautifully maintained Woods in Westchester, this townhome offers a wonderful opportunity to create a home that reflects your own style and vision. Privately situated amid mature landscaping, the setting is peaceful and inviting, with a sunny patio and private balcony providing comfortable outdoor spaces to relax and enjoy the surroundings. The interior features a bright eat-in kitchen, spacious living area, a versatile loft ideal for a home office or den, central air, second-floor laundry, and an attached garage. Residents enjoy a sparkling pool, tennis court, walking paths, a scenic pond, and professionally maintained grounds, creating an easy, low-maintenance lifestyle. The Woods is ideally located just minutes from the Croton-Harmon Metro-North station, major parkways, shopping, dining, parks, and the Hudson River waterfront. Situated with convenient access to the many conveniences and amenities of Croton-on-Hudson, Ossining, and the surrounding areas of Briarcliff Manor. Whether you're looking for low-maintenance living, outdoor amenities, or an easy Westchester lifestyle, 122 Woods Brooke Circle is the wonderful place for you!

122 Woods Brooke Circle, Ossining
$500,000
3 Beds ⋅ 3 Baths ⋅ 1005194 MLS
Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments. There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage was probably originally a stable. The water main and sewer lines were replaced in 2025

237 Spring Street, Ossining
$599,000
3 Beds ⋅ 1 Baths ⋅ 1010005 MLS
A beautifully cared-for 1929 Colonial with the sweetest feel, 16 Sherwood blends timeless character, warmth, and everyday ease. This darling home offers original charm, with beautiful wood floors, restored original interior doors with glass knobs, and thoughtful details throughout. A welcoming vestibule opens to a spacious living room anchored by a wood-burning fireplace with built-ins on either side. A French door leads to a wonderful three-season enclosed porch, extending the living space and creating the perfect spot for morning coffee, reading, or relaxed evenings. The formal dining room offers a classic setting for gathering, while the vintage charming kitchen has been meticulously maintained and includes a dishwasher, gas cooking, and easy access to the composite deck and lower level. Upstairs are three comfortable bedrooms and a nicely sized full bath. The lower level offers laundry, storage, and flexible space. Additional highlights include ductless AC, gas heat, a private driveway, detached two-car garage, low-maintenance deck, a welcoming front walkway, and beautifully established plantings that frame both the front and rear of the property. Set on a level property in one of Ossining’s lovely neighborhoods, close to parks, schools, shops, restaurants, the Hudson River, village conveniences, and under two miles to Metro-North. Classic, comfortable, and truly special.

16 Sherwood Avenue, Ossining
$540,000
3 Beds ⋅ 2 Baths ⋅ 1001582 MLS
Full of warmth, character, and timeless appeal, this charming colonial home offers a wonderful blend of classic details, comfortable living spaces, and an exceptional location in the heart of Ossining. Set on a beautiful property with a spacious yard, this special home provides the perfect backdrop for gardening, entertaining, outdoor play, or simply enjoying a quiet evening outdoors. Inside, you'll find inviting spaces filled with character, including a welcoming living room, formal dining room, bonus room ideal for a home office, den, or playroom, and a large eat-in kitchen that serves as the heart of the home. A convenient main-level laundry area, three bedrooms, one-and-a-half baths, and a full unfinished basement complete the home's functional and flexible layout. The outdoor space is truly a standout feature. The expansive yard offers endless possibilities for recreation, gardening, gatherings with family and friends, or creating your own private retreat. Whether hosting summer barbecues, enjoying morning coffee on the porch, or watching the seasons change, this property offers a lifestyle that is increasingly hard to find. Ideally located just minutes from downtown Ossining, you'll enjoy easy access to local restaurants, cafes, shops, parks, and the popular Ossining Farmers Market. Nature lovers will appreciate nearby waterfront parks, scenic trails, and recreation opportunities along the Hudson River. Commuters will love the convenience of the Ossining Metro-North station, offering direct access to New York City while allowing you to enjoy all the charm and community of Rivertown living. Rich in character, filled with potential, and situated in one of Westchester's most vibrant riverfront communities, 33 Maurice Avenue is a place you'll be proud to call home.

33 Maurice Avenue, Ossining
$599,000
3 Beds ⋅ 2 Baths ⋅ 1004276 MLS
Charming Cape Cod on a .23-acre lot in desirable Ossining — comfortable now with plenty of room to personalize. This 3-bedroom, 1.5-bath home offers classic curb appeal, a bright living area, and a flexible layout that adapts to your needs. The spacious yard provides room for gardening, play, or outdoor entertaining. Enjoy easy access to local shops, schools, parks, and commuter routes while making this home your own — whether you prefer simple cosmetic updates or a thoughtful remodel to add value. Move in now and add your finishing touches over time. Schedule a showing today to discover the possibilities.

5 Meadowbrook Drive, Ossining
$550,000
6 Beds ⋅ 3 Baths ⋅ 991931 MLS
Legal 2-family opportunity in the heart of Ossining offering exceptional value, versatility, and upside potential. Priced at $550,000, this spacious property features a 5-bedroom, 3 full bath layout plus a separate studio apartment with its own private entrance—ideal for investors or owner-occupants looking to generate rental income. Set on a 7,405 sq ft lot, the home offers approximately 2,276 sq ft of living space with classic architectural charm including a mansard-style roof, covered front porch, and original details throughout. The property features multiple living areas, generous room sizes, and flexible layout options to accommodate extended living or rental configurations. Interior spaces offer a blend of character and opportunity. Bright rooms with hardwood floors, large windows, and high ceilings provide great natural light. Kitchens and baths are functional with room for updates, making this a strong value-add opportunity. Separate living quarters allow for privacy between units, enhancing rental appeal. The exterior offers a large private driveway with ample off-street parking, a rare find in this area, along with a spacious backyard and patio area—perfect for outdoor use, entertaining, or future improvements. A detached structure and additional outdoor space provide even more potential. Located on a quiet residential street, the property is just minutes from downtown Ossining, shops, restaurants, parks, and the Hudson River waterfront. Commuters will appreciate easy access to Metro-North, offering a convenient commute to NYC. The area continues to see strong demand due to proximity to major employment hubs including White Plains, Tarrytown, and Stamford. With comparable multi-family properties in Ossining selling significantly higher, this property presents a compelling opportunity to build equity and maximize returns. Whether you are looking to invest, renovate, or live in one unit while renting the other, this is a property with strong income potential and long-term growth. A rare chance to own a legal 2-family with a separate studio in a sought-after Westchester location.

41 Ellis Place, Ossining
$599,000
3 Beds ⋅ 3 Baths ⋅ 989545 MLS
A charm-filled village home with river views, timeless details, and the ease of modern updates. This beautiful antique Colonial offers a rare blend of character, light, and convenience. From the moment you arrive, the Hudson River and Palisades set the tone, followed by a welcoming covered front porch and the warmth of beautiful woodwork and period details inside. The main level features an updated kitchen with counter seating, open to a bright breakfast room with walls of windows and access to the patio, along with a living room, reading nook, first-floor bedroom, and full bath. Upstairs, the primary suite offers river views, an updated ensuite bath, and walk-in closet, while a spacious second bedroom, updated hall bath, and second-floor laundry add everyday ease. A sunlit studio with glass doors provides flexible bonus space ready to suit your needs. Thoughtful improvements including updated heating and electrical systems, a new roof, driveway, patio, and retaining walls enhance the home, while lovely gardens and mature fruiting apple, plum, and peach trees add to its special appeal. All just moments from town, train, restaurants, parks, schools, and the farmers market.

41 Clinton Avenue, Ossining
$585,000
3 Beds ⋅ 1 Baths ⋅ 978657 MLS
Income-producing duplex in a desirable location! Has 5 bedrooms and two baths total. 3 bedrooms 1 bath in one unit, 2 bedrooms 1 bath in second unit. This well-maintained property offers two units with strong rental history and consistent cash flow. Ideal for investors or owner-occupants looking to offset their mortgage. Features include separate utilities, spacious layouts, and convenient access to transportation, shopping, and major highways. A rare opportunity to own a turnkey investment in a growing market.

58 State Street, 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.