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6 Reeback Drive, Ossining
$779,999
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

129-1 S Highland Avenue Unit #B3, Ossining
$225,000
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

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
$699,000
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

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

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

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.

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