Ossining Homes under $300,000

Ossining Homes under $300,000

Welcome to Ossining, New York – a charming village nestled in the heart of Westchester County, just 50 miles north of Manhattan. Known for its rich history and vibrant community, Ossining offers a perfect blend of suburban tranquility and urban accessibility, making it an ideal location for families, professionals, and retirees alike. With the picturesque Hudson River as its backdrop, residents enjoy scenic views and a plethora of outdoor activities, including hiking trails, parks, and waterfront access.

Ossining is not just about natural beauty; it boasts a thriving downtown area filled with unique shops, delightful eateries, and cultural attractions. The local arts scene is alive and well, with galleries, theaters, and community events that foster a strong sense of belonging among residents. Additionally, Ossining’s excellent school district and strong community programs make it a desirable place to raise children.

For those seeking affordable housing options, Ossining presents a fantastic opportunity with homes available for under $300,000. These properties range from charming single-family homes to cozy condos, providing a variety of choices for first-time homebuyers or those looking to downsize. With the current market offering competitive prices, now is the perfect time to invest in your dream home in this delightful village.

Whether you’re drawn to Ossining for its scenic beauty, community spirit, or affordability, you’ll find that this hidden gem has something for everyone. Come explore Ossining, where your ideal home awaits!

Newest Ossining Homes under $300,000

131 -2 S Highland Avenue Unit #A 5, Ossining
$160,000
1 Beds ⋅ 1 Baths ⋅ 1064424 MLS
Beautifully Updated One-Bedroom Co-op in Ossining Welcome to this charming and beautifully updated one-bedroom, one-bath co-op located on the second floor. Enter into spacious foyer perfect for a variety of uses, such as work space, dining, or reading nook. The updated kitchen features gorgeous white cabinetry, granite countertops, and a butcher-block breakfast bar, perfect for casual dining and entertaining. The kitchen opens to a spacious living room, creating a welcoming and comfortable living space. The updated bathroom adds a fresh, modern touch, while the generously sized bedroom offers plenty of room to relax and unwind. A wonderful opportunity to own a stylish, move-in-ready home that combines comfort, functionality, and modern updates. Don't miss the chance to make this lovely co-op your own!

131 -2 S Highland Avenue Unit #A 5, Ossining
133-3 S Highland Avenue Unit #5B, Ossining
$220,000
2 Beds ⋅ 1 Baths ⋅ 1065268 MLS
Welcome to Highland Terrace, a light-filled, top-floor end unit in a pet-friendly community. This bright and well-maintained two-bedroom apartment features an updated kitchen with granite counters, newer appliances, and a convenient pass-through to the living and dining area. The spacious living room offers plenty of space and great natural light, while both bedrooms include good sized closets. A flexible bonus space off the entrance is perfect for a dining nook or home office. Highland Terrace is a pet-friendly complex (up to two pets allowed) offering assigned parking, an outdoor pool, basketball court, and beautifully maintained grounds. Ideally located just minutes from shops, restaurants, parks, and the Ossining and Scarborough Metro-North stations, making commuting to NYC simple and convenient.

133-3 S Highland Avenue Unit #5B, Ossining
135 South Highland Ave Unit #3B3, Ossining
$223,000
2 Beds ⋅ 1 Baths ⋅ 1058239 MLS
Sun-drenched and spacious, this two-bedroom, one bathroom co-op in the desirable Highland Terrace offers the perfect blend of serene nature and urban convenience. The versatile layout begins with a welcoming foyer, currently utilized as a flexible bonus space. A generous kitchen features abundant cabinet storage and sleek stainless-steel appliances, flowing seamlessly into a bright, airy living room bathed in natural light. The primary bedroom provides expansive closet space, while the flexible second bedroom is ideal for guests, a home office, or additional living area. Residents enjoy exceptional community amenities, including a refreshing swimming pool, basketball court and access to the historic Old Croton Aqueduct Trail—a paradise for outdoor enthusiasts and their pets in this pet-friendly community. Ideally situated less than two miles from the Ossining Metro-North station, this home provides a seamless commute while keeping you close to the natural beauty and vibrant energy of the Hudson River region. An exceptional opportunity for those seeking space, style, and accessibility that combines privacy, luxury, and convenience—a rare opportunity to own a truly turnkey home in one of Ossining's most sought-after complexes. Close to all shopping and amenities. Laundry and storage located in the basement of this building. Come see your new home in the exquisite Hudson Valley! ***Be advised that there are carpet rules. 100% of all BR's & LR are required to have fully padded, tacked down carpet. ***

135 South Highland Ave Unit #3B3, Ossining
135 Main Street Unit #302, Ossining
$215,000
1 Beds ⋅ 1 Baths ⋅ 1057950 MLS
Why rent when you can own? Welcome to your new home! In the heart of the Village of Ossining, is this charming 1-bedroom condo that offers the perfect combination of comfort and convenience! Enjoy a vibrant, walkable lifestyle with easy access to the train station, restaurants, shops, farmers' market, seasonal festivals, waterfront park, community recreation center, library, and more. Pet-friendly for both cats and dogs, with a maximum of two pets per unit. There is also laundry facilities in the basement available to all residents. Each unit has its own storage unit for added convenience. Owners may also obtain parking permits for both Village and train station parking. A new parking garage is currently being built behind the building providing more parking options as seen in the aerial photos. This property is part of the "Fair and Affordable" housing program and is subject to HOME Program affordability requirements. Prospective purchaser(s) must meet applicable income eligibility guidelines, be a first time homebuyer and occupy the unit as their primary residence; investors are not permitted. As of September 2026, household income may not exceed 80% of the Westchester County Area Median Income (AMI), with the following limits: 1 occupant: $95,000, 2 occupants: $108,600, 3 occupants: $122,150 - Income limits are subject to change. There is a $30,000 Westchester County subsidy is available for this unit which has already been accounted for in the listing price. Note: Photos have been digitally enhanced for informational purposes only. Property is being sold as-is. AGENTS: Please review the confidential remarks and all MLS attachments for additional requirements, eligibility information, and further instructions.

135 Main Street Unit #302, Ossining
30 Campwoods Grounds, Ossining
$280,000
2 Beds ⋅ 1 Baths ⋅ 1057825 MLS
What an absolutely excellent opportunity! Come see this adorable cottage in the charming, unique, and AMAZING 44-home community that is Campwoods Grounds! As you walk through the property, you will notice the care that owners put into their homes...The attention to detail, the personal landscaping - in addition to the common areas, and the overall meticulousness is evident across the grounds. This two-bedroom cottage is ready for the lucky buyer(s) to add THEIR own personal touches, but plenty of wonderful features are already in place: A nice-sized eat in kitchen, beautiful hardwood floors downstairs, and a 120-square foot screened in porch are just some of these highlights. There are also two split heat/ac systems for efficiency, one up and one downstairs, as well as a gas furnace if desired for those absolutely frigid winter days/nights. The Campwoods Grounds community also boasts an extensive community garden, LARGE auditorium for neighborhood functions and other events, and a schedule of neighbohood get togethers to enjoy when you want to stay close to home. All of this, so convenient to all, and at a superb price point for the Ossining School District! Taxes with the STAR discount would be $4302/yr.

30 Campwoods Grounds, Ossining
4 Charter Circle Unit #4, Ossining
$225,000
2 Beds ⋅ 1 Baths ⋅ 1041072 MLS
Opportunity awaits at this 2-bedroom, 1-bath bi-level co-op in the High Meadow Cooperative! This home offers comfortable, functional living that has been lovingly lived-in and ready for your personal touch, it's a great chance to build equity and make it your own. The monthly maintenance covers heat, hot water, sewer, trash, and grounds — a simple, low-hassle way to own. Commuters will love the location: about 1 mile to the Scarborough Metro-North station for an easy 45-minute ride to Grand Central, plus shopping and restaurants nearby. Don't miss this value-priced opportunity in a convenient location! Make your appointment today!

4 Charter Circle Unit #4, Ossining
127-1 S Highland Avenue Unit #B5, Ossining
$228,000
2 Beds ⋅ 1 Baths ⋅ 1051780 MLS
Move right into this beautiful top-floor co-op in Highland Terrace! From the moment you enter, you will appreciate the spacious foyer with hardwood floors, suitable as a entryway drop zone, office space, or breakfast nook. Just beyond is the open galley-style kitchen, featuring granite countertops, a tile backsplash, and a double-basin sink with an under-sink water filtration system. The kitchen opens seamlessly to the living and dining area, complete with a breakfast bar that’s perfect for casual meals or entertaining. The living space features BRAND NEW carpeting, which continues into both bedrooms, and the entire unit has been freshly painted. Down the hallway, you will find a tiled bathroom with a BRAND NEW vanity, toilet, medicine cabinet, and light fixture, plus a bathtub that has just been reglazed. The primary bedroom offers ample closet space, and the second bedroom can function as a guest room, home office, or additional living space. Outside, enjoy the beautifully landscaped grounds, complete with a swimming pool and direct access to the Old Croton Aqueduct Trail. Bring your four-legged companions, as Highland Terrace is a pet-friendly community. Enjoy the best of both convenience and surroundings with this ideally situated home, just under two miles from the Ossining Metro-North station and close to the many stores, restaurants, recreation, and natural beauty of the Hudson River area. Come see it today!

127-1 S Highland Avenue Unit #B5, 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
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
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