Ossining Homes with On Street Parking features

Welcome to Ossining, New York—a charming town nestled in Westchester County, where picturesque landscapes meet a vibrant community spirit. This delightful area is not only known for its scenic views along the Hudson River but also for its exceptional school district, which plays a pivotal role in attracting families to the neighborhood.

The Ossining Union Free School District is renowned for its commitment to academic excellence and holistic student development. With a diverse array of programs and extracurricular activities, students are encouraged to explore their interests and talents. The district boasts a dedicated team of educators who strive to create an engaging learning environment, ensuring that every child receives the support they need to thrive. Parents can take comfort knowing their children have access to quality education, with schools that prioritize both academic achievement and personal growth.

In addition to its excellent educational offerings, Ossining’s real estate landscape includes homes with on-street parking—a convenient feature that enhances the overall living experience. Families can enjoy the ease of parking right outside their doors, making daily routines and gatherings a breeze. Whether you’re hosting friends or simply returning home after a long day, the accessibility of on-street parking adds a layer of comfort to your lifestyle.

Living in Ossining means embracing a community that values education, convenience, and a welcoming atmosphere. Explore the homes available in this charming town and discover the perfect place for your family to grow and thrive!

Newest Ossining Homes with On Street Parking features

$599,222

4 Beds ⋅ 2 Baths ⋅ 1050407 MLS

Wonderfully updated and beautifully maintained, this charming Village Colonial offers the perfect combination of character, comfort, and convenience. Located within a 10 minute walk to Metro North and the Hudson River, this home is ideal for commuters! Enter through the front porch to find inside, hardwood floors flowing throughout the home. The open living and dining area features elegant crown molding, built in shelving and cabinetry, and a welcoming layout that’s perfect for entertaining. A convenient first-floor bedroom and updated full bath provide flexibility for guests, a home office, or one-level living. The updated kitchen features a new floor, stainless steel appliances, and a stainless steel sink, with a door leading directly to an expansive, low-to-the-ground deck. Enjoy the private, level property—ideal for outdoor dining, entertaining, or simply relaxing. A 2006 addition included framing, siding windows, electrical and plumbing. Upstairs you'll find three generously sized bedrooms, including a spacious primary bedroom with a large walk-in closet. The renovated hall bath completes the second floor. The full, unfinished walk-out basement offers abundant storage and plenty of possibilities for future living space, recreation, a workshop, or a home gym. The driveway has parking for several vehicles. Freshly painted throughout with a new front door, this lovingly maintained home is move-in ready and waiting for its next owner. A wonderful opportunity to enjoy Village living with multiple parks, restaurants, waterfront community, schools & a fabulous farmer’s market. Enjoy the accessibility to NYC, with the peacefulness of suburban living. There are no audio recording devices inside this property.

81 Snowden Avenue, 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

$1,099,222

1034832 MLS

Exceptional opportunity to own a legal 6-unit multifamily property with stable, long-term tenants. All six units, 4-two bedroom units and 2-three bedroom units, are leased through September 2027, providing immediate, reliable rental income and a strong 7% cap rate. This well-maintained building is ideally situated in a convenient location directly across from Park School and within walking distance to shops, restaurants, the train station, and additional schools, making it an attractive location for tenants. The property's utility setup is designed to help minimize owner expenses. Tenants are responsible for their own gas and electric, while the landlord pays for water. The building features seven electric meters, six gas meters, and six individual water heaters. Street parking is readily available. Whether you're expanding your investment portfolio or seeking a turnkey income-producing property, this is a rare opportunity to acquire a well-maintained asset with dependable cash flow and long-term lease stability. There are no audio recording devices inside this property.

17 19 Edward Street, 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

$234,500

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

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