Ossining Homes with Attached Parking features

Welcome to Ossining, a vibrant community nestled in the heart of Westchester County, NY. Known for its rich history and picturesque landscapes along the Hudson River, Ossining offers a unique blend of suburban charm and urban convenience. One of the standout features of this area is its exceptional school district, which is dedicated to fostering a nurturing and stimulating environment for students of all ages. The Ossining Union Free School District is renowned for its commitment to academic excellence, offering a diverse curriculum and a wide array of extracurricular activities that encourage personal growth and development. Families can take comfort in knowing that their children have access to top-notch education, making Ossining an ideal place to call home.

In addition to its educational offerings, Ossining boasts a variety of homes that cater to modern living. Many properties in this delightful community come with attached parking, providing homeowners with the convenience and peace of mind that comes with secure, easy access to their vehicles. Imagine returning home after a long day and effortlessly parking right next to your front door. This feature not only enhances your day-to-day life but also adds value to your property.

Whether you’re drawn to the excellent schools, the scenic beauty, or the community spirit, Ossining is a place where families thrive and memories are made. Explore the homes available in this charming town, and discover the perfect blend of comfort, convenience, and community that awaits you!

Newest Ossining Homes with Attached Parking features

$539,999

1 Beds ⋅ 2 Baths ⋅ 1030990 MLS

Discover your dream home at 93 Bridle Path Road, nestled within the highly sought after Fox Hill Condominiums in Ossining, NY. This charming 2 level townhouse features a spacious 1 bedroom and a versatile loft, perfect for an office or study area. The first level boasts a modern galley kitchen with stainless steel appliances, a cozy living room with a wood burning fireplace, and a dining area that opens to a tranquil deck ideal for relaxing or entertaining. Enjoy the benefits of hardwood floors throughout, recessed lighting, and recently renovated kitchen and bathrooms. With a one car garage and additional driveway space, this property offers both convenience and comfort. Embrace the pet-friendly lifestyle and the serene, park-like setting of Fox Hill, which spans 45 wooded acres and includes amenities such as a pool, tennis court, basketball court, and playground. Located just 30 miles from New York City, with easy access to the Metro North rail line making your commute approximately 55 minutes, this home perfectly balances suburban tranquility with urban convenience. Don't miss the opportunity to make this peaceful retreat your own!

93 Bridle Path Road, Ossining

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 1021711 MLS

"Living at Beechwood has been a truly special experience. The beauty, serenity, and wonderful sense of community make it a place that feels like home from the moment you arrive. Some of my favorite memories have been simply sitting on the balcony, watching breathtaking sunsets paint the sky, greeting the peaceful sunrise with a cup of coffee, and enjoying the quiet glow of the moonlight in the evenings. The natural beauty that surrounds the home changes with every season, creating a tranquil retreat that is both inspiring and relaxing. Combined with the warmth and kindness of the lovely neighbors, Beechwood offers a rare lifestyle where every day feels peaceful, welcoming, and connected to nature." (Seller's words) 32 Beechwood Way is part of an 80-acre private parkland. Beechwood was designed by Frederick Law Olmsted (who also designed Central Park in NYC and Prospect Park in Brooklyn). Its expansive lawns, grove of large beech trees, imported trees, and Italianate Garden with an alcove, fountain, and small pool with wisteria-covered gazebo have been well-preserved. Serene, tranquil, alluring is at the essence of Beechwood. Natural light abounds from large windows in living room and sky lights in entrance foyer. The primary bedroom has en-suite bath, double walk-in closet (it is a room all its own!), walk-in-shower for ease in entry/exit, & private terrace with seasonal Hudson River views. Scarborough Station/Metro North is less than a mile away (.9 miles). Working remotely? Two additional bedrooms on main & lower level easily accommodate your lifestyle. Efficient & responsive resident property manager. Entire house painted within the year. Floors refinished and stained in the last 2 years. Whole-house water filtration system installed less than a year ago. Roof less than 3 years old. Residents at Beechwood may avail themselves of the Olympic-size pool, library, & elegant formal ballroom to celebrate life events in style.

32 Beechwood Way, Briarcliff Manor

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1013378 MLS

Some homes ask you to imagine what they could be. This one is already there and waiting for you. This classic colonial has been lovingly updated and impeccably maintained by owners/designer who cared about every detail. Large, sun-drenched rooms, a layout that feels both timeless and completely livable, and the big-ticket items already handled: new roof, new HVAC, new kitchen and appliances, new bathrooms, new garage doors, mostly new windows, new Trex deck, freshly painted throughout, and beautiful landscaping. The to-do list has already been done! The kitchen tells you everything about how this home was tended. Expanded windows pour light across generous counter space, the pantry closet and large cabinets keep things organized, and an induction cooktop and eat-in area make everyday life feel a little more considered. Sliding doors open directly to the new Trex deck, because good kitchens don't end at the walls. Upstairs, four well-proportioned bedrooms and two fully updated bathrooms offer real comfort. The primary bedroom includes a stunning new bathroom and a fabulous walk-in closet that makes the everyday routine feel a little more special. On the first floor, a powder room and a flexible den with fireplace work as a home office, playroom, or guest room, depending on what this season of life calls for. A sunny mudroom and laundry room with its own separate entrance off the kitchen keep the household running smoothly, and the two-car garage rounds out a home that was designed to actually live in. The walk-out lower level adds a chapter still to be written. Full, unfinished, with high ceilings and direct outdoor access and windows, it's ready for whatever you decide it should become. The flat, beautifully landscaped backyard with a fire pit patio turns an ordinary evening into a reason to stay outside a little longer. Less than a mile to the Scarborough Train Station for an easy city commute, Briarcliff Manor recreation right down the road with pool, tennis, pickleball, and summer camps, and the award-winning Ossining School District, this is a community that feels like home.

629 Scarborough Road, Briarcliff Manor

$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

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 970496 MLS

Stately, 4-bedroom Colonial with Hudson River views, ideally set on a level 2/3-acre property with exceptional curb appeal. Located within the desirable walk-to-train Scarborough neighborhood , this home offers a seamless blend of timeless architecture and modern convenience—perfectly suited for today’s Westchester lifestyle. Spanning approximately 3,500 square feet, the residence features gracious, light-filled interiors and refined updates throughout. The renovated eat-in kitchen is thoughtfully appointed with a full suite of Wolf appliances, including range and wall ovens, a Sub-Zero refrigerator, quartzite counters and custom cabinetry—designed to accommodate both everyday living and effortless entertaining. A well-designed mudroom adds functionality with understated style and connects to the 2 car garage. Elegant formal living and dining rooms provide the perfect backdrop for entertaining, while the inviting family room opens through French doors to a patio, creating an effortless indoor-outdoor flow. The home offers 2 full baths and a powder room, along with generously scaled living and gathering spaces that create a warm, inviting atmosphere. The partially finished walkout lower level provides flexible space ideal for a media room, home office, or fitness area. Set on beautifully level grounds, the property offers both privacy and open space, with room for outdoor entertaining or future enhancements such as a pool. Enjoy tranquil river views and the ease of a commuter-friendly location, just moments from Metro-North, local shops, dining, and the vibrant character of the Rivertowns. A rare offering combining location, scale, and lifestyle in one of Westchester’s most desirable settings.

179 River Road, Briarcliff Manor

$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

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