Ossining Homes with Maintenance Grounds Amenities

Welcome to Ossining, New York—a charming community nestled in the picturesque Westchester County. Renowned for its rich history and vibrant culture, Ossining boasts a highly regarded school district that prioritizes academic excellence and holistic development. The Ossining Union Free School District is committed to fostering a nurturing environment, where students are encouraged to explore their passions and reach their full potential. With dedicated educators and a diverse curriculum, the district consistently ranks among the top in the state, making it an ideal choice for families seeking quality education.

In addition to its educational offerings, Ossining is known for its stunning homes that come equipped with maintenance grounds amenities. Imagine stepping into your backyard oasis, where beautifully manicured lawns and lush landscapes are maintained for you, allowing you to spend more time enjoying your home and less time worrying about upkeep. These properties provide the perfect balance of comfort and convenience, ensuring you can savor the serene surroundings without the hassle of regular maintenance.

Living in Ossining means embracing a lifestyle that combines the tranquility of suburban living with easy access to urban amenities. The area is dotted with charming shops, delightful eateries, and scenic parks, all within a short distance. Whether you’re taking a stroll along the Hudson River or enjoying a community event, Ossining offers a warm and welcoming atmosphere that makes it feel like home. Discover the perfect blend of education, community, and convenience in Ossining—where your dream home awaits!

Newest Ossining Homes with Maintenance Grounds Amenities

$575,000

1 Beds ⋅ 2 Baths ⋅ 1049345 MLS

Welcome to The Brooke Club, an established residential community offering a wonderful combination of comfort, amenities, and convenience. Beautifully upgraded and thoughtfully maintained, this attached single-family home offers a flexible and distinctive floor plan complemented by a substantial list of meaningful improvements. On the main level, at the heart of the home, is a renovated chef's kitchen featuring quartz countertops, updated flooring, and a suite of Bosch appliances. Separate living and dining areas provide wonderful spaces for everyday living and entertaining as well as a fireplace. There is also a renovated full bathroom, separate laundry closet, pantry and direct access to the attached garage. The 2nd level offers an impressive primary suite providing a private retreat, complete with a beautifully renovated full bathroom and custom cedar-lined walk-in closet. The dramatic lofted mezzanine is multi-functional with cathedral ceilings adding architectural interest and valuable living space, plus a bonus room which can easily serve as a second bedroom. The home lives comfortably like a 2-bedroom, with excellent flexibility for guests, a home office or den. The private rear patio provides an inviting extension of the living space for outdoor dining, entertaining, or simply relaxing with park-like views and breathtaking seasonal sunsets. An attached garage plus 2 in driveway, offer the convenience of 3-car parking. Numerous upgrades and improvements have created a truly turn-key home designed to be enjoyed today and grown into for the long term, allowing its next owner to move in with confidence and make it their own for years to come. Residents of The Brooke Club enjoy updated community amenities, including an indoor pool complex and fitness center. Conveniently positioned near major parkway access and Metro-North, this location provides easy connections throughout Westchester, to New York City, and points north and south.

5-03 Brooke Club Drive, Ossining

$590,000

2 Beds ⋅ 3 Baths ⋅ 1039859 MLS

Love the NYC loft lifestyle, but not the NYC-sized floor plan—or price tag? Welcome to The Penthouse. Set within a reimagined historic 1820s schoolhouse, this dramatic tri-level penthouse loft delivers the attitude of a downtown loft with the space, light and breathing room Manhattan forgot to include. The result? Something seriously cool—and anything but ordinary. The Entertaining Level sets the tone with soaring volume, exposed brick elements, original wood beams, exposed copper piping, hardwood floors and distinctive low-set windows that help fill the space with natural light. An elevated kitchen with granite counters and stainless-steel appliances overlooks the expansive open-concept living and dining area, creating one incredible backdrop for entertaining or simply hanging out at home. A powder room completes the level. Then there’s The Loft—perched above and overlooking the entertaining space below. Skylights bring in even more natural light, while the open design gives you a completely different perspective on the architecture of The Penthouse. Home office, studio, lounge, reading retreat or creative escape—it’s the kind of flexible space that makes loft living so much fun. The Private Level changes gears completely. Two generously sized bedrooms each enjoy their own private en-suite bath. The oversized primary suite features a huge walk-in closet and spacious bath with double sinks and a jetted whirlpool tub. The second bedroom has its own beautifully refreshed en-suite bath with brand-new tile. In-unit laundry is conveniently tucked into this level as well. And here’s something you won’t see in the photos: some of the most impressive improvements in The Penthouse are hidden behind the finished walls. Extensive sound-control upgrades were incorporated into select walls and ceilings using additional framing and separation, ROCKWOOL mineral-wool insulation, spray foam and heavier 5/8-inch drywall. The primary-bedroom ceiling received its own extensive insulated assembly, all designed with acoustic comfort and reduced sound transmission in mind. Drenched in natural light? Absolutely. Drenched in noise? This renovation took that on from the inside out. And then there’s Ossining. Hudson River waterfront parks, marinas, downtown shops and cafes, the Old Croton Aqueduct Trail and Metro-North are all nearby—giving you the space and character of Hudson Valley living without giving up your connection to NYC. And when Manhattan calls? Metro-North express service can have you at Grand Central in under 50 minutes. Two assigned parking spaces and dedicated private storage round it all out—two more things Manhattan generally forgets to include. Historic character. Downtown attitude. Suburban breathing room. Three incredible levels. Serious sound-control improvements. This isn’t another suburban condo. This is The Penthouse—and that’s exactly the point.

88 Broadway Unit #PH4, Ossining

$349,900

1 Beds ⋅ 1 Baths ⋅ 1047960 MLS

Set among the mature landscaping and beautifully maintained grounds of Briarcliff Woods, this one-bedroom condo offers a peaceful setting for easy Hudson Valley living. The comfortable one-level layout features a spacious living room centered around a wood-burning fireplace, with sliding glass doors opening to a private balcony — a wonderful extension of the living space for relaxing outdoors. A dedicated dining area, separate kitchen, in-unit laundry, and excellent storage, including a generously sized walk-in closet, add everyday functionality, while the bedroom offers plenty of room to create a comfortable private retreat. One reserved parking space completes the package. Beyond the front door, Briarcliff Woods feels more like a landscaped retreat than a typical condo community, with a beautiful in-ground pool, tennis courts, clubhouse, an on-site superintendent, and well-cared-for grounds to enjoy throughout the seasons. Commuters will appreciate the convenient proximity to Croton-Harmon, with weekday jitney service from Briarcliff Woods to the station, express Metro-North service to Grand Central Terminal and Amtrak service to Penn Station, while the Ossining Metro-North station is also nearby. And when it’s time to stay closer to home, some of the best of the Hudson River Valley is just minutes away — waterfront parks, scenic walking and hiking trails, restaurants, shopping, seasonal events and the vibrant riverfront communities of Ossining and Croton-on-Hudson. It’s a wonderful combination of comfortable condo living, outdoor space, community amenities and easy access to everything that makes this corner of Westchester so appealing.

1 Briarcliff Drive S Unit #4, Ossining

$895,000

2 Beds ⋅ 3 Baths ⋅ 1045247 MLS

There is something very special about Mystic Pointe, you feel it as soon as you enter through the gates. 33 Mystic Drive is a tri-level, end unit, Biscayne model home in the heart of Mystic, overlooking the Nature Trail. It offers a traditional layout with an eat-in kitchen, living and dining areas with sliding glass doors to one of the decks, a powder room, and access to the two-car garage all on the main level. The upper level has two generous bedrooms, two full baths, and a den/office room. The lower level is a wonderful all-around everything room, with sliding glass doors to the oversized deck, a generous walk-in storage closet, a laundry room, plus an additional storage room and utility room. One of the few homes with double decks for double entertaining! And Mystic Pointe has so much to offer: two pools, one adult and one for children; a clubhouse with a full kitchen and gym; a tennis/pickleball court; and a warm, welcoming community with weekly bridge nights, book club, and so much more. And since you don't have to mow the lawn, shovel the snow, or repair the exterior of your home, you will have plenty of time to enjoy it all.

33 Mystic Drive, Ossining

$375,000

1 Beds ⋅ 2 Baths ⋅ 1044918 MLS

Discover an exceptional opportunity within the highly sought-after Liberty Knoll Town Home Community. Whether you are a first-time homebuyer seeking an entry into the Westchester market, a commuter desiring convenience with a walk to the Metro North Train Station or looking to downsize without compromising on quality and community, 3 Davids Lane presents a sophisticated, low-maintenance lifestyle. The main level boasts gleaming stainless-steel appliances in the kitchen updated powder room and built-in cabinetry with beverage center. The open layout extends to a private balcony which is perfect for al fresco dining or enjoying quiet moments. The upper level provides a tranquil retreat, featuring a generous sized bedroom with a large walk-in closet, a well-appointed updated full bathroom and a dedicated laundry area complete with washer and dryer. The home also has exceptional storage in the lower level. Residents enjoy access to an outdoor pool and well-equipped clubhouse. A children's playground and picnic facilities ensure endless outdoor enjoyment. The complex is proudly pet friendly. You're just moments away from the bustling Arcadian Shopping Center, home to essentials like Stop & Shop, CVS, various banks and popular eateries. 2 assigned parking spaces are directly in front of the home for easy access.

3 Davids Lane, 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. Pet-friendly, too.

32 Beechwood Way, Briarcliff Manor

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