Ossining, NY Real Estate Search

Ossining, NY 5 Bedroom Homes for Sale

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Newest Ossining, NY 5 Bedroom Homes for Sale

$9,000
5 Beds ⋅ 5 Baths ⋅ 1025513 MLS
Experience refined living at 45 Wolden Road, a fully furnished and move-in-ready residence offering five bedrooms, four-and-a-half bathrooms, expansive living spaces, a private in-ground pool, and generous driveway parking. Distinctive architectural details, multiple fireplaces, inviting outdoor entertaining areas, and nearly an acre of property create a private retreat designed for both everyday comfort and gracious hosting. Convenient access to Ossining’s Metro-North station provides Hudson Line service to Grand Central, making the home well suited for Manhattan commuters and those relocating to Westchester. Residents also enjoy a vibrant Hudson River community with downtown shops, waterfront destinations, local parks, recreational facilities, and access to the Ossining School District.

45 Wolden Road, Ossining
$699,000
5 Beds ⋅ 2 Baths ⋅ 1013271 MLS
FULLY AVAILABLE as of 7-7-2026. Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and offering a strong combination of space, convenience, and versatility. The building features a spacious three-bedroom second floor unit that is ready for immediate occupancy over a two-bedroom unit, providing an ideal opportunity for owner-occupants or investors. Both units benefit from updated finishes completed during the 2020 renovation, offering modern functionality while maintaining a practical layout. The second floor unit has a back enclosed porch with access to a fenced in back yard. The property is located within one mile of two Metro-North Hudson Line train stations, providing convenient access for commuters. Ideally situated close to local shops, parks, schools, major highways, and public transportation, this property offers excellent accessibility and everyday convenience. A solid option for those seeking a turnkey multi-family home in a well-connected Westchester location.

1 Edward Street, Ossining
$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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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.