Active Adult 55+ Homes for Sale in Westchester, NY

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Welcome to your dedicated resource for active adult 55+ homes for sale in Westchester, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Westchester, NY agent, Tierra Stanback specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the active adult 55+ properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Active Adult 55+ Homes for Sale in Westchester, NY

$448,500

2 Beds ⋅ 2 Baths ⋅ 982984 MLS

Welcome to 51 Jefferson Oval, Unit F, a beautifully renovated ground-floor residence in one of Yorktown Heights’ most desirable 55+ communities. Offering true one-level living with no stairs, this home combines comfort, quality, and convenience—complete with a private patio ideal for relaxing or entertaining. This move-in-ready 2-bedroom, 2-bath home has undergone a true, comprehensive renovation, extending well beyond cosmetic updates. The stunning white kitchen features quartz countertops, modern cabinetry, and updated finishes, while both bathrooms have been fully renovated with tasteful, high-quality materials. Significantly, the upgrades continue behind the walls, with updated electrical and plumbing systems throughout—a major value-add that provides long-term peace of mind and sets this home apart from typical surface-level renovations. The open-concept layout flows seamlessly between the kitchen, dining, and living areas, creating a bright and inviting space. Both bedrooms are generously sized, including a primary suite with its own fully updated bath. Additional improvements—including flooring, paint, trim, and doors—complete the home’s fresh, modern feel, delivering a truly turnkey experience. Located in a peaceful, well-maintained community close to shopping, dining, and everyday amenities, this is a rare opportunity to own a fully renovated home in a prime Yorktown Heights location.

51 Jefferson Oval Unit #F, Yorktown Heights

$3,250,000

4 Beds ⋅ 5 Baths ⋅ 979591 MLS

The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.

54 Cross Pond Road, Pound Ridge

$375,000

2 Beds ⋅ 2 Baths ⋅ 974096 MLS

Enjoy the easy lifestyle of living in Jefferson Village, a 55+ Active Adult Community. Walk right into this updated and well maintained 2-bedroom, 2 bath, plus detached garage Ascot Model boasting many updates over the years and lovingly maintained. New renovations include all new flooring and baseboards throughout, all interior doors, the whole interior just painted, all closets have new adjustable shelving. Water heater, refrigerator, stove, dishwasher, microwave, washer and dryer, 2 bathrooms, kitchen, outdoor deck supports, air handler, windows, awning, and air conditioning unit, have been previously updated. There is attic storage, and an updated stackable washer and dryer. Beautiful large pull in windows (easy to clean), bringing in the sunny days. Enjoy sitting on your very private deck and having your coffee. This unit is situated just a short walk to the Clubhouse and all the recreational amenities. Enjoy various bus trips, social dances, tennis, the inground pool, pickleball, vegetable garden, bocce, shuffleboard, a picnic area, a poolside summer DJ on holidays for your listening and dancing pleasure. There are many social dances and dinners and many clubs you may like to participate in. There is a billiards, an exercise room, a fully stocked library, a craft room, and an area for playing cards, darts, mahjong, and Ping-Pong, there is also a lounge area with a tv. Make this beautiful sought-after condo your own and enjoy a wonderful relaxing and fun lifestyle!

59 Kirby Close Unit #D, Yorktown Heights

$748,629

2 Beds ⋅ 2 Baths ⋅ 974690 MLS

Labor Day Special: Receive a $10,000 credit towards options on the Pinesbridge units at the Parkside at Underhill Farms. The special runs from now until Labor Day. Contact Anrea Salloway for complete details. This is an under-construction condominium building for people 55 years old and older. It is a brand new community offering pool, gym, club house and a beautiful pond with a fountain right in front of the building. The pond area has trails for pleasant relaxing walks and ice skating in the winter. The building is 4 stories but each unit is on one level. There is a parking garage underneath the building allowing you to park and take an elevator to your floor. No walking stairs is required. This new development is less than an hour from Manhattan. The units have 9 foot ceilings, choice of granite and quartz countertops, engineered hardwood floors, crown molding and stainless steel appliances. There are 5 different layouts to choose from. The community is walkable to downtown Yorktown Heights, convenient to shopping and only 1.7 miles to Taconic State Parkway. The building will be completed in the second quarter of 2027, but we have models for touring right now of other units with the same finishes. Experience new construction living at its finest at Underhill Farms - more than a home, it's a community. Pictures are renderings of one of the 5 unit layouts. Taxes are approximate.

370 Underhill Avenue, Yorktown Heights

$385,000

2 Beds ⋅ 1 Baths ⋅ 973165 MLS

Welcome to 18 Hastings Court—This 55+ active community is tucked away on a quiet cul-de-sac in the heart of Yorktown Heights, this home offers the perfect blend of space, comfort, and everyday convenience. From the moment you arrive, you’ll appreciate the setting—private, peaceful, and ideal for both relaxing and entertaining. Inside, the home features a functional layout with generous living spaces, great natural light, and flexibility for today’s adult lifestyle. Whether you’re hosting friends, working from home, or just enjoying a quiet night in, this home adapts to how you live. The kitchen flows seamlessly into the main living areas, creating an easy, connected feel that buyers are looking for right now. Bedrooms are well-sized, offering comfort and privacy, while additional space provides options for a home office, gym, or guest area. Step outside to your own private deck—perfect for morning coffee, summer dinners, or unwinding at the end of the day. It’s a great extension of the living space and gives you that indoor-outdoor feel buyers love. Conveniently located near shopping, dining, parks, and major commuter routes, this home offers the balance of suburban living with accessibility. If you’ve been waiting for the right opportunity in Yorktown Heights, this is one we’ll want to take a close look at.

18L Hastings Court, Yorktown Heights

$469,000

2 Beds ⋅ 2 Baths ⋅ 961695 MLS

BEAUTIFULLY UPDATED 2 bedroom/2 bath condo in this plush 55+ complex in Yorktown Heights! Let's start with the OPEN FLOOR PLAN accentuated by the lush, open kitchen equipped with granite counters (2021), modern cabinetry, stainless steel GE appliances and an array of updates including High Hat lighting & newer backsplash. The sun-drenched main bedroom is roomy and offers plenty of extra closet space from one end of the room to the other. And there's custom built closet shelving as a nice touch. The en suite features updated ceramic tile flooring, a tub/shower & vanity both replaced in 2021 while the hallway bathroom offers a beautifully tiled shower (2021) and washer/dryer from the same year. Enjoy the nice-sized living room and dining area (w/ updated flooring) and accompanying SGD to your deck which overlooks the well-manicured grounds. And you'll love the huge bay window in the dining room. Your own, private 1-car garage. For peace-of-mind, the water heater was replaced in 2020. JV is the area's premier 55+ complex, only 50 minutes north of NYC and just minutes to the Taconic, JV Mall, shopping and restaurants. This well-taken-care-of complex boasts a clubhouse with an expansive fitness facility, a large pool (with lifeguard), pickleball courts, private gardens and tennis!

41 Jefferson Oval Unit #G, Yorktown Heights

$135,000

1 Baths ⋅ 959941 MLS

Welcome to The Kenmore — a recently renovated and spacious studio offering comfort, convenience, and a prime location. This bright unit features an open layout, separate kitchen, and one full bath, complemented by lovely hardwood floors and an abundance of natural sunlight throughout. Ideally located within walking distance to the railroad, parks, shops, bus transportation, and the beach. Assigned parking provides added everyday convenience. A fantastic opportunity for easy living — schedule your showing today.

266 Pelham Road Unit #4E, New Rochelle

$890,000

6 Beds ⋅ 3 Baths ⋅ 911267 MLS

*Stunning 6 Bedroom Family Home in Private Setting* 12 Bacon Place *Overview:* Welcome to this exquisite 6 bedroom, 2 bathroom family home nestled in a serene and private area. Located just minutes from a bustling shopping mall, this property offers the perfect balance of tranquility and convenience. *Key Features:* - *Spacious Living Areas:* This beautiful home boasts ample space for families to grow and thrive. - *Finished Basement:* Currently rented for $3,000, this basement provides a fantastic opportunity for additional income. - *Private Setting:* Enjoy the peace and quiet of this secluded area, perfect for families seeking a relaxing environment. - *Big Driveway and Garage:* Ample parking and storage space, ideal for families with multiple vehicles or hobbies. - *Great Location:* Minutes from a shopping mall, providing easy access to amenities and services. *A Dream Home at a Great Price:* Don't miss this incredible opportunity to own a stunning family home in a desirable location. With its private setting, spacious living areas, and income-generating basement, this property is a rare find. Come and take advantage of this fantastic offer before it's gone! *Schedule a Viewing:* Contact us today to arrange a viewing and make this beautiful home yours!

12 Bacon Place, Yonkers

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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.