Pleasantville, NY Homes for Sale

Welcome to Pleasantville Country Club where luxury meets ease and every day feels like a retreat. Perfectly positioned just steps from the tennis and pickleball courts, this sun-drenched townhome places you in the heart of one of Westchester’s most coveted lifestyle communities. Whether you’re a player, a spectator, or simply someone who enjoys the hum of an active, close-knit neighborhood, this

Kile Boga-Ibric Houlihan Lawrence Inc.

This rare studio condo is a small starter home or pied-a-terre with mighty potential -- and a deeded one-care garage -- ideally located in one of Westchester's most desirable villages. This 500sf unit with a private entrance has an open main space with an in-line kitchen, a spacious bathroom, and a surprising amount of closet space. Being sold for the first time in 40 years, the low asking price

Allison Jaffe Key Real Estate Services, LLC

Welcome to 17-5 Foxwood Drive, nestled in the highly desirable Foxwood community. This beautifully updated, sun-filled 1-bedroom with a versatile den/office and 1.5 baths offers the perfect blend of space, comfort, and style, with thoughtful updates completed within the last six years.The expansive living and dining area is bright and inviting, offering generous room to entertain or unwind.

Kathryn Weinberger Compass Greater NY, LLC

Sun-filled and designed for easy living, this beautifully maintained 3-bedroom, 3-bath home offers the perfect blend of comfort and versatility. A private, level fenced yard creates an ideal setting for relaxing, entertaining, or everyday enjoyment. The walk-out lower level features its own private entrance and flexible living space complete with a studio setup, kitchenette, and recreation room,

Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

Welcome to this extraordinary estate, a gem dating back to the 1900s, situated on over an acre of picturesque land. This sunlit residence boasts 6 spacious bedrooms and 4 1/2 bathrooms, making it the perfect sanctuary for entertaining guests. Step inside to experience the remarkable craftsmanship that defines this home. With oversized rooms designed for both formal gatherings and casual moments,

Stacey Sporn William Raveis Real Estate

Welcome to this bright and well-maintained 2-bedroom, 1-bath condo located in the desirable Greenwood Complex. Situated on the second floor, this home overlooks the beautifully landscaped courtyard with mature trees, shrubs, and lush lawns, creating a peaceful setting. The spacious living room features a large triple window that fills the space with natural light and brand-new wall-to-wall

Patricia DelVecchio William Raveis Real Estate

Offered for the first time in over 90 years, this cherished village home presents a rare opportunity to become part of Pleasantville’s rich community fabric. Lovingly held by the same family for generations, this 3-bedroom, 1.5-bath residence is ready for its next chapter, offering endless potential for renovation, expansion, or personalization.The home features a classic layout filled with

Mary McCabe William Raveis-New York LLC

Welcome to this spacious contemporary home featuring three bedrooms and three baths, perfectly situated on a half-acre lot on a desirable cul-de-sac. Inside you'll find a bright dining room and an eat-in kitchen with a separate laundry room for added convenience. The kitchen enjoys easy outdoor access to a double deck, which is perfect for outdoor entertaining and offers a front-row seat to

Vanessa Catalano Julia B Fee Sothebys Int. Rlty

All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.

Karin Kimtis Compass Greater NY, LLC

Move right in to this 2-bedroom + loft, 2.5-bathroom townhouse in the highly sought-after Chappaqua School District. Freshly painted throughout and updated with brand-new quartz countertops, new dishwasher and new kitchen flooring, this home offers immediate comfort with the flexibility to personalize. The dining area features sliding doors that open to a grassy green space, while the kitchen

Karin Kimtis Compass Greater NY, LLC