Pleasantville, NY Homes for Sale

Welcome to Pleasantville Country Club, the golf community where luxury meets convenience in this pristine unit with walls of windows and an expansive sunny golf course view. perfectly sited on a cul-de-sac, this home offers a newly renovated (2025) spectacular open sparkling white designer kitchen with top-of-the line appliances and cabinetry, a breakfast bar and pantry storage, and gleaming

Sena Baron William Raveis-New York, LLC

Beautifully set between the Villages of Pleasantville and Chappaqua, this charming, well maintained split-level home offers the perfect blend of comfort, convenience, and community. Located within the highly regarded Pleasantville School District, you’ll enjoy easy access to both village centers, each filled with local favorites—from restaurants and farmers markets to the Jacob Burns Film Center.

Karin Morano Corcoran Legends Realty

Flexible floor plan in the heart of Mid-Westchester. Pride of ownership shines throughout this well maintained original-owner home. Featuring Andersen windows, brand new roof, brand new above ground oil storage tank, Weil Mclain boiler installed 2016, fully encapsulated continuous exterior foam insulation... this property offers both comfort and efficiency to the new owner. The spacious main

Rahul Soni Nestedge Realty

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.

The One You’ve Been Waiting For Has Arrived At the end of a quiet cul de sac in Pleasantville Country Club, one of Westchester County’s most sought after communities, lies a residence that feels less like a townhome and more like a private retreat. Here, luxury meets convenience and melts seamlessly into daily life, creating a rhythm that feels both elevated and effortless. A First Floor Primary

Kile Boga-Ibric Houlihan Lawrence Inc.

Set in the desirable Village of Pleasantville, this enchanting Colonial home, built in 1830 and sited on .78 acres, offers timeless character, unique architectural details, and endless potential. A true diamond in the rough, this residence, dubbed "Pierce House", is ready to be transformed into something truly spectacular. Far from cookie-cutter, this home tells a story. With its original charm

Grace LoBello William Raveis Real Estate

Don’t walk—run to this rare 3,500 square foot end-unit townhome in The Enclave, Pleasantville. Perfectly situated on one of the community’s most desirable lots, it offers a private oversized backyard, expansive deck, and patio. Inside, the light-filled open layout showcases a Chef’s kitchen with stainless steel appliances, a walk-in pantry, hardwood floors, custom millwork, and plantation

Sari Shaw Compass Greater NY, LLC

Executive Raised Ranch 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers plenty of storage .

Harry Donofrio Town and Village Real Estate

Beautiful Foxwood Condominium.. Picturesque Country Setting with Meticulously Kept Grounds.. Rarely Offered, Foxwood's 1st Floor " Somerset " Model.. Approximately 1,300 sq ft of 1 Level Living.. Light and Bright in the Most Private of Locations with Southern - Western Exposure and Wooded Views.. Eat in Kitchen with Large Dining Area, Additional Cabinetry and Plenty of Counter Space Throughout..

Vincent Vetrano Douglas Elliman Real Estate

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

Welcome to your dream home nestled in the serene cul-de-sac of Pleasantville. This stunning 4-bedroom, 4-bathroom residence spans an impressive 3917 square feet, offering luxurious living with a touch of modern elegance. Step inside to discover a home that was rebuilt in 2023 and designed by local architect Tim Lener. A beautiful open floor plan adorned with exquisite wood floors that flow

Karen O'Connor Compass Greater NY, LLC