Refine Search
Map
Sort by
$475,000
2 Beds ⋅ 1 Baths ⋅ 1030479 MLS
Welcome home to effortless, low-maintenance living in the highly sought-after Greenwood Condominium complex. Located on the first floor with seamless, step-free access, this bright and inviting 2-bedroom home pairs mid-century charm with smart, modern updates. Inside, refinished hardwood floors and generous natural light frame serene views of the beautifully landscaped grounds. The thoughtful layout features an updated eat-in kitchen, an expansive living and dining area, 2 generously sized bedrooms, a full hall bath, and six impressive closets - including an oversized front hall closet. Best of all, the unit comes with a one-car garage that offers covered parking and ample storage. There is also plenty of on-site guest parking and nearby common laundry. Situated in the heart of the Village of Pleasantville - just steps from the Pleasantville Metro North station, the renowned Jacob Burns Film Center, local dining, boutique shops, the Pleasantville famer's market, Pleasantville schools, and the PACE University campus - the location is unbeatable. With low monthly HOA and annual taxes, this property is an ideal match for first-time homebuyers, downsizers, or anyone seeking an easy Westchester commute.

590 Bedford Road Unit #3, Pleasantville
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 1013140 MLS
Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living. Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living room stretches the full width of the home and is bathed in natural light from eastern, southern, and western exposures. A wood-burning fireplace serves as a warm focal point, while a wall of windows showcases picturesque views of mature trees, a tranquil pond, and abundant wildlife. The formal dining room is perfectly suited for both holiday entertaining and intimate gatherings. The spacious eat-in kitchen, complete with two pantries, provides direct access to an expansive deck—ideal for outdoor dining—and the attached two-car garage. A convenient powder room completes the main level. Upstairs, you’ll find a gracious primary suite, three additional bedrooms, and a beautifully renovated full hall bath. The lower level offers remarkable versatility, featuring a welcoming family room with a fireplace, as well as a workshop, laundry area, ample storage space and more. Wood floors, crown molding, central air-conditioning and an oversized two car garage are just some of the special features you will enjoy. The grounds are truly extraordinary, highlighted by exquisite stonework, garden beds, and meticulously maintained landscaping. The backyard invites out door fun, recreation and relaxation, while serene water views create a breathtaking natural backdrop. This stately home boarders scenic Opperman's Pond, where all-season activities from fishing and birdwatching to ice skating - can be enjoyed. This exceptional property is more than a home—it will be your sanctuary offering comfort, beauty, and memories.

1 Woodland Drive, Pleasantville
$1,399,000
3 Beds ⋅ 4 Baths ⋅ 1018220 MLS
Enjoy carefree and resort-style living in the Pleasantville Country Club community! Perfectly situated as one of only ten homes at the end of a private cul-de-sac, this beautifully updated 3-bedroom, 3.5-bath townhome offers 3,434 square feet of elegant living space. The main level features a fabulous Kingswood gourmet kitchen, complete with a large granite center island, top-of-the-line appliances, and abundant counter space. Entertain with ease in the living room, accented by a cozy fireplace, or step out onto the spacious screened porch overlooking the 3rd green of the nine-hole golf course. Upstairs, the expansive primary suite offers a luxurious en-suite bath and generous closet space, accompanied by two additional bedrooms and a full hall bath. The lower level is an entertainer’s dream, featuring a bright, light-filled family room with a wall of doors opening to a beautifully landscaped private patio. This level also includes ample storage, a full bath, and French doors leading to a versatile space perfect for a guest room or private home office. Beyond the home, step out and enjoy the incredible community amenities, including a swimming pool, tennis and pickleball courts, workout facilities, and an on-site restaurant. With close proximity to the vibrant village of Pleasantville, this isn't just a home—it's a lifestyle waiting to be lived!

18 Brookview Drive, Pleasantville
$3,350,000
5 Beds ⋅ 6 Baths ⋅ 1023249 MLS
Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of thoughtfully curated living space designed for the most discerning buyer. From the moment you step inside, you're greeted by soaring ceilings, sun-filled interiors, and beautifully appointed living spaces that seamlessly blend everyday comfort with grand-scale entertaining. Every detail has been carefully considered, creating an atmosphere of refined luxury throughout. The home's versatile floor plan features five spacious bedrooms, including a desirable first-floor guest suite with a full bath—perfect for extended family, overnight guests, or a private executive home office. The spectacular primary suite is a private sanctuary unlike any other, offering a spacious bedroom retreat, expansive custom walk-in closets, and luxurious his-and-her spa-inspired bathrooms, providing the ultimate in comfort, privacy, and everyday indulgence. Designed for effortless indoor-outdoor living, the resort-style backyard is an entertainer's dream. Spend summer days relaxing beside the stunning in-ground pool and spa or host unforgettable gatherings beneath the covered patio, complete with built-in heaters, integrated speakers, and a fully equipped outdoor kitchen—allowing you to enjoy every season in style. The expansive walk-out lower level offers endless possibilities, whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, or additional living quarters. Its exceptional scale provides the flexibility to accommodate every lifestyle. Perfectly positioned in one of the area's most desirable neighborhoods, this remarkable estate is just minutes from Armonk's vibrant downtown, Metro-North, award-winning schools, fine dining, boutique shopping, parks, and convenient access to New York City.

15 Heritage Drive, Pleasantville
$1,499,000
3 Beds ⋅ 3 Baths ⋅ 1012440 MLS
Enjoy the best of Westchester living with a Pleasantville address in the highly sought-after Byram Hills School District. Just minutes from the Pleasantville Farmers Market, Jacob Burns Film Center, downtown Armonk, Chappaqua shopping, dining, and Metro-North, this beautifully updated ranch offers the perfect blend of convenience, privacy, and one-level living. The open-concept floor plan features hardwood floors, a stone fireplace, and a renovated eat-in kitchen with granite countertops, stainless steel appliances, custom cabinetry, and built-in seating. A stunning great room/tv room with 12-foot beamed ceilings, skylights, and sliding doors opens to an expansive deck, creating seamless indoor-outdoor living. The resort-style backyard is a private retreat with a heated saltwater pool (2021), new hot tub (2025), and mature landscaping. The primary suite offers a walk-in closet, radiant heated bath floors, and peaceful woodland views. Additional bedrooms, updated baths, a home office/library, laundry area, and a finished lower-level recreation space provide flexibility for today's lifestyle. Complete with a two-car attached garage and easy access to major commuting routes and the Pleasantville Metro-North station, this exceptional home delivers luxury, comfort, and convenience in one of Northern Westchester's most desirable locations.

15 Deerfield Lane S, Pleasantville
$435,000
1 Beds ⋅ 1 Baths ⋅ 1014284 MLS
Step into elegance and comfort in this beautifully maintained, rarely available second-floor Pembroke model condominium in the highly sought-after Foxwood community. This move-in-ready home offers the perfect blend of style, convenience, and low-maintenance living. The bright eat-in kitchen features attractive butcher block-style countertops, beautiful white cabinetry, abundant storage and plenty of space for casual dining. Just off the dining area, step onto your private covered balcony overlooking the beautifully maintained community grounds an ideal spot to enjoy your morning coffee or unwind after a long day. Back inside, you'll find a spacious living room filled with natural light, a convenient in-unit washer and dryer, a beautiful full bathroom and a generously sized bedroom featuring a ceiling fan and a large walk-in closet. Additional highlights include a secure private storage area. Common charges include heat, hot water, landscaping, snow removal, Tennis or Pickleball courts and access to three community swimming pools. Perfectly situated in the heart of Pleasantville, Foxwood is just minutes from the Jacob Burns Film Center, the renowned Pleasantville Farmers Market, shopping, dining, parks, and recreation. Commuters will appreciate being just 1.4 miles from the Metro-North train station, offering an easy commute to New York City, along with quick access to major highways. Enjoy the best of Central Westchester living where everything is close and convenience meets comfort.

8 Foxwood Drive Unit #8, Pleasantville
$2,100,000
6 Beds ⋅ 5 Baths ⋅ 944741 MLS
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, you’ll find ample space to create lasting memories. The property features an amazing garden and a fenced outdoor area ideal for summer gatherings and outdoor enjoyment. Conveniently located near Pleasantville, Armonk, and Chappaqua, you’ll have easy access to shopping, dining & Metro North. Don’t miss your chance to own this one-of-a-kind home.

235 Bear Ridge Road, Pleasantville

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.