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Single Family Homes for Sale in Pleasantville, NY

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Welcome to your dedicated resource for single family homes for sale in Pleasantville, 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 Pleasantville, NY agent, Jeremy Zucker specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Pleasantville, NY

$999,000
3 Beds ⋅ 2 Baths ⋅ 1027975 MLS
ATTEENTION WORK-AT -HOME PROFESSIONALS AND THOSE SEEKING MOTHER DAUGHTER SET UP! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to Bedford Road School, and 0.3 miles to both the Middle and High Schools, this home delivers effortless access to every part of town. Shops, dining, parks, the Farmers Market, and the Jacob Burns Film Center are all moments away, with easy ON/OFF access to the Saw Mill River Parkway for seamless commuting. County Tax classification code is R-02, the ground-floor unit is a standout feature — ideal as a professional home office (light business permitted) or as a 750 sq ft above ground living space. Previously used as a real estate office, it now functions as a comfortable residential space with endless potential with private entrance and second egress. . The main 3-bedroom apartment offers classic warmth and modern convenience, featuring a chef’s stove, EI kitchen w. SGD onto patio, formal dining room, sun room and living room. The second floor offers f primary bedroom, and two additional secondary bedrooms . The home has been fairly well maintained and is ready for you to personalize and make your own. This home offers off-street parking for at least three vehicles. With flexible zoning, walk-to-everything convenience, and timeless 1930’s character, 4 Depew Street is a one-of-a-kind Pleasantville opportunity. Zoning allows for 6 foot signage that is visible from Saw Mill River Parkway. .

4 Depew Street, 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 fa&#231;ade, 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
$689,000
3 Beds ⋅ 2 Baths ⋅ 1025216 MLS
Welcome to 660 Washington Avenue, a ranch-style home offering the ease of single-level living with the added benefit of flexible lower-level space. The main level features a sun-filled living room, dining area, eat-in kitchen, three comfortable bedrooms, and an updated full bath with radiant heated floors. Large windows throughout the home fill the interior with natural light and create a warm, inviting atmosphere. The walk-out lower level significantly expands the home's functionality, offering a spacious recreation area with direct access to the backyard patio, along with a private bedroom and full bath. This separate living area is ideal for extended family, in-laws, a live-in nanny, guests, or anyone seeking additional privacy and independence. Laundry, storage, and utility areas complete the lower level. Set on a beautifully landscaped property with mature trees providing privacy and shade, the home has been freshly painted and benefits from a newer furnace, heat pump, and HVAC system installed in 2021. Located just a short stroll from Chappaqua's train station, library, farmers market, downtown shops, restaurants, and community amenities, this home offers an exceptional combination of comfort, convenience, and versatility. Whether you're a first-time buyer, downsizing, or looking for a home with multi-generational living potential, 660 Washington Avenue presents a wonderful opportunity in one of Westchester County's most desirable communities.

660 Washington Avenue, 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
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 1021493 MLS
Welcome to 10 Crestview Drive, a beautifully updated 1990 colonial that perfectly blends classic elegance with updated modern luxury within the highly sought-after Heritage Court neighborhood. This exceptional property offers the rare combination of an intimate community feel and tremendous, serene privacy, all set on nearly an acre of flat, meticulously manicured grounds. Inside, you will find a bright and spacious layout featuring four well-proportioned bedrooms, all on the same level, and designed for ultimate comfort. The main floor features a three-car garage, mudroom, eat-in-kitchen with easy access to the deck, and backyard beyond, open floor plan, living room, dining room, and office. Also of note, this turnkey gem provides an unparalleled and truly unique opportunity for the next lucky buyers: a rare, one-time option to choose between the Chappaqua or the Byram Hills School District at closing. This is turnkey luxury at its finest!

10 Crestview Drive, Pleasantville
$879,000
3 Beds ⋅ 2 Baths ⋅ 1016376 MLS
There are homes that need a project list. This isn't one of them. An impeccably maintained split-level offering that rare opportunity to simply move in and start enjoying from day one. Every major improvement has already been completed, inviting you in with confidence. A stunningly redesigned kitchen, updated baths, central air, young roof and siding, and a brand new boiler and hot water heater means the heavy lifting has already been done. Offering the flexibility of a home that lives like 4-bedroom, the thoughtfully designed layout adapts beautifully to today's needs. A wood-burning fireplace adds cozy vibes to the main living space, while an expansive deck extends the living outdoors, creating the perfect setting for a quiet morning coffee to effortless entertaining. Add in exceptional curb appeal, abundant closet space, meticulous maintenance throughout and it’s easy to appreciate what makes this home so special. Ideally located in the highly regarded Pleasantville School District, this is the kind of home that lets you spend your weekends enjoying life instead of working on your house.

460 Washington Avenue, 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
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 994163 MLS
Welcome to this truly stunning residence in Pocantico Hills, where timeless design meets modern updates-all complemented by remarkably low taxes. This exceptional home features four spacious bedrooms and four full baths, including a brand-new roof (January 2024) and a newly painted chef’s kitchen designed for both function and style. At the heart of the home is the breathtaking Great Room, inspired by the historic Hingham Meeting House, showcasing intricate woodwork and soaring vaulted ceilings that create a dramatic yet inviting space. The main level offers a bright home office, a screened-in porch perfect for relaxing, and a full bath for added convenience. Upstairs, the primary suite serves as a private retreat, featuring a recently updated full bath (January 2026) and generous storage, including two cedar walk-in closets. Three additional bedrooms complete the upper level, two of which include their own en-suite full baths. The lower level provides abundant storage, while a separate Two-Story Guest House above the three-car garage adds incredible versatility, offering Two Additional bedrooms and two full baths—ideal for extended family or guests. Set on pristine, private grounds, the property is just moments from the scenic trails and outdoor beauty of Rockefeller State Preserve. Residents of Pocantico Hills benefit from a strong Pre-K starting at 3 YEARS OLD through 8th grade program, along with high school choice options including Pleasantville, Briarcliff Manor, and Sleepy Hollow. The community also features exceptional amenities such as an Olympic-sized swimming pool, tennis and pickleball courts, basketball courts, playgrounds, and ball fields. 2 Brand Above Ground New Oil Tanks (May 2026) This is a rare opportunity to own a truly distinctive home!

6 Raven Way, 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
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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.