Homes for Sale in Pleasantville, NY: Your Gateway to Westchester Living

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Discover an exceptional array of homes for sale in Pleasantville, NY, a charming village nestled in the heart of Westchester County. Prospective buyers will find diverse real estate options, from historic colonial homes to modern new constructions, all within a vibrant, family-friendly community. Pleasantville offers an idyllic blend of suburban tranquility and convenient access to New York City, making it a highly sought-after location. Explore properties near top-rated schools, lush parks, and a bustling downtown, perfectly suiting various lifestyles. Jeremy Zucker is your trusted guide to finding your dream home in Pleasantville.

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Explore Diverse Homes for Sale in Pleasantville, NY

Pleasantville's Unique Housing Market

Searching for homes for sale in Pleasantville, NY, reveals a dynamic and appealing real estate landscape. This picturesque village caters to a wide spectrum of preferences, ensuring that whether you’re a first-time homebuyer or seeking an upscale property, there’s a perfect match. The housing stock predominantly features single-family homes, though charming townhouses and some condominium complexes also dot the market.

Architectural Styles and Property Types

When considering homes for sale in Pleasantville, NY, prospective residents will encounter a rich tapestry of architectural styles. Classic Colonial homes, often featuring historical details and spacious layouts, are abundant. Additionally, you’ll find elegant Victorian and charming Cape Cod residences that exude timeless appeal. For those preferring modern aesthetics, a selection of contemporary homes and recently renovated properties offers updated amenities and open-concept designs. Furthermore, some luxurious estates provide expansive grounds and high-end finishes for discerning buyers.

Neighborhoods and Lifestyle in Pleasantville

Charming Pleasantville Neighborhoods

Pleasantville's appeal is significantly enhanced by its distinctive neighborhoods, each offering a unique character. As you explore homes for sale in Pleasantville, NY, you might discover the serene streets of the Bedford Road area, known for its larger lots and mature trees. Similarly, properties closer to the village center provide the convenience of walkability to shops, restaurants, and the train station. Other desirable enclaves include the quieter residential areas north of Manville Road, which often feature a mix of traditional and newer constructions.

Education and Family Living

Families consistently seek homes for sale in Pleasantville, NY, drawn by its outstanding school system. The Pleasantville Union Free School District is highly regarded, with schools like Pleasantville High School achieving excellent academic results. This focus on quality education makes the village particularly attractive to those prioritizing their children's schooling. Beyond academics, the community offers numerous youth sports leagues, cultural programs, and family-friendly events throughout the year, fostering a strong sense of community.

Vibrant Downtown and Local Amenities

The heart of Pleasantville beats strongest in its vibrant downtown area, which significantly adds to the allure of homes for sale in Pleasantville, NY. Residents enjoy easy access to the Jacob Burns Film Center, a renowned cultural institution, alongside an array of local boutiques, cafes, and diverse dining options. The Pleasantville Farmers Market, held seasonally, is a beloved local tradition offering fresh produce and artisanal goods. Moreover, numerous parks, such as Parkway Field and Nannahagan Park, provide ample opportunities for outdoor recreation, including playgrounds, sports fields, and walking trails.

Commuting and Accessibility from Pleasantville

Convenient Commuting Options

One of the primary advantages of investing in homes for sale in Pleasantville, NY, is its unparalleled accessibility. The Pleasantville Metro-North station offers direct commuter rail service to Grand Central Terminal in Manhattan, making it an ideal location for those who work in New York City but desire suburban living. The express train service significantly shortens travel times, enhancing the appeal for professionals and commuters alike.

Road Networks and Regional Access

Beyond rail, Pleasantville's strategic location provides excellent road access to major highways, including the Taconic State Parkway and Saw Mill River Parkway. This connectivity facilitates easy travel throughout Westchester County, allowing residents to conveniently reach neighboring towns, corporate centers, and recreational destinations. Thus, homes for sale in Pleasantville, NY, represent not just a beautiful place to live but also a highly connected hub.

Newest 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 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

$649,000

2 Beds ⋅ 2 Baths ⋅ 1024907 MLS

Welcome to this beautifully updated, move-in-ready 2-bedroom, 1.5-bath first-floor condominium offering 1,035 square feet of comfortable, low-maintenance living in the highly sought-after Foxwood community. This thoughtfully maintained home combines modern finishes, convenience, and an exceptional location in the heart of Pleasantville. Inside, you'll find beautiful hardwood floors throughout, creating a warm and inviting atmosphere. The updated kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous workspace, making it ideal for both everyday living and entertaining. The home has been meticulously maintained and enhanced with crown molding, high hat lighting, new windows, and beautifully renovated bathrooms completed within the past two years. Additional conveniences include an in-unit washer and dryer, a private storage unit, and one assigned parking space— conveniently located directly in front of the unit. Foxwood residents enjoy beautifully maintained grounds and outstanding community amenities, including three outdoor swimming pools and access to Village tennis courts. The community is pet-friendly, making it an ideal place for both homeowners and their furry companions. Ideally located in one of Pleasantville's most desirable neighborhoods, the home is just over a mile from the Pleasantville Metro-North station, providing an easy commute to New York City. Residents also enjoy convenient access to the village's vibrant downtown, offering charming restaurants, cafes, boutique shopping, parks, and year-round community events. Offering a rare combination of thoughtful updates, first-floor convenience, desirable amenities, and an unbeatable location, this exceptional home is truly move-in ready and presents a wonderful opportunity to enjoy everything Foxwood and Pleasantville have to offer.

16 Manville Lane Unit #2, 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

$349,000

1 Beds ⋅ 1 Baths ⋅ 1019926 MLS

Welcome to this spacious second-floor one-bedroom condo in the heart of the Village of Pleasantville! Offering a comfortable layout and an unbeatable location, this home is ready for its next owner to move right in and make it their own. The galley kitchen features natural oak cabinetry, a tile backsplash, tile flooring, and a cozy eat-in area. While the kitchen and bathroom retain their original 1980s finishes, they have been well maintained and offer a wonderful opportunity to update at your own pace. A fresh coat of paint is all that's needed to make this home shine from day one. The generously sized living room easily accommodates both a comfortable living/TV area and additional space for a dining area or home office. The spacious bedroom includes two double closets, providing excellent storage. New neutral wall-to-wall carpeting has been installed in the living room, bedroom, and the interior staircase leading to the apartment, creating a fresh, inviting feel throughout. Additional features include a dedicated one-car garage #50 and access to a common laundry room conveniently located beneath the 580 building. Ideally situated just 0.4 miles from the Metro-North train station, this condo is also within easy walking distance of the renowned Jacob Burns Film Center, charming shops, restaurants, and all that vibrant downtown Pleasantville has to offer. Whether you're a first-time buyer, downsizer, or commuter, this home offers outstanding value in one of Westchester's most desirable communities.

600 Bedford Road Unit #6, 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

$597,000

1 Beds ⋅ 2 Baths ⋅ 1013700 MLS

Welcome to Foxwood Condominiums in Pleasantville! This spacious first-floor 1-bedroom condo offers comfortable and convenient living with a versatile den, 1 full bath, and 1 half bath. Enjoy easy access with no stairs and relax on your private terrace, perfect for morning coffee or evening unwinding. Residents of Foxwood enjoy an array of amenities, including three swimming pools and a playground, all set within beautifully maintained grounds. The unit also includes a private locked storage unit located in the basement on the rear side of the building, providing valuable additional storage space. As an added bonus, public tennis courts are conveniently located near the entrance on Campus Drive, offering residents easy access to additional recreational opportunities. Ideally situated just 1.3 miles from the Pleasantville Metro-North train station, this home offers an easy commute while being close to shopping, dining, parks, and everything Pleasantville has to offer. Don't miss this opportunity to enjoy low-maintenance living in one of Pleasantville's most desirable condominium communities!

20 Foxwood Drive Unit #1, Pleasantville

$275,000

2 Beds ⋅ 1 Baths ⋅ 1012138 MLS

Updated and meticulously maintained co-op ideally located just moments from both the heart of Pleasantville and the Metro-North station, offering an effortless commute and vibrant village living. This inviting home features a modern, comfortable layout and quality finishes throughout. The updated kitchen offers clean lines, ample cabinetry, and functional workspace designed for everyday living and easy entertaining. The living and dining areas feel bright and open, with well-proportioned rooms that create a natural flow and a warm, welcoming atmosphere. The bedroom is generously sized with excellent closet space, while the updated bath reflects the same level of care and maintenance found throughout the home. Beautiful hardwood floors. Residents enjoy a peaceful residential setting while still incredibly close to everything. The Village of Pleasantville offers charming shops, restaurants, parks, and a lively downtown, all just a short distance away. Commuters will appreciate the easy access to the Metro-North Railroad station, making travel to NYC straightforward and convenient. One car garage is included. Attic area for additional storage. A rare combination of condition, location, and lifestyle, this is an excellent opportunity to enjoy low-maintenance living in one of Westchester’s most desirable villages.

73 Broadway Unit #2J, 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.