Pleasantville Real Estate

Welcome to Pleasantville, New York – a charming village nestled in the heart of Westchester County, known for its picturesque landscapes and vibrant community spirit. One of the standout features of this delightful area is its exceptional school district, which is highly regarded for its commitment to academic excellence and holistic student development.

The Pleasantville School District is dedicated to fostering a nurturing environment where children can thrive both academically and socially. With a focus on personalized learning, the district offers a wide range of programs that cater to diverse learning styles and interests. From advanced placement courses to innovative arts and athletics programs, students are encouraged to explore their passions while receiving a robust education.

Parents can take pride in the fact that Pleasantville's schools consistently receive high ratings for their performance, with dedicated educators who are committed to inspiring and guiding the next generation. The district emphasizes not only academic achievement but also character development, ensuring that students grow into well-rounded individuals ready to contribute positively to society.

In addition to strong academic offerings, the Pleasantville School District is actively involved in the community, fostering partnerships with local organizations and encouraging parental engagement. This collaborative spirit creates a supportive network that enriches the educational experience for students and families alike.

Choosing to settle in Pleasantville means investing in a future filled with opportunity for your children. With its top-notch schools, friendly neighborhoods, and a wealth of extracurricular activities, Pleasantville is a place where families can truly thrive. Come discover the magic of this community and see why so many are proud to call it home!

Newest Listings in Pleasantville

$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

$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

$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

$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

$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

$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

$875,000

4 Beds ⋅ 2 Baths ⋅ 996830 MLS

NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday living and entertaining. The spacious living room provides the ideal setting for gatherings and holidays, while multiple freshly stained multi-level decks create seamless indoor-outdoor living perfect for entertaining, summer barbecues, or relaxing evenings overlooking the expansive park-like property. The large yard offers endless possibilities for play, gardening, and recreation, plus three storage sheds for added convenience. Also included is a 11'x54' triangular shaped lot on north side of primary lot. .46 Acre Total Recent updates including a newer roof and boiler provide peace of mind, while the attached garage adds practicality and storage. Commuters will love the easy 5-minute walk to the Chappaqua train station with approximately 45-minute access to Grand Central Terminal. Rarely offered, this home also includes FREE school bus pickup within Pleasantville’s walking district. Ideally located just minutes from the farmers market, shops, restaurants, parks, and Metro-North, this move-in ready home delivers comfort, charm, and an exceptional lifestyle in one of Westchester’s most sought-after communities. Easy to show same day showings are ok now.

249 Mill River Road, Chappaqua

$199,000

1 Beds ⋅ 1 Baths ⋅ 983906 MLS

COMMONS OF PLEASANTVILLE. This beautifully updated one-bedroom Co-op in the charming Village of Pleasantville NY, offers the perfect blend of style and convenience . The unit features a brand new kitchen with sleek stainless steel appliances, a newly renovated bath, rich wood floors, and impressive high ceilings that create a bright and airy feel. Ideally located just moments from the metro-north train, commuting to NYC is a breeze, while the vibrant downtown-filled with shops, restaurants, cafes, farmers market, parks and The Jacob Burns Film Center. This unit is a wonderful opportunity for comfortable, low maintenance living in a highly desirable community.

310 Manville RD Unit #S4, 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.