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

$724,900

4 Beds ⋅ 1 Baths ⋅ 1047856 MLS

Nestled in the midst of an idyllic, tree-filled, half-acre setting, this charming, character-filled gem is ideal for working from home, relaxing and entertaining! Upon entry, the foyer opens to a formal living room with several architectural features of note -- a beautiful arched, vaulted ceiling, hardwood floors and a fireplace with stone trim. At the opposite end of the room is a huge picture window with expansive views of the glorious outdoors. Also on this level is a generously-proportioned master bedroom with custom woodwork and 4 windows that allow in natural light and views of the unspoiled park land located directly in front of this home. Three additional bedrooms are also on this level, one of which is currently used as an office. Step downstairs to a remodeled kitchen with a pocket door to a large, clean all-purpose room. Doors from this room and the kitchen lead out to an expansive stone patio with views over the property and out to the street. Guests can transition easily from the all-purpose room to the patio. Custom woodwork and built-ins are evident throughout this home, as well as upgraded lighting, shed ceilings and other notable features which give it a unique, eclectic style. Once outdoors, the large property lends itself to privacy, and yet there is ample room for gardening, for fur babies to roam and for relaxation and basking in the sun. Everything is here to conveniently work from home. However this home's proximity to the Pleasantville Metro-North Station makes commuting to New York City an equally desirable option. This home must be seen in person to be appreciated!

45 Leroy Street, Pleasantville

$1,300,000

3 Beds ⋅ 4 Baths ⋅ 1042845 MLS

Enjoy this beautifully updated, and stylishly appointed, corner unit home in the highly desirable Pleasantville Country Club community. You will appreciate the ease of a maintenance-free, resort-style living, where you can spend more time enjoying the wonderful amenities and less time worrying about upkeep. Offering three levels of spacious living, the home welcomes you with a dramatic two-story entryway leading to inviting living and dining rooms. The main level also features a comfortable family room with fireplace and an open kitchen with a sunny breakfast nook complete with built-in banquette seating. Sliders leading to a private deck overlooking the 6th hole of this beautiful golf course and a powder room finish off the main floor. The second floor offers a primary bedroom with ensuite bath and WIC, a second bedroom with an ensuite bath, along with a flexible office space or third bedroom featuring custom built-ins, ideal for working from home. The finished lower level provides a full bath and an expansive recreation room with sliders leading to a lower patio, creating additional space for entertaining, relaxing or enjoying the peaceful golf course setting. For added convenience and ease of living, the home includes an elevator and a two-car garage. Residents of the Pleasantville Country Club enjoy a well manicured property framed by perennial gardens and exceptional amenities including a golf course, tennis/pickleball, pool and clubhouse, all while enjoying a truly easy and convenient lifestyle. Additionally, this home is in the award winning Pleasantville school district and residents can enjoy the Farmers Market, Jacob Burns Theater, restaurants, shops and all that the charming village has to offer.

29 Country Club Lane, Pleasantville

$479,000

2 Beds ⋅ 1 Baths ⋅ 1036136 MLS

Easy Living in the Heart of Pleasantville! Welcome to this beautiful two-bedroom, first-floor condo in the desirable Greenwood Condominiums, offering no steps and effortless one-level living. Freshly painted and filled with natural light, this spacious home features a welcoming living room, updated kitchen with stainless steel appliances, warm wood cabinetry and a convenient breakfast bar, along with beautiful hardwood floors throughout. A detached one-car garage provides covered parking and additional storage. The location is hard to beat! Just steps from the Metro-North train station, Farmers Market, Jacob Burns Film Center, schools, shops, restaurants, and all that the Village of Pleasantville has to offer. Whether you're a first-time buyer, downsizing, or simply looking for a home that makes everyday life easier, this is easy living in an unbeatable village location.

590 Bedford Road Unit #1A, Pleasantville

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 1042508 MLS

There’s something truly special about this captivating Pleasantville Craftsman. It has the kind of charm and character that is hard to find in newer homes, along with a wonderful location right in the heart of Pleasantville. The moment you enter, you’ll notice the hardwood floors, large windows, and abundance of natural light filling the rooms. But the real star of the show may be the oversized front porch. It’s the kind of porch that makes you want to slow down, sit for a while, and enjoy the company of friends. Use it as a place to entertain, read the newspaper, enjoy your morning coffee, or simply relax. It truly feels like a second living room and adds so much to the personality of this home. The house has been recognized for its charm and has even been featured on Pleasantville home tours. There’s also plenty of opportunity to make the home work for your needs. The attic space could potentially be transformed into a primary bedroom suite, home office, study, playroom, or whatever space your wishes desire. You’re just blocks from Bedford Road Elementary, the library, the middle and high schools, and both uptown and downtown Pleasantville. Stroll to town for dinner, grab a coffee, browse the shops, catch a movie at the coveted Jacob Burn’s theatre or enjoy the many community events that make Pleasantville such a great place to live. The Metro-North station is also right in town making the commute to New York City and White Plains super convenient. For those who love the outdoors, Rockefeller State Park Preserve, Opperman’s Pond, the amazing Pleasantville town pool and other nearby parks offer beautiful places to walk, hike, and enjoy nature. The Pleasantville Music Festival and frequent town concerts contribute to the cultural elements that make this town one of a kind. This is a home with personality, history, and possibilities. You can move right in and enjoy it as it is or take advantage of the additional space and make it your own. If you’ve been looking for a home that feels welcoming the minute you arrive—and a community where you can truly put down roots—this Pleasantville Craftsman is a must see!

35 Grandview Avenue, Pleasantville

$879,000

3 Beds ⋅ 2 Baths ⋅ 1043937 MLS

Beautifully maintained and lovingly cared for, this inviting home is nestled on a private cul-de-sac and offers a true sense of sanctuary. The main level is filled with natural sunlight from large windows and two sliding glass doors, creating a warm and welcoming atmosphere throughout. The spacious living room features sliding glass doors leading to an expansive deck, seamlessly connecting the indoor and outdoor living spaces. The deck opens directly to both the kitchen and living room, making entertaining a breeze. The elegant dining room is highlighted by a picturesque bay window, while the eat-in kitchen offers granite countertops, stainless steel appliances, and sliding doors providing easy access to the deck. Three generously sized bedrooms, each with ample closet space, and a beautifully appointed full bathroom complete the main level. The finished lower level adds even more living and entertaining space, featuring a large family room with a stunning floor-to-ceiling stone fireplace and sliding glass doors leading to a covered patio. This private outdoor retreat is perfect for summer gatherings or relaxing with a favorite drink and watching TV—even on a rainy day. A versatile bonus room, ideal as a office, den or guest space, offers generous closet space, with an additional full bathroom conveniently located nearby. The fenced-in backyard provides added privacy and completes this wonderful outdoor setting. With a one-car attached garage and convenient nearby school bus pickup, this home is truly move-in ready. Simply unpack, settle in, and enjoy! Notable items: Driveway can hold 5 cars in addition to one car garage, school bus pickup steps from home, 6 zone built in ceiling speakers with Bluetooth easy connect lets you enjoy different music in different rooms or join them all together lastly, all light switches are smart so you can program them with your phone. A true delight!

3 Douglas Drive, Pleasantville

$389,000

1 Beds ⋅ 1 Baths ⋅ 1027741 MLS

Welcome to Pleasantville! This bright and inviting second-floor one-bedroom condo at Greenwood Condominium offers a wonderful blend of mid-century charm, thoughtful updates, and an unbeatable village location. Freshly painted and featuring brand-new Berber carpeting, this sun-filled home enjoys serene views of beautifully landscaped grounds. The spacious layout includes an expansive living and dining area, a generously sized bedroom, a full hall bath with tub and impressive closet space. The updated bath adds a fresh, modern touch while maintaining the home's comfortable character. A major bonus is the deeded one-car garage, providing covered parking and ample additional storage. The complex also offers plenty of guest parking, with convenient common laundry nearby. Ideally located in the heart of the Village of Pleasantville, you will l be just steps from the Pleasantville Metro-North station, renowned Jacob Burns Film Center, local restaurants, boutique shops, the popular Pleasantville Farmers' Market, Pleasantville schools, and Pace University's campus. Enjoy the convenience of village living with easy access to everything Pleasantville has to offer. With low monthly HOA fees and annual property taxes, this is a fantastic opportunity to own in one of Westchester's most desirable communities. A wonderful home in an exceptional location—this one will not last!

590 Bedford Road Unit ##22, Pleasantville

$1,900,000

1039538 MLS

Mixed-Use Investment Opportunity – Old Village of Pleasantville Rare mixed-use investment opportunity in the heart of the Old Village of Pleasantville. This distinctive Tudor-style property, originally constructed circa 1930, occupies a highly visible corner location at the southwest intersection of Broadway (Route 141) and Bedford Road. The property consists of four residential apartments and two retail storefronts, providing a diversified income stream from both residential and commercial tenants. The retail component includes Don Juan Restaurant, a well-established neighborhood fixture that has operated at the property for approximately 16 years, and Frankie’s Barber Salon, which has been a tenant for approximately 10 years. The long-term tenancy demonstrates the strength and stability of this location. The property benefits from approximately 10,000 vehicles passing the intersection daily, providing excellent exposure for the commercial tenants. The surrounding area is supported by a strong mix of established local businesses, including Bistro 146, Craft Pizza & Beer, Veterinary Care of Mt. Pleasant, and Phillips 66 Gas & Convenience Store.The Pleasantville Metro-North Train Station and Village Center are located less than one mile away, further enhancing the property's appeal to both residential and commercial tenants.

2 Broadway, Pleasantville

$925,000

3 Beds ⋅ 2 Baths ⋅ 1027975 MLS

ATTENTION 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

$1,399,000

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

$259,000

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

$995,000

1011121 MLS

Excellent location for a stand-alone building with great street exposure. Parking for approximately 10-12 cars. RO-3 zone allows a blend of residential and light commercial applications, including: Residential (1,2,3-family dwellings) Commercial (Professional business offices, retail stores, and mixed-use buildings). See the vision and make this space your own with some lite renovations. This building is also for lease - inquire within.

479 Marble Avenue, Pleasantville

$2,725,000

867179 MLS

The Marmaduke Forster House, nestled in the heart of Pleasantville, New York, is a living testament to history and architectural magnificence. This remarkable property, defined by its Queen Anne Victorian elegance and historic significance, offers an unparalleled opportunity for those pursuing a unique and promising investment in office spaces. The property comprises 13 offices, boasting a remarkable track record of consistently low vacancy rates. With a history dating back to 1785, the Marmaduke Forster House is a prominent staple in the Pleasantville community. Recognized by the Department of the Interior on its list of National Historic Places, this property showcases a wealth of historical context and heritage. Approaching this property, the immediate allure of architectural excellence is undeniable. The stately columns, symmetrical facade, and welcoming gabled roof draw attention, creating a striking first impression. The meticulously landscaped gardens and ample parking enhance the property's charm and functionality, ensuring an elegant and practical workspace. As you enter the property, you are transported to an era of luxury and meticulous craftsmanship. The grand entrance foyer, marked by soaring ceilings and intricate moldings, extends a warm embrace. Every corner has period-appropriate details, from original fireplaces to ornate woodwork. The Marmaduke Forster House offers versatile office spaces, accommodating diverse businesses and professional services. While preserving its historical charm, the Marmaduke Forster House was equipped with contemporary amenities. Updated HVAC and electrical systems ensure comfort and efficiency, while high-speed internet connectivity keeps your operations running smoothly. Additionally, modern kitchens and restroom facilities deliver convenience for all occupants. Pleasantville, New York, is experiencing a significant growth and redevelopment period. This thriving community is witnessing new development projects and revitalizing existing infrastructure. It's an exciting time for Pleasantville as it embraces the future while preserving its rich historic heritage. The property boasts a prime location within the village with many advantages. Easily accessible, it enjoys proximity to major highways and public transportation. The neighborhood provides numerous amenities, encompassing dining, shopping, and recreational activities. The Marmaduke Forster House is a rare and invaluable opportunity for prospective owners to acquire a piece of Pleasantville history. Its enduring architectural allure, versatile office spaces, and contemporary amenities highlight its status as a sound investment. Take the chance to make this unique property your own. Contact us today.

413-415 Bedford 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.