Pleasantville Real Estate

Welcome to Pleasantville, New York – a charming village nestled in the heart of Westchester County that perfectly blends small-town charm with modern conveniences. With its picturesque streets, vibrant community, and rich history, Pleasantville offers an idyllic setting for families, professionals, and retirees alike.

Pleasantville is renowned for its stunning landscapes, featuring lush parks and scenic walking trails that invite residents to embrace the great outdoors. The village is home to the beautiful Rockefeller State Park Preserve, where you can explore miles of hiking paths framed by serene woodlands and tranquil streams. For those who appreciate the arts, Pleasantville boasts a thriving cultural scene, highlighted by the Jacob Burns Film Center, which showcases independent films and hosts engaging community events.

Education is a cornerstone of Pleasantville, with its highly-rated schools that prioritize academic excellence and foster a nurturing environment. Families can rest assured knowing their children are receiving a top-notch education in a supportive community.

Conveniently located just 33 miles north of Manhattan, Pleasantville offers easy access to major highways and the Metro-North Railroad, making it an ideal location for commuters. The village features a delightful downtown area filled with boutique shops, inviting cafes, and delicious dining options, ensuring that residents have everything they need right at their fingertips.

Whether you’re looking to settle down or invest in a vibrant community, Pleasantville is a hidden gem that promises a quality of life that is hard to beat. Discover the warmth and charm of this delightful village – your new home awaits!

Newest Listings in 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

$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.