Pleasantville Homes under $1.5 million

Welcome to Pleasantville, New York—a charming gem nestled in the heart of Westchester County. Known for its quaint village atmosphere, Pleasantville offers a harmonious blend of suburban tranquility and vibrant community life. With tree-lined streets, historic architecture, and a welcoming spirit, it’s no wonder that this picturesque town has become a coveted destination for families and professionals alike.

Pleasantville boasts a rich cultural scene, highlighted by its renowned Jacob Burns Film Center, which showcases independent films and hosts engaging community events. The town also features beautiful parks, delightful local eateries, and boutique shops that add to its unique character. With highly-rated schools and a strong sense of community, Pleasantville is perfect for those looking to settle down in a nurturing environment.

For homebuyers seeking properties under $1.5 million, Pleasantville offers an impressive array of options. From charming single-family homes adorned with classic details to modern residences equipped with contemporary amenities, there’s something to suit every taste and lifestyle. Many homes are situated within walking distance to the train station, providing easy access to New York City for commuters.

Whether you’re looking for a cozy starter home or a spacious family residence, Pleasantville’s real estate market has a wealth of opportunities waiting for you. Embrace the idyllic lifestyle that this enchanting town has to offer, and discover why so many are proud to call Pleasantville home. Your dream home is just around the corner!

Newest Pleasantville Homes under $1.5 million

$850,000

3 Beds ⋅ 2 Baths ⋅ 1052833 MLS

Well-maintained two-family home ideally located in the heart of Pleasantville Village. Situated on a flat, usable lot, this property features a detached two-car garage plus ample driveway parking. Both kitchens and bathrooms have been updated, and the home offers low-maintenance vinyl siding and newer windows throughout. Key improvements include a roof approximately 14 years old and a furnace replaced just 8 years ago, providing added peace of mind. The full unfinished basement offers abundant storage space, mechanicals, and convenient walkout access. Enjoy the convenience of being just minutes from everything Pleasantville has to offer, including shopping, restaurants, delis, schools, the library, farmers market, parks, recreation facilities, and the Metro-North train station. With quick access to major highways and an easy commute to New York City, this property is an exceptional opportunity for both homeowners and investors alike.

7 Hopper Street, Pleasantville

$729,000

3 Beds ⋅ 1 Baths ⋅ 1050254 MLS

Welcome to 82 Birch Drive, a charming 3-bedroom, 1-bath home situated on two parcels along a quiet dead-end street in Pleasantville, offering a peaceful hillside setting surrounded by mature trees. Inside, hardwood floors throughout add warmth and character, while a beautiful arched doorway connects the living and dining rooms. The extended living room area features skylights and a high ceiling, bringing additional natural light and an open, airy feel to the space. The partially finished basement provides additional flexible space and was previously used as a home office, with additional areas available for storage and other needs. Outside, the two-parcel setting provides additional outdoor space to enjoy, along with ample parking. Located adjacent to Graham Hills Park, the home offers convenient access to outdoor recreation while remaining just minutes from the Pleasantville Metro-North station, downtown Pleasantville, shopping, dining, and major roadways. With its tranquil setting, hardwood floors, charming architectural details, extended living room, flexible lower-level space, ample parking, two-parcel property, and convenient location, 82 Birch Drive offers a wonderful combination of character, space, and convenience.

82 Birch Drive, Pleasantville

$1,225,000

4 Beds ⋅ 2 Baths ⋅ 1048225 MLS

Welcome to this beautifully situated 4-bedroom, 2-full-bath home in the heart of Pleasantville! Featuring a spacious primary bedroom, a large formal living room, and plenty of room to live, work, and entertain, this home offers both comfort and convenience. Enjoy the best of Pleasantville living with a truly walkable location close to schools, the train station, local farmers markets, and the popular Jacob Burns Film Center. A wonderful selection of restaurants, shops, and community amenities are all just moments away. With its inviting living spaces and unbeatable location, this home is a fantastic opportunity to enjoy all that Pleasantville has to offer!

1 Grandview Circle, Pleasantville

$619,000

2 Beds ⋅ 2 Baths ⋅ 1045921 MLS

Welcome to desirable Foxwood Condominiums in Pleasantville! A rare opportunity to unlock the full potential of this 2 bedroom 2 full bath Somerset unit. Entry Foyer with 2 Closets, Spacious Eat-in Kitchen with Dining area, additional Cabinetry, Formal Dining and Living Room with Picture Window and a Door Out to the Deck. Hall Bathroom, Hall Linen and Laundry Closets, Primary Bedroom with Primary Bath, Walk-in Closet and a 2nd Bedroom with sliding doors, closet. A true diamond in the rough. The property is being offered in its present condition. With the right vision, this home presents an opportunity to create a home tailored to your style in a sought after location. Heat and hot water are included in the common charges, along with full landscaping and snow removal. Amenities include 3 swimming pools, village tennis courts and playground. Foxwood is just minutes from everything Pleasantville has to offer, from Jacob Burns Film Center, to Saturday's Farmers' Market, to shopping, Restaurants, Metro north train and major highways.

16 Foxwood Drive Unit #8, Pleasantville

$689,000

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

590 Bedford Road Unit #1A, Pleasantville

$479,000

2 Beds ⋅ 1 Baths ⋅ 1036136 MLS

Easy One-Level Living, Just Six Minutes from the Village of Pleasantville. Enjoy the ease of true one-floor living in this first floor inviting two-bedroom condo, ideally located just a six-minute walk to the train and the heart of Pleasantville. With no steps, a detached garage, and low-maintenance ownership, this home offers the kind of convenience that makes everyday living simpler, and leaves more time to enjoy everything the village has to offer. The thoughtfully laid-out two-bedroom floor plan is equally appealing to buyers looking to downsize, first-time buyers ready to own, or anyone seeking an easy-to-maintain home in a walkable community. Everything you need is comfortably on one level, with no stairs to navigate and no exterior maintenance to worry about. Step outside and you're minutes from Pleasantville's shops, restaurants, the Jacob Burns Theater and the Metro-North train, making commuting or enjoying a spontaneous dinner and a movie downtown remarkably easy. The detached garage provides convenient parking and valuable storage, while the reasonable HOA helps keep ownership manageable. A rare combination for buyers looking for comfort, convenience, and an easy transition into their next chapter.

590 Bedford Road Unit #1A, Pleasantville

$1,125,000

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

$899,000

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

$1,325,000

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

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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.