Pleasantville Homes under $1.5 million

Welcome to Pleasantville, New York – a charming village nestled in the heart of Westchester County, renowned for its rich history, vibrant community, and exceptional school district. With its picturesque tree-lined streets and a close-knit atmosphere, Pleasantville is the perfect place for families seeking a welcoming environment.

The Pleasantville School District is celebrated for its commitment to academic excellence and holistic student development. With a diverse array of educational programs and dedicated faculty, students are encouraged to explore their interests and reach their full potential. The district encompasses several highly-rated schools, each fostering a love for learning and a strong sense of community. Parents can rest easy knowing their children are receiving a top-notch education, with numerous extracurricular activities that promote creativity, teamwork, and leadership skills.

For those looking to make Pleasantville their home, the real estate market offers a fantastic selection of homes under $1.5 million. Whether you’re searching for a cozy single-family residence, a charming colonial, or a contemporary gem, you’ll find a variety of options that cater to different tastes and lifestyles. Many homes boast spacious yards, modern amenities, and easy access to local parks, shops, and dining.

Living in Pleasantville means embracing a lifestyle that beautifully blends suburban tranquility with urban accessibility. With its excellent school district, welcoming community, and diverse housing options, Pleasantville is not just a place to live – it’s a place to thrive. Come discover your dream home in this idyllic village!

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

$929,000

4 Beds ⋅ 3 Baths ⋅ 1051611 MLS

Welcome to this inviting 4-bedroom, 2.5-bath home ideally located just outside the heart of Pleasantville Village. Enjoy the convenience of being within easy walking distance to town, with its restaurants, shops, entertainment, and everyday amenities. The home offers a flexible layout with a private in-law/guest suite, perfect for extended family, guests, or additional living space. A spacious backyard provides plenty of room for outdoor entertaining, play, gardening, or simply relaxing. A wonderful opportunity to enjoy the best of Pleasantville living in a convenient, walkable location

1 Brookfield Place, Pleasantville

$739,000

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

$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

$785,000

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

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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.