Pleasantville Homes with Attached Parking features

Welcome to Pleasantville, a charming village nestled in the heart of Westchester County, NY. Known for its scenic beauty and vibrant community, Pleasantville offers an exceptional quality of life that appeals to families, professionals, and retirees alike. One of the standout features of this delightful area is its highly regarded school district, which consistently ranks among the top in the state. Pleasantville School District is dedicated to fostering academic excellence and personal growth, providing students with a well-rounded education that prepares them for success in their future endeavors.

The district boasts a range of educational programs, dedicated teachers, and a strong sense of community involvement, ensuring that every child receives the support they need to thrive. With small class sizes and a commitment to innovative teaching methods, parents can feel confident that their children are receiving a top-notch education.

In addition to its stellar schools, Pleasantville is also home to a variety of beautiful homes, many of which come with attached parking features. This is a significant advantage in a bustling area, providing homeowners with the convenience of easy access to their vehicles while eliminating the hassle of street parking. Whether you’re looking for a cozy bungalow or a spacious family home, Pleasantville offers a diverse selection of properties that cater to various lifestyles and preferences.

Experience the charm of Pleasantville, where a strong sense of community, excellent schools, and beautiful homes with attached parking await you. Come and discover why so many choose to call this enchanting village home!

Newest Pleasantville Homes with Attached Parking features

$599,000

3 Beds ⋅ 1 Baths ⋅ 1030292 MLS

First time on the market in over 50 years—an exciting opportunity to create something truly your own in an exceptional location! Ideally situated between the vibrant Villages of Pleasantville and Chappaqua, this split-level home offers a wonderful canvas for its next owner to renovate, reimagine, and make their own. Inside, hardwood floors and abundant natural light set the stage for a fresh transformation. The main level offers excellent potential to create the open-concept kitchen, living, and dining space, so desirable for today’s lifestyle, with convenient access to the deck and backyard—perfect for entertaining, dining outdoors, or simply enjoying your own private outdoor space. Upstairs, three comfortable bedrooms and a full bath provide a traditional bedroom level, while the lower level offers valuable additional space with endless possibilities for a recreation room, home office, gym, or den, along with laundry, utilities, and garage access. And then there’s the location!! Enjoy the best of both Pleasantville and Chappaqua, with acclaimed restaurants, farmers markets, shops, the Jacob Burns Film Center, and Metro-North all nearby. Located within the highly regarded Pleasantville School District and approximately 1.5 miles from the Pleasantville train station and 0.8 mile from Chappaqua’s, commuting to NYC is a breeze. Bring your vision and create the home you’ve been waiting for—in a location that’s already hard to beat. Sold As Is.

582 Washington Avenue, Pleasantville

$750,000

3 Beds ⋅ 2 Baths ⋅ 1048774 MLS

Live in the heart of Pleasantville in a home as distinctive as its location. Just 0.4 mile from Metro North and moments from the village center, 3 Elm Street pairs an exceptionally convenient location with interiors that feel anything but expected. Fully renovated, this three bedroom Colonial features dark painted trim, rich color, patterned wallpaper and thoughtfully chosen finishes that give the home a collected, design forward feel. The formal dining room makes a memorable first impression, while the renovated kitchen mixes soft gray cabinetry, graphic flooring and a substantial center island. The adjoining living room is bright and comfortable, with direct access to the patio and fenced backyard. An oversized garage offers tremendous potential for a workshop, studio, gym or additional storage, while the generous driveway provides parking for multiple cars. Outside, the patio and fenced yard extend the living space with room for dinner, a garden or a quiet afternoon at home. This is an exceptional entry point into Pleasantville and the lifestyle that comes with it. Walk into the village for coffee, dinner or a show. Spend Saturday morning at the farmers market. Walk to Metro North for the commute into Manhattan, or enjoy the dog park, parades, festivals and community events throughout the year. There is an extraordinary amount of life packed into this 1.8 square mile village, and 3 Elm Street puts you right in the heart of it. This is a home that makes it remarkably easy to become part of the community around it.

3 Elm Street, 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

$849,999

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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