Refine Search
Sort by
$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

$819,000
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

board logo

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.