Chappaqua Homes with Pleasantville School district

Welcome to Chappaqua, New York, a charming hamlet nestled in the heart of Westchester County. Known for its picturesque landscapes and quaint, small-town atmosphere, Chappaqua offers residents a perfect blend of suburban tranquility and vibrant community life. With its tree-lined streets, historic architecture, and a strong sense of community, this idyllic locale has become a sought-after destination for families and professionals alike.

Chappaqua boasts a rich history, with roots dating back to the 1700s. Today, it is celebrated not only for its scenic beauty but also for its exceptional educational opportunities, particularly within the highly regarded Pleasantville School District. Families moving to Chappaqua will appreciate the commitment to academic excellence and the nurturing environment that the district provides. With top-notch schools, dedicated teachers, and a wide array of extracurricular activities, children in this area are well-prepared for future success.

The real estate market in Chappaqua offers a diverse range of homes, from charming colonial-style houses to modern architectural gems. Each property is surrounded by lush greenery, providing a serene escape just a short commute from New York City. With its proximity to major highways and the Metro-North train station, residents enjoy easy access to the hustle and bustle of the city while being able to retreat to their peaceful suburban oasis at the end of the day.

In Chappaqua, you’ll find not just a home, but a lifestyle—one filled with community events, local shops, and beautiful parks. Discover why so many families choose to call Chappaqua home, and experience the warmth and charm of this captivating hamlet for yourself!

Newest Chappaqua Homes with Pleasantville School district

$875,000

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

Start Your Search

© 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.