27 Bedford Road, Pleasantville, NY

About 27 Bedford Road

Set in the desirable Village of Pleasantville, this enchanting Colonial home, built in 1830 and sited on .78 acres, offers timeless character, unique architectural details, and endless potential. A true diamond in the rough, this residence, dubbed "Pierce House", is ready to be transformed into something truly spectacular. Far from cookie-cutter, this home tells a story. With its original charm and distinctive presence, it inspires imagination and offers a rare opportunity to create something exceptional. The expansive covered front porch sets the tone—perfectly welcoming for guests and spacious enough for a row of rocking chairs or even a full picnic table for outdoor dining and gatherings. Inside, you'll find spacious common rooms, 2 woodburning fireplaces, 5 bedrooms/4 full bathrooms and multiple options for hybrid workspaces, creative studios, or flexible living/bedroom configurations. The picturesque grounds feature a gently meandering brook, a charming trellis and archway. A rare find in Pleasantville, the expansive lot also includes a private tennis court awaiting revival—well-suited for recreation or open-air entertaining. Driveway entrance on Pierce Drive. Enjoy the best of both worlds: located within the Village of Pleasantville—with its cherished community traditions and vibrant local amenities—yet also in close proximity to the Chappaqua train station and town (sidewalk recently installed for improved access and safety). A one-of-a-kind opportunity to bring new life to a home rich with history, set in a location that blends charm, convenience, and character.

Listing Map