25 Old Route 55, Pawling, NY 12564

Description

Tucked away on five scenic acres in Pawling, this charming old farmhouse has quite the history. Originally built across the road, the house was quite literally picked up and moved across the creek to its current setting, where open lawns, mature trees, and a wooded hillside create a beautiful little world of its own.
Getting here is part of the charm. Cross a small bridge over the creek that borders the front of the property, follow the driveway in, and discover a classic country farmhouse surrounded by greenery, with a generous clearing that gently rises toward the forest. The property offers a lovely mix of open space and woodland, with a rustic outbuilding tucked among the trees and plenty of room to imagine what comes next.
Inside, there’s much to love. A slate-floored foyer welcomes you into the living room, where hardwood floors, warm wood trim, built-in shelving, and a substantial fireplace give the space its character. Large windows bring in beautiful natural light, while the adjoining dining room features French doors overlooking the grounds and an original wood staircase leading upstairs.
The kitchen has a functional layout, ample cabinetry, and a window overlooking the backyard and wooded hillside beyond. It’s easy to picture what this space could become with a thoughtful refresh, whether that’s a few simple updates or a completely reimagined Hudson Valley farmhouse kitchen. A full bathroom, generously sized laundry room, and two additional outdoor access points round out the first floor.
Upstairs, you’ll find three bright bedrooms with hardwood floors, including one with a sizable walk-in closet that could also serve as a small flex space. The second full bathroom is a delightful little time capsule, complete with vintage blue fixtures, double sinks, and a matching blue tub.
Outside, the possibilities extend well beyond the house. Picture gardens, long afternoons on the lawn, an outdoor dining area, or simply enjoying the changing seasons from your own five-acre retreat. The combination of open space, surrounding woods, and creek frontage makes this a particularly special setting.
With its classic farmhouse character, beautiful natural light, and wonderfully private setting, there’s already so much to appreciate here. The home would benefit from some TLC and thoughtful updates, whether your vision is to preserve its vintage charm or give it a more contemporary Hudson Valley feel. A special opportunity to make an old country house your own, with five lovely acres to enjoy along the way.
Just minutes from the charming Village of Pawling and its Metro-North station, with local favorites like McKinney & Doyle, Daryl’s House for live music, and independent shops and cafes to explore. Outdoor enthusiasts will appreciate nearby access to the Appalachian Trail, Great Swamp, and Pawling Nature Reserve, while the surrounding Harlem Valley offers farm stands, scenic backroads, and endless opportunities to get outside. And with the George Washington Bridge approximately 90 minutes away, a little country living doesn’t have to mean leaving the city too far behind.