Real Estate in Pawling, NY

Village charm, Appalachian Trail access, and Metro-North convenience in southeastern Dutchess.

Pawling is one of the most complete small towns in Dutchess County. It has a walkable village center, a Metro-North station with direct service to Grand Central, access to the Appalachian Trail, and a residential market that ranges from affordable condos to luxury estates. The Pawling Central School District is well-regarded, and the town's location along Route 22 puts it close to the Connecticut and Putnam County borders. Buyers relocating from Westchester or NYC consistently discover Pawling as the sweet spot where commuter access meets genuine small-town living.

Here's What You Get:

  • 1Metro-North commute analysis — real door-to-door times from Pawling station to Midtown.
  • 2Village, hamlet, and rural inventory coverage across every price point.
  • 3School district and community insight that helps relocating families make confident decisions.
Ryan Sylvestri

Ryan Sylvestri

Licensed Associate Real Estate Broker | ABR® | PSA

RE/MAX Town & Country | (845) 867-2646

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Pawling NY Real Estate | Homes for Sale | Hudson River Realtors