Step into the year our nation was born and own a piece of living American history. Originally constructed in 1776 by a Scottish stone mason and frontiersman, who fought in two Revolutionary War battles, this enduring stone home is more than a residence; it's a survivor. Once known as the Pawling Toll Gate and Toll House, it served as a gateway for travelers, a general store, a post office, and a gathering place woven into the early fabric of the region. Inside, the home carries its history with quiet strength. Hand-hewn beams stretch across the ceilings. Deep-set windows draw in southern light. Original fireplaces, now fitted with wood stove inserts, anchor the space. Wide-plank wood floors, laid in defiance of British colonial restrictions, remain underfoot, worn smooth by time, not replaced. The home offers 2 bedrooms and 2 full baths, with a layout that is both grounded and adaptable. The lower level provides a private, flexible space, ideal for a studio, retreat, or guest quarters. Outside, 2.2 acres open directly to the Empire State Trail and offer immediate access to the Appalachian Trail, putting miles of riding, hiking, and exploration right at your doorstep. This isn't nearby, it's connected. Behind the home, a substantial ~1,000 sq ft detached garage provides space for four or more vehicles, along with room for equipment, workshop use, or future conversion. It's not an afterthought, it's an asset. Located just minutes from the village of Pawling, Metro-North, shops, and dining, the property balances seclusion with accessibility. This is not just a home, it's a piece of early American infrastructure that has endured, adapted, and remained. Built by hand, shaped by history, and still standing with purpose.
Estimated Payment
$ 3,982.49 per month $2,856.95 Principal & Interest $960.75 Property Tax $164.79 Homeowner's InsuranceListing By
Agency Name: McGrath Realty Inc
Agency Contact: 845-855-5550
Shown By
Agent Name: Frank DeLucia
Agent Phone: (516) 578-2212
Agency Title: Coldwell Banker American Homes
168 Old Route 55 | MLS# 954200
This single family home located at 168 Old Route 55, Pawling, NY 12564 is currently listed for sale with an asking price of $565,000. This property was built in 1776 and has 2 bedrooms and 2 full baths with 2196 sq. ft. Old Route 55 is located within the Arlington school district. Search Pawling real estate on frankdelucia.cbamhomes.com today.