Price Reduced 5.68%
Price History
$599,000
2/5/2026
$565,000
4/22/2026
168 Old Route 55, Pawling, NY, 12564
8 rooms
2 beds
2 Full baths
1776
Other
2,196 sqft
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.
Status:
Active
Type:
Single-family residential
Garage:
2-car
Heating:
Electric, Other, Wood
Cooling:
Electric
Basement:
Finished, Full, Walk-Out Access
Parking:
6-car, Driveway, Garage
Acreage:
2.2
Est. Taxes:
$11,529
Assessment
$156,800
Construction
Stone
Utilities
Cable Available, Electricity Connected, Phone Available, Water Connected
Lot Description:
Back Yard, Part Wooded, Private
Elementary School:
Beekman
Middle School:
Union Vale Middle School
High School:
Arlington High School
School District:
Arlington
Days on Market:
79
Appliances:
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
MLS #:
954200
Community Info
School Info
Walk Score
Mass Transit
Yelp
Listing courtesy of McGrath Realty Inc 845-855-5550