168 Old Route 55, Pawling, NY 12564
Local realty services provided by:ERA Insite Realty Services
168 Old Route 55,Pawling, NY 12564
$565,000
- 2 Beds
- 2 Baths
- 2,196 sq. ft.
- Single family
- Active
Listed by: colleen mcgrath, valerie j. port
Office: mcgrath realty inc
MLS#:954200
Source:OneKey MLS
Price summary
- Price:$565,000
- Price per sq. ft.:$257.29
About this home
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....
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Home facts
- Year built:1776
- Listing ID #:954200
- Added:97 day(s) ago
- Updated:May 14, 2026 at 10:41 AM
Rooms and interior
- Bedrooms:2
- Total bathrooms:2
- Full bathrooms:2
- Rooms Total:8
- Dining Description:Eat-In Kitchen
- Kitchen Description:Dishwasher, Eat-in Kitchen, Microwave, Refrigerator, Stainless Steel Appliance(s), Walk Through Kitchen
- Basement:Yes
- Basement Description:Finished, Full, Walk-Out Access
- Living area:2,196 sq. ft.
Heating and cooling
- Heating:Electric, Wood
Structure and exterior
- Year built:1776
- Building area:2,196 sq. ft.
- Lot area:2.2 Acres
- Lot Features:Part Wooded, Private
- Construction Materials:Stone
- Levels:3 Story
Schools
- High school:Arlington High School
- Middle school:Union Vale Middle School
- Elementary school:Beekman
Utilities
- Water:Well
- Sewer:Septic Tank
Finances and disclosures
- Price:$565,000
- Price per sq. ft.:$257.29
- Tax amount:$11,529 (2025)
Features and amenities
- Appliances:Dishwasher, Dryer, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry features:Dryer, Washer
Parking
- Total parking spaces:6
- Parking description:Driveway, Garage
- Garage:Yes
- Garage spaces:2
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