USANYPawling168 Old Route 55
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$565,000

For Sale

3 months ago

168 Old Route 55, Pawling, NY

House

MLS® 954200

2 Bed

2 Bath

2196 sqft

6 Parking

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 2196 sqft
Garage Yes
Taxes $11,529
Days Active 84
Lot Size 
Approx. Age 1776
Avg. Price Per Sqft $257
MLS® Number 954200

Property Address: 168 Old Route 55, Pawling, NY, 12564-2210

Average square foot calculated using Size range provided by listing agent.

Description

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.
MLS® Number954200
Laundry Level
Central VacNo
FireplaceNo
Acreage
Exterior
GarageYes
Approx. Age1776
BasementFinished, Full, Walk-Out Access
DrivewayDriveway, Garage
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Bathroom 1:Second FloorNot available
Kitchen:First FloorNot available
Bedroom 1:Second FloorNot available
Living Room:First FloorNot available
Dining Room:First FloorNot available
Laundry:Lower LevelNot available
Bedroom 2:Second FloorNot available
Media Room:Lower LevelNot available
Bathroom 2:Lower LevelNot available

Price History

-End Date
Not Sold YetSold Price

For Sale

Feb 5, 2026List Date
$565,000List Price
  • Commute

Commute

Starting Address
Destination Address
168 Old Route 55, Pawling, NY

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