168 Old Route 55, Pawling, NY 12564

• 2 beds |
• 2 baths |
• 2,196 sqft

Property 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.

Listing Status:

Active

Data Last Updated:

May 11, 2026 at 7:20AM

Listing Office:

McGrath Realty Inc : 845-855-5550

MLS ID:

954200

Interior

• General: Beamed CeilingsBuilt-in FeaturesEat-in KitchenNatural WoodworkOriginal DetailsWalk Through Kitchen
• Appliances: DishwasherDryerElectric RangeMicrowaveRefrigeratorStainless Steel Appliance(s)Washer
• Basement: FinishedFullWalk-Out Access
• A/C: Electric
• Heating: ElectricOtherWood
• Fireplace: BasementLiving RoomWood Burning StoveFireplaceFireplaces: 2

Exterior

• General: LightingMailbox
• Style: Other
• Other Structures: Garage(s)Patio
• Parking: DrivewayGarageParking spaces: 6

Construction

• Windows: Oversized WindowsWood Frames
• General: Three Or More

Location

• Road/Access: Municipal
• Originating MLS: onekey2
• School District: Arlington
• County: Dutchess County

Lot

• Zoning: 134089-6857-00-454889-0000
• Fencing: Back Yard

Utilities

• Utilities: Cable AvailableElectricity ConnectedPhone AvailableWater Connected
• Water: Well
• Sewer: Septic Tank

Financial

• Source: onekey2