168 Old Route 55, Pawling, NY 12564

• 2 beds |
• 2 baths |
• 1,428 sqft

Property Description

Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a bet by lifting a 400lb hogshead of beer. Inside, the home breathes character. Hand-hewn beams stretch across the ceilings, deep-set windows welcome the southern sun, and original fireplaces with wood stove inserts serve as the heart of the home. You’ll walk on wide-plank "King’s Wood" floors (massive boards harvested in colonial defiance of the British Crown) that have felt the footsteps of figures like Emilio "Dee" DaBramo. While the history is meticulously preserved, the convenience is modern, featuring a kitchen with custom wood cabinetry, granite countertops and sleek stainless-steel appliances. With 2 bedrooms and 2 full baths, the layout is both intimate and versatile. The lower level offers a private sanctuary perfect for an artist’s studio, a quiet writer’s retreat, or a distinctive guest suite. Outside, the 2.2 acre property is a nature lover’s dream. Groomed trails wind through the land, passing dramatic natural stone features and leading directly to New York State land and the Appalachian Trail. Enjoy direct access to vast untouched nature while ensuring your backyard remains a private, wooded vista forever. Directly across the road, the Maybrook Trailway offers miles of adventure for cyclists and explorers. A two-story, two-car detached garage sits perched on the hill, offering even more potential for storage or creative conversion. Find yourself less than 10 minutes away from boutiques, restaurants, Pawling train station and the grocery store. This isnt just a house; it’s a legacy in a great location. From storied stone walls to the premium modern finishes, every inch of this home has been meticulously maintained to honor it’s 250-year legacy. From its revolutionary roots to its modern-day charm, this is a property without equal.

Listing Status:

Active

Data Last Updated:

February 7, 2026 at 11:21PM

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