Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
Listing photo for 168 Old Route 55, Pawling, NY
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168 Old Route 55,

Pawling, NY

$599,000

2 Beds
2 Baths
1,428 Sqft
2.20 Acres
2 Garages

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.

Facts & Features
MLS® # 954200
Price $599,000
Bedrooms 2
Bathrooms 2.00
Full Baths 2
Square Footage 1,428
Acres 2.20
Year Built 1776
Type Residential
Sub-Type Single Family Residence
Style Other
Status Active
MLS hgmls
Community Information
Address 168 Old Route 55
City Pawling
County Dutchess
State NY
Zip Code 12564
Amenities
Utilities Cable Available, Electricity Connected, Phone Available, Water Connected
Parking Spaces 6
Parking Driveway, Garage
# of Garages 2
Is Waterfront No
Has Pool No
Interior
Interior Features Beamed Ceilings, Built-in Features, Eat-in Kitchen, Natural Woodwork, Original Details, Walk Through Kitchen
Appliances Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Heating Electric, Other, Wood
Cooling Electric
Has Basement Yes
Basement Finished, Full, Walk-Out Access
Fireplace Yes
# of Fireplaces 2
Fireplaces Basement, Living Room, Wood Burning Stove
Exterior
Exterior Features Lighting, Mailbox
Lot Description Back Yard, Part Wooded, Private
Windows Oversized Windows, Wood Frames
Construction Stone
School Information
District Arlington
Elementary Beekman
Middle Union Vale Middle School
High Arlington High School
Additional Information
Date Listed February 5th, 2026
Days on Market 28
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of McGrath Realty Inc
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Listing information last updated on March 6th, 2026 at 2:50am EST.