BEDS2
BATHS2 full
SQUARE FEET2,196
MLS#954200
STATUSActive
PROPERTY TYPEResidential - Single Family
SCHOOLArlington
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.
Property Features
Property Type: Residential - Single Family
Basement: Yes
Basement: Finished, Full, Walk-Out Access
Cooling: Electric
Fireplaces: 2
Garage: 2
Heating: Electric, Other, Wood
Home Style: Other
Lot Size: 2.20 Acres
Taxes: $14,119
Year Built: 1776
Amenities
Beamed Ceilings
Built-in Features
Eat-in Kitchen
Natural Woodwork
Original Details
Walk Through Kitchen
Lighting
Mailbox
Feature Descriptions
Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Days on Site: 63
Exterior: Stone
Fencing: Back Yard
Fireplace Features: Basement, Living Room, Wood Burning Stove
Fireplace Y/N: Yes
GarageY/N: Yes
House Faces: South
Lot Features: Back Yard, Part Wooded, Private
Number Of Kitchens: 1
On Market Date: 2026-02-05
Other Structures: Garage(s)
Parcel Number: 134089-6857-00-454889-0000
Parking Features: Driveway, Garage
Parking Total: 6
Patio And Porch: Patio
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Rooms Total: 8
Security Features: Smoke Detector(s)
Sewer: Septic Tank
Utilities: Cable Available, Electricity Connected, Phone Available, Water Connected
Water: Well
Window Features: Oversized Windows, Wood Frames
Wooded: Yes
Local Schools
High School: Arlington High School
Middle School: Union Vale Middle School
Elementary School: Beekman
School District: Arlington
Listed By / Shown By
Listing By
Agency Name: McGrath Realty Inc
Agency Contact: 845-855-5550
Shown By
Agency Title: RealtyMark
Agency Phone: 888-240-0600
Estimate Your Payment
Estimated Payment
$ 2,684.41 per month $1,333.11 Principal & Interest $1,176.58 Property Tax $174.71 Homeowner's InsuranceChange Payment Information
168 Old Route 55 | MLS# 954200
This single family home located at 168 Old Route 55, Pawling, NY 12564 is currently listed for sale with an asking price of $599,000. This property was built in 1776 and has 2 bedrooms and 2 full baths with 2196 sq. ft. Old Route 55 is located within the Arlington school district. Search Pawling real estate on www.realtymark.net today.