168 Old Route 55, Pawling, NY

Name: 168 Old Route 55, For Sale in Pawling - eXp Realty
Brand: McGrath Realty Inc
SKU: 954200
Price: 599000 USD

House

For Sale

Listed price in listed location currency (USD).

$599,000

226

MLS® 954200

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 1428 sqft

Garage Yes

Taxes $14,119

Days Active 0

Lot Size 2.2 acres

Approx. Age 1776

Avg. Price Per Sqft $419

MLS® Number 954200

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

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

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.

MLS® Number954200

Laundry Level

Central VacNo

FireplaceNo

Acreage2.2

Exterior

GarageYes

Approx. Age1776

BasementFinished, Full, Walk-Out Access

DrivewayDriveway, Garage

Garage Spaces2

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Feb 5, 2026List Date

$599,000List Price

Commute

Commute

Starting Address

Destination Address

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