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Residential Land with Home for Sale in Pawling, New York

168 Old Route 55, Pawling, NY 12564

$599,000
2.2 acres
Active
ago
Est $4,112/mo

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.

1,428
Sq feet
2
Beds
2
Full baths
1776
Built

Location

Street address
168 Old Route 55
School district
Arlington
Elevation
695 feet
Coordinates
41.587, -73.6584

Property details

Acreage
2.2 acres
MLS #
MLSLI 954200
Posted

Property taxes

2025
$14,119

Parcels

  • 134089-6857-00-454889-0000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Independent

Lot

Features
Back Yard, Part Wooded, Private

Exterior

Parking Spaces
6
Parking
Driveway, Garage
Pool
Patio
Features
Lighting, Mailbox

Structure

Stories
3
Basement
Finished, Full, Walk-Out Access
Water
Well
Sewer
Septic Tank
Heating
Electric, Wood
Materials
Stone
Windows
Wood Frames

Interior

Room Count
8
Rooms
Basement, Bathroom x 2, Bedroom x 2, Dining Room, Laundry Room x 2
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Features
Beamed Ceilings, Built-In Features, Eat-In Kitchen, Natural Woodwork, Original Details, Walk Through Kitchen

Nearby schools

NameTypeDistrict
BeekmanElementaryArlington
Union Vale Middle SchoolMiddleArlington
Arlington High SchoolHighArlington

Listing history

DateEventPriceChangeSource
Feb 5, 2026New listing$599,000MLSLI
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This 2.2-acre property is located at 168 Old Route 55 in Pawling, NY 12564. The property is available for sale for $599,000. It has a 1,428 sq ft 2 bedroom, 2 bath house built in 1776.

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