168 Old Route 55

Pawling, NY 12564
  • $565,000

    Price
  • 2

    Bed
  • 2

    Bath
  • 2,196

    SqFt

About the Listing KEVMCG - 62138,34656

Step into the year our nation was born and own a piece of living American history. Originally constructed in 1776 by a Scottish stone mason and frontiersman, who fought in two Revolutionary War battles, this enduring stone home is more than a residence; it’s a survivor. Once known as the Pawling Toll Gate and Toll House, it served as a gateway for travelers, a general store, a post office, and a gathering place woven into the early fabric of the region. Inside, the home carries its history with quiet strength. Hand-hewn beams stretch across the ceilings. Deep-set windows draw in southern light. Original fireplaces, now fitted with wood stove inserts, anchor the space. Wide-plank wood floors, laid in defiance of British colonial restrictions, remain underfoot, worn smooth by time, not replaced. The home offers 2 bedrooms and 2 full baths, with a layout that is both grounded and adaptable. The lower level provides a private, flexible space, ideal for a studio, retreat, or guest quarters. Outside, 2.2 acres open directly to the Empire State Trail and offer immediate access to the Appalachian Trail, putting miles of riding, hiking, and exploration right at your doorstep. This isn’t nearby, it’s connected. Behind the home, a substantial ~1,000 sq ft detached garage provides space for four or more vehicles, along with room for equipment, workshop use, or future conversion. It’s not an afterthought, it’s an asset. Located just minutes from the village of Pawling, Metro-North, shops, and dining, the property balances seclusion with accessibility. This is not just a home, it’s a piece of early American infrastructure that has endured, adapted, and remained. Built by hand, shaped by history, and still standing with purpose.

Listing Highlights

Status Active
Days on Site 79
Property Type Residential
MLS ® 954200
Year Built 1776
Total Square Footage 2,196
Lot/Acreage 2.2
School District Arlington
Elementary School Beekman
Middle School Union Vale Middle School
High School Arlington High School

Interior Details

  • Bedrooms: 2
  • Bathrooms: 2 Full
  • Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
  • Air Cond: Electric
  • Heating: Electric,Wood
  • Fireplaces: 2, Basement,Living Room,Wood Burning Stove
  • Floor:
  • Above Ground Sq Ft:
  • Below Ground Sq Ft: n/a
  • Basement: Finished,Full,Walk-Out Access
  • Other: Beamed Ceilings,Built-in Features,Eat-in Kitchen,Natural Woodwork,Original Details,Walk Through Kitchen
  • Water: Well

Exterior Details

  • Lot Description: Back Yard,Part Wooded,Private,No Waterfront
  • Garage Capacity: 2 car
  • Parking Spaces: 6
  • Roof:
  • Others: Lighting,Mailbox
  • Sewer: Septic Tank
  • Parking Features: Driveway,Garage

Financial Details

  • Tax Amount: $11,529
  • Taxes w/Assessments: N/A
  • Tax/Property ID: 134089-6857-00-454889-0000
  • Tax Year: N/A

Payment Calculator

Monthly Payment

  • in Principal and Interest
  • in Taxes
Years
% Down Payment
% Mortgage Rate

Questions About..

168 Old Route 55 Pawling, NY 12564

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Never Miss A New Property

Get notified any time there's a new home on the market in this neighborhood!

Don't worry! We'll never spam you or sell your details. You can unsubscribe whenever you'd like.

Originating MLS: onekey2

home

Are you buying or selling a home?

Buying
Selling
Both
home

When are you planning on buying a new home?

1-3 Mo
3-6 Mo
6+ Mo
home

Are you pre-approved for a mortgage?

Yes
No
Using Cash
home

Would you like to schedule a consultation now?

Yes
No

When would you like us to call?

Thanks! We’ll give you a call as soon as possible.

home

When are you planning on selling your home?

1-3 Mo
3-6 Mo
6+ Mo

Would you like to schedule a consultation or see your home value?

Schedule Consultation
My Home Value

or another way