168 Old Route 55, Pawling, NY 12564

Local realty services provided by:Better Homes and Gardens Real Estate Green Team
168 Old Route 55,Pawling, NY 12564
$599,000
  • 2 Beds
  • 2 Baths
  • 1,428 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sat, Feb 14
    11:00 am - 01:00 pm
Listed by: colleen mcgrath, valerie j. port
Office: mcgrath realty inc
MLS#:954200
Source:OneKey MLS

Price summary

  • Price:$599,000
  • Price per sq. ft.:$419.47

About this home

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

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Home facts

  • Year built:1776
  • Listing ID #:954200
  • Added:6 day(s) ago
  • Updated:February 12, 2026 at 04:28 PM

Rooms and interior

  • Bedrooms:2
  • Total bathrooms:2
  • Full bathrooms:2
  • Living area:1,428 sq. ft.

Heating and cooling

  • Heating:Electric, Wood

Structure and exterior

  • Year built:1776
  • Building area:1,428 sq. ft.
  • Lot area:2.2 Acres

Schools

  • High school:Arlington High School
  • Middle school:Union Vale Middle School
  • Elementary school:Beekman

Utilities

  • Water:Well
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$599,000
  • Price per sq. ft.:$419.47
  • Tax amount:$14,119 (2025)
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