168 Old Route 55, Pawling, NY, 12564 | $565,000

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.

Features

  • Rooms: 8
  • Bedrooms: 2
  • Baths: 2 full
  • Style: Other
  • Year Built: 1776
  • Garage: 2-car
  • Heating: Electric, Other, Wood
  • Cooling: Electric
  • Basement: Finished, Full, Walk-Out Access
  • Approx Sq. Feet: 2,196
  • Acreage: 2.2
  • Est. Taxes: $11,529
  • Lot Desc: Back Yard, Part Wooded, Private
  • Elem. School: Beekman
  • Middle School: Union Vale Middle School
  • High School: Arlington High School
  • School District: Arlington
  • Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
  • MLS#: 954200
  • Days on Market: 79 days
  • Website: https://www.raveis.com
    /prop/954200/168oldroute55_pawling_ny?source=qrflyer
Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to the buying decision should be independently verified.

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Jae AhnSales Associate

203.803.9999

Jae.Ahn@raveis.com

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Joseph MollicaVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 130058

203.952.8600

Joseph.Mollica@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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203.610.1536

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Our Insurance Division:

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168 Old Route 55, Pawling, NY, 12564

$565,000

Jae Ahn

Sales Associate

William Raveis Real Estate

Phone: 203.803.9999

Jae.Ahn@raveis.com

Joseph Mollica

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.952.8600

Joseph.Mollica@raveis.com

NMLS Mortgage Loan Originator ID 130058

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $452,000 $452,000 $452,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.875% 6.250% 5.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.324% 6.398% 5.614%
Monthly Tax Payment $961 $961 $961
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $2,674 $2,783 $3,663
Total Monthly Payment $3,727 $3,836 $4,716

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.