168 Old Route 55
Pawling, NY 12564
2
Bed
2
Bath
2,194Sqft
2.20Acres(Lot)
Set on 2.7 private acres, this historic 1776 stone Toll Gate House at 168 Old Route 55 offers a rare blend of Hudson Valley history and modern comfort. Built in the year America declared independence—and meticulously renovated/restored in 1981—this remarkable property is more than a home; it’s a living piece of local history with timeless character, thoughtful updates, and an unbeatable location just 8 minutes from Metro-North and close to all shopping, dining, and village amenities in Pawling. Constructed with enduring craftsmanship, the home features a solid bluestone foundation, with matching bluestone also carried through the windowsills—subtle details that speak to its strength, authenticity, and lasting quality. The home welcomes you with classic stone exterior charm and interiors t
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
-
Bedroom Information
Total beds: 2Bathroom Information
Total Baths: 2 Full Baths: 2Room Information
Rooms Total: 6 Basement: Finished, Full, Walk-Out Access -
Flooring Information
Hardwood -
Interior Features
Beamed Ceilings, Granite Counters, In-Law Floorplan, Natural Woodwork, Open Floorplan, Pantry, Recessed Lighting, Storage Appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer Laundry Features: Inside Window Features: Wood Frames -
Heating & Cooling
Has Heating: Yes Heating: Wood Stove, Electric, Wood Cooling: None
-
Building Information
Year Built: 1776 Building Area Total: 2244 Construction Materials: Stone Patio And Porch Features: Patio Private Pool: No -
Exterior Features
Exterior Features: Garden, Fire Pit, Lighting, Playground
-
Lot Information
Lot Size Acres: 2.2 Lot Size Square Feet: 95832 Lot Description: Back Yard, Cleared, Garden, Level, Near Public Transit, Private, Secluded
-
Listing Price Information
Listing Price: $565000
-
Tax Information
Parcel Number: 134089-6857-00-454889-0000 Annual Tax: $11571
-
Virtual Tour
Parking Information
Parking Total: 8 Detached, Driveway, Garage, OversizedGarage Information
Has Garage: Yes Garage Space: 4
-
School Information
Elementary School: BeekmanJunior High School: Union Vale Middle SchoolSenior High School: Arlington High School -
Utility Information
Cable Available, Electricity Connected, Phone Available -
Location Information
Direction: Gravel driveway is to the east of the house, between the mailbox for 167, and the second white mailbox. WaterSource: Private, Well
How much is this property worth?
Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.
Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 41 AND 43 Meeting House.., Pawling, NY, 12564 | $1,799,000 | 5 | 6 | 5,390 | 5,390 SqFt |
| 34 Meeting House Road, Pawling, NY, 12564 | $2,500,000 | 3 | 4 | 2,292 | 2,292 SqFt |
| 15 Kirby Hill Road, Pawling, NY, 12564 | $14,995,000 | 4 | 4 | 3,942 | 3,942 SqFt |
| 809 Quaker Hill Road, Pawling, NY, 12564 | $3,100,000 | 3 | 3 | 3,600 | 3,600 SqFt |
| 618 Quaker Hill Road, Pawling, NY, 12564 | $5,000,000 | 8 | 13 | 15,000 | 15,000 SqFt |
| 1141 Old Quaker Hill Road, Pawling, NY, 12564 | $499,999 | 2 | 1 | 1,347 | 1,347 SqFt |
| 57 Buhleir Road, Pawling, NY, 12564 | $629,900 | 3 | 2 | 1,768 | 1,768 SqFt |
| 188 N Quaker Hill Road, Pawling, NY, 12564 | $595,000 | 3 | 3 | 2,636 | 2,636 SqFt |
| 17 Townsend Boulevard, Pawling, NY, 12564 | $460,000 | 2 | 2 | 1,088 | 1,088 SqFt |
| 128 Old Pawling Road, Pawling, NY, 12564 | $900,000 | 4 | 4 | 3,434 | 3,434 SqFt |
Similar Homes To 168 Old Route 55
Nearby For Sale
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved
ByOwner last updated this listing 06/10/2026 @ 19:26
More Cities with for Sale by Owner Homes
- Pawling Homes For Sale By Owner
- Sherman Homes For Sale By Owner
- Patterson Homes For Sale By Owner
- Poughquag Homes For Sale By Owner
- Wingdale Homes For Sale By Owner
- Holmes Homes For Sale By Owner
- Stormville Homes For Sale By Owner
- New Fairfield Homes For Sale By Owner
- Dover Plains Homes For Sale By Owner
- New Milford Homes For Sale By Owner
- Lagrangeville Homes For Sale By Owner
- Carmel Homes For Sale By Owner
- Hopewell Junction Homes For Sale By Owner
- Verbank Homes For Sale By Owner
- Brewster Homes For Sale By Owner
- Bridgewater Homes For Sale By Owner
- Kent Homes For Sale By Owner
- Brookfield Homes For Sale By Owner
- Millbrook Homes For Sale By Owner
- Roxbury Homes For Sale By Owner
Homes around $565,000
Verify Your Email
Please enter the 6-digit verification code
sent to your email address.