168 Old Rte 55

Pawling, NY 12564

$599,000
Price
2
Beds
1,428 Sq. Ft.
$419 / Sq. Ft.
1,428
Sq. Ft.
$419
per Sq. Ft.
Living Room with fireplace and wood burning stove insert
Fireplace with wood burning stove insert.
Stairway to 2nd Level
Open Concept dining area
Stainless Steel appliances
Upstairs Bathroom
Upstairs Bathroom
Upstairs Bathroom with Tub/shower combination
Fireplace in lower level with wood burning stove insert
Laundry area located in lower level
Balthroom in lower level
Bathroom in lower with pedastal sink
Bathroom in lower level with shower stall
Two car garage with storage on second level
The bustling Village of Pawling where Restaurants, Shops & the Train Station are less then 10 minutes away!
Open Concept Floor Plan
Main Level Floor Plan
2nd Level Floor Plan
Lower Level Floor Plan

Description

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...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. Listed by Colleen McGrath • McGrath Realty Inc
    P: (845)-855-5550 C: (845)-803-4341 cmcgrath@mcgrathny.com
  2. Listed by Valerie J. Port • McGrath Realty Inc
    P: (845)-855-5550 C: (845)-590-2482 VALERIE.PORT.REALTOR@GMAIL.COM

Property Details for 168 Old Rte 55

City/Township
Pawling
Architectural Style
Other
Garage Spaces
2.00
Waterfront
No
LISTING UPDATED: 02/06/2026 11:15 AM

Property Details for 168 Old Rte 55

StatusActive
MLS #954200
Days on Market1
Taxes$14,119 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1776
Lot Size2.20 AC / 95,832 SF
CountyDutchess County

Location

Listing Courtesy of McGrath Realty Inc
Add your commute

Building Information for 168 Old Rte 55

Stories-Year Built1776Building Size-Lot Size2.20 AC / 95,832 SF

Payment Calculator

$4,096 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,919

Property Taxes

$1,177

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 168 Old Rte 55

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • Levels: Three Or More
  • Country: US
  • State Or Province: NY
School Information
  • School District: Arlington
  • Elementary School District: Arlington
  • Elementary School: Beekman
  • Middle Or Junior School District: Arlington
  • Middle Or Junior School: Union Vale Middle School
  • High School District: Arlington
  • High School: Arlington High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: Second
  • Room Type: Bedroom 1
Room 2 Information
  • Room Level: Second
  • Room Type: Bedroom 2
Room 3 Information
  • Room Level: Second
  • Room Type: Bathroom 1
  • Room Description: Full bathroom with shower/tub combination
Room 4 Information
  • Room Level: First
  • Room Type: Living Room
Room 5 Information
  • Room Level: First
  • Room Type: Kitchen
Room 6 Information
  • Room Level: First
  • Room Type: Dining Room
Room 7 Information
  • Room Level: Lower
  • Room Type: Laundry
Room 8 Information
  • Room Level: Lower
  • Room Type: Media Room
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134089-6857-00-454889-0000
  • Tax Assessed Value: $156,800.00
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Back Yard, Basement, Beamed Ceilings, Built-in Features, Eat in Kitchen, Garage(s), Lighting, Living Room, Mailbox, Natural Woodwork, Original Details, Other, Oversized Windows, Patio, Smoke Detector(s), Walk Through Kitchen, Well, Wood Burning Stove, Wood Frames
  • Interior Features: Beamed Ceilings, Built-in Features, Eat-in Kitchen, Natural Woodwork, Original Details, Walk Through Kitchen
  • Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
  • Number Of Kitchens: 1.0
  • Total Rooms: 8
  • Basement: Finished, Full, Walk-Out Access
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Fireplace Features: Basement, Living Room, Wood Burning Stove
  • Location Amenities: Other/See Remarks, Stainless Steel Appliances, Walk Out Basement, Exposure South, Wood Burning Stove, Eat in Kitchen, Original Details, Walk Through Kitchen, Privacy, Patio, Oversized Windows
  • Security Features: Smoke Detector(s)
  • Spa: No
  • Window Features: Oversized Windows,Wood Frames
  • Living Area: 1,428.00
  • Foundation Details: Stone
  • Basement: Yes
Exterior Features
  • Exterior Features: Lighting, Mailbox
  • Exterior Property Features: Lighting, Mailbox, Patio, Driveway, Garage, Back Yard, Oversized Windows, Wood Frames, Part Wooded, Private
  • Elevation Certificate: No
  • Fencing: Back Yard
  • Patio And Porch Features: Patio
  • Construction Materials: Stone
  • Road Frontage Type: Municipal
  • Road Responsibility: Public Maintained Road
  • Other Structures: Garage(s)
  • Horse: No
  • Pool Private: No
  • Direction Faces: South
Lot Information
  • Lot Features: Back Yard, Part Wooded, Private
  • Additional Parcel: No
  • Site Features: Back Yard, Part Wooded, Private
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage
  • Parking Total: 6.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Electric
  • Heating: Electric, Other, Wood
  • Heat Fuel Type: Electric, Other, Wood
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Available, Electricity Connected, Phone Available, Water Connected
Green Features
  • Green Features: Oversized Windows, Wood Frames, Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Electric, Other, Wood, Lighting, Mailbox
Agent
Payment and Rate
  • Down Payment Resource: Yes

Property History for 168 Old Rte 55

DateEvent & SourcePriceAppreciation
Jul 16, 2018

Sold (Public Record)

Public Record #628610024

$365,000—
Jul 16, 2018

Sold (Public Record)

Public Record #628610024

$365,000

+2.7% / yr

Apr 19, 2013

Sold (Public Record)

Public Record #366573118

$317,500—
Apr 19, 2013

Sold (Public Record)

Public Record #366573118

$317,500—
Apr 19, 2013

Sold (Public Record)

Public Record #366573118

$317,500

-10.5% / yr

Sep 3, 2010

Sold (Public Record)

Public Record #298642069

$425,000—
Sep 3, 2010

Sold (Public Record)

Public Record #298642069

$425,000—
Sep 3, 2010

Sold (Public Record)

Public Record #298642069

$425,000—
DateEvent & SourcePrice
07/16/2018

Sold (Public Record)

Public Record #628610024

$365,000
07/16/2018

Sold (Public Record)

Public Record #628610024

$365,000

+2.7% / yr

04/19/2013

Sold (Public Record)

Public Record #366573118

$317,500
04/19/2013

Sold (Public Record)

Public Record #366573118

$317,500
04/19/2013

Sold (Public Record)

Public Record #366573118

$317,500

-10.5% / yr

09/03/2010

Sold (Public Record)

Public Record #298642069

$425,000
09/03/2010

Sold (Public Record)

Public Record #298642069

$425,000
09/03/2010

Sold (Public Record)

Public Record #298642069

$425,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 168 Old Rte 55

Taxable ValueLand$27,500Additions$129,300Total$156,800
Tax Record2024$11,621 ($968 / month)
Home Facts
Beds2Baths2Total Finished SqFt1,428 SqFtAbove Grade Finished SqFt1,428 SqFtStories2Lot Size95,832 SqFtStyleSingle Family ResidenceYear Built1776ZoningR-3CountyDUTCHESSAPN134089 6857-00-454889-0000Fireplace TypeHas Fireplace

Schools near 168 Old Rte 55

This home is within Arlington Central School District.
Rating
School
Type
Grades
Distance
Beekman School
Public - K to 5
Union Vale Middle School
Public - 6 to 8
Arlington High School
Public - 9 to 12
Vail Farm Elementary School
Public - K to 5
Rating
School
Distance
Beekman School
PublicK to 5

Union Vale Middle School
Public6 to 8

Arlington High School
Public9 to 12

Vail Farm Elementary School
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 168 Old Rte 55, Pawling, NY 12564

168 Old Rte 55 is a single family home for sale in Pawling, NY 12564. This property was listed for sale on February 5, 2026 by McGrath Realty Inc, it's currently listed at $599,000. It has been on the market for a total of 1 days and was last sold on July 16, 2018. This listing's school district is Arlington Central School District. Nearby schools include Beekman School, Union Vale Middle School and Arlington High School. 168 Old Rte 55 is a 2-bed, 2-bath, 1,428 sqft single family home built in 1776.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of McGrath Realty Inc

Based on information submitted to the MLS GRID as of 02/06/2026 11:15 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the 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. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.