168 Old Rte 55

Pawling, NY 12564

$565,000
Price
2
Beds
2,194 Sq. Ft.
$258 / Sq. Ft.
2,194
Sq. Ft.
$258
per Sq. Ft.
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Virtual Tour
a front view of a house with a garden
a view of a wooden door
a living room with furniture and a large window
a living room with furniture and a fireplace
a living room with furniture and a rug
a living room with furniture and a rug
a living room with couch and a dining table with wooden floor
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a kitchen with granite countertop wood cabinets and stainless steel appliances
a kitchen with a table chairs and stove
a view of a dining room with furniture and wooden floor
a bedroom with a bed and a window
a bedroom with a bed and a dresser
a view of a room with furniture wooden floor and windows
a bathroom with a sink a toilet and a mirror
a view of a bathroom with a shower and a window
a bedroom with a bed and a window
a bedroom with furniture and a baby crib
a bedroom with a bed and a fireplace
a living room with furniture and a rug
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a utility room with dryer and washer
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Description

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...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 that balance old-world warmth with everyday livability. A modernized kitchen features stainless steel appliances, granite counters, a copper backsplash, and painted wood cabinets that blend contemporary function with nostalgic farmhouse appeal. The open dining area showcases a stone wall, exposed 200-year-old beams, and rustic character that immediately reminds you of the home’s storied past. The primary bedroom is spacious and inviting, complete with a dressing nook and a striking stone chimney that adds warmth and atmosphere. The second bedroom offers exposed stone walls for added texture and historic charm, while the second floor bathroom evokes the feeling of an English garden with soft, serene character and whimsical detail. A finished lower level provides additional flexible living space, ideal for recreation, work, guests, or relaxation. Practicality is equally impressive. A large modern two-level detached garage built in 2012 offers room for multiple vehicles and endless possibilities for a studio, workshop, gym, or creative space. Outside, the property unfolds into a serene English-style garden with a stone patio, firepit, and private trails leading toward nearby Appalachian Trail corridors and surrounding natural preserves. It’s a setting that feels both peaceful and connected to the beauty of the Hudson Valley landscape. Steeped in history and enhanced for modern living, this is the kind of home that rarely comes along. From its role as a toll gate house, general store, post office, and legendary tavern to its renovated and restored present-day life as a distinctive residence, the property carries a story that is as compelling as its surroundings. Whether you’re drawn to its historic pedigree, its warm and inviting interiors, or its close proximity to Metro-North and the charming Village of Pawling, this is a truly special place to call home.

Property Details for 168 Old Rte 55

City/Township
Pawling
Architectural Style
Carriage House, Chalet, Colonial, Cottage, Farmhouse, Saltbox
Garage Spaces
4.00
Waterfront
No
LISTING UPDATED: 06/02/2026 04:25 PM

Property Details for 168 Old Rte 55

StatusActive
MLS #1004011
Days on Market10
Taxes$11,571 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeSingle Family
Year Built1776
Lot Size2.20 AC / 95,832 SF
CountyDutchess County
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Location

Listing Courtesy of RE/MAX Classic Realty
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Building Information for 168 Old Rte 55

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

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$3,780 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,815

Property Taxes

$964

HOA Dues

$0

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Property Information for 168 Old Rte 55

Summary
Location and General Information
  • Senior Community YN: No
  • Directions: Gravel driveway is to the east of the house, between the mailbox for 167, and the second white mailbox.
  • Year Built Effective: 1981
  • Property Attached: No
  • Structure Type: Detached
  • Levels: Three Or More
  • Property Condition: Updated/Remodeled
  • State Or Province: NY
  • Water Access YN: No
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: Lower
  • Room Type: Den
  • RoomDescription 1: Multi-purpose space with cozy stone fireplace for guest space, au pair suite, family room, exercise room, etc
Room 2 Information
  • Room Level: Lower
  • Room Type: Office
  • Room Description: Spacious home office
Room 3 Information
  • Room Level: Lower
  • Room Type: Bathroom 1
  • Room Description: Renovated full bath with shower
Room 4 Information
  • Room Level: Lower
  • Room Type: Laundry
  • Room Description: Clean, efficient laundry nook, simple and functional with practical space for every day use
Room 5 Information
  • Room Level: First
  • Room Type: Living Room
  • Room Description: Living room w/ historic exposed wood beams, 200 year old hardwood plank flooring, authentic slate window sills and wood burning stove with solid stone surround
Room 6 Information
  • Room Level: First
  • Room Type: Dining Room
  • Room Description: Open dining area with a stone wall, exposed 200-yr-old beams and charming rustic character
Room 7 Information
  • Room Level: First
  • Room Type: Kitchen
  • Room Description: Open concept kitchen blends modern convenience with nostalgic farmhouse charm, featuring stainless steel appliances, granite counters, copper backsplash and painted solid wood cabinets.
Room 8 Information
  • Room Level: Second
  • Room Type: Primary Bedroom
  • Room Description: Spacious primary bedroom includes a charming dressing nook and a striking stone chimney that adds warmth and character.
Room 9 Information
  • Room Level: Second
  • Room Type: Bedroom 2
  • Room Description: Spacious bedroom features exposed stone wall that adds rustic character and timeless Hudson Valley charm.
Room 10 Information
  • Room Level: Second
  • Room Type: Bathroom 2
  • Room Description: A charming second bath reminiscent of an English garden with soft natural details and a serene, whimsical feel.
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134089-6857-00-454889-0000
  • Tax Assessed Value: $156,800.00
  • Additional Fees: No
  • Tax Source: Municipality
  • Tax Year: 2025.0
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Back Yard, Beamed Ceilings, Carriage House, Chalet, Colonial, Cottage, Family Room, Farmhouse, Fire Pit, Garage(s), Garden, Granite Counters, Greenhouse, Hardwood Floors As Seen, In-Law Floorplan, Inside, Lighting, Living Room, Mailbox, Masonry, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Oversized Windows, Pantry, Patio, Playground, Recessed Lighting, Saltbox, Shed(s), Storage, Well, Wood Burning Stove, Wood Frames
  • Interior Features: Beamed Ceilings, Granite Counters, In-Law Floorplan, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Pantry, Recessed Lighting, Storage
  • Appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer
  • Number Of Kitchens: 1.0
  • Total Rooms: 6
  • Basement: Finished, Full, Walk-Out Access
  • Attic Description: Partial
  • Fireplaces Total: 2
  • Fireplace Features: Family Room, Living Room, Masonry, Wood Burning Stove
  • Location Amenities: Stainless Steel Appliances, Walk Out Basement, Exposure South, Wood Burning Stove, Hardwood Floors As Seen, Granit Countertops, Open Kitchen, Original Details, Pantry, Storage, Garden, Privacy, Greenhouse, Patio, Oversized Windows
  • Laundry Features: Inside
  • Spa: No
  • Window Features: Oversized Windows, Wood Frames
  • Flooring: Hardwood
  • Living Area: 2,194.00
  • Foundation Details: Stone
  • Basement: Yes
Exterior Features
  • Exterior Features: Fire Pit, Garden, Lighting, Mailbox, Playground
  • Exterior Property Features: Fire Pit, Garden, Lighting, Mailbox, Playground, Patio, Detached, Driveway, Garage, Oversized, Back Yard, Oversized Windows, Wood Frames, Borders State Land, Cleared, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded
  • 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), Greenhouse, Shed(s)
  • Pool Private: No
  • Direction Faces: South
Lot Information
  • Lot Features: Back Yard, Borders State Land, Cleared, Garden, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded
  • Site Features: Back Yard, Borders State Land, Cleared, Garden, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded
  • Building Area Units: Square Feet
Parking
  • Parking Features: Detached, Driveway, Garage, Oversized
  • Parking Total: 8.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: None
  • Heating: Electric, Wood
  • Heat Fuel Type: Electric, Wood
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Available, Electricity Connected, Phone Available
Green Features
  • Green Features: Oversized Windows, Wood Frames, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer, Electric, Wood, Fire Pit, Garden, Lighting, Mailbox, Playground
Virtual Tour
Agent
Payment and Rate
  • Down Payment Resource: Yes

Property History for 168 Old Rte 55

DateEvent & SourcePriceAppreciation
May 28, 2026

Listed (Active)

ONEKEY #1004011

$565,000—
May 14, 2026

Withdrawn

ONEKEY #954200

$565,000—
Feb 5, 2026

Listed (Active)

ONEKEY #954200

$599,000—
DateEvent & SourcePrice
05/28/2026

Listed (Active)

ONEKEY #1004011

$565,000
05/14/2026

Withdrawn

ONEKEY #954200

$565,000
02/05/2026

Listed (Active)

ONEKEY #954200

$599,000

For completeness, we 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 Record2025$11,571 ($964 / 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 May 28, 2026 by RE/MAX Classic Realty, it's currently listed at $565,000. It has been on the market for a total of 10 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, 2,194 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 RE/MAX Classic Realty

Based on information submitted to the MLS GRID as of 06/02/2026 04:25 PM. 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.