168 Old Route 55, Pawling, NY 12564
168 Old Route 55, Pawling, NY 12564,Video Tour
168 Old Route 55, Pawling, NY 12564
168 Old Route 55, Pawling, NY 12564
168 Old Route 55, Pawling, NY 12564
168 Old Route 55, Pawling, NY 12564
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$ 565,000
Est. payment | /mo

2 Beds

2 Baths

2,194 SqFt


$ 565,000
Est. payment | /mo

2 Beds

2 Baths

2,194 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 2,194 sqft

Price per Sqft $257

MLS Listing ID 1004011

Style Carriage House,Chalet,Colonial,Cottage,Farmhouse,Saltbox

Bedrooms 2

Full Baths 2

HOA Y/N No

Rental Info No

Year Built 1776

Annual Tax Amount $11,571

Lot Size 2.200 Acres

Acres 2.2

Property Sub-Type Single Family Residence

Source onekey2

Property 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 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.

Location

State NY

County Dutchess County

Rooms

Basement Finished, Full, Walk-Out Access

Interior

Interior Features Beamed Ceilings, Granite Counters, In-Law Floorplan, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Pantry, Recessed Lighting, Storage

Heating Electric, Wood

Cooling None

Flooring Hardwood

Fireplaces Number 2

Fireplaces Type Family Room, Living Room, Masonry, Wood Burning Stove

Fireplace Yes

Appliance Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer

Laundry Inside

Exterior

Exterior Feature Fire Pit, Garden, Lighting, Mailbox, Playground

Parking Features Detached, Driveway, Garage, Oversized

Garage Spaces 4.0

Fence Back Yard

Utilities Available Cable Available, Electricity Connected, Phone Available

Total Parking Spaces 8

Garage true

Private Pool No

Building

Lot Description Back Yard, Borders State Land, Cleared, Garden, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded

Foundation Stone

Sewer Septic Tank

Water Well

Level or Stories Three Or More

Structure Type Stone

Schools

Elementary Schools Beekman

Middle Schools Union Vale Middle School

High Schools Arlington

School District Arlington

Others

Senior Community No

Special Listing Condition None

Virtual Tour https://my.matterport.com/show/?m=mdEH674e15Y&mls=0

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
Listed by RE/MAX Classic Realty • Alea R. Vorillas

Nearby Locations

Diana H. Murphy

"My job is to find and attract mastery-based agents to the office, protect the culture, and make sure everyone is happy! "

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168 Old Route 55