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Pending
    • $565,000

    168 Old Route 55, Pawling, NY 12564

    2beds
    2,194sqft
    Loading
    Single Family Residence, Residential
    Built in 1776
    2.2 Acres Lot
    $-- Zestimate®
    $258/sqft
    $-- HOA

    What's special

    Striking stone chimneyStone patioOpen dining areaStainless steel appliancesClassic stone exterior charmRustic characterPainted wood cabinets
    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.
    54 days
    |
    383
    |
    10
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    RE/MAX Classic Realty 914-243-5200,

    Alea R. Vorillas 718-986-7441

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1004011MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Description: Spacious primary bedroom includes a charming dressing nook and a striking stone chimney that adds warmth and character.
      • Level: Second
      Bedroom 2
      • Description: Spacious bedroom features exposed stone wall that adds rustic character and timeless Hudson Valley charm.
      • Level: Second
      Bathroom 1
      • Description: Renovated full bath with shower
      • Level: Lower
      Bathroom 2
      • Description: A charming second bath reminiscent of an English garden with soft natural details and a serene, whimsical feel.
      • Level: Second
      Den
      • Description: Multi-purpose space with cozy stone fireplace for guest space, au pair suite, family room, exercise room, etc
      • Level: Lower
      Dining room
      • Description: Open dining area with a stone wall, exposed 200-yr-old beams and charming rustic character
      • Level: First
      Kitchen
      • Description: Open concept kitchen blends modern convenience with nostalgic farmhouse charm, featuring stainless steel appliances, granite counters, copper backsplash and painted solid wood cabinets.
      • Level: First
      Laundry
      • Description: Clean, efficient laundry nook, simple and functional with practical space for every day use
      • Level: Lower
      Living 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
      • Level: First
      Office
      • Description: Spacious home office
      • Level: Lower
      Heating
      • Electric, Wood
      Cooling
      • None
      Appliances
      • Included: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer
      • Laundry: Inside
      Features
      • Beamed Ceilings, Granite Counters, In-Law Floorplan, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Pantry, Recessed Lighting, Storage
      • Flooring: Hardwood
      • Windows: Oversized Windows, Wood Frames
      • Basement: Finished,Full,Walk-Out Access
      • Attic: Partial
      • Number of fireplaces: 2
      • Fireplace features: Family Room, Living Room, Masonry, Wood Burning Stove
      Interior area
      • Total structure area: 2,244
      • Total interior livable area: 2,194 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 8
      • Parking features: Detached, Driveway, Garage, Oversized
      • Garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Patio & porch: Patio
      • Exterior features: Fire Pit, Garden, Lighting, Mailbox, Playground
      • Fencing: Back Yard
      Lot
      • Size: 2.2 Acres
      • Features: Back Yard, Borders State Land, Cleared, Garden, Level, Near Public Transit, Near School, Near Shops, Private, Secluded
      • Residential vegetation: Partially Wooded
      Details
      • Additional structures: Garage(s), Greenhouse, Shed(s)
      • Parcel number: 1340896857004548890000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Carriage House,Chalet,Colonial,Cottage,Farmhouse,Saltbox
      • Property subtype: Single Family Residence, Residential
      Materials
      • Stone
      • Foundation: Stone
      Condition
      • Updated/Remodeled
      • Year built: 1776
      • Major remodel year: 1981

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available, Electricity Connected, Phone Available

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Pawling

      Financial & listing details

      • Price per square foot: $258/sqft
      • Tax assessed value: $156,800
      • Annual tax amount: $11,571
      • Date on market: 5/28/2026
      • Cumulative days on market: 151 days
      • Listing agreement: Exclusive Right To Sell
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/10/2026Pending sale$565,000$258/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1004011 Report a problem
        5/28/2026Listed for sale$565,000$258/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1004011 Report a problem
        5/14/2026Listing removed$565,000$258/sqft
        Source: OneKey® MLS as distributed by MLS GRID #954200 Report a problem
        4/22/2026Price change$565,000-5.7%$258/sqft
        Source: OneKey® MLS as distributed by MLS GRID #954200 Report a problem
        2/5/2026Listed for sale$599,000+64.1%$273/sqft
        Source: OneKey® MLS as distributed by MLS GRID #954200 Report a problem
        7/16/2018Sold$365,000$166/sqft
        Source: OneKey® MLS as distributed by MLS GRID #H4804762 Report a problem
        6/1/2018Pending sale$365,000$166/sqft
        Source: BHHS HUDSON VALLEY PROPERTIES LG #368404 Report a problem
        2/5/2018Listed for sale$365,000$166/sqft
        Source: BHHS HUDSON VALLEY PROPERTIES LG #368404 Report a problem
        12/13/2017Listing removed$365,000$166/sqft
        Source: Berkshire Hathaway HomeServices Hudson Valley Properties #4720587 Report a problem
        9/12/2017Price change$365,000-2.7%$166/sqft
        Source: BHHS HUDSON VALLEY PROPERTIES LG #4720587 Report a problem
        5/9/2017Listed for sale$375,000+18.1%$171/sqft
        Source: BHHS Hudson Valley Properties #4720587 Report a problem
        4/26/2013Sold$317,500-2.6%$145/sqft
        Source: OneKey® MLS as distributed by MLS GRID #H3233804 Report a problem
        1/15/2013Price change$325,900-3.6%$149/sqft
        Source: Prudential Serls Prime Properties #3233804 Report a problem
        10/17/2012Pending sale$338,000$154/sqft
        Source: Prudential Serls Prime Properties #309184 Report a problem
        10/1/2012Price change$338,000-6.1%$154/sqft
        Source: Prudential Serls Prime Properties #309184 Report a problem
        9/15/2012Price change$360,000-5.2%$164/sqft
        Source: Prudential Serls Prime Properties #309184 Report a problem
        9/9/2012Price change$379,900-2.6%$173/sqft
        Source: Prudential Serls Prime Properties #309184 Report a problem
        7/22/2012Listed for sale$389,900-8.3%$178/sqft
        Source: Prudential Serls Prime Properties #309184 Report a problem
        9/3/2010Sold$425,000-5.3%$194/sqft
        Source: Smart MLS #98442389 Report a problem
        8/9/2010Pending sale$449,000$205/sqft
        Source: GILLIAN STEWART REAL ESTATE #282358 Report a problem
        2/23/2010Price change$449,000-7.4%$205/sqft
        Source: GILLIAN STEWART REAL ESTATE #282358 Report a problem
        11/8/2009Listed for sale$485,000+51.6%$221/sqft
        Source: Gillian Stewart Real Estate, LLC #2934064 Report a problem
        11/15/2007Sold$320,000$146/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $156,800
        2024-- $156,800
        2023-- $156,800
        2022-- $156,800
        2021-- $156,800
        2020-- $156,800
        2019-- $156,800 +19%
        2018-- $131,800
        2017$8,654 $131,800
        2016-- $131,800
        2015-- $131,800
        2014-- $131,800
        2012-- $131,800
        2011-- $131,800
        2010-- $131,800
        2009-- $131,800
        2008-- $131,800
        2007-- $131,800
        2006-- $131,800
        2005-- $131,800
        2004-- $131,800
        2003-- $131,800
        2002-- $131,800 +15.4%
        2001-- $114,250
        2000-- $114,250
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.
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        Climate risks

        Neighborhood: 12564

        Getting around

        7 / 100
        Car-Dependent
        13 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Beekman
        • Middle: Union Vale Middle School
        • High: Arlington High School

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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