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Sold for $565,000
    • $565,000

    168 Old Route 55, Pawling, NY 12564

    2beds
    2,194sqft
    Single Family Residence, Residential
    Built in 1776
    2.2 Acres Lot
    $555,700 Zestimate®
    $258/sqft
    $3,443 Estimated rent

    Home value

    $555,700

    $528,000 - $583,000

    $3,443/mo

    Zestimate® history
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    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Alea R. Vorillas 718-986-7441,

    RE/MAX Classic Realty 914-243-5200

    Bought with:

    Jonathan Archie, 10401381072

    eXp Realty

    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

    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: 111 days
    • Listing agreement: Exclusive Right To Sell
    • Electric utility on property: Yes

    Price history

    DateEventPrice
    8/6/2026Sold$565,000$258/sqft
    Source: OneKey® MLS as distributed by MLS GRID #1004011 Report a problem
    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
    9/8/2010Sold$425,000-5.3%$194/sqft
    Source: Public Record 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

    Neighborhood: 12564

    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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