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For sale
    • Price cut: $225K (5/26)
    $725,000

    50 Southbury Road, Roxbury, CT 06783

    5beds
    1,365sqft
    : 
    $4,391/mo
    Get pre-qualified
    Single Family Residence
    Built in 1817
    2 Acres Lot
    $-- Zestimate®
    $531/sqft
    $-- HOA

    What's special

    Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.
    60 days
    |
    1,610
    |
    149
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    MADONNA & PHILLIPS TEAM AT WILLIAM PITT SOTHEBY’S INTERNATIONAL REALTY,

    Jeffrey Phillips (917)284-8276,

    William Pitt Sotheby's Int'l 860-868-6600,

    Co-Listing Agent: Mark Madonna 860-800-3344,

    William Pitt Sotheby's Int'l

    Source: Smart MLS,MLS#: 24178189MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: Main
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Other
      Bedroom
      • Level: Other
      Living room
      • Level: Main
      Heating
      • Baseboard, Electric
      Cooling
      • None
      Appliances
      • Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
      • Laundry: Main Level
      Features
      • Basement: Partial
      • Attic: None
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 1,365
      • Total interior livable area: 1,365 sqft
      • Finished area above ground: 1,365
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 1
      • Parking features: Detached
      • Garage spaces: 1
      Features
      • Patio & porch: Deck, Patio
      • Exterior features: Garden, Stone Wall
      • On waterfront: Yes
      • Waterfront features: Waterfront, Pond, Walk to Water
      Lot
      • Size: 2 Acres
      • Features: Few Trees, Sloped
      Details
      • Additional structures: Guest House
      • Parcel number: 866798
      • Zoning: A

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Wood Siding
      • Foundation: Block, Stone
      • Roof: Wood
      Condition
      • New construction: No
      • Year built: 1817

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Roxbury

      Financial & listing details

      • Price per square foot: $531/sqft
      • Tax assessed value: $375,340
      • Annual tax amount: $4,879
      • Date on market: 5/26/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/26/2026Price change$725,000-23.7%$531/sqft
        Source: Smart MLS #24178189 Report a problem
        8/7/2025Listed for sale$950,000+660%$696/sqft
        Source: Smart MLS #24117695 Report a problem
        12/30/2014Sold$125,000-77.5%$92/sqft
        Source: Public Record Report a problem
        6/14/2013Listing removed$555,000$407/sqft
        Source: Litchfield Hills Sotheby's International Realty #L143355 Report a problem
        7/22/2011Listed for sale$555,000$407/sqft
        Source: Litchfield Hills Sotheby's International Realty #98509011 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,879 +3.2%$375,340
        2024$4,729 $375,340
        2023$4,729 +3.2%$375,340 +24.9%
        2022$4,582 -1%$300,470
        2021$4,627 -2.5%$300,470
        2020$4,747 -0.3%$300,470
        2019$4,762 $300,470
        2018$4,762 +4%$300,470 -6.8%
        2017$4,579 +3.6%$322,480
        2016$4,418 $322,480
        2015$4,418 +2.2%$322,480
        2014$4,321 +0.7%$322,480
        2013$4,289 +6.7%$322,480 -2.9%
        2012$4,019 +1.7%$332,130
        2011$3,952 +4.4%$332,130
        2010$3,786 +4.6%$332,130
        2009$3,620 $332,130
        2008$3,620 -14%$332,130 +21.5%
        2007$4,211 +1.4%$273,470 +1.4%
        2006$4,151 $269,570
        2005$4,151 $269,570
        2004$4,151 $269,570
        2003$4,151 +3.6%$269,570 +31.5%
        2001$4,006 $205,020
        2000$4,006 $205,020
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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.
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        Climate risks

        Neighborhood: 06783

        Getting around

        8 / 100
        Car-Dependent
        7 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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