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For sale
  • $950,000

    50 Southbury Road, Roxbury, CT 06783

    5beds
    2,000sqft
    : 
    Single Family Residence
    Built in 1817
    8.71 Acres Lot
    $-- Zestimate®
    $475/sqft
    $-- HOA

    What's special

    Wood-burning fireplaceSpring-fed pondOriginal hand-hewn beamsMature treesLush gardensWide-plank oak floorsFormal dining room
    Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. 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. Whether you envision building a bespoke estate or simply enjoying the charm and privacy of the existing homes, this rare offering blends history, potential, and natural beauty in one of Litchfield County's most coveted locations. Total acreage includes 2 acre main house lot with 6.71 acre buildable lot. Total square footage is combined main house and guest house.
    141 days
    |
    1,163
    |
    90
    |

    Zillow last checked: 8 hours ago

    Listing updated: October 07, 2025 at 03:35pm

    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#: 24117695MLS Logo

    Tour with a local agent

    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
    • Window Unit(s)
    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: 2,000
    • Total interior livable area: 2,000 sqft
    • Finished area above ground: 2,000
    • 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: 8.71 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: $475/sqft
    • Tax assessed value: $375,340
    • Annual tax amount: $4,879
    • Date on market: 8/7/2025
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    Estimated market value

    Not available

    Estimated sales range

    Not available

    Not available

    Price history

    Price history
    DateEventPrice
    8/7/2025Listed for sale$950,000+660%$475/sqft
    Source: Smart MLS #24117695 Report a problem
    12/30/2014Sold$125,000-77.5%$63/sqft
    Source: Public Record Report a problem
    6/14/2013Listing removed$555,000$278/sqft
    Source: Litchfield Hills Sotheby's International Realty #L143355 Report a problem
    7/22/2011Listed for sale$555,000$278/sqft
    Source: Litchfield Hills Sotheby's International Realty #98509011 Report a problem

    Public tax history

    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%

    Find assessor info on the county website

    BuyAbility℠ payment

    Est. payment
    $5,426/mo
    Principal & interest
    $3684
    Property taxes
    $1409
    Home insurance
    $333

      Climate risks

      Neighborhood: 06783

      Nearby schools

      GreatSchools rating

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