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For sale
    • Price cut: $100.1K (2/28)
    $999,900

    27 Middle Quarter Road, Woodbury, CT 06798

    3beds
    2,042sqft
    : 
    Single Family Residence
    Built in 1825
    1.49 Acres Lot
    $-- Zestimate®
    $490/sqft
    $-- HOA

    What's special

    Wide board antique flooringWalk-up atticTwo post-and-beam barnsTwo additional bedroomsBeautifully landscaped level lot
    Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury! The home is under renovation and will be complete in 3 to 6 months. Buyers can still make some changes or upgrades. This MQ commercial zone provides flexibility to run businesses, add square feet for more business opportunity, or develop this parcel into a mixed use property with a commercial and residential component. Call for specifications and there is still time to make changes.
    92 days
    |
    910
    |
    28
    |

    Zillow last checked: 7 hours ago

    Listing updated: February 28, 2026 at 08:48am

    Listed by:

    Timothy Drakeley (203)510-9184,

    Drakeley Real Estate, Inc. 203-263-4336

    Source: Smart MLS,MLS#: 24146826MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Workshop
      Primary bedroom
      • Features: High Ceilings, Cathedral Ceiling(s), Bedroom Suite, Full Bath, Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Features: Wide Board Floor
      • Level: Upper
      Bedroom
      • Features: Wide Board Floor
      • Level: Main
      Dining room
      • Features: Fireplace, Wide Board Floor
      • Level: Main
      Kitchen
      • Features: Cathedral Ceiling(s), Beamed Ceilings
      • Level: Main
      Library
      • Features: Wide Board Floor
      • Level: Upper
      Living room
      • Features: Fireplace, Wide Board Floor
      • Level: Main
      Heating
      • Forced Air, Hot Water, Propane
      Cooling
      • Central Air
      Appliances
      • Included: Allowance, Water Heater
      • Laundry: Main Level
      Features
      • Open Floorplan
      • Windows: Storm Window(s)
      • Basement: Partial,Full
      • Attic: Walk-up
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 2,042
      • Total interior livable area: 2,042 sqft
      • Finished area above ground: 2,042

      Property

      Parking
      • Total spaces: 4
      • Parking features: Barn, Detached
      • Garage spaces: 4
      Features
      • Patio & porch: Patio
      • On waterfront: Yes
      • Waterfront features: Waterfront, Brook
      Lot
      • Size: 1.49 Acres
      • Features: Level, Open Lot
      Details
      • Additional structures: Barn(s)
      • Parcel number: 936023
      • Zoning: MQ
      • Horses can be raised: Yes

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Concrete Perimeter, Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1825
      Details
      • Warranty included: Yes

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Underground Utilities, Cable Available
      Green energy
      • Energy efficient items: Windows

      Community & HOA

      Community
      • Features: Basketball Court, Golf, Private School(s)
      • Subdivision: Middle Quarter
      HOA
      • Has HOA: No
      Location
      • Region: Woodbury

      Financial & listing details

      • Price per square foot: $490/sqft
      • Tax assessed value: $284,830
      • Annual tax amount: $6,728
      • Date on market: 1/2/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        2/28/2026Price change$999,900-9.1%$490/sqft
        Source: Smart MLS #24146826 Report a problem
        1/2/2026Listed for sale$1,100,000+57.2%$539/sqft
        Source: Smart MLS #24146826 Report a problem
        10/10/2025Listing removed$699,900$343/sqft
        Source: Smart MLS #24049803 Report a problem
        3/12/2025Price change$699,900-39.1%$343/sqft
        Source: Smart MLS #24049803 Report a problem
        11/9/2024Listed for sale$1,150,000+259.4%$563/sqft
        Source: Smart MLS #24049803 Report a problem
        4/9/2024Sold$320,000-34.1%$157/sqft
        Source: Smart MLS #170625141 Report a problem
        1/3/2024Sold$485,401$238/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$6,728 +1.9%$284,830
        2024$6,600 +0.9%$284,830 +26.5%
        2023$6,542 -0.4%$225,110
        2022$6,566 $225,110
        2021$6,566 $225,110
        2020$6,566 $225,110
        2019$6,566 +0.6%$225,110 -8.3%
        2018$6,525 -2.1%$245,500
        2017$6,668 +3.3%$245,500
        2016$6,454 +0.8%$245,500
        2015$6,400 +1.5%$245,500
        2014$6,307 +9.4%$245,500 -0.4%
        2013$5,766 -3.4%$246,410
        2012$5,971 +7.9%$246,410
        2011$5,534 +4.5%$246,410 -0.2%
        2010$5,295 +1.5%$246,830
        2009$5,216 -9.2%$246,830 +4.6%
        2008$5,744 +1.6%$235,880
        2007$5,652 +5.1%$235,880
        2006$5,376 +6.4%$235,880
        2005$5,053 $235,880
        2004$5,053 +83.5%$235,880 +133.5%
        2003$2,753 -31.6%$101,040 -51.2%
        1997$4,024 $206,880

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $6,639/mo
        Principal & interest
        $5156
        Property taxes
        $1483
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          Climate risks

          Neighborhood: 06798

          Getting around

          42 / 100
          Car-Dependent
          27 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Mitchell
          • High: Nonnewaug

          Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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