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  • Price cut: $25K (5/19)
    $574,900

    2 Judd Hill Road, Woodbury, CT 06798

    3beds
    1,470sqft
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    Single Family Residence
    Built in 1958
    0.96 Acres Lot
    $567,900 Zestimate®
    $391/sqft
    $-- HOA

    What's special

    Serene and private settingSpacious first-floor bedroomNewly updated kitchen
    Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace. Additional highlights include a new furnace and septic tank installed in 2025, a newer whole-house propane generator, and a roof approximately 10 years old. This one-of-a-kind Woodbury retreat offers privacy, comfort, and thoughtful updates in a beautiful country setting. Come see it and don't miss the opportunity to own your own oasis in Woodbury.
    38 days
    |
    793
    |
    52
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Timothy Drakeley (203)510-9184,

    Drakeley Real Estate, Inc. 203-263-4336

    Source: Smart MLS,MLS#: 24172678MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Hardwood Floor
      • Level: Main
      Bedroom
      • Level: Upper
      Bedroom
      • Features: Softwood Floor
      • Level: Upper
      Den
      • Features: Hardwood Floor
      • Level: Main
      Dining room
      • Level: Main
      Kitchen
      • Features: Kitchen Island
      • Level: Main
      Living room
      • Features: Fireplace, Hardwood Floor
      • Level: Main
      Heating
      • Forced Air, Oil
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Main Level
      Features
      • Basement: Full
      • Attic: Access Via Hatch
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 1,470
      • Total interior livable area: 1,470 sqft
      • Finished area above ground: 1,470
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached, Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Patio & porch: Deck
      Lot
      • Size: 0.96 Acres
      • Features: Level
      Details
      • Parcel number: 932289
      • Zoning: OS80
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1958

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Golf, Lake, Library, Private School(s), Tennis Court(s)
      HOA
      • Has HOA: No
      Location
      • Region: Woodbury

      Financial & listing details

      • Price per square foot: $391/sqft
      • Tax assessed value: $168,840
      • Annual tax amount: $3,988
      • Date on market: 5/5/2026
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        Estimated market value

        $567,900

        $540,000 - $596,000

        $3,272/mo

        Price history

        DateEventPrice
        5/19/2026Price change$574,900-4.2%$391/sqft
        Source: Smart MLS #24172678 Report a problem
        5/5/2026Listed for sale$599,900+9.1%$408/sqft
        Source: Smart MLS #24172678 Report a problem
        1/9/2026Sold$550,000-3.3%$374/sqft
        Source: Smart MLS #24134430 Report a problem
        12/7/2025Pending sale$569,000$387/sqft
        Source: Smart MLS #24134430 Report a problem
        11/6/2025Price change$569,000-5%$387/sqft
        Source: Smart MLS #24134430 Report a problem
        10/18/2025Listed for sale$599,000+84.3%$407/sqft
        Source: Smart MLS #24134430 Report a problem
        2/28/2025Sold$325,000+1.6%$221/sqft
        Source: Smart MLS #24071100 Report a problem
        2/3/2025Pending sale$319,900$218/sqft
        Source: Smart MLS #24071100 Report a problem
        2/1/2025Listed for sale$319,900$218/sqft
        Source: Smart MLS #24071100 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,988 +3.3%$168,840 +1.3%
        2024$3,860 +5.3%$166,600 +32.1%
        2023$3,664 -0.4%$126,080
        2022$3,678 $126,080
        2021$3,678 $126,080
        2020$3,678 $126,080
        2019$3,678 +3.2%$126,080 -6%
        2018$3,565 -2.1%$134,130
        2017$3,643 +3.3%$134,130
        2016$3,526 +0.8%$134,130
        2015$3,497 +1.5%$134,130
        2014$3,446 -11%$134,130 -18.9%
        2013$3,872 -3.4%$165,470
        2012$4,009 +7.9%$165,470
        2011$3,716 +4.7%$165,470
        2010$3,549 +1.5%$165,470
        2009$3,496 +9.4%$165,470 +26.1%
        2008$3,196 +1.6%$131,260
        2007$3,145 +5.1%$131,260
        2006$2,991 +6.4%$131,260
        2005$2,812 $131,260
        2004$2,812 +45.2%$131,260 +84.7%
        2003$1,936 -23.2%$71,050 -45.2%
        1997$2,521 $129,620

        Find assessor info on the county website

        Monthly payment

        Est. payment

          Payment breakdown

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          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: 06798

          Getting around

          1 / 100
          Car-Dependent
          16 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Mitchell
          • Middle: Woodbury
          • 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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