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For sale
    • Price cut: $200K (8/31)
    $1,590,000

    40 Ruffin Road, Woodbury, CT 06798

    4beds
    2,732sqft
    : 
    $10,454/mo
    Get pre-qualified
    Single Family Residence
    Built in 1881
    6.3 Acres Lot
    $-- Zestimate®
    $582/sqft
    $-- HOA

    What's special

    Relax by the poolCharming vintage homeVulcan stoveAdorable potting shedDetached three-bay garageHeated workshopInground pool
    It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE. This private setting is less than five minutes to Historic Woodbury's town center and only 10 minutes to Washington Depot. Woodbury is Voted top three best places to live in CT according to Travel & Leisure. POTENTIAL FOR TWO LOTS TO BE SPLIT OFF OR SECONDARY/GUEST HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.
    78 days
    1,097
    91

    Zillow last checked:

    Listing updated:

    Listed by:

    Mary Ann Bennett (203)206-7048,

    Drakeley Real Estate, Inc. 203-263-4336

    Source: Smart MLS,MLS#: 24184948MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Workshop
      Primary bedroom
      • Features: Bookcases, Bedroom Suite, Built-in Features, Full Bath, Wall/Wall Carpet
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Den
      • Features: Wide Board Floor
      • Level: Main
      Great room
      • Features: Beamed Ceilings, Dining Area, Fireplace, French Doors, Patio/Terrace, Wide Board Floor
      • Level: Main
      Kitchen
      • Features: Built-in Features, Dining Area, Dry Bar, Pantry, Wide Board Floor
      • Level: Main
      Living room
      • Features: Bay/Bow Window, Wide Board Floor
      • Level: Main
      Office
      • Features: Wide Board Floor
      • Level: Main
      Heating
      • Hot Water, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Gas Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Main Level
      Features
      • Wired for Data, Central Vacuum
      • Doors: French Doors
      • Basement: Crawl Space,Full,Interior Entry
      • Attic: Access Via Hatch
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,732
      • Total interior livable area: 2,732 sqft
      • Finished area above ground: 2,732

      Property

      Parking
      • Total spaces: 20
      • Parking features: Barn, Detached, Driveway, Garage Door Opener, Private, Gravel
      • Garage spaces: 5
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Screened, Porch, Patio
      • Exterior features: Rain Gutters, Garden, Stone Wall
      • Has private pool: Yes
      • Pool features: Vinyl, In Ground
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront, River Front
      Lot
      • Size: 6.3 Acres
      • Features: Level, Landscaped
      Details
      • Additional structures: Shed(s), Barn(s)
      • Parcel number: 933676
      • Zoning: OS100

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Concrete Perimeter, Stone
      • Roof: Asphalt,Wood
      Condition
      • New construction: No
      • Year built: 1881

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Golf, Health Club, Library, Medical Facilities, Private School(s), Stables/Riding, Tennis Court(s)
      • Security: Security System
      HOA
      • Has HOA: No
      Location
      • Region: Woodbury

      Financial & listing details

      • Price per square foot: $582/sqft
      • Tax assessed value: $425,110
      • Annual tax amount: $10,645
      • Date on market: 6/19/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/31/2026Price change$1,590,000-11.2%$582/sqft
        Source: Smart MLS #24184948 Report a problem
        7/17/2026Price change$1,790,000-5.8%$655/sqft
        Source: Smart MLS #24184948 Report a problem
        6/19/2026Listed for sale$1,900,000+204%$695/sqft
        Source: Smart MLS #24184948 Report a problem
        12/9/1999Sold$625,000$229/sqft
        Source: Smart MLS #98053129 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,041 +1.9%$425,110
        2024$9,850 +3%$425,110 +29.2%
        2023$9,560 -0.4%$328,960
        2022$9,596 $328,960
        2021$9,596 $328,960
        2020$9,596 $328,960
        2019$9,596 -2.1%$328,960 -10.7%
        2018$9,797 -2.1%$368,570
        2017$10,010 +3.3%$368,570
        2016$9,690 +0.8%$368,570
        2015$9,609 +1.5%$368,570
        2014$9,469 +8%$368,570 -1.6%
        2013$8,768 -17.6%$374,700 -14.7%
        2012$10,639 +7.9%$439,070
        2011$9,862 +4.7%$439,070
        2010$9,418 +1.5%$439,070
        2009$9,278 -5.2%$439,070 +9.2%
        2008$9,792 +1.6%$402,120
        2007$9,635 +5.1%$402,120
        2006$9,164 +6.4%$402,120
        2005$8,613 -0.7%$402,120 -0.7%
        2004$8,674 +66.3%$404,970 +111.5%
        2003$5,217 +4.6%$191,440 -25.3%
        1997$4,988 $256,440
        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.
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        Climate risks

        Neighborhood: 06798

        Getting around

        3 / 100
        Car-Dependent
        18 / 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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