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For sale
    • $1,329,000

    286 Black Rock Turnpike, Redding, CT 06896

    5beds
    4,158sqft
    : 
    $8,871/mo
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    Single Family Residence
    Built in 1708
    2.37 Acres Lot
    $1,321,100 Zestimate®
    $320/sqft
    $-- HOA

    What's special

    The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous maintenance, and thoughtful updates throughout. Offering more than 4,100 square feet of living space, this distinguished 12 room residence features 5 bedrooms, 4 updated full baths, and an updated half bath. Details include the original historic front door, exposed beams, paned windows, hardwood floors, five fireplaces (one gas fireplace in the family room and four wood-burning fireplaces), and abundant natural light throughout. Designed for both elegant entertaining and comfortable everyday living, the home offers gracious living and dining spaces with exceptional versatility, including a private entrance to a potential home office, study, or guest suite with Jotul cast iron gas stove. The chef's kitchen serves as the heart of the home, featuring high-end appliances, modern finishes, a large center island, generous pantry with prep sink, additional refrigerator, and abundant workspace. The kitchen flows seamlessly to the expansive deck, creating a wonderful indoor-outdoor living experience. The beautifully landscaped grounds provide a private retreat enhanced by brick walkways, stone retaining walls, mature trees, and a gated driveway with additional parking. A spectacular 1,000-square-foot stone patio with a working stone fireplace offers an exceptional setting for outdoor entertaining, dining, and relaxation. The property's 720-square-foot barn with loft provides three-car garage capacity, workshop space, storage, and potential for a studio or hobby area. Additional amenities include a storage shed and basketball court, adding to the property's versatility and appeal. Meticulously maintained and thoughtfully updated, the home features oil-fired forced-air heat, central air conditioning, a new oil tank, updated 200 amp electrical service, new balcony roof, and new cedar fencing enhancing privacy and curb appeal. This extraordinary Greek Revival estate offers a rare combination of historic character, modern comfort, privacy, and exceptional outdoor amenities. Move-in ready and rich in history, it presents a unique opportunity to own one of Connecticut's treasured historic properties while enjoying the conveniences of today's lifestyle. Located in Fairfield County, Redding is a picturesque New England community known for its natural beauty, privacy, and strong sense of community. Surrounded by rolling hills, preserved open space, and miles of scenic trails, Redding offers a peaceful country lifestyle with convenient access to excellent schools, local amenities, neighboring towns, and commuter routes to New York City.
    11 days
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    1,184
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    64
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    Zillow last checked:

    Listing updated:

    Listed by:

    Nora C. Ryan (203)410-5939,

    Houlihan Lawrence WD 203-787-7800

    Source: Smart MLS,MLS#: 24191583MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Balcony/Deck, Bedroom Suite, Ceiling Fan(s), Fireplace, Full Bath, Walk-In Closet(s)
      • Level: Upper
      • Area: 238 Square Feet
      • Dimensions: 14 x 17
      Bedroom
      • Features: Full Bath, Hardwood Floor
      • Level: Upper
      • Area: 273 Square Feet
      • Dimensions: 13 x 21
      Bedroom
      • Features: Balcony/Deck, Ceiling Fan(s), Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 187 Square Feet
      • Dimensions: 11 x 17
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 143 Square Feet
      • Dimensions: 11 x 13
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 165 Square Feet
      • Dimensions: 11 x 15
      Bathroom
      • Level: Main
      Bathroom
      • Level: Upper
      Den
      • Features: Hardwood Floor
      • Level: Main
      • Area: 108 Square Feet
      • Dimensions: 9 x 12
      Dining room
      • Features: High Ceilings, Beamed Ceilings, Fireplace, Hardwood Floor
      • Level: Main
      • Area: 154 Square Feet
      • Dimensions: 11 x 14
      Family room
      • Features: High Ceilings, Balcony/Deck, Wet Bar, Gas Log Fireplace, Hardwood Floor
      • Level: Main
      • Area: 340 Square Feet
      • Dimensions: 17 x 20
      Kitchen
      • Features: Remodeled, Balcony/Deck, Built-in Features, Fireplace, Kitchen Island, Pantry
      • Level: Main
      • Area: 340 Square Feet
      • Dimensions: 17 x 20
      Living room
      • Features: High Ceilings, Beamed Ceilings, Fireplace, Patio/Terrace, Hardwood Floor
      • Level: Main
      • Area: 420 Square Feet
      • Dimensions: 20 x 21
      Other
      • Features: Full Bath, Tile Floor
      • Level: Lower
      • Area: 340 Square Feet
      • Dimensions: 17 x 20
      Heating
      • Forced Air, Oil, Propane
      Cooling
      • Ceiling Fan(s), Central Air, Whole House Fan, Zoned
      Appliances
      • Included: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Lower Level
      Features
      • Central Vacuum
      • Doors: Storm Door(s)
      • Basement: Full,Heated,Storage Space,Interior Entry,Partially Finished,Liveable Space
      • Attic: Access Via Hatch
      • Number of fireplaces: 5
      Interior area
      • Total structure area: 4,158
      • Total interior livable area: 4,158 sqft
      • Finished area above ground: 3,788
      • Finished area below ground: 370
      Video & virtual tour

      Property

      Parking
      • Total spaces: 8
      • Parking features: Barn, Detached, Paved, Off Street, Driveway, Garage Door Opener, Private
      • Garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Patio, Porch, Deck
      • Exterior features: Lighting, Balcony, Fruit Trees, Garden
      • Fencing: Wood,Partial,Fenced
      Lot
      • Size: 2.37 Acres
      • Features: Wooded, Dry, Sloped, Landscaped
      Details
      • Additional structures: Barn(s), Shed(s)
      • Parcel number: 268852
      • Zoning: R-2
      • Other equipment: Generator Ready

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Antique
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Concrete Perimeter, Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1708

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available
      Green energy
      • Energy efficient items: Insulation, Thermostat, Doors

      Community & HOA

      Community
      • Features: Library, Medical Facilities, Park, Private School(s), Shopping/Mall, Stables/Riding
      • Subdivision: Redding Center
      HOA
      • Has HOA: No
      Location
      • Region: Redding

      Financial & listing details

      • Price per square foot: $320/sqft
      • Tax assessed value: $852,700
      • Annual tax amount: $25,189
      • Date on market: 7/15/2026
      • Exclusions: Please see inclusion/exclusion form.

        Estimated market value

        $1,321,100

        $1.26M - $1.39M

        $7,134/mo

        Price history

        DateEventPrice
        7/18/2026Listed for sale$1,329,000+92.9%$320/sqft
        Source: Smart MLS #24191583 Report a problem
        8/10/2018Sold$689,000-1.4%$166/sqft
        Source: Smart MLS #170075110 Report a problem
        5/4/2018Listed for sale$699,000+12.7%$168/sqft
        Source: William Raveis Real Estate #170075110 Report a problem
        10/30/2014Sold$620,000-35.4%$149/sqft
        Source: Smart MLS #99071336 Report a problem
        10/31/2003Sold$960,000+104.3%$231/sqft
        Source: Smart MLS #98176712 Report a problem
        4/15/1996Sold$470,000+14.8%$113/sqft
        Source: Public Record Report a problem
        6/29/1992Sold$409,500$98/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$25,189 +2.9%$852,700
        2024$24,490 +3.7%$852,700
        2023$23,611 +24.4%$852,700 +49.8%
        2022$18,974 +0.4%$569,100 -1.1%
        2021$18,903 $575,600
        2020$18,903 $575,600
        2019$18,903 +3.5%$575,600
        2018$18,258 -3.5%$575,600 -9.9%
        2017$18,930 +1.3%$639,100
        2016$18,687 +1.1%$639,100
        2015$18,476 $639,100
        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: 06896

        Getting around

        1 / 100
        Car-Dependent
        13 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Redding
        • High: Joel Barlow

        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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