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For sale
    • $789,000

    287 South Bear Hill Road, Chaplin, CT 06235

    4beds
    2,900sqft
    : 
    $5,692/mo
    Get pre-qualified
    Single Family Residence
    Built in 1997
    3.39 Acres Lot
    $769,800 Zestimate®
    $272/sqft
    $-- HOA

    What's special

    Cedar sidingVaulted ceilingsFirst-floor primary suiteStunning mahogany entryGated drivewayCentral vacBosch stainless appliances
    Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses, kennels, or hobby farming. The property also includes a chicken coop, goat building, fenced garden with 12 raised beds, pond, two running streams, and a fire pit area. Inside, the home has been extensively updated with a stunning mahogany entry, Brazilian Walnut (IPE) flooring, vaulted ceilings, fireplace, and a beautifully designed chef's kitchen with soapstone counters, custom cabinetry, and Bosch stainless appliances including an induction stove. The first-floor primary suite offers vaulted ceilings, two walk-in closets, and a renovated bath with porcelain tile and granite vanity. A sunroom with marble floors and skylights opens to the back deck, while a spacious bonus room with private entrance offers ideal in-law, office, or gym potential. Additional features include dual heat with Central Wood Boiler and oil backup, Kubota whole-house generator, underground utilities, central vac, artesian well, cedar siding, and gated driveway. A truly exceptional property with endless possibilities.
    83 days
    |
    607
    |
    42
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Team Rio of Executive Real Estate,

    Amy P. Rio (860)916-6048,

    Better Homes and Gardens Real Estate Executive Real Estate 860-633-8800

    Source: Smart MLS,MLS#: 24175652MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Bonus Room, Solarium
      Primary bedroom
      • Features: Vaulted Ceiling(s), Ceiling Fan(s), Full Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Main
      • Area: 336 Square Feet
      • Dimensions: 12 x 28
      Bedroom
      • Features: Walk-In Closet(s), Wall/Wall Carpet
      • Level: Upper
      • Area: 285 Square Feet
      • Dimensions: 15 x 19
      Bedroom
      • Features: Wall/Wall Carpet
      • Level: Upper
      • Area: 132 Square Feet
      • Dimensions: 11 x 12
      Bedroom
      • Features: Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 196 Square Feet
      • Dimensions: 14 x 14
      Dining room
      • Features: Bay/Bow Window
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 12 x 11
      Kitchen
      • Features: Remodeled, Breakfast Bar, Breakfast Nook, Hardwood Floor
      • Level: Main
      • Area: 143 Square Feet
      • Dimensions: 13 x 11
      Living room
      • Features: Vaulted Ceiling(s), Ceiling Fan(s), Fireplace, Hardwood Floor
      • Level: Main
      • Area: 300 Square Feet
      • Dimensions: 15 x 20
      Office
      • Features: Hardwood Floor
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 11 x 12
      Rec play room
      • Features: Hardwood Floor
      • Level: Main
      • Area: 418 Square Feet
      • Dimensions: 19 x 22
      Sun room
      • Features: Skylight, French Doors, Marble Floor
      • Level: Main
      • Area: 228 Square Feet
      • Dimensions: 12 x 19
      Heating
      • Hot Water, Electric, Oil, Wood
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Main Level
      Features
      • Open Floorplan
      • Windows: Thermopane Windows
      • Basement: Full,Unfinished,Walk-Out Access
      • Attic: Pull Down Stairs
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,900
      • Total interior livable area: 2,900 sqft
      • Finished area above ground: 2,900

      Property

      Parking
      • Total spaces: 2
      • Parking features: Barn
      • Garage spaces: 2
      Features
      • Patio & porch: Deck, Covered
      • Exterior features: Garden
      Lot
      • Size: 3.39 Acres
      • Features: Secluded, Wooded, Level, Cleared
      Details
      • Additional structures: Barn(s)
      • Parcel number: 1681632
      • Zoning: RA

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard, Cedar
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1997

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available
      Green energy
      • Green verification: ENERGY STAR Certified Homes
      • Energy efficient items: Windows

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Chaplin

      Financial & listing details

      • Price per square foot: $272/sqft
      • Tax assessed value: $330,700
      • Annual tax amount: $10,875
      • Date on market: 5/14/2026

        Estimated market value

        $769,800

        $731,000 - $808,000

        $3,603/mo

        Price history

        DateEventPrice
        5/14/2026Listed for sale$789,000$272/sqft
        Source: Smart MLS #24175652 Report a problem
        3/1/2026Listing removed$789,000$272/sqft
        Source: Smart MLS #24121168 Report a problem
        10/8/2025Price change$789,000-7.6%$272/sqft
        Source: Smart MLS #24121168 Report a problem
        8/28/2025Listed for sale$853,500+252.8%$294/sqft
        Source: Smart MLS #24121168 Report a problem
        3/5/2008Sold$241,900-26.4%$83/sqft
        Source: Smart MLS #G476209 Report a problem
        12/6/2007Sold$328,704$113/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,180 +4.8%$324,400
        2024$9,716 +24.2%$324,400 +47.2%
        2023$7,824 +2.9%$220,400
        2022$7,604 +6.2%$220,400
        2021$7,163 $220,400
        2020$7,163 $220,400
        2019$7,163 -1.2%$220,400 -1.2%
        2018$7,248 -7.3%$223,000
        2017$7,816 $223,000
        2016$7,816 -4%$223,000
        2015$8,140 $223,000
        2014$8,140 +6.9%$223,000 -11.7%
        2013$7,616 $252,600
        2012$7,616 $252,600
        2011$7,616 $252,600
        2010$7,616 +1%$252,600
        2009$7,540 -29.1%$252,600 -15.7%
        2007$10,632 +5%$299,500
        2006$10,123 +9.8%$299,500 +7.2%
        2005$9,217 +60.2%$279,300 +103.9%
        2003$5,754 -17.7%$137,000 -30.1%
        2002$6,989 $196,000 +29.8%
        1996-- $150,950
        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: 06235

        Getting around

        0 / 100
        Car-Dependent
        17 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Chaplin

        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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