287 South Bear Hill Road, Chaplin, Connecticut

$789,000

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4

Beds

3

Baths

2,900

Square feet

3.39

Acres

About 287 South Bear Hill Road

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.

Features of 287 South Bear Hill Road

MLS® # 24175652
Price $789,000
Bedrooms 4
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 2,900
Acres 3.39
Type Single Family For Sale
Style Colonial
Status Under Contract

Community Information

Address 287 South Bear Hill Road
Area N/A
City Chaplin
County Windham
State Connecticut
Zip Code 06235

Amenities

Features Energy Star Rated, Thermopane Windows
Parking Barn
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Interior Features Cable - Available, Open Floor Plan
Appliances Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Water, Electric, Oil, Wood
Cooling Window Unit
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Unfinished, Walk-out, Full With Walk-Out

Exterior

Exterior Clapboard, Cedar
Exterior Features Barn, Deck, Garden Area, Covered Deck
Lot Description Secluded, Treed, Level Lot, Cleared
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Chaplin
High Per Board of Ed

Additional Information

Date Listed May 14th, 2026
Days on Market 81
Zoning RA
RE / Bank Owned No

Listing Details

OfficeBetter Homes and Gardens Real Estate Executive Real Estate

Listing Map

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