287 South Bear Hill Road
Chaplin, CT, 06235 $ 789,000
Bedrooms4 Baths2.1 Sq 2,900 Monthly Estimate*
$ 4,858
for $789,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,900 square foot home was built in 1997 on a lot size of 3.39.
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.
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FeaturesGeneralZoning RA
Neighborhood N/A
County Windham
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 3.39
Directions gps
High School Per Board of Ed
City Chaplin
Elementary School Chaplin
Sq Ft Total 2900
DOM 26
Year Built 1997
Style Colonial
Year Built Source Public Records
Energy Features Energy Star Rated Thermopane Windows
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InteriorCooling System Window Unit
Total Rooms 8
Basement Description Full Unfinished Walk-out Full With Walk-Out
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ExteriorWater Source Private Well
Lot Description Secluded Treed Level Lot Cleared
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* Excluded FeaturesList ByBetter Homes And Gardens Real Estate Executive Real EstateBroker
amy.executive@gmail.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $4,858
- Monthly Property Taxes
- $848
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Chaplin, CT
Average List Price $435,600
Percent of Sale Price 45%
About Chaplin, CT 2,325 Population
3% Since 2002
$ 77,241 Median Income
46.07 Median Age
28% Households with Children
Trends Information provided by ATTOM Data Solutions.
4798888 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 5/14/2026 | $789,000 | | Listed Price |