287 South Bear Hill Road Chaplin, CT $ 789,000
287 South Bear Hill Road
$ 789,000
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287 South Bear Hill Road

Chaplin, CT, 06235
$ 789,000
Bedrooms4 Baths2.1 Sq 2,900

Monthly Estimate*

$ 4,858

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Single Family Home for sale in Chaplin, CT

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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Single Family Active

Price

$ 789,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 10,180

Style

Lot Size

3.39

Year Built

1997

Town/City

Chaplin

MLS | Web ID

24175652

Features
General
Zoning 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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Interior
Cooling System Window Unit
Total Rooms 8
Basement Description Full Unfinished Walk-out Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Secluded Treed Level Lot Cleared
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* Excluded Features
List By
Amy Rio

Listing Agent

Better Homes And Gardens Real Estate Executive Real Estate

Broker

amy.executive@gmail.com

Email

Affordability Calculator

$5,706
Per Month
85%
15%
0%
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.
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Nearby
4798888 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
5/14/2026$789,000 Listed Price

Map


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287 South Bear Hill Road, Chaplin, CT, 06235 is a Single Family Home for sale at $789,000 with 2,900 sqft and a lot size of 3.39. 287 South Bear Hill Road has 4 bedrooms, 2.1 baths, and was built in 1997. The property's zip code is 06235 which is in Chaplin, CT