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
| Office | Better Homes and Gardens Real Estate Executive Real Estate |
|---|