287 South Bear Hill Road, Chaplin, CT 06235

• 4 beds |
• 3 baths |
• 2,900 sqft

Property Description

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.

Listing Status:

Active

Date Added:

May 14, 2026

Data Last Updated:

June 27, 2026 at 12:50PM

Listing Office:

Better Homes and Gardens Real Estate Executive Real Estate : (860) 633-8800

Listing Agent:

Amy Rio : (860) 916-6048

MLS ID:

24175652

Interior

• General: Cable - AvailableOpen Floor Plan
• Rooms: Bonus RoomSolarium
• Appliances: Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
• Laundry: Main Level
• Basement: FullUnfinishedWalk-outFull With Walk-Out
• A/C: Window Unit
• Heating: Hot WaterElectricOilWood
• Fireplace: Fireplaces: 1

Exterior

• General: BarnDeckGarden AreaCovered Deck
• Style: Colonial

Construction

• Roofing: Asphalt Shingle

Location

• County: Windham

Lot

• Zoning: RA1681632

Utilities

• Water: Private Well
• Sewer: Septic