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287 S Bear Hill Road
Chaplin CT 06235 US

$789,000

Active Listing ID 24175652
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4 bed
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3.00 Bath (2 Full , 1 Half)
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Lot: 3.39 Acres
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Other

$789,000

Active Listing ID 24175652
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287 S 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.

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Property Features

  • Facts
  • Lot Size: 3.39 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 2
  • 1/2 Bathrooms: 1
  • Cooling System: Window Unit(s)
  • Exterior Finish: Barn, Deck, Garden Area, Covered Deck
  • Heating Fuels: Hot Water(Heating)
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

  • School
  • Chaplin(Elementary)
  • Per Board of Ed(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 789000
  • unparsedaddress: 287 S Bear Hill Road
  • postalcity: Chaplin
  • stateorprovince: CT
  • country: US
  • postalcode: 06235
  • bathroomsfull: 2
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 3.39
  • lotsizeunits: Acres
  • lotsizearea: 3.39
  • livingarea: 2900
  • livingareaunits: Square Feet
  • latitude: 41.783457
  • longitude: -72.114041
  • listagentfullname: Amy Rio
  • listagentemail: amy.executive@gmail.com
  • listagentkey: 3yd-CTMLS-PAYNEA
  • listagentmlsid: PAYNEA
  • listagentpreferredphone: 8609166048
  • listagentofficephone: 8606338800
  • listofficekey: 3yd-CTMLS-EXRE01
  • listofficemlsid: EXRE01
  • disclaimer: Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CTMLS
  • yearbuilt: 1997
  • listingcontractdate: 2026-05-14
  • listagenturl: http://buyexecutive.com/
  • countyorparish: Windham
  • elementaryschool: Chaplin
  • highschool: Per Board of Ed
  • appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • cooling: Window Unit(s)
  • heating: Hot Water(Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Cable - Available, Open Floor Plan
  • exteriorfeatures: Barn, Deck, Garden Area, Covered Deck
  • architecturalstyle: Colonial
  • rooms: Bedroom 3, Bathroom 2, Bathroom 1, Bedroom 1, Bathroom 3, Basement, Bedroom 2, Bedroom 4
  • patioandporchfeatures: Deck
  • basement: Full, Unfinished
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -72.114044, 41.78346
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Listing Changed: 5/31/2026 12:52:31 PM GMT
Source Updated Date: 6/4/2026 12:54:43 AM GMT

Courtesy of: Amy Rio, Better Homes and Gardens Real Estate Executive Real Estate, amy.executive@gmail.com

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.