287 S Bear Hill Rd

Chaplin, CT 06235

$789,000
Price
4
Beds
2,900 Sq. Ft.
$272 / Sq. Ft.
2,900
Sq. Ft.
$272
per Sq. Ft.
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a front view of a house with garden
a front view of a house with a yard
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and a microwave oven with wooden cabinets
a kitchen with stainless steel appliances granite countertop a stove and white cabinets
a view of livingroom with furniture and floor to ceiling window
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a view of a room with gym equipment and floor to ceiling window
a view of a room with wooden floor
a view of entryway and hall with wooden floor
an empty room with windows and closet
a view of an empty room with a window
a bedroom with a bed a table and chair
a bedroom with a bed and a window
a bathroom with a sink a toilet and a mirror
a sign on the side of a building
a front view of a house with a yard and garage
a front view of a house with a garage
a view of a room with wooden walls

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...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.
  1. Listed by Amy F Rio • Better Homes and Gardens Real Estate Executive Real Estate
    P: (860)-916-6048 C: (860)-916-6048 amy.executive@gmail.com

Property Details for 287 South Bear Hill Road

Basement Description
Full, Unfinished, Walk-out, Full With Walk-Out
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Barn
Swimming Pool
No
LISTING UPDATED: 05/15/2026 07:40 PM

Property Details for 287 South Bear Hill Road

StatusActive
MLS #24175652
Days on Market20
Taxes$10,180 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1997
Lot Size3.39 AC / 147,668 SF
CountyWindham County
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Location

Listing Courtesy of Better Homes and Gardens Real Estate Executive Real Estate, Amy F Rio
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Building Information for 287 South Bear Hill Road

Stories-Year Built1997Building Size-Lot Size3.39 AC / 147,668 SF

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$4,780 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,932

Property Taxes

$848

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 287 South Bear Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: gps
  • Elementary School: Chaplin
  • Flood Zone: No
  • High School: Per Board of Ed
  • Latitude: 41.782769
  • Longitude: -72.113365
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,180
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Deck, Garden Area, Covered Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Pull-Down Stairs
  • Cooling System: Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Cable - Available, Open Floor Plan
  • Laundry Room Info: Main Level
  • Rooms Additional: Bonus Room, Solarium
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Vaulted Ceiling,Ceiling Fan,Fireplace,Hardwood Floor
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.0
Room 2
  • Room Entry Order: 10
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 3
  • Room Entry Order: 2
  • Room Features: Bay/Bow Window
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 12.0
Room 4
  • Room Entry Order: 3
  • Room Features: Remodeled,Breakfast Bar,Breakfast Nook,Hardwood Floor
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 13.0
Room 5
  • Listing Key: 51CA572FA49C88D0E0631A01100A5BAC
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Ceiling Fan,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 28.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 11.0
Room 7
  • Room Entry Order: 6
  • Room Features: Skylight,French Doors,Marble Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 12.0
Room 8
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Rec/Play Room
  • Room Width: 19.0
Room 9
  • Listing Key: 51CA572FA49C88D0E0631A01100A5BAC
  • Room Entry Order: 8
  • Room Features: Walk-In Closet,Wall/Wall Carpet
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 10
  • Room Entry Order: 9
  • Room Features: Wall/Wall Carpet
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Color: Brown
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Cedar
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1997
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor
  • In Law Apartment: Possible
  • Sq Ft Description: Above grade
  • Living Area SQFT Per Public Records: 2168
Lot Information
  • Lot Description: Secluded, Treed, Level Lot, Cleared
  • Parcel Number: 1681632
  • Sq Ft Est Heated Above Grade: 2900.0
  • Sq Ft Total: 2900.0
  • Zoning: RA
Utilities
  • Energy Features: Energy Star Rated, Thermopane Windows
  • Heat Fuel Type: Electric, Oil, Wood
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 287 South Bear Hill Road

DateEvent & SourcePriceAppreciation
Mar 6, 2008

Closed (Public Record)

Public Record #234378734

$241,900—
Mar 6, 2008

Closed (Public Record)

Public Record #734378734

$241,900

+3.7% / yr

Feb 4, 2000

Closed (Public Record)

Public Record #92824835

$179,900—
DateEvent & SourcePrice
03/06/2008

Closed (Public Record)

Public Record #234378734

$241,900
03/06/2008

Closed (Public Record)

Public Record #734378734

$241,900

+3.7% / yr

02/04/2000

Closed (Public Record)

Public Record #92824835

$179,900

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 287 South Bear Hill Road

Taxable ValueLand$31,600Additions$292,800Total$324,400
Tax Record2024$10,180 ($848 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt2,168 SqFtAbove Grade Finished SqFt2,168 SqFtUnfinished Basement SqFt1,542 SqFtStories2Lot Size147,668 SqFtStyleSingle Family ResidenceYear Built1997ZoningRACountyNORTHEASTERN CONNECTICUTAPNCHAP M:53 B:52Fireplace TypeHas Fireplace

Schools near 287 South Bear Hill Road

This home is within Chaplin School District.
Rating
School
Type
Grades
Distance
Chaplin Elementary School
Public - PK to 6
Parish Hill High School
Public - 7 to 12
Rating
School
Distance
Chaplin Elementary School
PublicPK to 6

Parish Hill High School
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 287 South Bear Hill Road, Chaplin, CT 06235

287 South Bear Hill Road is a single family home for sale in Chaplin, CT 06235. This property was listed for sale on May 14, 2026 by Better Homes and Gardens Real Estate Executive Real Estate, it's currently listed at $789,000. It has been on the market for a total of 20 days and was last sold on March 6, 2008. This listing's school districts are Regional School District 11, Chaplin School District. Nearby schools include Chaplin Elementary School and Parish Hill High School. 287 South Bear Hill Road is a 4-bed, 3-bath, 2,900 sqft single family home built in 1997.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Better Homes and Gardens Real Estate Executive Real Estate, Amy F Rio

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.