287 South Bear Hill Road
Chaplin, CT 06235
4 Beds
2.5 Baths
2,900 sqft (on 3.39 acres)
4 Beds
2.5 Baths
2,900 sqft
(on 3.39 acres)
Home Highlights
Parking
Garage
Outdoor
Deck
Climate Control
Heating & Cooling
Price/Sqft
$272
Listed
78 days ago
Local Information
- Map ViewExplore the area around 287 South Bear Hill Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
Home Details for 287 South Bear Hill Road
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Interior Details Basement: Full,Unfinished,Walk-Out AccessNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Office, Rec Play Room, Sun Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2900 Square Feet |
Appliances & Utilities Utilities: Cable AvailableAppliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Hot Water,Electric,Oil,WoodHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Hot Water |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane Windows |
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Exterior Home Features Roof: AsphaltPatio / Porch: Deck, CoveredOther Structures: Barn(s)Exterior: GardenFoundation: Concrete PerimeterGardenNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Barn |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2900 Square Feet |
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Days on Market: 78 |
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Year Built Year Built: 1997 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Clapboard, CedarNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1681632 |
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Price List Price: $789,000Price Per Sqft: $272 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: Chaplin |
School Information Elementary School: ChaplinHigh School: Per Board of Ed |
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Listing Agent Listing ID: 24175652 |
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Building Area Building Area: 2900 Square Feet |
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No HOA |
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Lot Area: 3.39 Acres |
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Energy Efficiency Features: Windows |
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BasementMls Number: 24175652Attic: Pull Down StairsAttribution Contact: (860) 916-6048Above Grade Unfinished Area: 2900 |
Last check for updates: about 5 hours ago
Listing courtesy of Amy P. Rio, (860) 916-6048
Better Homes and Gardens Real Estate Executive Real Estate, (860) 916-6048
Source: Smart MLS, MLS#24175652
Also Listed on Smart MLS.
Market trends in Chaplin
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
10
2MoM
Price History for 287 South Bear Hill Road
| Date | Price | Event | Source |
|---|---|---|---|
| 05/14/2026 | $789,000 | Listed For Sale | Smart MLS #24175652 |
| 03/01/2026 | $789,000 | ListingRemoved | Smart MLS #24121168 |
| 10/08/2025 | $789,000 | PriceChange | Smart MLS #24121168 |
| 08/28/2025 | $853,500 | Listed For Sale | Smart MLS #24121168 |
| 03/05/2008 | $241,900 | Sold | Smart MLS #G476209 |
| 12/06/2007 | $328,704 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $10,180 |
| Assessment | $324,400 |
Home facts updated by county records
Comparable Sales for 287 South Bear Hill Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.45 | Single-Family Home | $300,000 | 04/30/26 | 2 | 1 | 904 | |
0.97 | Single-Family Home | $401,000 | 08/22/25 | 4 | 3 | 2,726 | |
0.84 | Single-Family Home | $640,000 | 03/23/26 | 5 | 2.5 | 3,268 | |
0.55 | Single-Family Home | $320,000 | 11/13/25 | 2 | 2 | 1,080 | |
0.82 | Single-Family Home | $375,000 | 10/15/25 | 3 | 2 | 1,848 | |
1.42 | Single-Family Home | $365,000 | 10/08/25 | 3 | 2.5 | 2,440 | |
1.19 | Single-Family Home | $510,000 | 08/18/25 | 3 | 2 | 1,638 | |
0.95 | Single-Family Home | $324,000 | 06/08/26 | 2 | 1 | 1,500 | |
1.23 | Single-Family Home | $305,000 | 02/06/26 | 3 | 1 | 1,267 | |
1.21 | Single-Family Home | $340,000 | 03/13/26 | 5 | 3.5 | 2,496 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETAspen Realty Group
OFF MARKETCountryside Realty
Assigned Schools
These are the assigned schools for 287 South Bear Hill Road.
- Parish Hill High School
- 7-12
- Public
- 184 Students
4/10GreatSchools RatingParent Rating AverageClasses are small and individualized attention can be helpful. However, the students are very sheltered from what the real world is like and many have difficulty in higher education because of this. Most of the teachers care about the students a but are not always well versed in current educational methods and tend to not follow state guidelines. Some of the courses are put together with no regard to standards or needs for required state testing. This puts students at a deficit when they take college classes. The top students at the school earn well deserved accolades for their grades but are not academically equivalent to students from a larger high school who earn the same grades, they have a hard time competing in a larger and more diverse school.Other Review6y ago - Chaplin Elementary School
- PK-6
- Public
- 150 Students
4/10GreatSchools RatingParent Rating AverageThe new principal has done a fantastic job creating a positive, cooperative learning environment.Other Review3y ago 
Check out schools near 287 South Bear Hill Road.
What Locals Say about Chaplin
At least 3 Trulia users voted on each feature.
100 % Say there's wildlife
100 % Say car is needed
88 % Say there's holiday spirit
83 % Say parking is easy
83 % Say it's dog friendly
71 % Say people would walk alone at night
60 % Say yards are well-kept
50 % Say they plan to stay for at least 5 years
39 % Say neighbors are friendly
33 % Say kids play outside
33 % Say it's quiet
29 % Say there are community events
25 % Say it's walkable to restaurants
25 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Amy P. Rio, Better Homes and Gardens Real Estate Executive Real Estate, (860) 916-6048
Agent Phone: (860) 916-6048
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
287 South Bear Hill Road, Chaplin, CT 06235 is a 4 bedroom, 3 bathroom, 2,900 sqft single-family home built in 1997. This property is currently available for sale and was listed by Smart MLS on May 14, 2026. The MLS # for this home is MLS# 24175652.