288 Bedlam Road
Chaplin, Connecticut 06235
- Beds
- 3
- Baths
- 1
- SqFt
- 1,710
- Acres
- 1.00
- Year Built
- 1830
- Neighborhood
- South Chaplin
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Step into a beautifully restored piece of history with this enchanting 1830s home, nestled on a serene, private acre featuring a sprawling backyard complete with a tranquil babbling brook. This property captures the balance of historic character and modern ease. The main level offers a sun-drenched layout with a convenient primary bedroom featuring a brand-new floor, and a fully renovated bathroom with new framing and subfloor. A cozy wood stove serves as the heart of the home, while upstairs, a thoughtfully remodeled space adds to the bright, refreshed aesthetic. Extensively updated for worry-free living, this residence boasts updated electrical and plumbing systems, a new well system, and an efficient mini-split ductless system. As a result of a recent home inspection, the seller is upgrading the septic system by installing a brand-new septic tank and adding a UV light filtration system for the well. Modern conveniences-from new appliances and lighting to fresh carpeting-blend seamlessly with the home's original spirit. The exterior impresses with a new roof on both the home and garage, a rebuilt deck off the primary bedroom, and charming curb appeal. A rare opportunity to own a meticulously cared-for historic home in a tranquil country setting.
Key Facts
- City/Town
- Chaplin
- Neighborhood
- South Chaplin
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1830
- Days on Market
- 83 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,710 sq ft
- Lot Size
- 1.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $6,580 / Annually
Market Snapshot
The Chaplin Market
Single Family · trailing 12 months
Active Listings
5
5 under contract
Median List Price
$369,900
5 active listings
Median Closed Price
$365,000
25 sales
Median Days on Market
22
5 active listings
Median $ / Sq Ft
$216
5 active listings
Sale-to-List Ratio
103.1%
25 sales
How this home compares
List Price
$369,900
vs $369,900 median
In line with median
Price / Sq Ft
$216
vs $216 median
In line with median
Days on Market
83 days
vs 22 days median
61 days longer than median
Based on 5 active and 25 closed sales (trailing 12 mo) of single family in Chaplin. Source: SmartMLS · As of September 23, 2026.
Location
288 Bedlam Road, Chaplin, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$1,959
- Property Taxes$548
- Insurance$123
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chaplin
- Neighborhood
- South Chaplin
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1830
- New Construction
- No/Resale
- Living Area
- 1,710 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- WoodOther
- Cooling
- Ductless
- Fireplaces
- 1
- Appliances
- Gas CooktopOven/RangeRefrigeratorDishwasher
- Basement
- FullUnfinishedHatchway AccessFull With Hatchway
Exterior & Lot
- Lot Size
- 1.00 acres
- Zoning
- RA
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $6,580 / Annually
- Days on Market
- 83
- MLS #
- 24188389
- MLS Status
- Active
- Financing
- FHA,VA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/23/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/23/2026 at 10:00 PM UTC.