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288 Bedlam Road

Chaplin, Connecticut 06235

ACTIVE$369,900
Beds
3
Baths
1
SqFt
1,710
Acres
1.00
Year Built
1830
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

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

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

Property + 3 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,630

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Georgia Labonne

(860) 303-7096

William Pitt Sotheby's Int'l

(860) 536-5900

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.