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288 Bedlam Road

Chaplin, Connecticut 06235

ACTIVE$344,900
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. This property perfectly captures the balance of historic character and modern ease, offering a warm, welcoming retreat from the everyday. The main level features a flexible, sun-drenched layout highlighted by a convenient primary bedroom and a fully renovated bathroom with new framing and subfloor for peace of mind. A cozy wood stove serves as the heart of the home, creating an inviting atmosphere for both relaxed evenings and intimate gatherings. Upstairs, you will find a thoughtfully remodeled space that adds to the home's bright, refreshed aesthetic. Extensively updated for worry-free living, this residence boasts significant mechanical improvements, including updated electrical and plumbing systems, a new well system, and an efficient mini-split ductless system. Modern conveniences-from new appliances and lighting to fresh carpeting-blend seamlessly with the home's original spirit. The exterior is equally impressive, featuring a new roof on both the home and garage, a rebuilt deck off the primary bedroom, and charming curb appeal with a brick mailbox and landscape lighting. This is a rare opportunity to own a meticulously cared-for home that offers the best of both worlds: the soul of a historic property and the comfort of modern upgrades, all 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
33 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

59

6 active listings

Median $ / Sq Ft

$222

6 active listings

Sale-to-List Ratio

103.1%

27 sales

How this home compares

List Price

$344,900

vs $409,450 median

15.8% below median

Price / Sq Ft

$202

vs $222 median

9.0% below median

Days on Market

33 days

vs 59 days median

26 days fresher than median

Based on 6 active and 27 closed sales (trailing 12 mo) of single family in Chaplin. Source: SmartMLS · As of August 5, 2026.

Location

288 Bedlam Road, Chaplin, Connecticut

Property + 5 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,436

per month

  • Principal & Interest$1,773
  • Property Taxes$548
  • Insurance$115
  • 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
33
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 8/5/2026. 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 8/5/2026 at 12:31 AM UTC.