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. 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
Active Listings
6
1 under contract
Median List Price
$409,450
6 active listings
Median Closed Price
$365,000
27 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 30, 2026per 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
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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 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.