58 Tower Hill Road
Chaplin, Connecticut 06235
- Beds
- 3
- Baths
- 2
- SqFt
- 1,871
- Acres
- 2.90
- Year Built
- 1840
- Neighborhood
- Tower Hill
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Country Roads, Take Me Home! Tucked away in a peaceful setting just a short walk to downtown Chaplin Village, this unique and charming antique home blends historic character with surprisingly spacious, light-filled living. Oversized rooms, hardwood floors, and abundant built-ins showcase the home's timeless appeal, while the flexible layout offers endless possibilities. The inviting country-style eat-in kitchen is the heart of the home, complemented by a large den/sitting room or possible dining room, perfect for gatherings, along with a warm and welcoming living room filled with antique charm. A first-floor primary bedroom adds convenience, while the expansive rear addition offers incredible versatility - ideal for a luxurious primary suite, in-law setup, or an impressive great room. Outside, enjoy 2.9 acres of peaceful Chaplin charm featuring beautiful stone walls, a relaxing back patio, and a workshop with 50-amp service. Full of warmth, history, and opportunity, this special property is ready to welcome you home.
Key Facts
- City/Town
- Chaplin
- Neighborhood
- Tower Hill
- Property / Style
- Single Family · Antique
- Year Built
- 1840
- Days on Market
- 64 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,871 sq ft
- Lot Size
- 2.90 acres
- Garage / Parking
- 5 total
- Property Taxes
- $6,363 / Annually
Market Snapshot
The Chaplin Market
Single Family · trailing 12 months
Active Listings
6
2 under contract
Median List Price
$462,450
6 active listings
Median Closed Price
$361,250
26 sales
Median Days on Market
61
6 active listings
Median $ / Sq Ft
$256
6 active listings
Sale-to-List Ratio
103.1%
26 sales
How this home compares
List Price
$399,000
vs $462,450 median
13.7% below median
Price / Sq Ft
$213
vs $256 median
16.8% below median
Days on Market
64 days
vs 61 days median
In line with median
Based on 6 active and 26 closed sales (trailing 12 mo) of single family in Chaplin. Source: SmartMLS · As of July 29, 2026.
Location
58 Tower Hill Road, Chaplin, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,034
- Property Taxes$530
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chaplin
- Neighborhood
- Tower Hill
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Antique
- Year Built
- 1840
- New Construction
- No/Resale
- Living Area
- 1,871 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Split SystemWindow Unit
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Off Kitchen
- Appliances
- Oven/RangeRefrigeratorDishwasher
- Basement
- PartialSump PumpConcrete Floor
- Interior Features
- Cable - Available
Exterior & Lot
- Lot Size
- 2.90 acres
- Zoning
- RA
- Garage / Parking
- 5 total parking spacesOff Street ParkingDrivewayUnpavedPrivateUnpavedCrushed StoneGravel
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Red
- Roof
- Asphalt Shingle
- Foundation
- MasonryStone
- Exterior Features
- ShedPorchDeckGarden AreaCovered DeckPatio
- Lot Description
- Lightly WoodedSloping Lot
Listing & Financials
- Property Taxes
- $6,363 / Annually
- Days on Market
- 64
- MLS #
- 24178105
- MLS Status
- Under Contract - Continue to Show
Similar Properties
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Co-Listed By
John Fulton
Home Selling Team
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 12:50 PM UTC.