64 Chestnut Street
Windham, Connecticut 06226
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,494
- Acres
- 0.21
- Year Built
- 1917
- Neighborhood
- Willimantic
- 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
Located in the Historic Hill section of romantic Willimantic, this charming Craftsman-era bungalow offers the perfect blend of historic character and modern convenience, just minutes from downtown shops, restaurants, and local attractions. Before you even step inside, beautifully maintained gardens welcome you to the expansive front porch-an ideal spot to relax and enjoy the neighborhood's timeless charm. Inside, natural light fills the home, highlighting the sparkling hardwood floors, original turn-of-the-century woodwork, and classic architectural details that reflect the craftsmanship of a bygone era. The main level features a light and bright floor plan, including a fully remodeled kitchen, an updated half bath, and a dedicated first-floor office-perfect for working from home, studying, or creating a private retreat. Upstairs, you'll find three generously sized bedrooms and a tastefully remodeled full bath, providing comfortable living space while preserving the home's historic appeal. Rich in character and enhanced with thoughtful updates, this special Historic Hill home offers a rare opportunity to enjoy the best of Willimantic's past and present in a convenient location close to downtown.
Key Facts
- City/Town
- Windham
- Neighborhood
- Willimantic
- Property / Style
- Single Family · Cottage
- Year Built
- 1917
- Days on Market
- 41 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,494 sq ft
- Lot Size
- 0.21 acres
- Garage / Parking
- 1 garage · 4 total
- Property Taxes
- $5,700 / Annually
Market Snapshot
The Windham Market
Single Family · trailing 12 months
Active Listings
13
40 under contract
Median List Price
$299,900
13 active listings
Median Closed Price
$271,000
166 sales
Median Days on Market
19
13 active listings
Median $ / Sq Ft
$203
13 active listings
Sale-to-List Ratio
100.7%
166 sales
How this home compares
List Price
$340,000
vs $299,900 median
13.4% above median
Price / Sq Ft
$228
vs $203 median
12.3% above median
Days on Market
41 days
vs 19 days median
22 days longer than median
Based on 13 active and 166 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of July 28, 2026.
Location
64 Chestnut Street, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,734
- Property Taxes$475
- Insurance$113
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- Willimantic
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Cottage
- Year Built
- 1917
- New Construction
- No/Resale
- Living Area
- 1,494 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Steam
- Heat Fuel
- Natural Gas
- Cooling
- Wall Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullGarage AccessInterior AccessConcrete FloorFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.21 acres
- Zoning
- NPR2
- Garage / Parking
- 1 garage space4 total parking spacesUnder House GaragePavedOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In Street
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Masonry
- Exterior Features
- GazeboGarden AreaCovered Deck
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $5,700 / Annually
- Days on Market
- 41
- MLS #
- 24183909
- MLS Status
- Under Contract - Continue to Show
Similar Properties
Homes with a close match in area, property type, and price.
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 7/28/2026. 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 7/28/2026 at 8:05 AM UTC.