81 Chestnut Street
Windham, Connecticut 06226
- Beds
- 3
- Baths
- 2
- SqFt
- 2,412
- Acres
- 0.36
- Year Built
- 1918
- Neighborhood
- Willimantic
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Step into timeless elegance with this beautiful Colonial home, nestled in the historic Hill section of town. Built in 1918, this character-filled residence showcases the original charm and craftsmanship that make historic homes so special. From the moment you enter, you'll appreciate the stunning original woodwork, period lighting fixtures, welcoming entryway, and classic fireplace. Large windows throughout the home fill every room with natural light, highlighting the beautiful hardwood floors and architectural details. The main level features a spacious living room, formal dining room, kitchen, full bathroom, and a convenient first-floor bedroom. Upstairs, you'll find two to three additional bedrooms, a second full bathroom, and a large family room offering flexible living space for today's lifestyle. Enjoy relaxing on the covered front porch or take advantage of the home's original sleeping porch, a unique feature that adds to its historic appeal. Many of the home's mechanical systems have been updated, providing peace of mind while preserving its vintage character. Ideally located within walking distance to downtown, you'll have easy access to local restaurants, galleries, shops, and community events. This is a rare opportunity to own a home filled with charm, character, and history.
Key Facts
- City/Town
- Windham
- Neighborhood
- Willimantic
- Property / Style
- Single Family · Colonial
- Year Built
- 1918
- Days on Market
- 46 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,412 sq ft
- Lot Size
- 0.36 acres
- Garage / Parking
- 1 garage · 2 total
- Property Taxes
- $8,020 / 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
$309,000
vs $299,900 median
In line with median
Price / Sq Ft
$128
vs $203 median
36.9% below median
Days on Market
46 days
vs 19 days median
27 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
81 Chestnut Street, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,576
- Property Taxes$668
- Insurance$103
- 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
- Colonial
- Year Built
- 1918
- New Construction
- No/Resale
- Living Area
- 2,412 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Steam
- Heat Fuel
- Natural Gas
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorWasher
- Basement
- FullUnfinishedStorageInterior AccessConcrete FloorFull With Hatchway
- In-Law Apartment
- PossibleSecond Floor
- Interior Features
- Cable - Available
Exterior & Lot
- Lot Size
- 0.36 acres
- Zoning
- NPR2
- Garage / Parking
- 1 garage space2 total parking spacesDetached GarageOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- ShingleBrick
- Color
- Brown and Brick
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch-ScreenedPorch-EnclosedSidewalkShedPorchGarden AreaStone Wall
- Lot Description
- Historic District
Listing & Financials
- Property Taxes
- $8,020 / Annually
- Days on Market
- 46
- MLS #
- 24180787
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA
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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 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 6:15 AM UTC.