1008 Windham Road
Windham, Connecticut 06266
- Beds
- 5
- Baths
- 1 | 1
- SqFt
- 2,340
- Acres
- 0.67
- Year Built
- 1950
- Neighborhood
- South Windham
- 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
Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but the elbow grease will make you TONS of equity. Come look and make an offer!!!
Key Facts
- City/Town
- Windham
- Neighborhood
- South Windham
- Property / Style
- Single Family · Colonial
- Year Built
- 1950
- Days on Market
- 19 days
- Beds
- 5
- Baths
- 1 full · 1 half
- Living Area
- 2,340 sq ft
- Lot Size
- 0.67 acres
- Garage / Parking
- 5 total
- Property Taxes
- $5,422 / 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
$269,000
vs $299,900 median
10.3% below median
Price / Sq Ft
$115
vs $203 median
43.3% below median
Days on Market
19 days
vs 19 days median
In line with 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
1008 Windham Road, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,372
- Property Taxes$452
- Insurance$90
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- South Windham
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1950
- New Construction
- No/Resale
- Living Area
- 2,340 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Windham
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- None
- Appliances
- Oven/RangeRefrigerator
- Basement
- PartialPartial With Walk-Out
- In-Law Apartment
- Possible
Exterior & Lot
- Lot Size
- 0.67 acres
- Zoning
- R3
- Garage / Parking
- 5 total parking spacesOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Color
- Red
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Deck
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $5,422 / Annually
- Days on Market
- 19
- MLS #
- 24190067
- MLS Status
- Active
- Financing
- Renovation
Similar Properties
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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 7:01 AM UTC.