371 Prospect Street
Windham, Connecticut 06226
- Beds
- 6
- Baths
- 2
- SqFt
- 2,181
- Acres
- 0.41
- Year Built
- 1908
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Whether you're looking for abundant living space, room for extended household members, or an investment opportunity, this spacious 5-bedroom, 2-bath home offers exceptional flexibility in a prime Windham location. The home features generously sized bedrooms, updated bathrooms, and a versatile floor plan that can easily adapt to a variety of needs. A possible sixth bedroom on the first floor provides even more options for a home office, guest room, or additional living space. Previously utilized as a 6-bedroom rental, the home offers an abundance of space and functionality. A detached 2-car garage and expansive driveway provide ample parking, while the generous .41-acre lot offers a surprisingly spacious yard with plenty of room to enjoy the outdoors. Located just steps from Eastern Connecticut State University and close to shopping, dining, and major commuter routes, this property combines space, convenience, and versatility in one unique package. Whether you're searching for a spacious primary residence or a property with strong income potential, this home is full of opportunity.
Key Facts
- City/Town
- Windham
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1908
- Days on Market
- 56 days
- Beds
- 6
- Baths
- 2 full
- Living Area
- 2,181 sq ft
- Lot Size
- 0.41 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,022 / Annually
Market Snapshot
The Windham Market
Single Family · trailing 12 months
Active Listings
15
25 under contract
Median List Price
$217,500
15 active listings
Median Closed Price
$275,000
161 sales
Median Days on Market
38
15 active listings
Median $ / Sq Ft
$151
15 active listings
Sale-to-List Ratio
101.9%
161 sales
How this home compares
List Price
$362,500
vs $217,500 median
66.7% above median
Price / Sq Ft
$166
vs $151 median
9.9% above median
Days on Market
56 days
vs 38 days median
18 days longer than median
Based on 15 active and 161 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of October 17, 2026.
Location
371 Prospect Street, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$2,008
- Property Taxes$585
- Insurance$121
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1908
- New Construction
- No/Resale
- Living Area
- 2,181 sq ft
Schools
- Elementary
- North Windham
- Middle
- Per Board of Ed
- High
- Windham
Interior
- Heating
- Steam
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 2
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedConcrete FloorFull With Hatchway
Exterior & Lot
- Lot Size
- 0.41 acres
- Zoning
- NPR1
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Beige
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- SidewalkPatio
- Lot Description
- Level LotCleared
Listing & Financials
- Property Taxes
- $7,022 / Annually
- Days on Market
- 56
- MLS #
- 24200868
- MLS Status
- Under Contract
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 10/17/2026. 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 10/17/2026 at 10:01 PM UTC.