55 Main Street
Windham, Connecticut 06266
- Beds
- 4
- Baths
- 2
- SqFt
- 1,386
- Acres
- 0.09
- Year Built
- 1866
- Neighborhood
- Willimantic
- Property Type
- 2 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
Investors Take Notice! Bring your vision and unlock the potential of this Victorian-style two-family property at 55 Main Street in Willimantic. Each unit offers 2 bedrooms and 1 bath, with both bathrooms recently updated with brand-new finishes. While the property would benefit from additional updating and improvements, the opportunity to build equity and maximize its potential is well worth exploring. Ideally located across from Recreation Park, near Eastern Connecticut State University and UConn, and within walking distance to local amenities and the bus line. Whether you're an investor seeking your next project or an owner-occupant looking to offset your mortgage with rental income, this property offers exciting possibilities. Bring your ideas, envision the possibilities, and schedule your showing today!
Key Facts
- City/Town
- Windham
- Neighborhood
- Willimantic
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1866
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,386 sq ft
- Lot Size
- 0.09 acres
- Garage / Parking
- 2 total
- Property Taxes
- $4,138 / Annually
Market Snapshot
The Windham Market
Multi-Family · trailing 12 months
Active Listings
7
5 under contract
Median List Price
$349,900
7 active listings
Median Closed Price
$323,000
17 sales
Median Days on Market
50
7 active listings
Median $ / Sq Ft
$183
7 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$299,000
vs $349,900 median
14.5% below median
Price / Sq Ft
$216
vs $183 median
18.0% above median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 7 active and 17 closed sales (trailing 12 mo) of multi-family in Windham. Source: SmartMLS · As of October 24, 2026.
Location
55 Main Street, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$1,643
- Property Taxes$345
- Insurance$100
- 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
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1866
- New Construction
- No/Resale
- Living Area
- 1,386 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Steam
- Heat Fuel
- Gas In StreetOilPropane
- Cooling
- None
- Laundry
- Basement Hook-Up(s)
- Laundry Location
- basement
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.09 acres
- Zoning
- B3
- Garage / Parking
- 2 total parking spacesDrivewayPavedOff Street ParkingPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Shingle
- Foundation
- Masonry
- Exterior Features
- SidewalkStone Wall
- Lot Description
- Corner LotLevel Lot
Listing & Financials
- Property Taxes
- $4,138 / Annually
- Days on Market
- 0
- MLS #
- 24216737
- 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 10/24/2026. 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 10/24/2026 at 7:05 AM UTC.