57 Main Street
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 0
- SqFt
- 3,660
- Acres
- 0.13
- Year Built
- 1962
- Neighborhood
- Winchester Center
- Property Type
- Multi-Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS #24112471. Property has brand new paved parking lot not shown in current picture and some new siding on outside. Come see this great investment opportunity.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winchester Center
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1962
- Days on Market
- 364 days
- Beds
- 3
- Baths
- 0 baths
- Living Area
- 3,660 sq ft
- Lot Size
- 0.13 acres
- Property Taxes
- $5,133 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
6
7 under contract
Median List Price
$524,450
6 active listings
Median Closed Price
$305,000
17 sales
Median Days on Market
16
6 active listings
Median $ / Sq Ft
$191
6 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$375,000
vs $524,450 median
28.5% below median
Price / Sq Ft
$102
vs $191 median
46.6% below median
Days on Market
364 days
vs 16 days median
348 days longer than median
Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
57 Main Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,912
- Property Taxes$428
- Insurance$125
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winchester Center
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- Other
- Style
- Units on different Floors
- Year Built
- 1962
- New Construction
- No/Resale
- Living Area
- 3,660 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Steam
- Heat Fuel
- Electric
- Cooling
- None
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.13 acres
- Zoning
- CB-2
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In Street
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $5,133 / Annually
- Days on Market
- 364
- MLS #
- 24112807
- MLS Status
- Under Contract
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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 6:10 AM UTC.