95 Williams Avenue
Winchester, Connecticut 06098
- Beds
- 6
- Baths
- 3
- SqFt
- 2,887
- Acres
- 0.49
- Year Built
- 1870
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large .49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that is always appreciated in a multi-family home. According to the property card, the home is classified as a three-family property. The two units on the left side were previously combined, creating the larger four-bedroom residence that exists today. A future owner may have the opportunity to separate the space again and restore the property to a three-unit configuration, subject to any required municipal approvals. Whether you're looking for an investment property, an owner-occupied multi-family with rental income, or a property with the potential for a future three-unit configuration, 95 Williams Street offers an unusual combination of space, versatility, privacy and possibilities that are increasingly hard to find. Property being sold AS IS, WHERE IS.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1870
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 3 full
- Living Area
- 2,887 sq ft
- Lot Size
- 0.49 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $3,652 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
8
2 under contract
Median List Price
$447,450
8 active listings
Median Closed Price
$324,950
20 sales
Median Days on Market
73
8 active listings
Median $ / Sq Ft
$159
8 active listings
Sale-to-List Ratio
100.2%
20 sales
How this home compares
List Price
$374,900
vs $447,450 median
16.2% below median
Price / Sq Ft
$130
vs $159 median
18.2% below median
Days on Market
0 days
vs 73 days median
73 days fresher than median
Based on 8 active and 20 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of September 25, 2026.
Location
95 Williams Avenue, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$2,001
- Property Taxes$304
- 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
- N/A
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units are Side-by-Side
- Year Built
- 1870
- New Construction
- No/Resale
- Living Area
- 2,887 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- FullStorage
Exterior & Lot
- Lot Size
- 0.49 acres
- Zoning
- TSF
- Garage / Parking
- 2 garage spaces6 total parking spacesDetached GarageOff Street ParkingUnassigned Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Asbestos
- Roof
- Asphalt Shingle
- Foundation
- BrickStone
- Exterior Features
- Porch
- Lot Description
- Lightly Wooded
Listing & Financials
- Property Taxes
- $3,652 / Annually
- Days on Market
- 0
- MLS #
- 24207726
- MLS Status
- Active
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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 9/25/2026. 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 9/25/2026 at 4:51 AM UTC.