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95 Williams Avenue

Winchester, Connecticut 06098

ACTIVE - NEW$374,900
Beds
6
Baths
3
SqFt
2,887
Acres
0.49
Year Built
1870
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

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

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

Property + 8 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,430

per 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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Listed By

Annie Simard

(860) 841-2633

LPT Realty

(877) 366-2213

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.