50 High Street
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 2
- SqFt
- 3,044
- Acres
- 0.56
- Year Built
- 1900
- Neighborhood
- Winsted
- 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
Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 3,044 sq ft
- Lot Size
- 0.56 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $2,256 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
5
4 under contract
Median List Price
$499,900
5 active listings
Median Closed Price
$324,900
21 sales
Median Days on Market
36
5 active listings
Median $ / Sq Ft
$175
5 active listings
Sale-to-List Ratio
100.3%
21 sales
How this home compares
List Price
$324,900
vs $499,900 median
35.0% below median
Price / Sq Ft
$107
vs $175 median
38.9% below median
Days on Market
0 days
vs 36 days median
36 days fresher than median
Based on 5 active and 21 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of August 18, 2026.
Location
50 High Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$1,672
- Property Taxes$188
- Insurance$108
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winsted
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 3,044 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Fireplaces
- 1
- Basement
- FullFull With Hatchway
Exterior & Lot
- Lot Size
- 0.56 acres
- Zoning
- R-3
- Garage / Parking
- 2 garage spaces6 total parking spacesBarnDetached GarageOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- ClapboardWood
- Color
- Blue
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch-Wrap AroundPorch-EnclosedPorchBarn
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $2,256 / Annually
- Days on Market
- 0
- MLS #
- 24199721
- MLS Status
- Active
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 8/18/2026. 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 8/18/2026 at 2:50 AM UTC.