50 High Street, Winchester, Connecticut

$324,900

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4

Beds

2

Baths

3,044

Square feet

0.56

Acres

About 50 High Street

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.

Features of 50 High Street

MLS® # 24199721
Price $324,900
Bedrooms 4
Bathrooms 2.00
Full Baths 2
Square Footage 3,044
Acres 0.56
Type Multi-Family For Sale
Sub-Type 2 Family
Style Units on different Floors
Status Under Contract - Continue to Show

Community Information

Address 50 High Street
Area Winsted
City Winchester
County Litchfield
State Connecticut
Zip Code 06098

Amenities

Features Thermopane Windows
Parking Spaces 6
Parking Barn, Detached Garage, Off Street Parking
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Heating Hot Water, Natural Gas
Cooling Window Unit
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Full With Hatchway

Exterior

Exterior Clapboard, Wood
Exterior Features Porch-Wrap Around, Porch-Enclosed, Porch, Barn
Lot Description Level Lot
Roof Asphalt Shingle
Foundation Stone

School Information

Elementary Per Board of Ed
High Gilbert

Additional Information

Date Listed August 17th, 2026
Days on Market 23
Zoning R-3
RE / Bank Owned No

Listing Details

OfficeNorthwest CT Realty

Listing Map

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Listing information last updated on September 10th, 2026 at 1:42pm EDT.