50 High Street Winchester, CT $ 324,900
50 High Street
$ 324,900
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50 High Street

Winchester, CT, 06098
$ 324,900
Bedrooms4 Baths2.0 Sq 3,044

Monthly Estimate*

$ 2,051

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Multi-Family Home for sale in Winchester, CT

for $324,900 with 4 bedrooms and 2 full baths. This 3,044 square foot home was built in 1900 on a lot size of 0.56.

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.

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Multi-Family Active

Price

$ 324,900

Bedrooms

4

Full Bath

2

Property Type

Multi-Family

Taxes

$ 2,256

Style

Lot Size

0.56

Year Built

1900

Town/City

Winchester

MLS | Web ID

24199721

Features
General
Zoning R-3
Neighborhood Winsted
County Litchfield
Tax Year July 2025-June 2026
Property Type Multi-Family For Sale
Status Active
Acres 0.56
Directions 50 High St
High School Gilbert
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 3044
DOM 0
Year Built 1900
Style Units on different Floors
Year Built Source Public Records
Energy Features Thermopane Windows
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Interior
Cooling System Window Unit
Total Number of Units 2
Total Rooms 12
Basement Description Full Full With Hatchway
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Exterior
Water Source Public Water Connected
Lot Description Level Lot
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* Excluded Features
List By
David Sartirana

Listing Agent

Northwest Ct Realty

Broker

dsart3@hotmail.com

Email

Affordability Calculator

$2,239
Per Month
92%
8%
0%
Monthly Principal & Interest
$2,051
Monthly Property Taxes
$188
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
2060047 Elementary School
1415485 Middle School
Gilbert High School High School
Pricing History
DatePricePrice ChangeDescription
8/17/2026$324,900 Listed Price

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50 High Street, Winchester, CT, 06098 is a Multi-Family Home for sale at $324,900 with 3,044 sqft and a lot size of 0.56. 50 High Street has 4 bedrooms, 2.0 baths, and was built in 1900. The property's zip code is 06098 which is in Winchester, CT