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50 High Street, Winchester, CT 06098

Multi-Family For Sale · 2 Family

$324,900
$107/sqft
50 High Street, Winchester, CT
Active
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4
Bedrooms
2
Bathrooms
3,044
Sq Ft
0.56
Acres
1900
Year Built

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.

Listed by David Sartirana (860) 806-0225 with Northwest CT Realty (860) 379-7245

Listing Snapshot

Price $324,900 Days on Our Site 0 days
Property Tax $2,256/yr Style Units on different Floors
Year Built 1900 Total Sq Ft 3,044
Lot Size 0.56 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 2
Total Rooms 12 Half Baths 0

Key Features

Outdoor
  • Porch-Wrap Around
  • Porch-Enclosed
  • Porch
  • Barn

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Barn, Detached Garage, Off Street Parking

Systems & Utilities

Heat Hot Water
Fuel Natural Gas
Cooling Window Unit
Hot Water Natural Gas, Upright Tank
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Gilbert

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $188/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Aug 17, 2026 Listed $324,900

Frequently Asked Questions

How much does 50 High Street in Winchester, CT cost?
This property is listed at $324,900, which works out to $107 per square foot.
How many bedrooms does 50 High Street have?
This home has 4 bedrooms and 2 bathrooms.
What is the square footage of 50 High Street?
The home is 3,044 square feet, situated on 0.56 acres.
When was 50 High Street in Winchester built?
This property was built in 1900.
Is 50 High Street, Winchester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 50 High Street, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Gilbert as the high school.
How do I schedule a tour of 50 High Street, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

David Sartirana · (860) 806-0225

Northwest CT Realty · (860) 379-7245

MLS# 24199721 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Aug 17, 2026 10:22 PM UTC