720 Main Street Winchester, CT $ 395,000
720 Main Street
$ 395,000
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720 Main Street

Winchester, CT, 06098
$ 395,000
Bedrooms3 Baths1.1 Sq 1,909

Monthly Estimate*

$ 2,464

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Multi-Family Home for sale in Winchester, CT

for $395,000 with 3 bedrooms and 1 full bath, 1 half bath. This 1,909 square foot home was built in 1900 on a lot size of 0.07.

Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates, a new roof, windows, a deck, a kitchen, and an on-demand hot water system. The unit was renovated down to the studs. Separate gas and electric meters make it ideal for owner-occupier or investment use. On-street parking only, but surrounded by other downtown businesses with strong walkability and visibility. Excellent location near Highland Lake, Route 44, and all downtown amenities. Great opportunity to live and work in the same building or generate dual rental income. Bring your vision and make this Main Street property shine again! Also listed as a commercial property- MLS# 24138743

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Multi-Family Active

Price

$ 395,000

Bedrooms

3

Full Bath

1

Half Bath

1

Property Type

Multi-Family

Taxes

$ 1,395

Style

Lot Size

0.07

Year Built

1900

Town/City

Winchester

MLS | Web ID

24138050

Features
General
Zoning CB-3
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Multi-Family For Sale
Status Active
Acres 0.07
Directions GPS Friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 1909
DOM 17
Year Built 1900
Style Units on different Floors Other
Year Built Source Public Records
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Interior
Cooling System None
Total Number of Units 2
Total Rooms 7
Basement Description None
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Exterior
Water Source Public Water Connected
Lot Description Level Lot
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* Excluded Features
List By
Ryan Marconi

Listing Agent

The Washington Agency

Broker

ryan@thewashingtonagency.com

Email

Affordability Calculator

$2,581
Per Month
95%
5%
0%
Monthly Principal & Interest
$2,464
Monthly Property Taxes
$116
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% 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
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
11/12/2025$395,000 Listed Price

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720 Main Street, Winchester, CT, 06098 is a Multi-Family Home for sale at $395,000 with 1,909 sqft and a lot size of 0.07. 720 Main Street has 3 bedrooms, 1.1 baths, and was built in 1900. The property's zip code is 06098 which is in Winchester, CT