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436 Main Street, Winchester, CT 06098

Multi-Family For Sale · 2 Family

$750,000
$139/sqft

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4
Bedrooms
2
Bathrooms
5,389
Sq Ft
0.1
Acres
1910
Year Built

About This Home

One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)***Price includes thriving restaurant with 10 year track record with all equipment included. See attachment for equipment list***

Listed by Anthony Gioia (860) 459-8911 with The Washington Agency (860) 482-7044

Listing Snapshot

Price $750,000 Days on Market 143 days
Property Tax $4,690/yr Style Units on different Floors
Year Built 1910 Total Sq Ft 5,389
Lot Size 0.1 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 0
Total Rooms 14 Half Baths 2

Structure & Parking

Construction Brick
Roof Flat

Systems & Utilities

Heat Heat Pump, Hot Air
Fuel Natural Gas
Cooling Ductless
Hot Water 40 Gallon Tank
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $391/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Oct 27, 2025 Listed $750,000

Frequently Asked Questions

How much does 436 Main Street in Winchester, CT cost?
This property is listed at $750,000, which works out to $139 per square foot.
How many bedrooms does 436 Main Street have?
This home has 4 bedrooms and 2 bathrooms.
What is the square footage of 436 Main Street?
The home is 5,389 square feet, situated on 0.1 acres.
When was 436 Main Street in Winchester built?
This property was built in 1910.
Is 436 Main 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 436 Main Street, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 436 Main 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

Anthony Gioia · (860) 459-8911

The Washington Agency · (860) 482-7044

MLS# 24135030 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Mar 2, 2026 8:28 PM UTC