436 Main Street Winchester, CT $ 750,000
436 Main Street
$ 750,000
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436 Main Street

Winchester, CT, 06098
$ 750,000
Bedrooms4 Baths2.2 Sq 5,389

Monthly Estimate*

$ 4,679

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Multi-Family Home for sale in Winchester, CT

for $750,000 with 4 bedrooms and 2 full baths, 2 half baths. This 5,389 square foot home was built in 1910 on a lot size of 0.1.

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***

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Multi-Family Active

Price

$ 750,000

Bedrooms

4

Full Bath

2

Half Bath

2

Property Type

Multi-Family

Taxes

$ 4,690

Style

Lot Size

0.1

Year Built

1910

Town/City

Winchester

MLS | Web ID

24135030

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 0.1
Directions GPS friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 5389
DOM 1
Year Built 1910
Style Units on different Floors
Year Built Source Public Records
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Interior
Cooling System Ductless
Total Number of Units 5
Total Rooms 14
Basement Description Crawl Space
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Exterior
Water Source Public Water Connected
Lot Description Level Lot
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* Excluded Features
List By
Anthony Gioia

Listing Agent

The Washington Agency

Broker

tony@thewashingtonagency.com

Email

Affordability Calculator

$5,070
Per Month
92%
8%
0%
Monthly Principal & Interest
$4,679
Monthly Property Taxes
$391
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
10/27/2025$750,000 Listed Price

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436 Main Street, Winchester, CT, 06098 is a Multi-Family Home for sale at $750,000 with 5,389 sqft and a lot size of 0.1. 436 Main Street has 4 bedrooms, 2.2 baths, and was built in 1910. The property's zip code is 06098 which is in Winchester, CT