380 Main Street Winchester, CT $ 999,000
380 Main Street
$ 999,000
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380 Main Street

Winchester, CT, 06098
$ 999,000
Bedrooms-- Baths5.0 Sq 6,200

Monthly Estimate*

$ 6,308

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Commercial Property for sale in Winchester, CT

for $999,000 with 5 full baths. This 6,200 square foot building was built in 1900 on a lot size of 0.17.

Rare opportunity to own a well-established, 38-year restaurant with a loyal, built-in clientele and strong community presence. This fully turnkey operation offers exceptional versatility and income potential, featuring a spacious dining area with seating for up to 156 guests, plus an upstairs 20-seat bar-ideal for expanding service or hosting private events. The property includes five apartments, with three currently functioning units and two additional units ready for completion-perfect for added value and increased revenue. A dedicated 12-15 car parking lot, along with ample street parking, ensures convenience for patrons and tenants alike. Guests can also enjoy outdoor dining with seating for approximately 24, enhancing the overall dining experience. The basement area is fully equipped for dough preparation and offers abundant storage, supporting full-scale catering capabilities and high-volume operations. Endless possibilities await with this unique investment-ideal for restaurateurs or investors seeking a thriving business with multiple income streams.

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Commercial Active

Price

$ 999,000

Full Bath

5

Property Type

Commercial

Taxes

$ 6,015

Style

Lot Size

0.17

Year Built

1900

Town/City

Winchester

MLS | Web ID

24134408

Features
General
Zoning CB-3
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Location Downtown
Property Type Commercial For Sale
Status Active
Acres 0.17
Directions GPS friendly
City Winchester
Sq Ft Total 6200
DOM 1
Year Built 1900
Present Use Restaurant & Apartments
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Interior
Utilities Available Electric Gas
Cooling System Ductless Wall Unit Window Unit
Total Number of Units 6
Total Rooms 0
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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

$6,809
Per Month
93%
7%
0%
Monthly Principal & Interest
$6,308
Monthly Property Taxes
$501
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
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
6/23/2026$999,000 Listed Price

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380 Main Street, Winchester, CT, 06098 is a Commercial Property for sale at $999,000 with 6,200 sqft and a lot size of 0.17. 380 Main Street has 5.0 baths and was built in 1900. The property's zip code is 06098 which is in Winchester, CT