380 Main Street, Winchester, Connecticut

$999,000

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5

Baths

6,200

Square feet

0.17

Acres

About 380 Main Street

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.

Features of 380 Main Street

MLS® # 24134408
Price $999,000
Bathrooms 5.00
Full Baths 5
Square Footage 6,200
Square Footage Public Records
Acres 0.17
Type Commercial For Sale
Status Active

Community Information

Address 380 Main Street
Area N/A
City Winchester
County Litchfield
State Connecticut
Zip Code 06098

Amenities

Utilities Electric, Gas
Parking Spaces 12
Parking On Street Parking, Off Street Parking
Is Waterfront No
Has Pool No

Interior

Heating Hot Air, Electric, Natural Gas
Cooling Ductless, Wall Unit, Window Unit
Fireplace No
Has Basement No

Exterior

Lot Description Level Lot
Roof Flat, Rubber
Foundation Concrete

Additional Information

Date Listed June 23rd, 2026
Days on Market 79
Zoning CB-3
RE / Bank Owned No

Listing Details

OfficeThe Washington Agency

Listing Map

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Listing information last updated on September 10th, 2026 at 2:26pm EDT.