# 380 Main Street, Winchester, CT 06098 > **TL;DR:** 0bd/5ba commercial, $999,000 ($161/sqft), built 1900, 6,200 sqft. > A/C. Est. $5,342/mo. Listed 132 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $999,000 | | Price/sqft | $161 | | Bathrooms | 5 full | | Square Feet | 6,200 | | Year Built | 1900 | | Lot Size | 7,405 sqft (0.17 acres) | | Property Type | Commercial (Other) | | Status | Active | | Days on Market | 132 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,051 | | Estimated Insurance | $291 | | **Total** | **$5,342** | ## Key Amenities - A/C ## Property Highlights - Built in 1900 - 0.17 acre lot - 12 parking spaces ## Description ### Agent Description 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. ## Location - **Address:** 380 Main Street, Winchester, CT 06098 - **County:** Litchfield ## Listing Agent - **Name:** Anthony Gioia - **Brokerage:** The Washington Agency - **Broker Phone:** (860) 482-7044 x222 ## Photos ![380 Main Street - Photo 1](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1467844375r.jpg) ![380 Main Street - Photo 2](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1736709206r.jpg) ![380 Main Street - Photo 3](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f2958824588r.jpg) ![380 Main Street - Photo 4](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1715898145r.jpg) ![380 Main Street - Photo 5](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1683489321r.jpg) ![380 Main Street - Photo 6](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f307300456r.jpg) ![380 Main Street - Photo 7](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f2777048140r.jpg) ![380 Main Street - Photo 8](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f4268566581r.jpg) ![380 Main Street - Photo 9](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f2195624167r.jpg) ![380 Main Street - Photo 10](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1249501883r.jpg) ![380 Main Street - Photo 11](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f54738609r.jpg) ![380 Main Street - Photo 12](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f1497257051r.jpg) ![380 Main Street - Photo 13](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f3099067553r.jpg) ![380 Main Street - Photo 14](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f3122814998r.jpg) ![380 Main Street - Photo 15](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f66019499r.jpg) ![380 Main Street - Photo 16](http://lh.rdcpix.com/f4cc485216198445b7c9607757c9686el-f2826733612r.jpg) --- **MLS#:** 24134408 | **Updated:** 2026-10-25 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/380-main-street-winchester-ct-06098-9a0b52fd08c74f3daf05eaae369887c7) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/380-main-street-winchester-ct-06098-9a0b52fd08c74f3daf05eaae369887c7#listing", "url": "https://www.propertysimple.ai/listing/380-main-street-winchester-ct-06098-9a0b52fd08c74f3daf05eaae369887c7", "name": "380 Main Street, Winchester, CT 06098", "description": "Rare opportunity to own a well-established, 38-year restaurant with a loyal, built-in clientele and strong community presence. 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