Winchester, CT Retail Properties & Spaces for Sale

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$750,000

5,389 SF

Turnkey Restaurant with Apartments

436 Main Street, Winchester, CT 06098

Thriving restaurant with apartments in high-traffic Litchfield County location.

Turnkey, award‑winning restaurant with 10‑year track record and loyal customer base.
Includes 4 apartments in addition to the restaurant.
Prime location in the heart of Litchfield County with high traffic.
Restaurant is fully equipped with all infrastructure items included (valued over $100k).
Restaurant has 65 indoor seats and 35 outdoor seats.

Updated: Oct 27, 2025

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Versatile Commercial Building in Winchester

$280,000

4,852 SF

Versatile Commercial Building in Winchester

1 Lake Street, Winchester, CT 06098

4,852 SF commercial building in Litchfield County.

Prime location in highly desirable Litchfield County with exceptional visibility on a prominent corner lot.
Versatile 4,852 sq ft open layout customizable for retail, office, showroom, or mixed‑use.
Flexible Town Center zoning allows for numerous commercial uses (retail, office, restaurant, etc.).
Clear‑span construction enables easy interior reconfiguration.
Includes separate men's and women's bathrooms, a handicap/family restroom, and a kitchen.

Updated: Jun 17, 2025

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$395,000

1,909 SF

Mixed-Use Building in Downtown Winsted

Two-story mixed-use building with commercial space and residential apartment.

720 Main Street, Winchester, CT 06098

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$395,000

1,909 SF

Mixed-Use Building in Downtown Winsted

Two-story mixed-use building with commercial space and residential apartment.

720 Main Street, Winchester, CT 06098

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$595,000

0.58 Acres

Commercial Property on Route 44

High-visibility commercial property with auto sales and repair business.

404 New Hartford Road, Barkhamsted, CT 06063

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$595,000

Versatile Commercial Property in Winchester

Adaptable building suitable for retail, storage, or automotive uses.

45 Willow St, Winchester, CT 6098

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Barkhamsted Commercial Opportunity For Sale

$899,900

4,342 SF

Barkhamsted Commercial Opportunity For Sale

4,342 sq ft building on high-visibility road in Barkhamsted, CT.

110 New Hartford Road, Barkhamsted, CT 06063

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$1,900,000

12,000 SF

New 12,000 SF Steel Building

Newly constructed flex space with expansion potential on 20+ acres.

144 Rowley St, Winchester, CT 6098

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Prime Commercial Property, Winchester CT

$290,000

4,852 SF

Prime Commercial Property, Winchester CT

Versatile commercial building in Litchfield County with customization options.

1 Lake St, Winchester, CT 6098

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$595,000

0.58 Acres

Route 44 Auto Sales Property

High-visibility commercial property on Route 44 with auto sales/repair.

404 New Hartford Road, Barkhamsted, CT 6063

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Based on your search, we've compiled 35 Potential Opportunities for your consideration. Besides 10 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 17 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Former Showroom Office Building For Sale

$589,900

3,412 SF

Former Showroom Office Building For Sale

3,412 SF commercial building on corner lot for sale.

2407 Winsted Road, Torrington, CT 6790

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$625,000

New Hartford Drive-Thru Opportunity

Former Dunkin' with drive-thru; retail, medical, or office potential.

495 Main Street, New Hartford, CT 6057

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$64,000

1,652 SF

Commercial Building on Winsted Road

Commercial building on 0.39 acres with retail/office potential.

1380 Winsted Road, Torrington, CT 6790

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$235,000

Retail/Office Building in New Hartford

Former laundromat building suitable for retail or office venture.

10 Town Hill Road, New Hartford, CT 6057

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Potential Development Sites for Consideration

Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

Contact for pricing

0.15 Acres

Prime Lot Near Downtown

Convenient .15-acre lot near shopping, dining, and entertainment.

48 Bridge Street, Winchester, CT 06098

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Contact for pricing

0.44 Acres

Versatile Lot Near Downtown

Prime 0.44-acre lot near downtown with city utilities available.

124 Rockwell Street, Winchester, CT 06098

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$45,000

0.58 Acres

Prime Commercial Lot on Route 44

0.58-acre business-zoned lot with high visibility on Route 44.

408 New Hartford Road, Barkhamsted, CT 06063

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$49,000

0.37 Acres

Private Lot Near Downtown

0.37-acre lot near downtown and Highland Lake.

PARKING LOT • 0.07 Acres

Value Estimation by Request

Elm St, Winchester, CT 06098

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Winchester, CT Retail Properties & Spaces Investment Opportunities Market Analysis

Explore 27 retail properties & spaces for sale in Winchester, CT, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 23,958 square feet of properties for sale, with an estimated market value of $1,820,000.

Sale prices for stores in Winchester, CT start at $280,000, averaging $455,000, and reaching up to $750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Winchester, CT Retail Properties & Spaces for Sale

Turnkey Restaurant with Apartments

Thriving restaurant with apartments in high-traffic Litchfield County location.

Versatile Commercial Building in Winchester

4,852 SF commercial building in Litchfield County.

Mixed-Use Building in Downtown Winsted

Mixed-Use Building in Downtown Winsted

Commercial Property on Route 44

Versatile Commercial Property in Winchester

Barkhamsted Commercial Opportunity For Sale

New 12,000 SF Steel Building

Prime Commercial Property, Winchester CT

Route 44 Auto Sales Property

Explore Opportunities in Nearby Cities

Former Showroom Office Building For Sale

New Hartford Drive-Thru Opportunity

Commercial Building on Winsted Road

Retail/Office Building in New Hartford

Potential Development Sites for Consideration

Prime Lot Near Downtown

Versatile Lot Near Downtown

Prime Commercial Lot on Route 44

Private Lot Near Downtown

Explore Off-Market Properties in Winchester, CT

Boyd St

18th Riveredge Drg18

Rowley St

29th Riveredge Dr

3rd Riveredge Dr

7th Riveredge Dr

20th Riveredge Dr

9th Riveredge Dr

22nd Riveredge Dr

5th Riveredge Dr

2nd Riveredge Dr

13th Riveredge Dr

Litchfield Ave

Elm St

Winchester, CT Retail Properties & Spaces Investment Opportunities Market Analysis

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