Winchester, KY Retail properties for sale

Historic Mixed-Use Building in Winchester

$429,000

3,538 SF

Historic Mixed-Use Building in Winchester

39 S Main St, Winchester, KY 40391

Renovated historic building with restaurant and apartment in downtown Winchester.

Renovated historic building in Downtown Winchester.
Restaurant space with full hood system and commercial kitchen.
Live/work layout potential with apartment upstairs.
Booming Downtown Winchester location.
Hardwood floors and tin ceiling.

Updated: Sep 12, 2025

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Renovated Commercial Building with Parking

$299,999

2,310 SF

Renovated Commercial Building with Parking

16 N Main St, Winchester, KY 40391

Recently renovated commercial building with large parking lot in downtown.

Largest back parking lot in the downtown area.
Recently renovated: new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing, and new electrical.
Numerous new business grants available through Winchester First.
Prime location: directly across from a brand‑new apartment building, surrounded by retail and restaurants, and near the Leeds Center for the Arts.
Plumbed for 4 bathrooms, laundry room, and back office.

Updated: Oct 29, 2025

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$299,900

0.12 Acres

Downtown Winchester Mixed-Use Building

Renovated mixed-use building in downtown Winchester, near new apartments.

18 N Main St, Winchester, KY 40391

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Established Business in Historic Downtown

$399,000

1,536 SF

Established Business in Historic Downtown

Turn-key bar and liquor store with established clientele.

137 East Broadway St, Winchester, KY 40391

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$300,000

1,675 SF

Winchester Commercial Property For Sale

Commercial property with metal/pole barn near I-64 exit 96.

1045 Early Dr, Winchester, KY 40391

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$614,900

2,906 SF

Freestanding Retail Building on Bypass

Highly visible retail building in a busy commercial corridor.

838 Bypass Rd, Winchester, KY 40391

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Income-Producing Property Near Downtown Winchester

$439,900

2,269 SF

Income-Producing Property Near Downtown Winchester

Income opportunity: salon with apartment in prime location near downtown.

1125 W Lexington Ave, Winchester, KY 40391

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$525,000

5,094 SF

Mixed-Use Property in Winchester, KY

Versatile property with commercial space and residential income potential.

808 Bypass Rd, Winchester, KY 40391

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Versatile Commercial Building in Winchester

$249,000

4,180 SF

Versatile Commercial Building in Winchester

4,180 SF building suitable for automotive, warehouse, or retail.

300 W Broadway St, Winchester, KY 40391

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Renovated Mixed-Use Building, Winchester, KY

$314,900

3,132 SF

Renovated Mixed-Use Building, Winchester, KY

Mixed-use property with renovated storefront and residential space.

27-29 S Main St, Winchester, KY 40391

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$314,900

3,132 SF

27 Main St

Individual retail properties • 3,132 SF

27 Main St, Winchester, KY 40391

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$1,750,000

20,548 SF

The Winchester Opera House

Individual retail properties • 20,548 SF

101 Main St, Winchester, KY 40391

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$1,325,000

Winchester Rally's: Sale-Leaseback Opportunity

High-traffic QSR, 10-year NNN lease.

1478 Lexington Ave, Winchester, KY 40391

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Former Car Wash on 1.07 Acres

Freestanding car wash on 1.07 acres with outstanding visibility.

160 Codella Dr, Winchester, KY 40391

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Based on your search, we've compiled 29 Potential Opportunities for your consideration. Besides 14 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 7 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.

$1,200,000

1.30 Acres

Richmond Rd Retail Outlot

1.3-acre prime retail land, Lexington, KY

2891 Richmond Rd, Lexington, KY 40509

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$6,306,524

7,755 SF

Lexington Retail Center Investment

Prime Lexington retail, 100% occupied, strong tenants.

2887 Richmond Rd, Lexington, KY 40509

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$250,000

3,500 SF

Downtown Mt Sterling Retail Building

Retail building in high-traffic downtown location with parking.

111 W Locust St, Mt Sterling, KY 40353

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Downtown Mt Sterling Commercial Property

$282,500

2,156 SF

Downtown Mt Sterling Commercial Property

Commercial property with reliable income and expansion potential in Mt Sterling.

10-12 Court St, Mt Sterling, KY 40353

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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.

$650,000

3.00 Acres

Prime Land Near Winchester Bypass

Land available near Winchester Bypass amidst new commercial development.

205 Codella Dr, Winchester, KY 40391

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$200,000

0.81 Acres

Bypass Frontage Retail Land

Retail land with bypass frontage, utilities, and B-3 zoning.

550-A Bullion Blvd, Winchester, KY 40391

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$1,350,000

3.02 Acres

Prime Land in Winchester, KY

3+ acres of commercial land in Winchester, Kentucky.

155 April Way, Winchester, KY 40391

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$775,000

3.00 Acres

Winchester Land For Sale

Prime land opportunity in Winchester, Kentucky, near major retailers.

609 Bullion Blvd, Winchester, KY 40391

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Explore Off-Market Properties in Winchester, KY

Consider similar Off-Market properties in Winchester, KY. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

1518 Bypass Rd

Neighborhood centers • 53,989 SF

Value Estimation by Request

1518 Bypass Rd, Winchester, KY 40391

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1525 Lexington Ave

Restaurants • 5,498 SF

Value Estimation by Request

1525 Lexington Ave, Winchester, KY 40391

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1910 Bypass Rd

Retail properties • 62,525 SF

Value Estimation by Request

1910 Bypass Rd, Winchester, KY 40391

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10 Court St

Office space • 1,800 SF

Value Estimation by Request

10 Court St, Winchester, KY 40391

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272 Redwing Dr

Neighborhood centers • 17,500 SF

Value Estimation by Request

272 Redwing Dr, Winchester, KY 40391

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1501 Byp Rd

RESTAURANT • 7,020 SF

Value Estimation by Request

1501 Byp Rd, Winchester, KY 40391-2714

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Winchester, KY Retail Properties Investment Opportunities Market Analysis

Explore 20 retail properties for sale in Winchester, KY, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 190,090,787 square feet of properties for sale, with an estimated market value of $6,986,499.

Prices for stores in Winchester, KY start at $249,000, averaging $499,035, and reaching up to $1,750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

Winchester, KY Retail Properties for Sale

Historic Mixed-Use Building in Winchester

Renovated historic building with restaurant and apartment in downtown Winchester.