Winchester, KY Commercial real estate for sale

Renovated Mixed-Use Building, Winchester, KY

$299,000

3,132 SF

Renovated Mixed-Use Building, Winchester, KY

27-29 S Main St, Winchester, KY 40391

Renovated mixed-use building with storefront, apartment, and parking.

Prime Location: Directly across from the Court House on Main Street.
Live/Work Opportunity: Perfect building to live upstairs and operate your business downstairs.
Renovated Downstairs: Completely renovated storefront with new HVAC, exposed brick, and new flooring.
Partially Renovated Upstairs: Demo complete, new back deck, walls up, plaster work completed, and new back windows installed.
Opportunity Zone: Located in an Opportunity Zone.

Updated: Jan 5

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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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Historic Church Near Downtown Winchester

Pending

$199,900

2,844 SF

Historic Church Near Downtown Winchester

1927 church with stained glass, hardwood floors, and full basement.

152 W Broadway St, Winchester, KY 40391

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Renovated Commercial Building with Parking

$299,999

2,310 SF

Renovated Commercial Building with Parking

Recently renovated commercial building with large parking lot in downtown.

16 N Main St, Winchester, KY 40391

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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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$1,200,000

7,744 SF

Winchester Industrial Property For Sale

3.9-acre industrial property with 7,800 Sq Ft building in Winchester, KY

101 Jefferson St, Winchester, KY 40391

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$1,799,900

20,252 SF

Winchester Industrial Facility For Sale

20,252 sqft industrial warehouse with highway access and racking.

599 Blt Way, Winchester, KY 40391

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$1,300,000

4,331 SF

Medical Office Building on Bypass Road

Class A medical office building near Walmart with investment potential.

2570 Bypass Rd, Winchester, KY 40391

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Winchester Office Building with Flex Space

$1,650,000

10,136 SF

Winchester Office Building with Flex Space

10,136 SF office building with conversion potential and pole barn.

273 Shoppers Dr, Winchester, KY 40391

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Winchester Commercial Property - I-64 Access

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31,200 SF

Winchester Commercial Property - I-64 Access

High-Visibility Commercial Property, 5 Acres, Two Buildings

1000 Early Dr, Winchester, KY 40391

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$1,350,000

3.02 Acres

Winchester Commercial Land - 3 Acres

High-traffic location, development potential.

155 April Way, Winchester, KY 40391

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$4,800,000

57,050 SF

Winchester Industrial Park Gem

57,050 SF Warehouse, 5.79 Acres

1805 Fortune Dr, Winchester, KY 40391

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Winchester KY Commercial Land Opportunity

$775,000

3.00 Acres

Winchester KY Commercial Land Opportunity

High-traffic location, development potential.

529 Bullion Blvd, Winchester, KY 40391

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5,000 SF

Winchester KY Industrial Building

New 5,000 SF Industrial Building - 2025 Completion

495 Gawthrop Dr, Winchester, KY 40391

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Contact for pricing

8.40 Acres

Winchester Shopping Center Investment

High-traffic retail center, 8.4 acres

1918 Bypass Rd, Winchester, KY 40391

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2.57 Acres

Winchester Commercial Land Lease

High-visibility commercial lot, I-64 access.

507 Tech Dr, Winchester, KY 40391

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$775,000

2.60 Acres

Winchester KY Commercial Land Opportunity

High-traffic location, development potential.

529 Bullion Blvd, Winchester, KY 40391

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1,800 SF

Downtown Winchester Commercial Space

Prime location, renovated office/retail space.

10 Court St, Winchester, KY 40391

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Winchester, KY Commercial Real Estate Investment Opportunities Market Analysis

Explore 913 commercial real estate investment opportunities in Winchester, KY with 98 listings featured on our commercial real estate marketplace. The current inventory includes 516,831,503 square feet of properties with an estimated value of $183,540,899.

Estimated prices for commercial real estate in Winchester, KY begin at $49,500, with an average of $374,573 and extend to $5,646,000.

In Winchester, KY, current investment values show:

Other commercial real estate positioned at $334,567
Land measuring $502,562
Residential land & home lots assessed at $399,796
Commercial land calculated at $937,806

Winchester, KY Commercial Real Estate for Sale

Renovated Mixed-Use Building, Winchester, KY

Renovated mixed-use building with storefront, apartment, and parking.