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Winchester, KY Retail Space for Lease

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Downtown Winchester Retail Space Available
$2,000 / Mo
3,920 SF

Downtown Winchester Retail Space Available

29 S Main St, Winchester, KY 40391

Retail space in downtown Winchester with parking and grant opportunities.

  • Prime downtown Winchester location directly across from the Court House.
  • Large back parking lot.
  • Suitable for various business types: cafe, ice cream shop, boutique, photography studio, etc.
  • Exposed back walls and huge display windows.
  • Downtown Winchester actively seeking new businesses.
Updated: Oct 13, 2025
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Renovated Restaurant Space in Winchester
$2,500 / Mo
3,000 SF

Renovated Restaurant Space in Winchester

30 N Main St, Winchester, KY 40391

Beautifully renovated restaurant space with seating for 100 in Winchester.

  • Prime location in the heart of booming Downtown Winchester.
  • Seating capacity for 100 patrons.
  • Renovated in 2020, preserving historical charm with hardwood floors and tin ceilings.
  • Well‑appointed bar area.
  • Opportunity for sidewalk dining.
Updated: Sep 12, 2025
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Commercial Space in Winchester, KY
Pending
$1,700 / Mo
958 SF

Commercial Space in Winchester, KY

Versatile commercial space suitable for various business types.

174 Pedro Way, Winchester, KY 40391
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Retail Space in Colby Station
$10 SF/Yr
365,904 SF

Retail Space in Colby Station

Prime retail space in high-traffic shopping center, Winchester, Kentucky.

1946 Bypass Rd, Winchester, KY 40391
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Retail Space in Kroger Plaza
$19 SF/Yr
1,000 SF

Retail Space in Kroger Plaza

Retail or office space available in Winchester's primary retail corridor.

1615 Bypass Rd, Winchester, KY 40391
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Based on your search, we've compiled 14 Potential Opportunities for your consideration. Besides 5 Active listings in Winchester, KY, we suggest exploring alternatives. Consider Similar 4 Spaces in Nearby Cities, and Similar 5 Properties for Sales.

Explore Retail space for Lease in Nearby Cities

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

Retail Space in Pleasant Ridge
$25 SF/Yr
1,877 SF

Retail Space in Pleasant Ridge

Retail space available in Lexington's Pleasant Ridge Shoppes.

1908 Bryant Rd, Lexington, KY 40509
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Lexington Retail Space: Liberty Rd
$25 SF/Yr
35,460 SF

Lexington Retail Space: Liberty Rd

Prime Retail/Office Space, Lexington, KY

2985 Liberty Rd, Lexington, KY 40509
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Richmond, KY Commercial Space
$1,000 / Mo
1,000 SF

Richmond, KY Commercial Space

Commercial space suitable for retail or office use in Richmond.

105 S 3Rd St, Richmond, KY 40475
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Retail Space in Richmond, KY
$1,800 / Mo
1,950 SF

Retail Space in Richmond, KY

Retail property available for lease in Richmond, Kentucky.

309 Steep St, Richmond, KY 40475
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Explore Similar Spaces for Sale in Winchester, KY

Consider Similar Space for Sale. We found 5 Spaces in Nearby Locations matching your search parameters.

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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Downtown Winchester Mixed-Use Building
$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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Freestanding Retail Building on Bypass
$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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The Winchester Opera House
$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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27 Main St
$314,900
3,132 SF

27 Main St

Individual retail properties • 3,132 SF

27 Main St, Winchester, KY 40391
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Winchester, KY Retail space Leasing Opportunities Market Analysis

Explore Retail space leasing options in Winchester, KY with 10 listings featured on our commercial real estate exchange. The current inventory includes 16,325,535,279 square feet of properties with an estimated lease value of $66 SF/Yr.

Estimated lease rates for Retail space in Winchester, KY begin at $6 SF/Yr, with an average of $13 SF/Yr and extend to $21 SF/Yr.
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