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    Winchester, KY
    Retail

    Winchester, KY Retail Properties & Spaces for Sale

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    Storefront Property with Two-Level Tenants
    Updated: Jul 27
    Storefront Property with Two-Level Tenants

    1 N Main St, Winchester, KY 40391

    $225,000
    1,900 sqft
    Very visible corner location on Lexington Avenue and Main Street
    Recently updated storefront building
    Upstairs and downstairs units with tenants in both levels
    Opportunity Zone location
    About 1,900 SF of retail‑oriented space
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    This listing looks promising.

    Here's a quick look at some key insights for

    1 N Main St, Winchester, KY

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    • Est. Cap Rate

      8%
      Above avg (5.9%)

    • Est. NOI

      $18K
      Annual

    • Price @ 7% Cap

      $258K
      Above asking
    View Property Analytics
    Storefront Bar with Liquor Sales
    Updated: Dec 20, 2025
    Storefront Bar with Liquor Sales

    137 East Broadway Street, Winchester, KY 40391

    $374,000
    1,536 sqft 0.17 AC lot
    1,536 SF brick storefront on a 0.174‑acre parcel
    Two pool tables, barstools, tables, televisions, pool sticks, and dartboard included
    All inventory remains with the business
    Recently replaced HVAC unit, walk‑in compressors, and cooler
    Liquor store authorized to serve mixed drinks and open liquor in Kentucky
    View details
    Mixed-Use Triplex with Storefront
    Mixed-Use Triplex with Storefront

    502 W Lexington Avenue, Winchester, KY 40391

    $340,000
    4,798 sqft 0.18 AC lot

    Brick property offers a street-facing commercial space and two upstairs two-bedroom apartments.

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    Car Wash with Multiple Bays
    Car Wash with Multiple Bays

    126 Shoppers Drive, Winchester, KY 40391

    $780,000
    3,080 sqft 0.79 AC lot

    Car wash facility features three drive-in bays plus an automatic wash, with an included two-bay oil change operation.

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Mixed-Use Property with Income Home
    Mixed-Use Property with Income Home

    35-37 Hays Street, Winchester, KY 40391

    $470,000
    1,440 sqft 0.13 AC lot

    Mixed-use building with a kitchen and laundry area plus a separate 3-bedroom residence leased through 2027.

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    Renovated Retail Storefront
    Renovated Retail Storefront

    16 N Main Street, Winchester, KY 40391

    $299,999
    2,310 sqft 0.18 AC lot

    Renovated storefront with a new roof and four skylights, plus new hardwood floors throughout.

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    Winchester Land Near Bypass Road
    Winchester Land Near Bypass Road

    529 Bullion Boulevard, Winchester, KY 40391

    $575,000
    2.60 AC lot

    Land available in Winchester, Kentucky, near retail centers.

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    Two-Frontage Retail/Office Building
    Two-Frontage Retail/Office Building

    930 Bypass Road, Winchester, KY 40391

    Contact for pricing
    2,384 sqft

    Two bottom-floor storefronts offer one rented retail space and one suited for office use on Bypass Road.

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    Historic Downtown Retail Building
    Historic Downtown Retail Building

    27 S Main St, Winchester, KY 40391

    Contact for pricing

    Renovated main level retail space features large windows, open floor plan, exposed brick, and a back parking lot.

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    Former Car Wash on 1.07 Acres
    Former Car Wash on 1.07 Acres

    160 Codella Dr, Winchester, KY 40391

    Contact for pricing

    Freestanding car wash on 1.07 acres with outstanding visibility.

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    Historic Office Building with Parking
    Historic Office Building with Parking

    59 S Main St, Winchester, KY 40391

    Contact for pricing

    Multi-story building with rear parking, newly repaired roof, and first-floor new HVAC, with floors suited for offices or retail.

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    Office Building with Garage
    Office Building with Garage

    1210 W Lexington Ave, Winchester, KY 40391

    Contact for pricing

    Well-cared-for office building with a garage, adaptable layout, and multiple built-in storage areas.

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    Mixed-Use Downtown Corner Property
    Mixed-Use Downtown Corner Property

    2 N Main St, Winchester, KY 40391

    Contact for pricing

    Mixed-use building with renovated, fully occupied apartments above ground-floor retail space on a downtown corner.

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    Winchester Land for Sale
    Winchester Land for Sale

    529 Bullion Blvd, Winchester, KY 40391

    Contact for pricing
    1.00 AC lot

    Land for sale in Winchester, Kentucky, near major retailers.

    View details
    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.

    Opportunities in Nearby Cities

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

    Automotive-Ready Live-Work Building
    Automotive-Ready Live-Work Building

    311 Main Street, N Middletown, KY 40357

    $159,000
    770 sqft 0.24 AC lot

    Versatile Main Street property with a garage, office space, and an upstairs one-bedroom apartment.

    View details
    Flex Space with Apartment
    Flex Space with Apartment

    311 Main St N, N Middletown, KY 40357

    $159,000
    770 sqft

    Garage, office, and upper-level residential accommodations support a flexible live-work configuration.

    View details
    Retail Space with Pylon Sign
    Retail Space with Pylon Sign

    1973 Bryant Rd, Lexington, KY 40509

    Contact for pricing
    10,695 sqft

    Retail property with a pylon sign and two access points off Bryant Rd.

    View details
    Retail Strip Center in Lexington
    Retail Strip Center in Lexington

    3090, 3094 & 3100 Old Todds Road, Lexington, KY 40509

    Contact for pricing
    30,418 sqft

    Retail strip center with diverse tenant mix and high traffic.

    View details

    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.

    Downtown Winchester Land Assemblage
    Downtown Winchester Land Assemblage

    33-41 Winn Avenue, Winchester, KY 40391

    $490,000
    1.53 AC lot

    1.53 acres of vacant land in downtown Winchester, Kentucky.

    View details
    Commercial Land in Winchester, KY
    Commercial Land in Winchester, KY

    507 Tech Drive, Winchester, KY 40391

    Contact for pricing
    2.57 AC lot

    Commercial land with I-64 visibility and paved driveway.

    View details
    148 Acres Winchester Development Land
    148 Acres Winchester Development Land

    1395 Two Mile Road, Winchester, KY 40391

    $2,500,000
    148.00 AC lot

    148 acres of land zoned for planned development.

    View details
    Lexington Land for Ground Lease
    Lexington Land for Ground Lease

    5540 Athens Boonesboro Road, Lexington, KY 40509

    $138,000
    1.38 AC lot

    1.38 acres of land available for ground lease.

    View details

    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

    1518 Bypass Rd, Winchester, KY 40391

    Value Estimation by Request
    53,989 sqft
    View details
    1120-1140 Bypass Rd
    Individual retail properties

    1120-1140 Bypass Rd, Winchester, KY 40391

    Value Estimation by Request
    4,800 sqft 0.98 AC lot
    View details
    1525 Lexington Ave
    Restaurants

    1525 Lexington Ave, Winchester, KY 40391

    Value Estimation by Request
    5,498 sqft 2.25 AC lot
    View details
    1910 Bypass Rd
    Retail properties & Spaces

    1910 Bypass Rd, Winchester, KY 40391

    Value Estimation by Request
    62,525 sqft 8.43 AC lot
    View details
    10 Court St
    Office Units

    10 Court St, Winchester, KY 40391

    Value Estimation by Request
    1,800 sqft
    View details
    272 Redwing Dr
    Neighborhood centers

    272 Redwing Dr, Winchester, KY 40391

    Value Estimation by Request
    17,500 sqft
    View details
    1501 Byp Rd
    RESTAURANT

    1501 Byp Rd, Winchester, KY 40391-2714

    Value Estimation by Request
    7,020 sqft 1.09 AC lot
    View details

    Winchester, KY Retail Properties & Spaces Market Trends and Statistics

    Explore 21 retail properties & spaces for sale in Winchester, KY, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 17,448 square feet of properties for sale, with an estimated market value of $3,063,999.

    Sale prices for stores in Winchester, KY start at $225,000, averaging $437,714, and reaching up to $780,000 — 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Storefront properties 11
    Shopping centers 3
    Automotive properties 2
    Car washes 2
    Grocery and convenience stores 2

    Demographics Overview

    Population 37K
    Population Growth (5Y) +3.5%
    Median Household Income $67,910
    College Educated 15.1%

    High-Yield Neighborhoods for Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    40391 $411.6K

    Taxes & Financing

    Tax Rate (average for all types) 0.91%
    Property Tax per SF $10.57 per SF
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Clark County

    New Delisted

    Total CRE Inventory on Market (SF)

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