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    Winchester, KY
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    Winchester, KY Restaurants for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    6 results
    Mixed-Use Property on High-Traffic Bypass
    $500,000
    5,054 SF

    Mixed-Use Property on High-Traffic Bypass

    808 Bypass Road, Winchester, KY 40391

    Versatile commercial space with apartment near I-64.

    • High‑traffic, high‑visibility location on the bypass, less than half a mile from I‑64.
    • Mixed‑use property with commercial space and attached apartment with private entrance.
    • Commercial space includes a kitchen, service counter, dining/event space, and drive‑up window.
    • Unfinished space plumbed for a second one‑bedroom apartment, offering additional income potential.
    • On‑site parking and outdoor seating for customers.
    Updated: Apr 21
    View details
    Established Turn-Key Business Opportunity
    $374,000
    1,536 SF

    Established Turn-Key Business Opportunity

    137 East Broadway Street, Winchester, KY 40391

    Well-established business with equipment and inventory included in historic Winchester.

    • Turn‑key ready business with all equipment and inventory included.
    • Rare Kentucky liquor license allowing mixed drinks and open liquor sales.
    • Well‑established clientele base.
    • Recently replaced HVAC unit, walk‑in compressors, and cooler.
    • Prime location in historic downtown Winchester.
    Updated: Dec 20, 2025
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    Historic Building in Downtown Winchester
    $415,000
    3,538 SF

    Historic Building in Downtown Winchester

    Renovated commercial building with restaurant and apartment in Winchester.

    39 S Main Street, Winchester, KY 40391
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    Turnkey Waterfront Restaurant with Apartment
    $531,000
    5,012 SF

    Turnkey Waterfront Restaurant with Apartment

    Renovated restaurant with indoor-outdoor dining and spacious upstairs apartment.

    220 Athens Boonsboro Road, Winchester, KY 40391
    View details
    Established Winchester Business For Sale
    $379,000
    1,536 SF

    Established Winchester Business For Sale

    Turn-key bar and restaurant with mixed drink license.

    137 E Broadway St, Winchester, KY 40391
    View details
    Commercial Lot with High Visibility
    $374,900
    1.29 Acres

    Commercial Lot with High Visibility

    1.29 acre commercial lot ideal for various businesses.

    395 Croxton Way, Winchester, KY 40391
    View details
    Based on your search, we've compiled 17 Potential Opportunities for your consideration. Besides 6 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 3 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.

    Prime Retail/Restaurant Outlot Opportunity
    $100,000
    1.30 Acres

    Prime Retail/Restaurant Outlot Opportunity

    1.3-acre outlot ideal for retail or restaurant with high visibility.

    2887 Richmond Road, Lexington, KY 40509
    View details
    Versatile Commercial Building in Clay City
    $150,000
    1,004 SF

    Versatile Commercial Building in Clay City

    Dual-unit commercial building with high visibility and income potential.

    5657 Main Street, Clay City, KY 40312
    View details
    Equipped Restaurant Building in Lexington
    $1,750,000
    3,500 SF

    Equipped Restaurant Building in Lexington

    3,500 SF restaurant with fully equipped kitchen for sale.

    3280 Eagle View Ln, Lexington, KY 40509
    View details
    Versatile Commercial Building in Clay City
    $150,000
    0.45 Acres

    Versatile Commercial Building in Clay City

    Two-unit commercial building in Clay City, Kentucky, for sale.

    5657 Main St, Clay City, KY 40312
    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.

    Lexington Land for Ground Lease
    $138,000
    1.38 Acres

    Lexington Land for Ground Lease

    1.38 acres of land available for ground lease.

    5540 Athens Boonesboro Road, Lexington, KY 40509
    View details
    Eastland Shopping Center Outlot
    $1,100,000
    1.01 Acres

    Eastland Shopping Center Outlot

    Prime commercial land in established shopping center facing Winchester Rd.

    1311 Winchester Road, Lexington, KY 40505
    View details
    Prime Commercial Land Opportunity
    $375,000
    2.91 Acres

    Prime Commercial Land Opportunity

    2.90-acre commercial parcel with high visibility and easy access.

    2275 N Broadway, Lexington, KY 40505
    View details
    Richmond, KY Out Parcel Land
    $1,400,000
    1.71 Acres

    Richmond, KY Out Parcel Land

    1.71 acre outparcel ideal for retail, restaurant, or office.

    2072 Merchant Drive, Richmond, KY 40475
    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

    1518 Bypass Rd

    Neighborhood centers • 53,989 SF
    Value Estimation by Request
    1518 Bypass Rd, Winchester, KY 40391
    View details
    1525 Lexington Ave

    1525 Lexington Ave

    Restaurants • 5,498 SF
    Value Estimation by Request
    1525 Lexington Ave, Winchester, KY 40391
    View details
    1501 Byp Rd

    1501 Byp Rd

    RESTAURANT • 7,020 SF
    Value Estimation by Request
    1501 Byp Rd, Winchester, KY 40391-2714
    View details

    Winchester, KY Restaurants Investment Opportunities Market Analysis

    Explore 9 restaurants for sale in Winchester, KY, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 16,676 square feet of properties for sale, with an estimated market value of $2,199,000.

    Sale prices for restaurant properties in Winchester, KY start at $374,000, averaging $439,800, and reaching up to $531,000 — 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

    Bars & Pubs 2
    Conventional restaurants 2

    Demographics Overview

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

    High-Yield Neighborhoods for Strategic Investment

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

    Neighborhood Average Price
    40391 $429K

    Taxes & Financing

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

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