Winchester, KY Restaurants for sale

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

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This listing looks promising.

Here's a quick look at some key insights for

137 East Broadway Street, Winchester, KY 40391

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Est. Cap Rate

4.8%
NOI ÷ price
Est. NOI

$18K
Annual
Price @ 7% Cap

$255K
Suggested

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Updated: Apr 21

Mixed-Use Property with Private-Entry Apartment

808 Bypass Road, Winchester, KY 40391

$500,000

5,054 sqft 0.42 AC lot

5,054 square feet on a 0.42‑acre site
Commercial space includes kitchen, service counter, dining/event area, and drive‑thru window
Attached apartment has a private entrance
Unfinished area is plumbed for a second one‑bedroom apartment
Outdoor seating and on‑site parking included

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Historic Opera House Venue

101 S Main, Winchester, KY 40391

$1,750,000

20,548 sqft 0.23 AC lot

Restored brick venue combines event, dining, gallery, and office areas in a flexible downtown commercial setting.

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Applebee’s Restaurant Property

1525 W Lexington Ave, Winchester, KY 40391

Contact for pricing

5,498 sqft 2.25 AC lot

Applebee’s restaurant building built in 2003 on 2.25 acres with an absolute net lease structure.

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Turnkey Waterfront Restaurant

220 Athens Boonsboro Road, Winchester, KY 40391

$531,000

5,012 sqft 1.23 AC lot

Renovated restaurant with indoor-outdoor dining, full bar, and an upstairs apartment at a waterfront property.

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Based on your search, we've compiled 16 Potential Opportunities for your consideration. Besides 5 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.

Freestanding Restaurant on Winchester Road

1015 Winchester Road, Lexington, KY 40505

$1,200,000

2,100 sqft

Freestanding restaurant with drive-thru for sale on Winchester Road.

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B-1 Commercial Land with Drive-Through Approval

1209 Winchester Road, Lexington, KY 40505

$919,900

0.40 AC lot

Corner-oriented commercial site with public sewer, water availability, and a previously approved conditional use permit for drive-through development.

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Equipped Restaurant Building in Lexington

3280 Eagle View Ln, Lexington, KY 40509

Contact for pricing

3,500 sqft

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

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Prime Retail/Restaurant Outlot Opportunity

2887 Richmond Road, Lexington, KY 40509

$100,000

1.30 AC lot

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

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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.

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.

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Eastland Shopping Center Outlot

1311 Winchester Road, Lexington, KY 40505

$1,100,000

1.01 AC lot

Prime commercial land in established shopping center facing Winchester Rd.

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Richmond, KY Out Parcel Land

2072 Merchant Drive, Richmond, KY 40475

$1,400,000

1.71 AC lot

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

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Platted B-3 Development Land

999 Dr Robert R Martin Bypass, Richmond, KY 40475

$3,200,000

16.00 AC lot

Zoned B-3 commercial development land with existing preliminary plat history along Robert Martin Bypass in Madison County.

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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.

Neighborhood centers

1518 Bypass Rd, Winchester, KY 40391

Value Estimation by Request

53,989 sqft

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Restaurants

1525 Lexington Ave, Winchester, KY 40391

Value Estimation by Request

5,498 sqft 2.25 AC lot

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RESTAURANT

1501 Byp Rd, Winchester, KY 40391-2714

Value Estimation by Request

7,020 sqft 1.09 AC lot

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Winchester, KY Restaurants Market Trends and Statistics

Explore 8 restaurants for sale in Winchester, KY, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 37,648 square feet of properties for sale, with an estimated market value of $3,155,000.

Sale prices for restaurant properties in Winchester, KY start at $374,000, averaging $788,750, and reaching up to $1,750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Neighborhood	Average Price
40391	$730.6K

Neighborhood

Average Price

40391

$730.6K