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    Winchester, KY
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    Winchester, KY Bed & Breakfasts for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    Turnkey Waterfront Restaurant with Apartment
    $531,000
    5,012 SF

    Turnkey Waterfront Restaurant with Apartment

    220 Athens Boonsboro Road, Winchester, KY 40391

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

    • Prime waterfront location.
    • Fully operational, renovated waterfront restaurant with real estate included.
    • Turnkey business with established income potential.
    • Spacious upstairs apartment for live‑in manager or short‑term rental income.
    • Indoor‑outdoor dining and full bar.
    Updated: Jun 18, 2025
    View details
    Based on your search, we've compiled 9 Potential Opportunities for your consideration. Besides 1 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, 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.

    Turn-Key Motel with Coffee Shop
    $699,000
    3,500 SF

    Turn-Key Motel with Coffee Shop

    Motel with furnished rooms, house, and functioning coffee shop.

    1165 S KY-11, Beattyville, KY 41311
    View details
    Kentucky Farm & Retreat Estate
    $4,250,000
    9,721 SF

    Kentucky Farm & Retreat Estate

    290-acre estate with hospitality compound and retreat center.

    790 McSwain Branch Road, Irvine, KY 40336
    View details
    Historic Beaumont Inn For Sale
    $3,300,000
    26.00 Acres

    Historic Beaumont Inn For Sale

    27-room English style country retreat and culinary staple.

    638 Beaumont Inn Drive, Harrodsburg, KY 40330
    View details
    Charming Two-Story Home
    $337,000
    2,760 SF

    Charming Two-Story Home

    Character-rich home suitable for a bed & breakfast.

    212 Clay St, Mount Sterling, KY 40353
    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.

    Land Near Red River Gorge
    $30,000
    1.42 Acres

    Land Near Red River Gorge

    1.42 acres near Red River Gorge, potential Air BNB.

    44 Indian Valley Retreat, Zoe, KY 41397
    View details
    23.93 Acres Near Windrock Park
    $350,000
    1,042,390 SF

    23.93 Acres Near Windrock Park

    23.93 acres zoned AG-1/Timber, near Windrock Bike Park.

    320 Frost Bottom Road, Oliver Springs, TN 37840
    View details
    Oliver Springs Land for Sale
    $350,000
    23.93 Acres

    Oliver Springs Land for Sale

    23.93 acre tract near Wind Rock Park.

    320 Frost Bottom Rd, Oliver Springs, TN 37840
    View details
    Unrestricted Lot with Mountain Views
    Contact for pricing
    0.30 Acres

    Unrestricted Lot with Mountain Views

    Sevierville, TN lot suitable for investment or cabin development.

    Black Oak Dr, Sevierville, TN 37876
    View details

    Winchester, KY Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 1 bed & breakfasts for sale in Winchester, KY on our real estate platform. These investment opportunities span a total of 5,012 square feet of properties for sale, with an estimated market value of $531,000.

    Sale prices for inns in Winchester, KY start at $531,000, averaging $531,000, 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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