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    Middlesboro, KY

    Middlesboro, KY Commercial Real Estate for Sale

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    15 properties
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    Downtown Restaurant Building
    Updated: Jun 3
    Downtown Restaurant Building

    1803 W Cumberland Avenue, Middlesboro, KY 40965

    $325,000
    12,210 sqft 0.60 AC lot
    12,210 SF commercial building in the Downtown Business District
    Long‑established restaurant tenant occupies 4,070 SF, with 8,140 SF additional open space available
    141 feet of road frontage in a downtown setting
    Ample on‑site parking for customers and employees
    Roof is flat; heating is forced air and cooling is a heat pump
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    High-Visibility Retail and Restaurant Building
    Updated: Jun 1
    High-Visibility Retail and Restaurant Building

    601 N 15th Street, Middlesboro, KY 40965

    $375,000
    3,200 sqft 0.57 AC lot
    3,200 SF building in the city limits of Middlesboro
    Built in 1998 with block construction
    Metal roof, central air, and heat pump HVAC
    Public sewer service
    Located on a high‑visibility street behind Middlesboro Mall with lots of parking
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    Versatile Commercial Building in Middlesboro
    Versatile Commercial Building in Middlesboro

    205 N 20th Street, Middlesboro, KY 40965

    $350,000
    3,330 sqft 0.53 AC lot

    Adaptable commercial building suitable for office or retail use.

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    Multi-Use Commercial Building
    Multi-Use Commercial Building

    205 N 20th St, Middlesboro, KY 40965

    $350,000
    3,330 sqft

    Commercial building suited for office or retail use, with an additional lot behind that conveys with the sale.

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    Versatile Retail and Office Building
    Versatile Retail and Office Building

    414 S 24th Street, Middlesboro, KY 40965

    $182,000
    1,608 sqft 0.25 AC lot

    For sale commercial building with flexible space for retail, office, or professional service use in Middlesboro.

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    Land with Heated Garage
    Land with Heated Garage

    904-A E Cumberland Avenue, Middlesboro, KY 40965

    $35,000
    0.28 AC lot

    Approximately 0.28-acre lot in Middlesboro city limits includes a well-maintained, heated 1,292 SF garage with utilities.

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    Middlesboro Land For Sale
    Middlesboro Land For Sale

    321 Chester Avenue, Middlesboro, KY 40965

    $275,000
    1.69 AC lot

    1.695 acres of B3 zoned land in Middlesboro, Kentucky.

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    Downtown Restaurant and Retail Building
    Downtown Restaurant and Retail Building

    1803 W Cumberland Avenue, Middlesboro, KY 40965

    $325,000
    12,210 sqft

    Multi-tenant building with operating restaurant plus substantial flexible space and 141 feet of road frontage.

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    Middlesboro, KY Land For Sale
    Middlesboro, KY Land For Sale

    205 Exeter Avenue, Middlesboro, KY 40965

    Contact for pricing
    0.13 AC lot

    Land with city utilities available in Middlesboro, Kentucky.

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    B-1 Zoned Commercial Land
    B-1 Zoned Commercial Land

    US 25E, Middlesboro, KY 40965

    $185,000
    1.50 AC lot

    1.5-acre commercial land parcel zoned B-1 in Middlesboro, KY.

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    High-Visibility Retail Restaurant Building
    High-Visibility Retail Restaurant Building

    601 N 15th Street, Middlesboro, KY 40965

    $375,000
    3,200 sqft

    A 1998-built retail and restaurant-ready building with ample parking, positioned on a high-visibility street in Middlesboro.

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    Middlesboro Commercial Land For Sale
    Middlesboro Commercial Land For Sale

    321 Chester Avenue, Middlesboro, KY 40965

    $275,000
    73,616 sqft 1.70 AC lot

    1.695 acres of B3-zoned land in Middlesboro, Kentucky.

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    Single-Tenant NNN Retail Building
    Single-Tenant NNN Retail Building

    239 N 12th St, Middlesboro, KY 40965

    Contact for pricing

    Single-tenant retail building leased to Fast Pace with a remaining 10 years on an original 15-year NNN term.

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    Krystal QSR Restaurant Property
    Krystal QSR Restaurant Property

    1225 N 12th St, Middlesboro, KY 40965

    Contact for pricing

    For-sale Krystal-branded QSR restaurant with a long-time franchisee tenant operating at the site.

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    Zoned Commercial Development Land
    Zoned Commercial Development Land

    423 N 10th St, Middlesboro, KY 40965

    Contact for pricing
    64.84 AC lot

    64.84-acre parcel with a family farm house, zoned commercial near Cumberland Gap National Park and LMU.

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    Based on your search, we've compiled 76 Potential Opportunities for your consideration. Besides 15 Active listings in Middlesboro, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 57 Off-Market properties to explore as potential leads

    Opportunities in Nearby Cities

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

    Automotive Garage with Lifts
    Automotive Garage with Lifts

    145 Providence Rd, Cumberland Gap, TN 37724

    $149,900
    1,500 sqft

    Metal garage includes a concrete pad and a four-post electric/hydraulic lift system, plus updated electrical and climate control.

    View details
    Dual-Access Office Building
    Dual-Access Office Building

    395 PATTERSON RD, Harrogate, TN 37752

    $825,000
    2,528 sqft

    Established office building with dual roadway access, designed for professional services including medical and legal uses.

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    Self-Storage Facility For Sale
    Self-Storage Facility For Sale

    2390 HWY 63, Cumberland Gap, TN 37724

    $439,900
    2,500 sqft

    2,500 SF self-storage facility available for purchase.

    View details
    Harrogate, TN 5-Acre Land
    Harrogate, TN 5-Acre Land

    Shawanee Rd, Harrogate, TN 37752

    $250,000
    5.65 AC lot

    5.65-acre tract with barn, spring, and fencing in Harrogate.

    View details

    Off-Market Properties in Middlesboro, KY

    Consider similar Off-Market properties in Middlesboro, 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.

    1106 Cumberland Ave
    COMMERCIAL (GENERAL)

    1106 Cumberland Ave, Middlesboro, KY 40965-1054

    $2,220,000
    Estimated value
    33,744 sqft
    View details
    2016 Cumberland Ave
    COMMERCIAL (GENERAL)

    2016 Cumberland Ave, Middlesboro, KY 40965-2829

    Value Estimation by Request
    9,794 sqft 0.09 AC lot
    View details
    2014 Cumberland Ave
    COMMERCIAL (GENERAL)

    2014 Cumberland Ave, Middlesboro, KY 40965-2829

    Value Estimation by Request
    2,500 sqft
    View details
    1005 Winchester Ave
    COMMERCIAL (GENERAL)

    1005 Winchester Ave, Middlesboro, KY 40965-1545

    Value Estimation by Request
    3,000 sqft
    View details
    1911 Cumberland Ave
    RETAIL STORES (PERSONAL SERVICES)

    1911 Cumberland Ave, Middlesboro, KY 40965-1230

    Value Estimation by Request
    3,850 sqft
    View details
    1909 Cumberland Ave
    COMMERCIAL (GENERAL)

    1909 Cumberland Ave, Middlesboro, KY 40965-1230

    Value Estimation by Request
    3,236 sqft
    View details
    132 21st St
    COMMERCIAL (GENERAL)

    132 21st St, Middlesboro, KY 40965-2813

    Value Estimation by Request
    5,880 sqft 0.07 AC lot
    View details
    205 Avondale Ave
    COMMERCIAL (GENERAL)

    205 Avondale Ave, Middlesboro, KY 40965-1037

    Value Estimation by Request
    4,184 sqft 0.21 AC lot
    View details
    1817 Cumberland Ave
    COMMERCIAL (GENERAL)

    1817 Cumberland Ave, Middlesboro, KY 40965-1228

    $710,000
    Estimated value
    30,000 sqft 0.41 AC lot
    View details

    Middlesboro, KY Commercial Real Estate Market Trends and Statistics

    Explore 72 commercial real estate for sale in Middlesboro, KY, showcased through 15 active listings on our real estate platform. These investment opportunities span a total of 112,704 square feet of properties for sale, with an estimated market value of $3,052,000.

    Sale prices for business properties in Middlesboro, KY start at $35,000, averaging $277,454, and reaching up to $375,000 — 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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    Demographics Overview

    Population 12K
    Population Growth (5Y) -5.8%
    Median Household Income $30,980
    College Educated 20.5%

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    40965 $281.1K

    Taxes & Financing

    Tax Rate (average for all types) 1.06%
    Property Tax per SF $2.60 per SF
    Tax Rate vs County Average 0.06 pp below county avg
    Average Loan-to-Value 65.0%

    Total CRE Inventory on Market (SF)

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