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For sale
  • $960,000

    508 & 512 E Winchester Ave, Middlesboro, KY 40965

    2beds
    6,696sqft
    : 
    $6,312/mo
    Get pre-qualified
    Multi Family
    Built in 1980
    -- sqft lot
    $-- Zestimate®
    $143/sqft
    $-- HOA

    What's special

    Generous lot sizesAmple parkingGreen space
    Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each building offers significant square footage ideal for multiple residential units, making them well-suited for investors seeking strong cash flow potential in the Middlesboro market. The generous lot sizes allow for ample parking, green space, or future expansion opportunities. Situated along Winchester Avenue, the properties benefit from convenient access to local amenities, major thoroughfares, and the broader Middlesboro community. Whether you're an experienced multifamily investor or looking to expand your portfolio, this paired offering represents a solid foundation for long-term rental income and value appreciation.
    110 days
    |
    88
    |
    2
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Beth Combs 606-269-1807,

    Turn Key Realty

    Source: Imagine MLS,MLS#: 26007224MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Heating
      • Electric
      Cooling
      • Electric
      Appliances
      • Laundry: Electric Dryer Hookup, Washer Hookup
      Interior area
      • Total structure area: 6,696
      • Total interior livable area: 6,696 sqft

      Property

      Parking
      • Total spaces: 12
      Lot
      • Size: 0.55 Acres
      Details
      • Parcel number: 0694206012.00 069.42.06.011.00

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Multi Family
      Materials
      • Roof: Shingle
      Condition
      • Year built: 1980

      Community & HOA

      Community
      • Security: Fire Sprinkler System
      • Subdivision: City Limits
      Location
      • Region: Middlesboro

      Financial & listing details

      • Price per square foot: $143/sqft
      • Date on market: 4/7/2026
      • Listing terms: Cash,Conventional

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $918/mo

        Price history

        DateEventPrice
        4/7/2026Listed for sale$960,000$143/sqft
        Source: Imagine MLS #26007224 Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 40965

        Getting around

        58 / 100
        Somewhat Walkable
        61 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Middlesboro Ind

        Source: Imagine MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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