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Pending
    • $239,000

    221 S Highland St, Winchester, KY 40391

    6beds
    3,007sqft
    : 
    $1,576/mo
    Get pre-qualified
    Triplex
    Built in 1930
    -- sqft lot
    $231,400 Zestimate®
    $79/sqft
    $-- HOA

    What's special

    Eat-in kitchenLarge eat-in kitchenStorage buildingLaundry room
    Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 3 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in kitchen. The main level unit rents for $1299 per month. The upper unit rents for $895 per month. When the lower level is rented it rents for $799 per month. You will find plenty of parking in the back. There is a carport and storage building that also goes with this property.
    31 days
    |
    355
    |
    23
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Libby VanMeter 859-771-4811,

    Marshall Lane Real Estate - Lexington

    Source: Imagine MLS,MLS#: 26015897MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 3
      • Full bathrooms: 3
      Heating
      • Baseboard, Electric, Floor Furnace, Other
      Cooling
      • Electric, Window Unit(s)
      Appliances
      • Laundry: Electric Dryer Hookup, Washer Hookup
      Interior area
      • Total structure area: 3,007
      • Total interior livable area: 3,007 sqft

      Property

      Parking
      • Total spaces: 5
      Lot
      • Size: 6,969 Square Feet
      • Dimensions: 50 x 150
      Details
      • Parcel number: 054301201600
      • Zoning: R-1C

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Triplex
      • Attached to another structure: Yes
      Materials
      • Roof: Shingle
      Condition
      • Year built: 1930

      Community & HOA

      Community
      • Features: Park, Tennis Court(s), Pool, Pickleball
      • Subdivision: Downtown
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $79/sqft
      • Tax assessed value: $185,500
      • Annual tax amount: $1,855
      • Date on market: 7/2/2026

        Estimated market value

        $231,400

        $220,000 - $243,000

        $1,173/mo

        Price history

        DateEventPrice
        7/24/2026Pending sale$239,000$79/sqft
        Source: Imagine MLS #26015897 Report a problem
        7/2/2026Listed for sale$239,000-0.4%$79/sqft
        Source: Imagine MLS #26015897 Report a problem
        6/1/2026Listing removed$239,900$80/sqft
        Source: Imagine MLS #26006685 Report a problem
        4/16/2026Price change$239,900-2.6%$80/sqft
        Source: Imagine MLS #26006685 Report a problem
        4/1/2026Listed for sale$246,400$82/sqft
        Source: Imagine MLS #26006685 Report a problem
        4/1/2026Listing removed$246,400$82/sqft
        Source: Imagine MLS #26000780 Report a problem
        2/13/2026Price change$246,400-1%$82/sqft
        Source: Imagine MLS #26000780 Report a problem
        1/12/2026Price change$248,900-1.4%$83/sqft
        Source: Imagine MLS #26000780 Report a problem
        12/16/2025Price change$252,500-1.9%$84/sqft
        Source: Imagine MLS #25504956 Report a problem
        11/30/2025Price change$257,500-1.9%$86/sqft
        Source: Imagine MLS #25504956 Report a problem
        11/18/2025Price change$262,500-2.7%$87/sqft
        Source: Imagine MLS #25504956 Report a problem
        10/29/2025Listed for sale$269,900+1.9%$90/sqft
        Source: Imagine MLS #25504956 Report a problem
        8/2/2024Listing removed--
        Source: Imagine MLS #24008911 Report a problem
        6/28/2024Price change$264,900-1.9%$88/sqft
        Source: Imagine MLS #24008911 Report a problem
        5/30/2024Price change$269,900-3.6%$90/sqft
        Source: Imagine MLS #24008911 Report a problem
        5/6/2024Listed for sale$279,900+50.9%$93/sqft
        Source: Imagine MLS #24008911 Report a problem
        12/1/2022Sold$185,500-6.8%$62/sqft
        Source: Imagine MLS #22023667 Report a problem
        10/27/2022Pending sale$199,000$66/sqft
        Source: Imagine MLS #22023667 Report a problem
        10/27/2022Listed for sale$199,000$66/sqft
        Source: Imagine MLS #22023667 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$1,855 +123.4%$185,500
        2023$830 $185,500 +48.6%
        2022$830 +0.3%$124,800
        2021$828 -1.6%$124,800
        2020$841 +574.1%$124,800
        2019$125 $124,800
        2018$125 -1.9%$124,800
        2017$127 -84.9%$124,800
        2016$845 $124,800
        2015$845 +551.5%$124,800 +40.5%
        2013$130 $88,800 -27.6%
        2011-- $122,700
        2010-- $122,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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.
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        Climate risks

        Neighborhood: 40391

        Getting around

        74 / 100
        Very Walkable
        43 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: GRC

        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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