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For sale
    • Price cut: $15K (7/7)
    $165,000

    229 S Highland St, Winchester, KY 40391

    4beds
    3,462sqft
    : 
    $1,110/mo
    Get pre-qualified
    Single Family Residence
    Built in 1930
    4,791 Square Feet Lot
    $-- Zestimate®
    $48/sqft
    $-- HOA

    What's special

    Detailed woodworkTimeless architectural details throughoutOriginal hardwood floorsCorner lot
    Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.
    92 days
    |
    2,697
    |
    218
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Michelle R Blackburn 859-707-5955,

    RE/MAX Creative, Winchester

    Source: Imagine MLS,MLS#: 26008701MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: First
      Bedroom 1
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Second
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: Second
      Bathroom 3
      • Level: Second
      Dining room
      • Level: First
      Family room
      • Level: First
      Foyer
      • Level: First
      Kitchen
      • Level: First
      Living room
      • Level: First
      Heating
      • Forced Air, Natural Gas
      Cooling
      • Electric
      Appliances
      • Included: Refrigerator
      Features
      • Flooring: Hardwood
      • Basement: Crawl Space,Interior Entry,Walk-Out Access
      • Number of fireplaces: 3
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 3,462
      • Total interior livable area: 3,462 sqft
      • Finished area above ground: 3,462
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 1
      • Parking features: Basement, Garage Faces Side
      • Garage spaces: 1
      Features
      • Levels: Two
      • Fencing: None
      Lot
      • Size: 4,791 Square Feet
      Details
      • Parcel number: 054301201400

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • HardiPlank Type, Wood Siding
      • Foundation: Stone
      • Roof: Metal
      Condition
      • Year built: 1930

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected, Natural Gas Connected, Water Connected

      Community & HOA

      Community
      • Subdivision: South Park Addition
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $48/sqft
      • Tax assessed value: $205,900
      • Annual tax amount: $2,059
      • Date on market: 4/22/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $2,195/mo

        Price history

        DateEventPrice
        7/7/2026Price change$165,000-8.3%$48/sqft
        Source: Imagine MLS #26008701 Report a problem
        4/22/2026Listed for sale$180,000$52/sqft
        Source: Imagine MLS #26008701 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$2,059 +1.5%$205,900
        2023$2,028 $205,900
        2022$2,028 +72.1%$205,900 +71.6%
        2021$1,179 +49.7%$120,000 +50%
        2020$787 +670.4%$80,000 +14.3%
        2019$102 $70,000
        2018$102 $70,000
        2017$102 $70,000
        2016$102 $70,000
        2015$102 $70,000
        2013$102 $70,000
        2011-- $70,000
        2010-- $70,000
        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.
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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
        • Elementary: Shearer
        • Middle: Robert Campbell
        • 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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