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For sale
    • Price cut: $10K (6/8)
    $340,000

    443 S Maple St, Winchester, KY 40391

    4beds
    3,261sqft
    : 
    $2,175/mo
    Get pre-qualified
    Single Family Residence
    Built in 1905
    0.39 Acres Lot
    $331,300 Zestimate®
    $104/sqft
    $-- HOA

    What's special

    Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.
    129 days
    |
    820
    |
    66
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Terra Long 859-707-7366,

    Keller Williams Commonwealth,

    Shane T Underwood 859-699-2969,

    Keller Williams Commonwealth

    Source: Imagine MLS,MLS#: 26008225MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Level: First
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Second
      Bathroom 1
      • Description: Full Bath
      • Level: First
      Bathroom 2
      • Description: Full Bath
      • Level: Second
      Den
      • Level: First
      Dining room
      • Level: First
      Kitchen
      • Level: First
      Living room
      • Level: First
      Other
      • Description: Sun Room
      • Level: First
      Utility room
      • Description: in closet by full bath
      • Level: First
      Heating
      • Forced Air
      Cooling
      • Electric, None
      Appliances
      • Included: Double Oven, Dishwasher, Refrigerator, Range
      • Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
      Features
      • Flooring: Carpet, Hardwood, Vinyl
      • Windows: Blinds
      • Basement: Unfinished
      • Number of fireplaces: 3
      • Fireplace features: Living Room, Den
      Interior area
      • Total structure area: 3,261
      • Total interior livable area: 3,261 sqft
      • Finished area above ground: 3,261
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 1
      • Parking features: Attached Garage, Basement, Driveway, Garage Door Opener, Off Street, Garage Faces Side
      • Garage spaces: 1
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Exterior features: Awning(s)
      • Fencing: None
      • Has view: Yes
      • View description: Neighborhood
      Lot
      • Size: 0.39 Acres
      • Features: Many Trees
      Details
      • Parcel number: 054201800100

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Stone
      • Roof: Shingle
      Condition
      • Year built: 1905

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Subdivision: Downtown
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $104/sqft
      • Tax assessed value: $199,000
      • Annual tax amount: $1,912
      • Date on market: 4/18/2026

        Estimated market value

        $331,300

        $315,000 - $348,000

        $1,949/mo

        Price history

        DateEventPrice
        6/8/2026Price change$340,000-2.9%$104/sqft
        Source: Imagine MLS #26008225 Report a problem
        4/18/2026Listed for sale$350,000$107/sqft
        Source: Imagine MLS #26008225 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$1,912 +48.7%$199,000 +13.7%
        2024$1,287 -2.9%$175,000
        2023$1,325 $175,000
        2022$1,325 +0.3%$175,000
        2021$1,321 -1.1%$175,000
        2020$1,336 +574.1%$175,000
        2019$198 $175,000
        2018$198 -1.2%$175,000
        2017$201 -0.5%$175,000
        2016$202 $175,000
        2015$202 -0.6%$175,000 +25.9%
        2013$203 $139,000 -33.1%
        2011-- $207,700
        2010-- $207,700
        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.
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        Climate risks

        Neighborhood: 40391

        Getting around

        64 / 100
        Somewhat Walkable
        42 / 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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