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Pending
    • Price cut: $10K (6/24)
    $375,000

    382 S Main St, Winchester, KY 40391

    4beds
    3,310sqft
    : 
    $2,398/mo
    Get pre-qualified
    Single Family Residence
    Built in 1893
    0.27 Acres Lot
    $362,000 Zestimate®
    $113/sqft
    $-- HOA

    What's special

    Inviting front porchBasement-entry garageUpdated kitchenScreened-in porchMultiple living spacesSoaring ceilingsBeautiful original woodwork
    Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.
    124 days
    |
    287
    |
    12
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    Zillow last checked:

    Listing updated:

    Listed by:

    Michelle R Blackburn 859-707-5955,

    RE/MAX Creative, Winchester

    Source: Imagine MLS,MLS#: 26008931MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: Second
      Bedroom 1
      • Level: First
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Second
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: Second
      Bathroom 3
      • Level: Third
      Dining room
      • Level: First
      Foyer
      • Level: First
      Foyer
      • Level: Second
      Kitchen
      • Level: First
      Living room
      • Level: First
      Other
      • Description: Finished attic could be bedroom or recreation room
      • Level: Third
      Heating
      • Forced Air, Natural Gas
      Cooling
      • Central Air, Ceiling Fan(s), Electric
      Appliances
      • Included: Dryer, Dishwasher, Refrigerator, Washer, Range
      • Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
      Features
      • Entrance Foyer, Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
      • Flooring: Carpet, Hardwood, Vinyl
      • Doors: Storm Door(s)
      • Windows: Insulated Windows, Skylight(s), Blinds, Screens
      • Basement: Full,Sump Pump,Unfinished,Walk-Out Access
      • Number of fireplaces: 4
      • Fireplace features: Dining Room, Gas Log, Living Room, Master Bedroom
      Interior area
      • Total structure area: 3,310
      • Total interior livable area: 3,310 sqft
      • Finished area above ground: 3,310
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Basement, Driveway, Garage Door Opener, Garage Faces Side
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Exterior features: Other
      • Fencing: Wood
      Lot
      • Size: 0.27 Acres
      • Features: Landscaped, Many Trees
      Details
      • Additional structures: Shed(s)
      • Parcel number: 054202100900

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Stone
      • Roof: Dimensional Style,Shingle
      Condition
      • Year built: 1893

      Utilities & green energy

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

      Community & HOA

      Community
      • Subdivision: Thomson Addition
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $113/sqft
      • Tax assessed value: $209,000
      • Annual tax amount: $1,537
      • Date on market: 4/24/2026

        Estimated market value

        $362,000

        $344,000 - $380,000

        $2,138/mo

        Price history

        DateEventPrice
        8/18/2026Pending sale$375,000$113/sqft
        Source: Imagine MLS #26008931 Report a problem
        8/5/2026Contingent$375,000$113/sqft
        Source: Imagine MLS #26008931 Report a problem
        6/24/2026Price change$375,000-2.6%$113/sqft
        Source: Imagine MLS #26008931 Report a problem
        6/10/2026Price change$385,000-2.5%$116/sqft
        Source: Imagine MLS #26008931 Report a problem
        5/14/2026Price change$395,000-4.8%$119/sqft
        Source: Imagine MLS #26008931 Report a problem
        4/24/2026Listed for sale$415,000+299%$125/sqft
        Source: Imagine MLS #26008931 Report a problem
        8/31/1998Sold$104,000$31/sqft
        Source: Imagine MLS #9806775 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$1,537 +30.4%$209,000 +27.3%
        2024$1,179 -27.1%$164,200
        2023$1,617 $164,200
        2022$1,617 +0.3%$164,200
        2021$1,613 -0.2%$164,200
        2020$1,616 +574.1%$164,200
        2019$240 $164,200
        2018$240 $164,200
        2017$240 $164,200
        2016$240 $164,200
        2015$240 $164,200
        2013$240 $164,200
        2011-- $164,200
        2010-- $164,200
        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

        56 / 100
        Somewhat Walkable
        31 / 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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