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Sold for $370,000
  • $370,000

    382 S Main St, Winchester, KY 40391

    4beds
    3,310sqft
    Single Family Residence
    Built in 1893
    0.27 Acres Lot
    $370,200 Zestimate®
    $112/sqft
    $2,098 Estimated rent

    Home value

    $370,200

    $337,000 - $407,000

    $2,098/mo

    Zestimate® history
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    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Michelle R Blackburn 859-707-5955,

    RE/MAX Creative, Winchester

    Bought with:

    Alyssa Ryan, 270324

    Marshall Lane Real Estate - Lexington

    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
    • New construction: No
    • 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: $112/sqft
    • Tax assessed value: $209,000
    • Annual tax amount: $1,537
    • Date on market: 4/24/2026

    Price history

    DateEventPrice
    9/4/2026Sold$370,000-1.3%$112/sqft
    Source: Imagine MLS #26008931 Report a problem
    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

    Neighborhood: 40391

    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.

    Sell for more on Zillow
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    $370,200
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    With Zillow Showcase(estimated)
    $377,604
    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $370,200
    2% more
    +$7,404
    With Zillow Showcase(estimated)
    $377,604