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For sale
    • Price cut: $5K (8/31)
    $239,900

    377 Crescent Ave, Winchester, KY 40391

    3beds
    1,533sqft
    : 
    $1,581/mo
    Get pre-qualified
    Single Family Residence
    Built in 1940
    8,276 Square Feet Lot
    $237,400 Zestimate®
    $156/sqft
    $-- HOA

    What's special

    Inviting living spacesBeautiful hardwood floorsWelcoming covered front porchSeparate dining room
    "Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!
    85 days
    1,530
    124

    Zillow last checked:

    Listing updated:

    Listed by:

    Bill VanWinkle 859-582-2810,

    Joyce Marcum Realty

    Source: Imagine MLS,MLS#: 26013350MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: Second
      Kitchen
      • Level: First
      Living room
      • Level: First
      Heating
      • Electric, Heat Pump, Natural Gas
      Cooling
      • Electric
      Appliances
      • Included: Dishwasher, Microwave, Refrigerator, Range
      • Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
      Features
      • Ceiling Fan(s)
      • Flooring: Hardwood, Tile
      • Windows: Insulated Windows
      • Basement: Concrete,Interior Entry,Sump Pump,Unfinished,Walk-Up Access
      • Number of fireplaces: 1
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 1,533
      • Total interior livable area: 1,533 sqft
      • Finished area above ground: 1,533
      • Finished area below ground: 0

      Property

      Parking
      • Parking features: Off Street
      Features
      • Levels: Two
      • Fencing: Privacy,Wood
      • Has view: Yes
      • View description: Neighborhood
      Lot
      • Size: 8,276 Square Feet
      • Features: Few Trees
      Details
      • Additional structures: Shed(s)
      • Parcel number: 054202101200

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Block
      • Roof: Metal,Shingle
      Condition
      • Year built: 1940

      Utilities & green energy

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

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $156/sqft
      • Tax assessed value: $219,900
      • Annual tax amount: $2,113
      • Date on market: 6/10/2026

        Estimated market value

        $237,400

        $226,000 - $249,000

        $1,539/mo

        Price history

        DateEventPrice
        8/31/2026Price change$239,900-2%$156/sqft
        Source: Imagine MLS #26013350 Report a problem
        8/11/2026Price change$244,900-1.1%$160/sqft
        Source: Imagine MLS #26013350 Report a problem
        7/10/2026Price change$247,500-0.8%$161/sqft
        Source: Imagine MLS #26013350 Report a problem
        6/24/2026Price change$249,500-2%$163/sqft
        Source: Imagine MLS #26013350 Report a problem
        6/10/2026Listed for sale$254,500+15.7%$166/sqft
        Source: Imagine MLS #26013350 Report a problem
        2/2/2024Sold$219,900$143/sqft
        Source: Imagine MLS #23023799 Report a problem
        12/19/2023Pending sale$219,900$143/sqft
        Source: Imagine MLS #23023799 Report a problem
        12/18/2023Listed for sale$219,900+37.4%$143/sqft
        Source: Imagine MLS #23023799 Report a problem
        5/29/2020Sold$160,000+3.2%$104/sqft
        Source: Imagine MLS #20008245 Report a problem
        4/29/2020Pending sale$155,000$101/sqft
        Source: Realty World Adams #20008245 Report a problem
        4/28/2020Listed for sale$155,000+19.3%$101/sqft
        Source: Realty World Adams #20008245 Report a problem
        3/25/2019Listing removed$129,900$85/sqft
        Source: @Home Realty #1825697 Report a problem
        3/10/2019Pending sale$129,900$85/sqft
        Source: @Home Realty #1825697 Report a problem
        3/6/2019Listed for sale$129,900$85/sqft
        Source: @Home Realty #1825697 Report a problem
        2/22/2019Pending sale$129,900$85/sqft
        Source: @Home Realty #1825697 Report a problem
        2/16/2019Price change$129,900-3.7%$85/sqft
        Source: @Home Realty #1825697 Report a problem
        11/19/2018Price change$134,900-9.5%$88/sqft
        Source: @Home Realty #1825697 Report a problem
        11/14/2018Listed for sale$149,000+106.9%$97/sqft
        Source: @Home Realty #1825697 Report a problem
        11/21/2014Sold$72,000-9.9%$47/sqft
        Source: Imagine MLS #1410251 Report a problem
        8/27/2014Price change$79,900-11.1%$52/sqft
        Source: Hunter Real Estate #1410251 Report a problem
        7/29/2014Price change$89,900-5.3%$59/sqft
        Source: Hunter Real Estate #1410251 Report a problem
        5/29/2014Listed for sale$94,900-18.9%$62/sqft
        Source: Hunter Real Estate #1410251 Report a problem
        2/20/2004Sold$117,000$76/sqft
        Source: Imagine MLS #307360 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$2,113 -3.9%$219,900
        2024$2,199 +39.5%$219,900 +37.4%
        2023$1,576 $160,000
        2022$1,576 +0.3%$160,000
        2021$1,572 +21.1%$160,000 +21.3%
        2020$1,298 +611.3%$131,900 +5.5%
        2019$183 $125,000 -13%
        2018$183 -13%$143,600
        2017$210 $143,600
        2016$210 $143,600
        2015$210 $143,600
        2013$210 $143,600
        2011-- $143,600
        2010-- $143,600
        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.
        See how much you could borrow to make a competitive offer.
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        Climate risks

        Neighborhood: 40391

        Getting around

        51 / 100
        Somewhat Walkable
        30 / 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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