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For sale
  • $484,900

    414 Fairholme Way, Winchester, KY 40391

    4beds
    2,418sqft
    : 
    Single Family Residence
    Built in 2025
    0.37 Acres Lot
    $-- Zestimate®
    $201/sqft
    $-- HOA

    What's special

    Step into a lifestyle where modern luxury and brand-new construction come together seamlessly in Fairholme Estates of Winchester. Perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm fireplace create an inviting centerpiece for the open-concept living space—designed for both effortless entertaining and cozy nights at home. The timeless kitchen is equal parts beautiful and functional, featuring quartz countertops, a spacious walk-in pantry, and a dedicated coffee bar nook ready to elevate your morning routine. Just beyond, a dedicated dining area creates the perfect backdrop for weeknight dinners, holiday gatherings, and lingering conversations with family and friends. The primary suite feels like a private retreat, offering a spa-inspired en-suite complete with a soaking tub, tiled walk-in shower, dual vanities, and an expansive custom closet designed with luxury in mind. A split-bedroom floor plan provides ideal privacy with three additional bedrooms and two full bathrooms, creating flexibility for guests, family, or a home office setup. Outdoor living provides a screened back patio made for slow mornings, relaxing evenings, and enjoying the peaceful views. Whether you're gardening, unwinding after a long day, or gathering on the front porch with friends as the sun sets over the golf course, this space was designed to be enjoyed. And the location? Exceptional. Nestled just minutes from charming downtown Winchester's local shops, restaurants, and small-town charm, with quick access to I-64 for an easy commute. Plus, the oversized tall garage offers incredible vertical storage opportunities for hobbies, equipment, and all of life's extras. A rare opportunity to enjoy the ease of new construction, elevated design, and a lifestyle centered around comfort, connection, and beautiful surroundings. This isn't just a home—it's your next chapter.
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    Zillow last checked:

    Listing updated:

    Listed by:

    Morgan Withrow 859-699-9049,

    The Brokerage

    Source: Imagine MLS,MLS#: 26011136MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: First
      Kitchen
      • Level: First
      Heating
      • Electric
      Cooling
      • Electric
      Appliances
      • Included: Disposal, Dishwasher, Microwave, Refrigerator, Cooktop, Oven
      • Laundry: Main Level
      Features
      • Breakfast Bar, Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s), Soaking Tub
      • Flooring: Carpet
      • Basement: Crawl Space
      • Number of fireplaces: 1
      • Fireplace features: Electric, Living Room
      Interior area
      • Total structure area: 2,418
      • Total interior livable area: 2,418 sqft
      • Finished area above ground: 2,418
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached Garage, Driveway, Garage Faces Side
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      Lot
      • Size: 0.37 Acres
      Details
      • Parcel number: 055100401500

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch
      • Property subtype: Single Family Residence
      Materials
      • Brick Veneer, Vinyl Siding
      • Foundation: Block
      • Roof: Dimensional Style
      Condition
      • New Construction
      • Year built: 2025

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Subdivision: Fairholme Estates
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $201/sqft
      • Tax assessed value: $28,000
      • Annual tax amount: $280
      • Date on market: 5/17/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $2,555/mo

        Price history

        DateEventPrice
        5/17/2026Listed for sale$484,900+1%$201/sqft
        Source: Imagine MLS #26011136 Report a problem
        4/16/2026Listing removed$479,900$198/sqft
        Source: Imagine MLS #25505996 Report a problem
        4/8/2026Price change$479,900-2%$198/sqft
        Source: Imagine MLS #25505996 Report a problem
        3/13/2026Price change$489,900-2%$203/sqft
        Source: Imagine MLS #25505996 Report a problem
        11/12/2025Listed for sale$499,900+1165.6%$207/sqft
        Source: Imagine MLS #25505996 Report a problem
        3/5/2025Sold$39,500$16/sqft
        Source: Imagine MLS #20019593 Report a problem
        2/3/2025Pending sale$39,500$16/sqft
        Source: Imagine MLS #20019593 Report a problem
        6/28/2024Price change$39,500+14.5%$16/sqft
        Source: Imagine MLS #20019593 Report a problem
        2/19/2024Listed for sale$34,500$14/sqft
        Source: Imagine MLS #20019593 Report a problem
        10/20/2023Listing removed--
        Source: Imagine MLS #20019593 Report a problem
        10/19/2022Listed for sale$34,500$14/sqft
        Source: Imagine MLS #20019593 Report a problem
        10/1/2022Listing removed--
        Source: Imagine MLS #20019593 Report a problem
        9/30/2021Listed for sale$34,500$14/sqft
        Source: Imagine MLS #20019593 Report a problem
        9/22/2021Listing removed--
        Source: Imagine MLS #20019593 Report a problem
        4/13/2021Listed for sale$34,500$14/sqft
        Source: Imagine MLS #20019593 Report a problem
        1/14/2021Listing removed--
        Source: Imagine MLS Report a problem
        12/4/2020Listed for sale$34,500$14/sqft
        Source: Tom Goebel & Company #20019593 Report a problem
        10/23/2020Pending sale$34,500$14/sqft
        Source: Tom Goebel & Company #20019593 Report a problem
        9/21/2020Listed for sale$34,500$14/sqft
        Source: Tom Goebel & Company #20019593 Report a problem
        5/1/2020Listing removed$34,500$14/sqft
        Source: Keller Williams Bluegrass #1919810 Report a problem
        2/9/2020Listed for sale$34,500$14/sqft
        Source: Keller Williams Bluegrass #1919810 Report a problem
        12/19/2019Pending sale$34,500$14/sqft
        Source: Keller Williams Bluegrass #1919810 Report a problem
        3/18/2019Listed for sale$34,500$14/sqft
        Source: Tom Goebel & Company #1120284 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$280 +60.6%$28,000 +58.2%
        2023$174 $17,700
        2022$174 +0.3%$17,700
        2021$174 -0.2%$17,700
        2020$174 +574.1%$17,700
        2019$26 $17,700
        2018$26 $17,700
        2017$26 $17,700
        2016$26 $17,700
        2015$26 $17,700

        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.
          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

          21 / 100
          Car-Dependent
          21 / 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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