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For sale
    • $2,750,000

    4664 Lexington Rd, Winchester, KY 40391

    8beds
    13,433sqft
    : 
    $18,160/mo
    Get pre-qualified
    Single Family Residence
    Built in 1996
    35 Acres Lot
    $-- Zestimate®
    $205/sqft
    $-- HOA

    What's special

    Classic tobacco barnFully finished basementRefined finishesGraceful winding drivewayOpen pasturesClassic architectural detailsSweeping valley views
    Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.
    126 days
    914
    36

    Zillow last checked:

    Listing updated:

    Listed by:

    Adam Boardman 859-338-8243,

    Block + Lot Homes,

    Gregory Leveridge 859-421-8959,

    Block + Lot Homes

    Source: Imagine MLS,MLS#: 26009631MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 8
      • Bathrooms: 8
      • Full bathrooms: 7
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: First
      Bedroom 1
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Second
      Bedroom 5
      • Level: Second
      Primary bathroom
      • Level: First
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: Second
      Bathroom 3
      • Level: Second
      Bathroom 4
      • Level: Second
      Bathroom 5
      • Level: First
      Kitchen
      • Level: First
      Living room
      • Level: First
      Heating
      • Forced Air, Natural Gas
      Cooling
      • Central Air
      Appliances
      • Included: Double Oven, Dishwasher, Refrigerator, Cooktop
      • Laundry: Main Level
      Features
      • Entrance Foyer, Eat-in Kitchen, Walk-In Closet(s), Soaking Tub
      • Flooring: Carpet, Hardwood, Tile
      • Basement: Exterior Entry,Finished,Full,Walk-Out Access
      • Number of fireplaces: 2
      • Fireplace features: Gas Log, Kitchen, Living Room, Master Bedroom
      Interior area
      • Total structure area: 13,433
      • Total interior livable area: 13,433 sqft
      • Finished area above ground: 8,259
      • Finished area below ground: 5,174

      Property

      Parking
      • Total spaces: 4
      • Parking features: Attached Garage, Driveway, Garage Faces Side
      • Garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Wood
      • Has view: Yes
      • View description: Rural, Trees/Woods, Farm
      Lot
      • Size: 35 Acres
      • Features: Secluded
      Details
      • Additional structures: Barn(s), Workshop
      • Parcel number: 022000000601
      • Horses can be raised: Yes

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Brick Veneer
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Year built: 1996

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Electricity Connected, Water Connected

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $205/sqft
      • Tax assessed value: $2,120,000
      • Annual tax amount: $15,052
      • Date on market: 5/1/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $20,531/mo

        Price history

        DateEventPrice
        5/1/2026Listed for sale$2,750,000-13.4%$205/sqft
        Source: Imagine MLS #26009631 Report a problem
        10/14/2025Listing removed$3,175,000$236/sqft
        Source: Imagine MLS #25011994 Report a problem
        6/6/2025Listed for sale$3,175,000-9.3%$236/sqft
        Source: Imagine MLS #25011994 Report a problem
        10/15/2024Listing removed$3,500,000$261/sqft
        Source: Imagine MLS #24009597 Report a problem
        5/15/2024Listed for sale$3,500,000$261/sqft
        Source: Imagine MLS #24009597 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$15,052 -4.1%$1,615,400
        2024$15,691 +1.6%$1,615,400
        2023$15,443 $1,615,400 +0.4%
        2022$15,443 +69.4%$1,608,300 +66%
        2021$9,119 -0.3%$968,800
        2020$9,148 -0.5%$968,800
        2019$9,195 +1%$968,800
        2018$9,100 -2.3%$968,800
        2017$9,310 $968,800
        2016$9,310 $968,800
        2015$9,310 +4.9%$968,800
        2013$8,874 $968,800 -27.2%
        2011-- $1,330,500
        2010-- $1,330,500
        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

        1 / 100
        Car-Dependent
        16 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Strode Station
        • 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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