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For sale
  • $2,950,000

    486 Chesterfield Way, Simpsonville, KY 40067

    4beds
    7,352sqft
    : 
    $19,557/mo
    Get pre-qualified
    Single Family Residence
    Built in 1999
    43.51 Acres Lot
    $2,735,400 Zestimate®
    $401/sqft
    $-- HOA

    What's special

    Tranquil pondMotorized blindsPond aeratorFour-board fencingRolling pastureOpen pastureIron entrance gates
    Turning off Chesterfield Way onto the newly sealed blacktop driveway, the pace of life immediately begins to slow. The drive winds through rolling pasture, four-board fencing, and across a picturesque tree-lined stream before arriving at the iron entrance gates. Beyond them, mature trees frame both sides of the lane, creating a beautiful approach that feels like a welcome home every time you arrive. This is more than a home it's a private estate encompassing over 43 acres of peaceful Western Shelby County countryside, where open pasture, eleven acres of mature timber, a winding creek with natural stone banks, a tranquil pond, and miles of natural beauty create a setting that feels far removed from the everyday. Ten acres of woods have recently been cleared and mulched, making it easy to explore the property, enjoy the creek, or simply take in the privacy, all while being just five minutes from Simpsonville and only twenty minutes from Louisville. Meticulously maintained, the home blends timeless design with thoughtful updates. The soaring two-story great room is filled with natural light, while new Andersen doors open to a covered porch and a recently built deck overlooking the backyard. The kitchen has been refreshed with countertops, a backsplash, and a gas cooktop supplied by a newly installed gas line, creating a space equally suited for everyday meals or entertaining a full house. The first-floor primary suite serves as a private retreat with bay windows overlooking the backyard, engineered wood flooring, motorized blinds, a spa-inspired bath, and a dressing room centered around a custom island. Upstairs are two additional bedrooms and a loft, while the finished walkout basement offers a spacious family room, wet bar, game room with pool table, fitness room, and a fourth bedroom tucked behind sliding barn doors. French doors lead directly to the backyard, seamlessly connecting indoor and outdoor living. The outdoor amenities rival those of a private resort. The in-ground pool features a tanning shelf and four elegant fountains, while the nearby timber pavilion with its impressive stone fireplace provides the perfect gathering place long after the sun goes down. Guests can enjoy complete privacy in the carriage house, which includes a one-bedroom apartment with its own kitchen, bathroom, laundry, and covered veranda. Attached is a 43-foot climate-controlled show garage with durable polyurea flooring. The property also includes a 36x60 tool shed, farm and 4-board fencing, and deed restrictions that allow horses and barns. Major improvements have already been completed, including geothermal heating with a new exchanger and coils, a 2019 roof, new windows and Andersen doors, resurfaced pool deck and porches, a repaved entrance and driveway, an 18-foot automatic front gate with a sensor, and a pond aerator. Public water, septic service, and no HOA dues complete this truly exceptional property. Plat and restrictions are attached.
    19 days
    |
    1,591
    |
    99
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Zachary Tipton 502-633-0220,

    Torrey Smith Realty Co., LLC

    Source: Metro Search Inc. LLC DBA Apex MLS,MLS#: 1722813MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 5
      Primary bedroom
      • Description: Main House
      • Level: First
      Bedroom
      • Description: Main House
      • Level: Second
      Bedroom
      • Description: Main House
      • Level: Second
      Primary bathroom
      • Description: Main House
      • Level: First
      Full bathroom
      • Description: Main House
      • Level: First
      Full bathroom
      • Description: Main House
      • Level: Second
      Full bathroom
      • Description: Main House
      • Level: Basement
      Full bathroom
      • Description: Guest House
      • Level: First
      Dining area
      • Description: Main House
      • Level: First
      Dining room
      • Description: Main House
      • Level: First
      Family room
      • Description: Main House
      • Level: Basement
      Game room
      • Description: Main House
      • Level: Basement
      Kitchen
      • Description: Main House
      • Level: First
      Kitchen
      • Description: Main House
      • Level: Basement
      Kitchen
      • Description: Guest House
      • Level: First
      Laundry
      • Description: Main House
      • Level: First
      Living room
      • Description: Main House
      • Level: First
      Living room
      • Description: Guest House
      • Level: First
      Office
      • Description: Main House
      • Level: Basement
      Study
      • Description: Main House
      • Level: First
      Heating
      • MiniSplit/Ductless, Electric, Geothermal
      Cooling
      • Central Air
      Features
      • Basement: Walkout Finished
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 5,063
      • Total interior livable area: 7,352 sqft
      • Finished area above ground: 5,063
      • Finished area below ground: 2,289

      Property

      Parking
      • Total spaces: 6
      • Parking features: Detached, Attached
      • Attached garage spaces: 6
      Features
      • Stories: 2
      • Patio & porch: Screened Porch, Deck, Patio, Porch
      • Exterior features: See Remarks
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Split Rail
      • On waterfront: Yes
      • Waterfront features: Creek, Lake Front
      Lot
      • Size: 43.51 Acres
      • Features: Cul-De-Sac, Cleared
      Details
      • Additional structures: Guest House, Pergola, Outbuilding
      • Parcel number: 01400026D

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Synthetic Stucco, Brick, Stone Veneer
      • Foundation: Concrete Perimeter
      • Roof: Metal,Shingle
      Condition
      • Year built: 1999

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Electricity Connected, Propane
      Green energy
      • Energy generation: GeoThermal

      Community & HOA

      Community
      • Subdivision: None
      HOA
      • Has HOA: No
      Location
      • Region: Simpsonville

      Financial & listing details

      • Price per square foot: $401/sqft
      • Tax assessed value: $1,811,533
      • Annual tax amount: $20,449
      • Date on market: 8/3/2026
      • Electric utility on property: Yes

        Estimated market value

        $2,735,400

        $2.60M - $2.87M

        $5,363/mo

        Price history

        DateEventPrice
        8/3/2026Listed for sale$2,950,000+28.3%$401/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1722813 Report a problem
        7/6/2023Sold$2,300,000-11.2%$313/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1632691 Report a problem
        6/17/2023Pending sale$2,590,000$352/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1632691 Report a problem
        3/18/2023Listed for sale$2,590,000+15.4%$352/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1632691 Report a problem
        2/8/2023Listing removed$2,245,000$305/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        2/8/2023Price change$2,245,000-2.2%$305/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        1/12/2023Price change$2,295,000-4.2%$312/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        12/12/2022Price change$2,395,000-33.5%$326/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        10/17/2022Price change$3,600,000+16.1%$490/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1624306 Report a problem
        9/23/2022Price change$3,100,000+24.2%$422/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1613988 Report a problem
        9/23/2022Price change$2,495,000-10.9%$339/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        7/30/2022Price change$2,800,000-17%$381/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1618913 Report a problem
        6/30/2022Price change$3,375,000-6.3%$459/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1613988 Report a problem
        6/3/2022Listed for sale$3,600,000+297.8%$490/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1613988 Report a problem
        11/6/2019Sold$905,000+16.8%$123/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1534384 Report a problem
        9/22/2019Price change$775,000-18.4%$105/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        9/22/2019Pending sale$950,000+22.6%$129/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        8/30/2019Price change$775,000-18.4%$105/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        8/21/2019Price change$950,000+14.5%$129/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        6/11/2019Price change$830,000-21%$113/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        6/10/2019Price change$1,050,000+26.5%$143/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        6/8/2019Listed for sale$830,000-7.3%$113/sqft
        Source: RE/MAX Performance Realty #1534384 Report a problem
        10/17/2016Listing removed$894,900$122/sqft
        Source: Coldwell Banker Larry K. Rogers Realty, Inc. #1445279 Report a problem
        4/20/2016Listed for sale$894,900-0.6%$122/sqft
        Source: Coldwell Banker Larry K. Rogers Realty, Inc. #1445279 Report a problem
        1/1/2016Listing removed$900,000$122/sqft
        Source: Louisville - WEICHERT, REALTORS - ABG Properties #1426629 Report a problem
        1/30/2015Listed for sale$900,000+13.9%$122/sqft
        Source: Louisville - WEICHERT, REALTORS - ABG Properties #1409839 Report a problem
        10/8/2002Sold$790,000$107/sqft
        Source: Agent Provided Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$20,449 -1%$1,811,533
        2024$20,648 +147.5%$1,811,533 +151.3%
        2023$8,342 +11.9%$720,900 +12.5%
        2022$7,454 -2.5%$640,900
        2021$7,646 +3.2%$640,900 +3.6%
        2020$7,405 $618,900 +9.5%
        2019$7,405 +17.9%$565,000
        2018$6,280 $565,000
        2017$6,280 -4.7%$565,000
        2016$6,589 $565,000
        2015$6,589 $565,000
        2014$6,589 $565,000
        2013$6,589 $565,000
        2012-- $565,000
        2011-- $565,000
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        Climate risks

        Neighborhood: 40067

        Getting around

        0 / 100
        Car-Dependent
        7 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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