486 Chesterfield Way, Simpsonville, KY 40067

bedrooms 4
bathrooms 5
|House
NZD $5,172,672
USD $2,950,000
Published on: 04 Aug 2026
Last updated on: 18 Oct 2026
486 Chesterfield Way, Simpsonville, KY 40067
486 Chesterfield Way, Simpsonville, KY 40067
486 Chesterfield Way, Simpsonville, KY 40067
+61
486 Chesterfield Way, Simpsonville, KY 40067
  • 61
Property ID: 110109662111
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Residential, Simpsonville, KY

486 Chesterfield Way, Simpsonville, KY 40067
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.

Property Details

Basic Info

Property Type
House
Listing Status
Pending
Land Size
176,078.88 m2
Building Size
683.02 m2
Year Built
1999
Rooms
4 bedroom(s), 5 bathroom(s)
Architecture Style
Other
Num Floors
2
County
Shelby
Parcel ID
014-00-026D
Provider
Greater Louisville Association of REALTORS®
Brokerage Office Name
Torrey Smith Realty Co., LLC
Brokerage Office Phone
(502) 633-0220
Neighbourhoods
30-Shelby County
Address
486 Chesterfield Way, Simpsonville, KY 40067
Contact Agent
Zachary Tipton
Torrey Smith Realty Co., LLC
529 Main Street , Shelbyville, KY 40065
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Zachary Tipton
529 Main Street , Shelbyville, KY 40065
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      Property ID: 110109662111

      Original Property ID: 3yd-GLARKY-1722813
      Data provided by Greater Louisville Association of REALTORS®, MLS #: 1722813
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