486 Chesterfield Way
Simpsonville, KY, 40067 $ 2,950,000
Bedrooms4 Baths5.0 Sq 7,765 Monthly Estimate*
$ 18,627
for $2,950,000 with 4 bedrooms and 5 full baths. This 7,765 square foot home was built in 1999 on a lot size of 43.51.
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.
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FeaturesGeneralHeating MiniSplit/Ductless Electric Geothermal
Cooling Central Air
Utilities Electricity Connected Propane
Roof Metal Shingle
HOA Fee 0
Garage Spaces 6
Architectural Style Traditional
Construction Materials Synthetic Stucco Brick Stone Veneer
Year Built 1999
Stories Count 2
Property Subtype Single Family Residence
Waterfront Features Creek Lake Front
County Shelby
Property Type Residential
HOA false
Attached Garage true
Subdivision Name NONE
Garage Y/N true
Green Energy Generation GeoThermal
Other Structures Guest House Pergola Outbuilding
Total Rooms 20
Full Baths 5
Status Active
Directions Shelbyville Road To Todds Point Road. Take a left on Chesterfield Way. Property is on the right.
City Simpsonville
High School District Shelby
MLS Area 30-Shelby County
Lot Size Units Acres
Lot Size Square Feet 1895295.6
MLS Area Minor 30-Shelby County
Virtual Tour https://my.matterport.com/show/?m=U8Xzs2dybhC
Standard Status Active
Tax Lot 13 & 14
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InteriorBasement Walkout Finished
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 5063
Half Baths 0
Total Bedrooms 4
Below Grade Finished Area 2702
Total Baths 5
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ExteriorExterior Amenities See Remarks
Fencing Split Rail
Parking Features Detached Attached
Lot Features Cul-De-Sac Cleared
Water Source Public
Lot Size Area 43.51
Foundation Details Poured Concrete
Building Area Total 5063
Lot Size Acres 43.51
Waterfront Y/N true
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* Excluded FeaturesList ByTorrey Smith Realty Co., LlcBroker
zach.tipton@smithclick.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $18,627
- Monthly Property Taxes
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- Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Simpsonville, KY
Average List Price $763,132
Percent of Sale Price 74%
About Simpsonville, KY 2,787 Population
55% Since 2002
$ 72,766 Median Income
34.07 Median Age
36% Households with Children
Trends Information provided by ATTOM Data Solutions.
0 Elementary School
0 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 8/3/2026 | $2,950,000 | | Listed Price |