486 Chesterfield Way Simpsonville, KY $ 2,950,000
486 Chesterfield Way
$ 2,950,000
Recently Listed
Share Save

486 Chesterfield Way

Simpsonville, KY, 40067
$ 2,950,000
Bedrooms4 Baths5.0 Sq 7,765

Monthly Estimate*

$ 18,627

486 Chesterfield Way, Simpsonville, KY 40067 - Image 1
486 Chesterfield Way, Simpsonville, KY 40067 - Image 2
486 Chesterfield Way, Simpsonville, KY 40067 - Image 3
486 Chesterfield Way, Simpsonville, KY 40067 - Image 4
486 Chesterfield Way, Simpsonville, KY 40067 - Image 5
486 Chesterfield Way, Simpsonville, KY 40067 - Image 6
486 Chesterfield Way, Simpsonville, KY 40067 - Image 7
486 Chesterfield Way, Simpsonville, KY 40067 - Image 8
486 Chesterfield Way, Simpsonville, KY 40067 - Image 9
486 Chesterfield Way, Simpsonville, KY 40067 - Image 10
486 Chesterfield Way, Simpsonville, KY 40067 - Image 11
486 Chesterfield Way, Simpsonville, KY 40067 - Image 12
486 Chesterfield Way, Simpsonville, KY 40067 - Image 13
486 Chesterfield Way, Simpsonville, KY 40067 - Image 14
486 Chesterfield Way, Simpsonville, KY 40067 - Image 15
486 Chesterfield Way, Simpsonville, KY 40067 - Image 16
486 Chesterfield Way, Simpsonville, KY 40067 - Image 17
486 Chesterfield Way, Simpsonville, KY 40067 - Image 18
486 Chesterfield Way, Simpsonville, KY 40067 - Image 19
486 Chesterfield Way, Simpsonville, KY 40067 - Image 20
486 Chesterfield Way, Simpsonville, KY 40067 - Image 21
486 Chesterfield Way, Simpsonville, KY 40067 - Image 22
486 Chesterfield Way, Simpsonville, KY 40067 - Image 23
486 Chesterfield Way, Simpsonville, KY 40067 - Image 24
486 Chesterfield Way, Simpsonville, KY 40067 - Image 25
486 Chesterfield Way, Simpsonville, KY 40067 - Image 26
486 Chesterfield Way, Simpsonville, KY 40067 - Image 27
486 Chesterfield Way, Simpsonville, KY 40067 - Image 28
486 Chesterfield Way, Simpsonville, KY 40067 - Image 29
486 Chesterfield Way, Simpsonville, KY 40067 - Image 30
486 Chesterfield Way, Simpsonville, KY 40067 - Image 31
486 Chesterfield Way, Simpsonville, KY 40067 - Image 32
486 Chesterfield Way, Simpsonville, KY 40067 - Image 33
486 Chesterfield Way, Simpsonville, KY 40067 - Image 34
486 Chesterfield Way, Simpsonville, KY 40067 - Image 35
486 Chesterfield Way, Simpsonville, KY 40067 - Image 36
486 Chesterfield Way, Simpsonville, KY 40067 - Image 37
486 Chesterfield Way, Simpsonville, KY 40067 - Image 38
486 Chesterfield Way, Simpsonville, KY 40067 - Image 39
486 Chesterfield Way, Simpsonville, KY 40067 - Image 40
486 Chesterfield Way, Simpsonville, KY 40067 - Image 41
486 Chesterfield Way, Simpsonville, KY 40067 - Image 42
486 Chesterfield Way, Simpsonville, KY 40067 - Image 43
486 Chesterfield Way, Simpsonville, KY 40067 - Image 44
486 Chesterfield Way, Simpsonville, KY 40067 - Image 45
486 Chesterfield Way, Simpsonville, KY 40067 - Image 46
486 Chesterfield Way, Simpsonville, KY 40067 - Image 47
486 Chesterfield Way, Simpsonville, KY 40067 - Image 48
486 Chesterfield Way, Simpsonville, KY 40067 - Image 49
486 Chesterfield Way, Simpsonville, KY 40067 - Image 50
486 Chesterfield Way, Simpsonville, KY 40067 - Image 51
486 Chesterfield Way, Simpsonville, KY 40067 - Image 52
486 Chesterfield Way, Simpsonville, KY 40067 - Image 53
486 Chesterfield Way, Simpsonville, KY 40067 - Image 54
486 Chesterfield Way, Simpsonville, KY 40067 - Image 55
486 Chesterfield Way, Simpsonville, KY 40067 - Image 56
486 Chesterfield Way, Simpsonville, KY 40067 - Image 57
486 Chesterfield Way, Simpsonville, KY 40067 - Image 58
486 Chesterfield Way, Simpsonville, KY 40067 - Image 59
486 Chesterfield Way, Simpsonville, KY 40067 - Image 60
486 Chesterfield Way, Simpsonville, KY 40067 - Image 61
View a Virtual Tour

Single Family Home for sale in Simpsonville, KY

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.

See more

Single Family Active

Price

$ 2,950,000

Bedrooms

4

Full Bath

5

Property Type

Single Family

Taxes

$ 0

Style

Traditional

Lot Size

43.51

Year Built

1999

Town/City

Simpsonville

County/Region

Shelby

MLS | Web ID

1722813

Features
General
Heating 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
See more
Interior
Basement 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
See more
Exterior
Exterior 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
See more
* Excluded Features
List By
Torrey Smith Realty Co., Llc

Broker

zach.tipton@smithclick.com

Email

Affordability Calculator

$18,627
Per Month
100%
0%
0%
Monthly Principal & Interest
$18,627
Monthly Property Taxes
--
Monthly Home Insurance
--
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

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
0 Elementary School
0 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
8/3/2026$2,950,000 Listed Price

Map


See all

486 Chesterfield Way, Simpsonville, KY, 40067 is a Single Family Home for sale at $2,950,000 with 7,765 sqft and a lot size of 43.51. 486 Chesterfield Way has 4 bedrooms, 5.0 baths, and was built in 1999. The property's zip code is 40067 which is in Simpsonville, KY