486 Chesterfield Way

Simpsonville, KY
$ 2,950,000 Beds 4 Baths 5 Sq 7,352 Virtual Tour
Monthly Estimate* How much can I afford?

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.

Pending

  • Price
  • $ 2,950,000
  • City
  • Simpsonville
  • Bedrooms
  • 4
  • Full Bathrooms
  • 5
  • County
  • Shelby
  • Half Bathrooms
  • 0
  • Area
  • Shelby County
  • Lot Size
  • 43.51 Acres
  • Zip
  • 40067
  • Sqr Footage
  • 7,352
  • Year Built
  • 1999
  • Style
  • Traditional
  • MLS#
  • 1722813
Listed By: Torrey Smith Realty Co., LLC
Data Source: Metro Search, Inc.

Features

General

Heating MiniSplit/Ductless,Electric,Geothermal
Cooling Central Air
Utilities Electricity Connected,Propane
Roof Metal,Shingle
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 Pending
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
Standard Status Pending
Tax Lot 13 & 14

Interior Features

Basement Walkout Finished
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 5063
Total Bedrooms 4
Below Grade Finished Area 2289
LivingAreaSource Other
Total Baths 5

Exterior Features

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

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Shelbyville, KY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
Agent Photo

Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School
Middle School
High School Unknown High School

Price History

8/3/2026 Listed $2,950,000

Property vs Zip Code Average in 40067

Price
AVG $950K
$2.95M
Year Built
AVG 1996
1999

486 Chesterfield Way Simpsonville, KY is a Single Family Home for sale at $2950000 with 7352 sqft and a lot size of 43.51 Acres Acre(s). 486 Chesterfield Way Simpsonville has 4 bedrooms, 5 baths and was built in 1999. The property's zip code is 40067 which is in Simpsonville, KY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.