About This Home

This 4-bedroom, 5-bathroom single family at 486 Chesterfield Way in Simpsonville, KY is listed for $2,950,000 ($401 per sqft). Built in 1999, the home offers 7,352 sqft of living space on a 43.51 acres lot.

Key Features

  • Built in 1999
  • 43.51 acre lot
  • 2 stories
  • Fireplace
  • Waterfront

Property Details

2 stories
5 full
6-car garage
1999

Amenities

FireplaceWaterfrontA/C
Listing Description

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 ban

ks, 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.

Monthly Cost Estimate

$15,777/mo

20% down · 6.5% · 30 years

Principal$2,133
Interest$12,783
Insurance$860

Estimates only. Actual payments may vary.

Location

486 Chesterfield Way

Simpsonville, KY 40067

Property Details

Construction

Synthetic Stucco Brick Stone Veneer

Outdoor Features

PorchDeckPatio

Heating

Ductless (Heating)Geothermal (Heating)Electric (Heating)

Cooling

Central Air

Questions & Answers

This 4-bedroom, 5-bathroom single family at 486 Chesterfield Way is listed at $2,950,000 ($401/sqft). The estimated monthly payment is $15,777 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1999, 43.51 acre lot, 2 stories, Fireplace, Waterfront.

This property is listed by Zachary Tipton.

ZT

Zachary Tipton

Agent at Torrey Smith Realty Co., LLC

Listed by Torrey Smith Realty Co., LLC · Broker phone: (502) 633-0220 · View on Broker Site · Broker website

MLS# 1722813· Source: Greater Louisville Association of REALTORS®· 91 days on PropertySimple

Copyright © 2026 Greater Louisville Association of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

486 Chesterfield Way, Simpsonville, KY 40067

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