486 Chesterfield Way, Simpsonville, KY 40067 | MLS# 1722813

$2,950,000
486 Chesterfield Way, Simpsonville, KY 40067, Simpsonville, NONE

Overview

  • Updated On:
  • September 7, 2026
  • 4 Bedrooms
  • 5 Bathrooms
  • 7,352 ft2

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 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 36×60 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.

Address: 486 Chesterfield Way, Simpsonville, KY 40067
Area:
State/County:
Zip: 40067
Country: United States

Property Id: 10751364
Price: $2,950,000
Property Size: 7,352 ft2
Property Lot Size: 44 ft2
Rooms: 20
Bedrooms: 4
Bathrooms: 5
BathroomsFull: 5
InternetConsumerCommentYN: 1
InternetAutomatedValuationDisplayYN: 1
ListAgentKey: 20131203230520330858000000
StreetNumberNumeric: 486
ListAgentFullName: Zachary Tipton
InternetAddressDisplayYN: 1
ListAgentMobilePhone: 502-321-4831
OnMarketDate: 2026-08-03
InternetEntireListingDisplayYN: 1
ListOfficeKey: 20131203192849642445000000
ListAgentLastName: Tipton
Cooling: Central Air
FireplacesTotal: 1
StatusChangeTimestamp: 2026-09-07T23:17:28Z
ListAgentFirstName: Zachary
MajorChangeType: Status Change
OffMarketDate: 2026-09-07
LotSizeUnits: Acres
DocumentsCount: 3
PatioAndPorchFeatures: Screened Porch, Deck, Patio, Porch
BuyerAgentMlsId: 22101
LotSizeSquareFeet: 1895295.6
ListingId: 1722813
YearBuilt: 1999
SourceSystemName: APEX MLS (Greater Louisville Association of REALTORS®)
SourceSystemKey: 20260709172909878143000000
ArchitecturalStyle: Traditional
Basement: Walkout Finished
StateOrProvince: KY
ListOfficeName: Torrey Smith Realty Co., LLC
LotFeatures: Cul-De-Sac, Cleared
OriginatingSystemKey: 20260709172909878143000000
PhotosCount: 61
PhotosChangeTimestamp: 2026-08-03T13:52:56Z
BuildingAreaTotal: 5063
Stories: 2
PurchaseContractDate: 2026-09-07
OriginatingSystemName: APEX MLS (Greater Louisville Association of REALTORS®)
Utilities: Electricity Connected, Propane
PoolFeatures: In Ground
OriginalListPrice: 2950000
Sewer: Septic Tank
ListingContractDate: 2026-08-03
StreetSuffix: Way
OriginatingSystemID: M00000290
StreetNumber: 486
StreetName: Chesterfield
ListAgentEmail: zach.tipton@smithclick.com
ModificationTimestamp: 2026-09-07T23:18:05Z
ListOfficeMlsId: 2095
MlsStatus: Pending
LotSizeArea: 43.51
SourceSystemID: M00000290
ParcelNumber: 014-00-026D
ListAgentMlsId: 22101
ParkingFeatures: Detached, Attached
DocumentsChangeTimestamp: 2026-08-03T13:49:33Z
Heating: MiniSplit/Ductless, Electric, Geothermal
MajorChangeTimestamp: 2026-09-07T23:17:31Z
Directions: Shelbyville Road To Todds Point Road. Take a left on Chesterfield Way. Property is on the right.
MLSAreaMajor: 30-Shelby County
LivingAreaSource: Other
GarageSpaces: 6
MLSAreaMinor: 30-Shelby County
BuyerOfficeMlsId: 2095
WaterSource: Public
FloorPlansChangeTimestamp: 2026-08-02T20:17:53Z
TaxLot: 13 & 14
AboveGradeFinishedArea: 5063
BuildingAreaSource: Other
FoundationDetails: Poured Concrete
BelowGradeFinishedArea: 2289
Fencing: Split Rail
Roof: Metal, Shingle
ConstructionMaterials: Synthetic Stucco, Brick, Stone Veneer

Outdoor Details
Garage Attached
Other Features
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Waterfront
See Remarks

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$15,125.23
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 11,437.73

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