12

Simpsonville, KY Homes for Sale with Garage

Section Image Section Image
  • /61

    $2,950,000

    • 4 Beds
    • 5 Baths
    • 7,352 Sq Ft

    486 Chesterfield Way, Simpsonville, KY 40067

    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

    Agent Photo

    Zach Tipton

    Torrey Smith Realty Co., LLC

    486 Chesterfield Way, Simpsonville, KY 40067
  • /87

    $1,499,900

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,265 Sq Ft

    37 Timberwood Dr, Simpsonville, KY 40067

    Welcome to your own private country retreat in sought-after Simpsonville, Kentucky! Situated on 10 beautifully laid-out acres at the end of a cul-de-sac, this exceptional property offers the perfect blend of comfort, recreation, and functionality. Fully fenced and surrounded by mature trees, you'll enjoy a peaceful setting complete with a pond, pavilion, treehouse, barn, and an impressive newly

    Cheryl Poore Weichert Realtors-H. Barry Smith Co.

    37 Timberwood Dr, Simpsonville, KY 40067
  • /59

    $899,900

    $90K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,897 Sq Ft

    1948 Todds Point Rd, Simpsonville, KY 40067

    Welcome to one of Simpsonville's most versatile luxury properties, where beautifully renovated living spaces, exceptional craftsmanship, and a rare 30x60 insulated shop come together on a private, beautifully landscaped homesite. This move-in-ready estate offers over 4,500 finished square feet designed for both everyday comfort and entertaining. The completely renovated kitchen features custom

    Melinda Spencer Move With Me Realty

    1948 Todds Point Rd, Simpsonville, KY 40067
  • /61

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 3,832 Sq Ft

    401 Old Stone Dr, Simpsonville, KY 40067

    Welcome home to this exceptional custom property nestled on 7.42 picturesque acres in the lush green countryside of Shelby County. Offering the perfect blend of luxury, comfort, and functionality, this stunning home features 5 spacious bedrooms, 4.5 bathrooms, and room for everyone to spread out. The heart of the home is the beautifully updated kitchen, designed to impress with three ovens, two

    Shelly Gardner Keller Williams Collective

    401 Old Stone Dr, Simpsonville, KY 40067
  • /105

    $999,950

    • 4 Beds
    • 2 Baths
    • 2,625 Sq Ft

    1219 Taylor Wood Rd, Simpsonville, KY 40067

    This 4-bedroom, 2-bath historic farmhouse is situated on 5 scenic acres (with an additional adjoining 5-acre tract available for purchase and possible owner financing) in the heart of Simpsonville and offers a rare combination of residential comfort, equestrian functionality, income potential, and Kentucky character. The property includes two barns, seven fenced paddocks, a pond, a detached

    Trish Segrest Segrest Flaherty Realtors LLC

    1219 Taylor Wood Rd, Simpsonville, KY 40067
  • /125

    $1,650,000

    • 5 Beds
    • 6 Baths
    • 7,141 Sq Ft

    107 My Kentucky Rose Cir, Simpsonville, KY 40067

    A rare offering to own this spectacular country estate in the gated community of Majestic Oaks, featuring over 7,000 square feet of living space on 5 verdant acres. The first floor has soaring 10 foot and vaulted ceilings, 3 fireplaces, 2 staircases, and extensive custom woodwork and built-ins. The first floor primary suite is the epitome of luxury, with a steam shower, quartz counters, towel

    Julie Pogue Julie Pogue Properties

    107 My Kentucky Rose Cir, Simpsonville, KY 40067
  • /58

    $1,699,000

    $26K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 4,731 Sq Ft

    2259 Taylor Wood Rd, Simpsonville, KY 40067

    Welcome to 2259 Taylor Wood Road in Simpsonville, Kentucky. This stunning custom home sits on 6 private acres with no HOA, offering the perfect blend of luxury, privacy, and space in the heart of Shelby County. Built in 2023, this home features 4,731 square feet above grade with 5 bedrooms, a bonus room, 3 full bathrooms and 2 half baths. From the moment you step inside you will notice the

    Sam Stone Lenihan Sotheby's Int'l Realty

    2259 Taylor Wood Rd, Simpsonville, KY 40067
  • /66

    $875,000

    $75K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,250 Sq Ft

    451 Todd Dr, Simpsonville, KY 40067

    *NEW PRICE* Welcome to a truly extraordinary estate in Simpsonville, KY where luxury, space, and timeless elegance come together on more than 5 breathtaking acres. From the moment you arrive, the grand scale and stunning curb appeal make an unforgettable impression. This custom home was designed for those who appreciate refined living, exceptional entertaining spaces, and the flexibility for

    Rhonda Roberts Keller Williams Collective

    451 Todd Dr, Simpsonville, KY 40067
  • /87

    $649,900

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,925 Sq Ft

    209 Champions Way, Simpsonville, KY 40067

    Priced UNDER Fair Market Value AND Move-In Ready! Ideally located between Louisville and Lexington, Simpsonville combines small-town charm with convenient access to shopping, dining, and I-64. Nestled in the heart of Kentucky's renowned horse country, you'll enjoy scenic rolling landscapes, beautiful horse farms, and a peaceful setting just minutes from modern conveniences. Situated in the highly

    Margo Whisman Weichert Realtors-H. Barry Smith Co.

    209 Champions Way, Simpsonville, KY 40067
  • /50

    $1,900,000

    • 4 Beds
    • 3.5 Baths
    • 7,224 Sq Ft

    22 Timberwood Dr, Simpsonville, KY 40067

    Exceptional opportunity in desirable Timberwood Farms. Situated on approx. 10 acres, this impressive property offers space, privacy, and a prime Simpsonville location with convenient access to I-64, Shelbyville, and Louisville.

    KRISTY GOOCH RE/MAX Elite Realty

    22 Timberwood Dr, Simpsonville, KY 40067
  • /61

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 3,177 Sq Ft

    1051 Champions Cir, Simpsonville, KY 40067

    The rolling hills and sweet community of Simpsonville welcome you to this STUNNING home in the beautiful Cardinal Club Estates. A quick commute out of the busy-ness of Louisville leads you to the beautiful setting where your next home awaits. Built in 2014 (with 2x6 exterior wall construction) , this home features the updated convenience of an incorporated large kitchen and gathering/family room,

    Jennifer Toadvine Keller Williams Collective

    1051 Champions Cir, Simpsonville, KY 40067
  • /11

    $489,900

    • 4 Beds
    • 2.5 Baths
    • 1,990 Sq Ft

    1204 Divot Way, Simpsonville, KY 40067

    Welcome to this exceptional 4 BEDROOM + 2 1/2 BATH NEW CONSTRUCTION home in the highly sought-after Villas at Cardinal Club. Offering 1,990 square feet of thoughtfully designed living space, this home delivers the perfect balance of style, comfort, and functionality. This home features a spacious first-floor primary suite, providing privacy and convenience, while three additional bedrooms

    Melinda Mathis Watts Torrey Smith Realty Co., LLC

    1204 Divot Way, Simpsonville, KY 40067

Home Price Trends

Median Sale Price
$372,500
Median Single Family Sale Price
$393,450
Median 2 Bedroom Sale Price
$219,450
Average Price Per Sq Ft
$198
Number of Homes for Sale
12
Last 12 months Home Sales
63
Months of Supply
2.30
Median List Price
$384,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home