Simpsonville, KY Homes for Sale with Acreage

Welcome to Cabin Chase Farm, a rare 59± acre luxury equestrian estate in the heart of Shelby County horse country in Simpsonville, KY. This exceptional property blends historic charm with modern luxury, centered around a beautifully preserved 1800s log cabin incorporated into a stunning 5-bedroom, 7-bath estate home. Vaulted living spaces, expansive windows, and a chef's kitchen designed for

Jennifer Channell Weichert Realtors-H. Barry Smith Co.

Welcome to a rare opportunity in the heart of Simpsonville — a fully renovated estate property offering over 4,500+ finished square feet, a separate-entry lower-level living space, and a 1,800 sq ft insulated pole barn with office, plumbing, and HVAC — all situated on a beautifully improved, private homesite. This home has undergone an extensive top-to-bottom renovation, blending modern design

Melinda Spencer Move With Me Realty

Welcome to this extraordinary farm located in Simpsonville, Kentucky, offering over 10 acres of prime Kentucky Bluegrass land and an increasingly rare opportunity to own a turnkey equestrian property in one of the most sought-after horse regions in the country. This exceptional property seamlessly blends the timeless character of a 1938 farmhouse with thoughtfully curated modern upgrades,

Shawn Willard Weichert Realtors-H. Barry Smith Co.

Welcome to 1058 Majestic Oaks Way in Majestic Oaks, the only gated community in Shelby County. Spanning nearly 8 acres of rolling countryside, this estate combines the elegance of Tuscan-inspired architecture with the relaxed beauty of Kentucky horse country. From the moment you arrive, the circular driveway makes a statement, leading to a residence where every detail has been thoughtfully

Sam Stone Lenihan Sotheby's Int'l Realty

Welcome to a truly exceptional 5.07 acre estate offering space, versatility, & endless possibilities in the heart of Shelby County. Nestled in Simpsonville just minutes from the Outlet Shoppes, downtown Shelbyville, & everyday conveniences, this unique estate is designed for the way people live today, whether that means multigenerational living, working from home, or pursuing your passion for

Tammy Ramsey Segrest Flaherty Realtors LLC

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

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

Welcome to 4199 Webb Road! 20 Acre Gated Fully Fenced Equestrian Farm. This very well maintained 3 Bedroom/4 Full Bath Home Features Expansive Porches, Huge Screened Back Porch And A Fabulous In-Ground Heated Pool Overlooking A Beautiful Lake! 7 Stall Barn (Very Functional) With Hay Storage For Approximately 300 Bale Of Hay. 3 Pastures, 4 Run In Sheds and Outdoor Nelson Waterers. This Property Is

Teresa Barnes Abbot Realty & Auction

Welcome to this extraordinary farm located in Simpsonville, Kentucky, offering just over 5 acres of prime Kentucky Bluegrass land and an increasingly rare opportunity to own a turnkey equestrian property in one of the most sought-after horse regions in the country. This exceptional property seamlessly blends the timeless character of a 1938 farmhouse with thoughtfully curated modern upgrades,

Shawn Willard Weichert Realtors-H. Barry Smith Co.

Located just minutes away from Simpsonville and the Jefferson Co. line, this beautiful pristine farm offers all the amenities of country living along with the convenience of urban benefits. With almost 156 acres of rolling ground, there are limitless opportunities. The historic farm home features 4 BRs and 1.5 baths with almost all original hardwood flooring throughout. Spend the mornings and

Steve Hornback Weichert Realtors-H. Barry Smith Co.