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$389,900
4 Beds ⋅ 3 Baths ⋅ 1724484 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly desirable Ardmore Crossing community! This move-in-ready two-story offers a versatile loft, 2-car garage, and an open-concept design perfect for everyday living and entertaining. The stunning kitchen features abundant cabinetry, generous counter space, and ample storage, flowing seamlessly into the spacious living area. The private primary suite boasts two custom oversized walk-in closets and a beautifully updated bath. Brand-new carpet throughout the second floor adds a fresh, modern touch. Enjoy the large patio, perfect for relaxing or hosting guests. Conveniently located near shopping, dining, parks, schools, and I-64 in a walkable neighborhood you'll love!

163 Ardmore Crossing Dr, Shelbyville
$999,950
4 Beds ⋅ 2 Baths ⋅ 1723903 MLS
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 garage with a finished apartment, and picturesque views across the surrounding countryside. Built in 1938, the farmhouse blends timeless charm with thoughtful modern updates. Rich hardwood floors, elegant crown molding, two fireplaces, and an abundance of natural light create a warm and inviting atmosphere throughout the home. Large windows capture sweeping views of the pastures, pond, rolling landscape, and memorable Kentucky sunsets. The spacious kitchen offers stainless steel appliances, a beautiful bay window, generous workspace, and an open layout designed for both everyday living and entertaining. A classic front porch provides the perfect place to enjoy peaceful mornings, while the expansive screened-in covered rear deck overlooks the property and creates an ideal setting for relaxing, dining, or hosting guests. Designed with equestrian use in mind, the 13-stall main barn features 12-by-12 stalls, built-in hay racks, wide aisles, a dedicated wash area, and a well-appointed tack room. The farm also includes seven fenced paddocks with run-in sheds and automatic waterers, creating an efficient and functional setup for horses and livestock. Adding to the property's unique equestrian history, the farm was once home to the owner's beloved horse, a granddaughter of the legendary Secretariat. A second historic dairy barn adds even more versatility and future potential. Its size, setting, and distinctive character make it suitable for agricultural use, storage, a creative space, a private gathering venue, or a future event or wedding destination. The detached garage provides additional value with an oversized heated and cooled space below and a finished studio apartment above. The apartment includes a full bath and kitchenette, making it ideal for guests, extended family, farm staff, tenants, a private office, or potential rental income. Located just minutes from Interstate 64 and moments from the Simpsonville outlet mall, the property offers the peace and beauty of rural Kentucky without sacrificing convenience. Its central location between Louisville and Lexington also provides easy access to many of the region's premier equestrian destinations, including Churchill Downs, Keeneland, and the Kentucky Horse Park. The home, barns, pond, and approximately 5 acres are being offered together, with the additional adjoining 5-acre tract available separately. Contact the listing agents for details regarding purchase options and possible owner-financing terms. Opportunities offering this level of historic character, usable acreage, equestrian infrastructure, scenic beauty, income potential, and flexibility are increasingly difficult to find in Simpsonville.

1219 Taylor Wood Rd, Simpsonville
$1
5 Beds ⋅ 4 Baths ⋅ 1722489 MLS
Sealed Bid Auction - Bids Due Friday, July 31, 2026 at 11:59 PM ET. For complete terms, bidder registration, and offering documents, visit www.ClaudiaSandersAuction.com. A once-in-a-generation opportunity to acquire Blackwood Hall, the historic residence of Colonel Harland Sanders for approximately 25 years and one of Kentucky's most significant hospitality landmarks. Built in 1866, this remarkable 5-bedroom, 4-bath home served as the Colonel's primary residence during the period when Kentucky Fried Chicken experienced unprecedented national and international growth. The property's original garage (no longer standing) served as the early headquarters of Kentucky Fried Chicken before operations later moved into the adjacent commercial building. Following the sale of Kentucky Fried Chicken, Colonel and Claudia Sanders personally selected Tommy and Cherry Settle to carry on their hospitality legacy. On August 1, 1974, the Sanders family moved out of Blackwood Hall as the Settle family moved in the very same day. The Settle family has faithfully preserved the home and its history for more than fifty years. The residence features approximately 5 bedrooms, 4 full bathrooms, gracious historic architecture, and exceptional character throughout. Blackwood Hall is eligible for inclusion on the National Register of Historic Places, offering the potential for historic rehabilitation tax credits, subject to buyer verification and approval by the appropriate agencies. Potential future uses include continued residential occupancy, boutique inn, bed & breakfast, executive retreat, museum, hospitality destination, bourbon tourism experience, or other adaptive uses, subject to zoning and governmental approvals. Blackwood Hall is being offered as part of the Claudia Sanders Dinner House & Blackwood Hall Sealed Bid Auction, creating a rare opportunity to become the next steward of one of Kentucky's most recognizable historic properties.

3200 Shelbyville Rd, Shelbyville
$799,999
3 Beds ⋅ 2 Baths ⋅ 1721748 MLS
Escape to your own private Kentucky paradise with this breathtaking 86-acre retreat, perfectly positioned in the heart of the world-famous Bourbon Trail and one of Kentucky's fastest-growing counties. Whether you're looking for a private residence, recreational getaway, family farm, or investment opportunity, this remarkable property offers endless possibilities at an exceptional new price of $799,999. Surrounded by rolling hills, mature woodlands, scenic creeks, and abundant wildlife, this property is a nature lover's dream. Miles of wooded trails invite hiking, ATV riding, horseback riding, hunting, or simply enjoying the peace and quiet that only a property of this size can provide. The charming cottage-style home is ideally situated to capture spectacular views in every direction. Inside, you'll find a warm and inviting open-concept living and dining area filled with natural light from expansive windows that bring the outdoors in. A stunning glass-enclosed sunroom offers panoramic views of the surrounding countryside, creating the perfect place to enjoy your morning coffee or unwind while watching wildlife throughout the seasons. The spacious kitchen features abundant cabinetry, generous countertop space, and a gas range, making it ideal for everyday living or entertaining family and friends. Upstairs, two comfortable bedrooms provide peaceful retreats, each overlooking the picturesque landscape and offering the tranquility of country living. Just steps from the main residence, a versatile detached outbuilding provides endless opportunities. Use it as a recreation room, guest quarters, home office, art or woodworking studio, fitness space, or hobby barn—the choice is yours. The acreage is equally impressive, offering plenty of room for horses, cattle, chickens, gardens, food plots, or future expansion. Whether your dream is homesteading, farming, hunting, creating hiking trails, or simply enjoying unmatched privacy, this property is ready to accommodate your vision. Conveniently located just 42 miles from Louisville and 43 miles from Lexington, you'll enjoy the perfect balance of peaceful rural living with easy access to major employment centers, world-class bourbon distilleries, horse farms, dining, and entertainment. With acreage becoming increasingly difficult to find in this desirable region, this property represents an outstanding value. Offered at the new price of $799,999, this is an incredible opportunity to own a legacy property in one of Kentucky's most sought-after locations. The home is being offered furnished, with select exclusions, making it even easier to begin enjoying your Kentucky retreat from day one.

2466 Back Creek Rd, Waddy
$300,000
3 Beds ⋅ 2 Baths ⋅ 1721267 MLS
Active STR with frequent bookings. Call listing agent to schedule showings. Please inquire directly for profit and loss statements. Public Remarks: Discover a rare investment opportunity in the heart of bourbon country! This income-producing short-term rental is a cozy, spacious, and bright 3-bedroom, 2-bathroom home offering peaceful views and the perfect setting for guests to relax and unwind. Situated on 2.47 acres overlooking open fields and a tranquil pond, the property also features a backyard patio with a firepit, creating an ideal outdoor space for entertaining and memorable evenings. Inside, you'll find a desirable layout with a first-floor primary bedroom and full bath, complete with a walk-in closet, plus a main-level laundry room for added convenience. The main level offers a welcoming kitchen, dining area, and comfortable family room, perfect for both owner use and guest stays. Upstairs, you'll find two additional bedrooms and a full bathroom, providing plenty of space for guests or extended stays. Whether you're looking to expand your rental portfolio or own a getaway that can generate revenue, this property checks all the boxes. Furniture is negotiable and may be purchased separately through a bill of sale outside of the real estate contract.

2767 Bardstown Trail, Waddy
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1720384 MLS
Exceptional opportunity to own a beautiful 38.97-acre farm offered in two tracts, conveniently located just one mile from Interstate 64 in Waddy, Kentucky. This versatile property features three homesites, making it ideal for multi-generational living, rental income, or future expansion. Tract 1 consists of 15.04 acres and includes the primary residence along with a modular home currently suitable for rental or guest accommodations. The main home offers 3 bedrooms, 2 bathrooms, and an unfinished basement providing ample storage or future living space potential. Tract 2 contains 23.93 acres and features an additional modular home and a picturesque 1-acre pond, creating a peaceful setting for country living. The farm lays exceptionally well with gently rolling to level ground, making it ideal for cattle, horses, hay production, or other agricultural uses. With easy interstate access, multiple residences, quality pastureland, and a scenic pond, this property offers a rare combination of convenience, income potential, and rural charm. Don't miss this unique opportunity to own a productive farm with multiple homes and endless possibilities in the heart of Shelby County.

904 Waddy Rd, Waddy
$680,000
3 Beds ⋅ 1 Baths ⋅ 1719471 MLS
Opportunity awaits on nearly 20 beautiful acres! This rare property offers endless potential for those seeking space, privacy, and the chance to create something truly special. The existing 3-bedroom, 1-bath home is in need of repairs and updates, making it an ideal candidate for renovation or a fresh start. Whether you're dreaming of a private homestead, recreational retreat, or future development, the expansive acreage provides the perfect canvas. Enjoy peaceful surroundings, room to roam, and the freedom to bring your vision to life. Properties with this much land and potential don't come along often—schedule your showing today and explore the possibilities!

8420 Frankfort Rd, Waddy
$279,900
3 Beds ⋅ 2 Baths ⋅ 1717011 MLS
Farm house located on 3.4 acres on quiet street. Home is in need of a fair amount of TLC, but has tons of potential. So many incredibly large rooms, with gorgeous trim work. The original doors are amazing. This home is such searching for the right buyer. Home is sold "as is". Agents see agent notes before scheduling showings.

546 Banta Ln, Pleasureville
$1,025,000
5 Beds ⋅ 5 Baths ⋅ 1715009 MLS
Country living at it's best. 15 acre farmstead ready for your horses, chickens, fishing, deer hunting and hay production. Pass thru the gates and down a tree lined drive to a modern farmhouse with covered wrap around porch. Inside, the vaulted great room opens to a fully renovated kitchen built for people who actually cook and entertain. Quartz counters, a custom wood range hood, double wall ovens, a farmhouse sink, butler's pantry/scullery, and a center island with seating for four anchor the space. The adjacent dining area holds a table for fourteen, and the gas log fireplace in the living room throws warmth clear across the open plan. The main floor primary suite opens to the rear deck & includes an updated bath with double vanities, walk-in tile shower, and a cedar-lined walk-in closet The second suite, converted from the attached garage, adds a private bath and its own entrance through a generous mudroom and would make an excellent In-law suite, guest quarters, home office, or accommodations for in-home carer or nanny. Upstairs, three more bedrooms and a full bath share a loft that overlooks the great room. The walkout basement adds a family room, game room, full bath, and a finished office currently used as a fifth bedroom. The unfinished mechanical room could be finished into a full apartment. Perfect for multi-generational living. Outside, the saltwater pool sits beside a 24x28 detached garage with a full-length deck. A 24x24 barn and fenced pasture handle horses or livestock. Fish from your own private pond and dock. Raise chickens in your own coop. The wooded creek corridor at the rear has produced deer every season. The front five acres yield hay each year. Located less than 5 minutes from I64 exit 43, Shelbyville and Frankfort are 12 minutes in either direction. Louisville is 35. Lexington is 45. Enjoy the peace and quiet of country living with quick access to any shopping/commuting needs.

779 Kings Hwy, Waddy
$1,025,000
5 Beds ⋅ 5 Baths ⋅ 1715003 MLS
Tucked behind a gated, tree-lined drive off Kings Highway, this 2002 farmhouse sits on 14.92 rolling acres bordered by working farms on every side. The stocked pond greets you at the front of the property. The covered wrap-around porch is the place you will drink your coffee from April through October. Inside, the vaulted great room opens to a fully renovated kitchen built for people who actually cook and entertain. Quartz counters, a custom wood range hood, double wall ovens, a farmhouse sink, butler's pantry/scullery, and a center island with seating for four anchor the space. The adjacent dining area holds a table for fourteen, and the gas log fireplace in the living room throws warmth clear across the open plan. The main floor primary suite opens to the rear deck & includes an updated bath with double vanities, walk-in tile shower, and a cedar-lined walk-in closet. The second suite, converted from the attached garage, adds a private bath and its own entrance through a generous mudroom and would make an excellent In-law suite, guest quarters, home office, or accommodations for in-home carer or nanny. Upstairs, three more bedrooms and a full bath share a loft that overlooks the great room. The walkout basement adds a family room, game room, full bath, and a finished office currently used as a fifth bedroom. The unfinished mechanical room could be finished into a full apartment. Perfect for multi-generational living. Outside, the saltwater pool sits beside a 24x28 detached garage with a full-length deck. A 24x24 barn and fenced pasture handle horses or livestock. The wooded creek corridor at the rear has produced deer every season. The front five acres yield hay each year. Shelbyville and Frankfort are 12 minutes in either direction. Louisville is 35. Lexington is 45. Feel the peace of country living with quick access to any shopping/commuting needs.

779 Kings Hwy, Waddy
$475,000
3 Beds ⋅ 2 Baths ⋅ 1713024 MLS
Looking for the perfect place to start a hobby farm on over 8 acres? Maybe a private retreat away from the city and neighbors? What about a large pole barn thats perfect as a workshop or a great place to store your boat/atv/cars? Well look no further, because this property has it all! The kitchen is fit for a chef with counter-space and cabinets to spare, a gas stove, and granite countertops. The living room has soaring ceilings and large windows with plenty of natural light. The primary suite features a tub, shower, and separate sinks as well! The back patio is perfect for entertaining or for a quiet evening watching the sunset. This turn key home was beautifully updated from head to toe in 2019, including; granite countertops, HVAC, water heater, roof, and more. Schedule a showing today!

9210 Mount Eden Rd, Waddy
$275,000
6 Beds ⋅ 2 Baths ⋅ 1709571 MLS
Check out this 3000+sf Home on 5.36 Acres with a Million Dollar View! This home needs extensive renovation but could easily be the Fixer-upper you have been looking for. The Property sits atop Frankfort Road overlooking the countryside with Fantastic Views adjacent to Jeptha Knobs. This is the perfect property for the investor or flipper. Plenty of Space to Build your New Horse Barn/Arena and space for animals. LOADS of Potential... Easy Access to I-64 Between Shelbyville and Frankfort. Call NOW for your private Viewing!

4200 Frankfort Rd, Shelbyville
$5,439,000
4 Beds ⋅ 2 Baths ⋅ 1680398 MLS
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 evenings on the covered porch enjoying the gorgeous views. Currently being used as a short term rental, this property has limitless possibilities. It also has two large ponds, along with over 2300' of frontage on Plum Creek. There are 3 platted five acre tracts included in the total acreage. An equipment barn built in 2018 is the perfect place to store your things. Don't miss this one!

4260 Fisherville Rd, Simpsonville