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5191 Bardstown Trail, Waddy
$765,000
2 Beds ⋅ 1 Baths ⋅ 1733107 MLS
Offered at an exceptional value - Don't pass up this opportunity to escape the hustle and bustle, slow down and enjoy the beauty of nature? Welcome to 5191 Bardstown Trail, where 78 acres of privacy and seclusion offer a rare opportunity for peaceful country living in Shelby County. Imagine starting your morning with coffee on the deck as the wildlife comes to life around you. As you enter the property, you'll cross a picturesque creek and make your way through a beautiful landscape of mostly wooded acreage, open fields, ravines, streams and abundant natural surroundings. Nestled toward the top of the hill is a charming 1.5-story log cabin that makes an ideal full-time residence, weekend getaway, recreational retreat or private escape. The cabin features 2 bedrooms, 1 full bath and a basement with an outside entrance. Inside, you'll find an inviting open-concept Kitchen and Family Room with a wood-burning stove that adds to the cozy cabin atmosphere. The Kitchen features granite countertops, a bar area for additional seating and plenty of space for gathering. A versatile loft provides additional living space and would make a great home office, reading area or retreat. Kitchen appliances and washer/dryer can remain. A 24' x 32' metal pole barn provides additional space for equipment, recreational vehicles, storage and more. The approximately 78 acres are divided into four separate tracts with a shared entrance, offering additional possibilities for the new owner. Enjoy the privacy and tranquility of your own Kentucky retreat while remaining conveniently located just 3 miles from the Waddy/Peytona I-64 Exit #43. Whether you're searching for a permanent country home, weekend retreat, hunting or recreational property, or simply a place to get away from it all, 5191 Bardstown Trail offers acreage, privacy and natural beauty that can be difficult to find. Come experience the peace and possibilities this special property has to offer! Check out the fall landscape pictures and drone shots!

5191 Bardstown Trail, Waddy

5665 Zaring Mill Rd, Shelbyville
$399,000
3 Beds ⋅ 3 Baths ⋅ 1732466 MLS
Welcome to 5665 Zaring Mill Rd, a well-loved home offered by its original owners for the first time. Set on very private acreage, this home gives you room to spread out and the kind of quiet you only find in the Shelby County countryside. The main level has an open layout where the kitchen, with its sunny bay window, flows right into the living room. A separate dining area is ready for family dinners, and a half bath on the main level is handy for guests. Step out back to the bright sunroom and take in the views of your land. Upstairs you'll find all three bedrooms, including a spacious primary suite with its own full bath. There's also a second full bath, a convenient upstairs laundry room, and a flexible bonus room that works well as an office, playroom, or reading nook. basement gives you lots of storage and room to grow, and the attached garage keeps life easy year-round. Acreage, privacy, and a solid floor plan make this one worth seeing in person.

5665 Zaring Mill Rd, Shelbyville

21 Braxton Ct, Simpsonville
$795,000
2 Beds ⋅ 3 Baths ⋅ 1732303 MLS
If privacy and serenity are what you are looking for, you will find them at 21 Braxton Court in Simpsonville. Nestled down a tree-lined drive in sought-after Braxton Estates, this iconic log cabin is a dream. The front porch is inviting and welcomes you in. Once through the door, you will experience the warmth of a ski lodge and the attention to detail only a custom home can provide. The large stone fireplace, rich wood on the walls, and custom chef's kitchen are only a few examples of what make this home special. The abundance of windows brings the outside in, creating a wilderness oasis and truly serene experience. The primary suite with a lovely ensuite bath is the perfect place to unwind with a jacuzzi tub. The first-floor laundry room, office (could easily be used as a bedroom), and additional half bath rounds out the first. Upstairs, a loft area offers a multitude of uses. It overlooks the two-story fireplace and brings the home's warmth in. A second bedroom and attached full bath are the perfect cherry on top. Outside this home has even more to offer. The screened porch overlooks the gorgeous lot with a mix of trees and open meadow. This property is too unique and special to just peer at online! Schedule your private showing today.

21 Braxton Ct, Simpsonville

1658 Vigo Rd, Shelbyville
$475,000
3 Beds ⋅ 3 Baths ⋅ 1732005 MLS
Located just outside Shelbyville, this custom-built brick ranch combines a tranquil country setting and expansive views with convenient access to the city. The home offers more than 2,500 square feet of thoughtfully designed living space, including a large living room, adjoining dining room, and generously sized country kitchen with an additional dining area for gatherings with family and guests. The family room features a brick fireplace for cozy winter evenings. Three spacious bedrooms include hardwood floors and ample closet space. The home also has 2.5 baths and a laundry area. Have a home business or need an office, there is a great area with outside entrance to accommodate you . The lower level provides abundant storage or room to pursue hobbies. Additional features include solid wood cabinetry, a blacktop driveway, mature shade trees, and an attached two-car garage. The property also offers wood fencing, a detached two-car garage with workshop space, a storage shed, and the potential availability of additional acreage. Take a minute to view this exceptional property. Just add your personal touch then imagine your family enjoying the best life.

1658 Vigo Rd, Shelbyville

1458 St Andrews Dr, Shelbyville
$584,900
4 Beds ⋅ 3 Baths ⋅ 1731564 MLS
Welcome to Brentwood, one of Shelby County's most sought after neighborhoods! Tucked away toward the back of this beautiful, established community, this spacious 4-bedroom, 3-full-bath home offers a wonderful sense of privacy and a peaceful setting away from the main neighborhood entrance. Located next to Shelbyville Country Club, and minutes from local schools, parks, and downtown Shelbyville, this property offers an incredible combination of location, comfort, and opportunity. With approximately 2,800 square feet of finished living space above grade, this home features a desirable main-level layout with a spacious family room, separate living room/library, large eat in kitchen, laundry room, and two bedrooms, including the primary suite. Upstairs, you'll find two additional generously sized bedrooms, a full bathroom, and convenient walk-in attic storage. Major updates have already been completed! Enjoy a brand-new roof, new HVAC system, beautiful new hardwood flooring throughout the main level, updated flooring in every bedroom, and fresh interior paint throughout the entire home. These improvements provide a fresh, modern feel while maintaining the character and charm of this established neighborhood. Need more room? The expansive 2,200-square-foot unfinished basement offers endless possibilities! Whether you envision additional living space, a home theater, recreation room, home gym, or simply an abundance of storage, the opportunity to make this space your own is already there. Outside, enjoy a beautiful lot offering privacy, mature surroundings, and plenty of room to relax. An oversized two-car garage provides additional convenience and storage. Homes in Brentwood are highly desirable, and opportunities to purchase in this established neighborhood don't come along every day. With its generous square footage, extensive updates, incredible basement potential, and attractive price point, this home offers a fantastic opportunity to enjoy everything Brentwood has to offer. Schedule your private showing today and discover the possibilities!

1458 St Andrews Dr, Shelbyville

1615 Harrington Mill Rd, Shelbyville
$2,950,000
3 Beds ⋅ 3 Baths ⋅ 1731382 MLS
Historic horse farm, located in the heart of Saddlebred country, and minutes from downtown Shelbyville features a beautifully renovated brick Federal style estate and superb equestrian horse facility. Built circa 1850, this home features modern updated amenities yet retains the charm of the age. Features include original hardwood flooring, six fireplaces, Living and Dining rooms with beautiful pocket doors, an expansive Foyer, and fabulous chandeliers in every room. The remodeled kitchen includes custom birchwood cabinetry, Dacor gas oven, warming drawer, and Butlers pantry with a wine cooler and ice maker. The second floor Primary suite features a large dressing room, remodeled bathroom with heated floors and steam shower, a sleeping porch, office, laundry and linen closets. There are 2 additional expansive bedrooms with a remodeled bathroom. Other features of the home include original windows with new storms and plantation shutters, a spacious elevator, updated plumbing and electrical, 2 HVAC systems, and a Trex deck off the remodeled kitchen. The 4 car garage, built in 2005, contains 3 bays for cars along with a 4th bay for equipment. The Barn has 20 stalls with an attached indoor arena and lounge with a viewing window. The property includes an additional outdoor riding ring, 2 spring fed ponds, 2 large run-in sheds, 2 porches, and a stunning large portico. The main entrance is gated for additional security and privacy.

1615 Harrington Mill Rd, Shelbyville

195 Locust Grove Rd, Shelbyville
$574,000
3 Beds ⋅ 3 Baths ⋅ 1731059 MLS
Escape to your own private homestead on 5 sprawling acres, just minutes from town and 4.5 miles from I-64! Sellers are offering a 2/1 rate buydown with a full-price offer. This updated 3BR, 2.5BA home features a remodeled kitchen with new appliances and gas range, new woodstove insert, renovated primary suite and bath, whole-house generator, and basement tornado safe room. A dedicated canning kitchen with gas cooktop, sink and dishwasher makes preserving your harvest easy. Outside, enjoy a fenced front yard with dog run, barn with heated/cooled tack or workshop room, paddock, and large storage shed. Ideal for animals, gardening and self-sufficient living. Rare Shelbyville homestead priced below appraised value!

195 Locust Grove Rd, Shelbyville

10053 Shelbyville Rd, Simpsonville
$12,500,000
6 Beds ⋅ 3 Baths ⋅ 1730842 MLS
A landmark Kentucky estate of extraordinary provenance, 10053 Shelbyville Road offers approximately 55 acres along one of the region's most coveted corridors near the Jefferson/Shelby County line. Built in the early 1800s, near the formation of the Commonwealth, the historic main residence is listed on the historic registry and is believed to be among the oldest homes in Kentucky, with the property recognized as one of the state's longest continuously farmed landholdings. The estate features a 5,336 sq, ft, main residence, an approximately 2,000 sq. ft. guest house, and expansive grounds suited for equestrian use, private farming, a family compound, or long-term legacy ownership. Rarely does a property combine this level of history, acreage, location, and future optionality. This is not simply a home - it is a generational Kentucky estate awaiting its next steward.

10053 Shelbyville Rd, Simpsonville

201 Cherokee Dr, Shelbyville
$649,900
3 Beds ⋅ 2 Baths ⋅ 1730079 MLS
This new construction in Town an Country is almost ready for its first owners! This 3 bed, 2 bath split-bedroom ranch offers 2,043 sq ft of one-level living with an open floor plan that flows easily from the kitchen to the dining and living areas, perfect for everyday life and entertaining alike. The kitchen shines with quartz countertops, and the split design puts the primary suite on its own side of the home for added privacy, with two additional bedrooms and a full bath on the other. Below, a full unfinished basement gives you room to grow, whether that's a rec room, home gym, extra bedrooms, or plenty of storage. An attached two-car garage adds convenience, and the location can't be beat: set in the established Town and Country subdivision right across from the country club.

201 Cherokee Dr, Shelbyville

108 1st St, Simpsonville
$335,000
3 Beds ⋅ 2 Baths ⋅ 1729967 MLS
Some houses have a little more personality than others. 108 First Street is one of them. Start your morning on the front porch with a cup of coffee and the sounds of Simpsonville waking up around you. Church bells across the street, a short walk to the farmers market, and Simpsonville Park just down the road give this home a location that is hard to duplicate. Inside, the character continues. This well-maintained older home has the details you hope to find, including beautiful original trim, solid-core doors, and a story-and-a-half layout that gives the home plenty of personality without sacrificing function. The kitchen has been renovated, the laundry is conveniently located on the main floor, and there are three bedrooms and two full bathrooms spread across approximately 1,788 square feet. The roughly .3-acre lot gives you just enough room to enjoy the outdoors without spending your weekends maintaining a huge yard. Garden, entertain, let the kids play, or simply sit on the porch and watch the neighborhood go by. And then there's the location. You're right in the heart of old-town Simpsonville, close enough to walk to some of the town's favorite spots while still being only minutes from I-64. If you like homes with character, a little history, and a location that lets you actually enjoy small-town living, 108 First Street deserves a look.

108 1st St, Simpsonville

6381 Frankfort Rd, Shelbyville
$409,000
3 Beds ⋅ 3 Baths ⋅ 1729897 MLS
This beautifully maintained white brick home offers 2196 sq ft of above-grade living space with scenic views of a neighboring 281-acre farm. Inside, rustic charm meets modern updates with exposed brick accents, an inviting living room, and an updated Kitchen featuring an island, double oven, and appliances that remain. The home includes 3 bedrooms and 2.5 baths, including a first-floor owner's suite with a slipper tub, separate shower, and walk-in closet. A wood-burning fireplace adds warmth to the kitchen area. Outside, enjoy a large covered rear patio overlooking peaceful farmland, along with a level yard featuring shade trees, perennial landscaping, and partial fencing. The property also includes an oversized two-car carport and a 19'x32' electrified barn suitable for storage, workshop space, or a potential garage.

6381 Frankfort Rd, Shelbyville

284 Saint Regis Dr, Shelbyville
$345,000
3 Beds ⋅ 3 Baths ⋅ 1729378 MLS
Welcome to 284 Saint Regis Drive in Cloverbrook Farms! This spacious two story home offers 3 bedrooms, 2.5 bathrooms, and 2,050 square feet of finished living space with plenty of room to spread out. The main level features multiple living areas and an open layout connecting the kitchen, dining space, and family room, creating a comfortable setup for both everyday living and entertaining. Upstairs, you'll find all three bedrooms, a convenient second floor laundry, and a versatile loft that provides additional space for a home office, playroom, or second living area. The unfinished 910 square foot basement offers even more possibilities for future finished living space, a home gym, recreation area, or additional storage. Step outside to enjoy the deck overlooking the fenced backyard, or take advantage of the attached garage for added parking and storage. Cloverbrook Farms also offers neighborhood amenities including a pool and playground. With generous living space, a flexible layout, and room to grow, 284 Saint Regis Drive is ready to welcome you home. Schedule your showing today!

284 Saint Regis Dr, Shelbyville

2280 Anderson Ln, Shelbyville
$1,899,000
5 Beds ⋅ 5 Baths ⋅ 1728798 MLS
Luxury newer construction on 15.01 acres in Shelbyville, KY! This exceptional custom-built 5-bedroom, 4.5-bath Kentucky estate combines modern farmhouse architecture, designer finishes and beautiful Shelby County countryside views. The open-concept interior showcases soaring ceilings, dramatic wood beams, wide-plank flooring and a stunning great room with floor-to-ceiling stone fireplace and custom built-ins. The chef-inspired kitchen features custom cabinetry, stone countertops, oversized island, professional-style gas range, pot filler, designer lighting and walk-in pantry. The luxurious primary suite offers a spa-inspired bath with freestanding soaking tub, oversized glass shower, dual vanities and custom finishes. A massive unfinished walkout basement, already roughed in for 2 additional bathrooms and a wet bar, provides incredible future living and entertainment potential with impressive ceiling height and double-door exterior access. Situated on 15.01 newly platted acres, this rare Shelbyville luxury home with acreage offers privacy, space and Kentucky country living while remaining convenient to Shelbyville, Simpsonville and the greater Louisville area.

2280 Anderson Ln, Shelbyville

1051 Champions Cir, Simpsonville
$734,500
4 Beds ⋅ 4 Baths ⋅ 1725347 MLS
The golf course is calling you to this STUNNING home in the beautiful Cardinal Club Estates and you can be in before the Holiday Season starts. Custom built in 2014 (with 2x6 exterior wall construction), with beautiful golf course views throughout, this home features many elevated elements most don't-custom millwork and oversized doors, just to name a couple. There is the convenience of a large kitchen and gathering/family room, and also the elegance of a formal living room and dining room. The split floor plan takes you to a generously sized primary suite, with double closets as well as an oversized bathroom. Two additional bedrooms (one currently used as an office) on the main floor share a Jack & Jill style bathroom, while a well appointed powder room provides convenience for guests. A spacious laundry room and second exterior door near the garage adds convenience while rounding out the first floor. While not a necessity at the time of building, the sellers opted to finish a large area above the garage to create a 4th bedroom and en-suite bath, certainly providing a very nice additional completed space that is conditioned with it's own HVAC unit. The basement is unfinished, but walls are framed and a bathroom roughed in, allowing for TONS of space for your creative finishes. There is a utility garage in the basement perfect for a golf cart or to keep yard tools, lawn equipment and other hobby items. The amount of storage space and closets on the main living level, as well as in the basement, will not leave you wanting more. Tall ceilings throughout help create an open, grand space while keeping the warm and inviting feeling of the home. You will find that most windows incorporate custom treatments or shutters. Access the expansive deck from the gathering room, living room, and primary suite, and enjoy BEAUTIFUL evenings this fall season overlooking the UofL Golf Course, and many sightings of wildlife. This home sits on the Hole 11 tee box, and has gorgeous views of the clubhouse and Hole 18 as well. The property has been lovingly and exceptionally well cared for - you can move right in and begin enjoying the peaceful nature of the City of Simpsonville and the golf course, yet still be conveniently located near the amenities of Louisville and Shelbyville.

1051 Champions Cir, Simpsonville

1219 Taylor Wood Rd, Simpsonville
$955,000
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

449 South Stallard Dr, Shelbyville
$659,900
3 Beds ⋅ 3 Baths ⋅ 1722246 MLS
Rare Home For Sale in STALLARD SPRINGS | 2,205 Sq Ft on 5 Private Acres for Under $700,000 This 3 bedroom, 2.5 bath home offers 2,205 square feet of thoughtfully designed living space with a dedicated office that could easily convert to a 4th bedroom if needed. Set on 5 scenic acres with panoramic views, the home features luxury vinyl plank flooring, quartz countertops, custom tile showers, and an open kitchen with premium appliances and generous counter space ideal for entertaining. Enjoy the peace of acreage living while taking advantage of community amenities including the nature trail, pickleball court, pavilion, and iconic silo gathering space. Space, flexibility, and connection all within one of Shelby County's most sought after communities.

449 South Stallard Dr, Shelbyville

904 Waddy Rd, 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

575 Moody Pike, Shelbyville
$1,249,900
4 Beds ⋅ 4 Baths ⋅ 1714943 MLS
Welcome to 575 Moody Pike where Southern charm meets historic beauty. Conveniently located less than 10 minutes from quaint downtown Shelbyville, this 13.46 +/- acre one-of-a-kind equestrian estate has been featured in Southern Living Magazine, Bourbon Barrel Retreats, USA Today, the Lane Report and more! The enchanting tree-lined drive leads to the stately 2 story brick home (circa 1860). Inside, enjoy refinished and original hardwood floor, beautiful millwork, an upgraded eat-in kitchen with granite countertops, custom cabinetry, upgraded appliances as well as an additional fabulous prep kitchen/butler's pantry. Gorgeous views are plentiful on this property. Retreat to the shaded gazebo adorned with grape vines for a cup of tea or coffee or relax by the bubbling lily pond from the comfort of a front porch rocking chair. Watch the sunrise from the all-season wrap around porch and sunsets through the pines from the well-appointed sunroom. Enjoy up to four fireplaces to create that special ambiance for the holidays or cooler months. Efficient geothermal heating and cooling keep the home comfortable all year round. This notable property has a huge historic 12+ stall concrete block and wooden barn that includes 2 foaling stalls, all fully renovated with rubber stall mats on top of an asphalt base and a loft that can easily accommodate 1000 square bales. A large heated and cooled tack room is complete with utility sink. The "milk room" next to the tack room provides ample storage options. Attached to the barn is extra covered storage that is large enough to protect several tractors, implements or round bales. This property also features three additional period-specific custom-built all-oak barns crafted by the Amish, complete with attached feed rooms equipped with electric access and concrete floors, plus storage! The first barn could easily house 4 stalls and is adorned with a stylish cupola wired for incredible nighttime aesthetics. The second barn could accommodate 2 stalls and has an attached feed room with a concrete floor and a large storage room and cupola. The third barn is big enough to house up to 6 small stalls or 3 large stalls plus run-in space and is next to an 80 x 190 ft. professionally installed riding arena with all-weather footing. Water and electric are run to all paddock areas, up to 15 paddocks of various sizes. Located in Bourbon country, this unique turnkey property is also income producing, whether as a Bed and Breakfast, wedding venue, derby/corporate events, retreats and/or Horse Boarding/Training/Breeding facility. The possibilities are endless. Or simply move in and enjoy this slice of heaven!

575 Moody Pike, Shelbyville

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