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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.

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

$12,500,000

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.

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

$335,000

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.

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

$734,500

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.

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

$955,000

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.

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

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