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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

$639,900

Situated in the established Cardinal Club community of Simpsonville, this beautiful 5 bed, 3.5 bath home offers approximately 3,636 sq. ft. of finished living space across three levels, with wonderful views toward the golf course. From the moment you arrive, the classic brick exterior, welcoming covered porch, mature landscaping, and attached two-car garage set the tone. Inside, the main level features beautiful hardwood flooring, crown molding, abundant natural light, and an inviting open flow between the living spaces. The spacious kitchen features granite countertops, beautiful cabinetry, ample storage, and generous workspace, with a bright adjoining breakfast room and formal dining room. The first-floor primary suite is a true retreat, featuring a large primary bath and California Closet organization. Finishing out the first floor are the laundry room and a half bath. Upstairs are three additional bedrooms and a full bath. The finished walkout basement features a large great room, additional bedroom, full bathroom, and gas fireplace. Outdoor living is just as inviting, with a spacious deck, covered patio and porch. Located in Cardinal Club Estates, residents have the opportunity to enjoy the community's semi-private golf and swim country club, with the golf course and neighborhood amenities right at your doorstep. Whether you're enjoying a quiet morning coffee, hosting, or unwinding after a day on the course, this home offers an exceptional combination of space, character, and location.

5 Beds ⋅ 4 Baths ⋅ 1730129 MLS

Situated in the established Cardinal Club community of Simpsonville, this beautiful 5 bed, 3.5 bath home offers approximately 3,636 sq. ft. of finished living space across three levels, with wonderful views toward the golf course. From the moment you arrive, the classic brick exterior, welcoming covered porch, mature landscaping, and attached two-car garage set the tone. Inside, the main level features beautiful hardwood flooring, crown molding, abundant natural light, and an inviting open flow between the living spaces. The spacious kitchen features granite countertops, beautiful cabinetry, ample storage, and generous workspace, with a bright adjoining breakfast room and formal dining room. The first-floor primary suite is a true retreat, featuring a large primary bath and California Closet organization. Finishing out the first floor are the laundry room and a half bath. Upstairs are three additional bedrooms and a full bath. The finished walkout basement features a large great room, additional bedroom, full bathroom, and gas fireplace. Outdoor living is just as inviting, with a spacious deck, covered patio and porch. Located in Cardinal Club Estates, residents have the opportunity to enjoy the community's semi-private golf and swim country club, with the golf course and neighborhood amenities right at your doorstep. Whether you're enjoying a quiet morning coffee, hosting, or unwinding after a day on the course, this home offers an exceptional combination of space, character, and location.

209 Champions Way, 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

$405,000

Looking for more room to spread out without giving up the spaces that bring everyone together? This 4-bedroom, 2.5-bath home in Todd's Station in Simpsonville offers a flexible layout, multiple living and entertaining spaces, a 2-car garage, and convenient access to I-64. A covered front porch welcomes you inside, where beautiful flooring carries through the main level. Just off the entry, the spacious dining room gives you room for holiday dinners, celebrations, or simply gathering around the table. At the heart of the home, the open great room brings the living room, kitchen, and dining area together, creating an easy flow for everyday life and entertaining. Just beyond, a vaulted sunroom adds the kind of flexible space that can change right along with you, whether it be a home office, playroom, game room, reading space, or additional place to relax. From the sunroom, step directly onto the large back deck, extending your living space outdoors with plenty of room for grilling, dining, entertaining, or unwinding at the end of the day. A half bath and laundry room conveniently located near the kitchen and 2-car garage complete your main level. Upstairs, the primary suite gives you a place to recharge with a spacious walk-in closet and ensuite bath featuring double sinks, a jetted tub, and separate shower. Three additional bedrooms and another full bath provide even more options for bedrooms, guests, hobbies, or work-from-home space. Located in Simpsonville's Todd's Station neighborhood, you're just minutes from I-64 and the Outlet Shoppes of the Bluegrass, making it easy to reach shopping, dining, and destinations throughout Shelby County and the Louisville area. If your next home needs to give you more space, more flexibility, and more ways to enjoy it, this one is ready to fit the way you live.

4 Beds ⋅ 3 Baths ⋅ 1728891 MLS

Looking for more room to spread out without giving up the spaces that bring everyone together? This 4-bedroom, 2.5-bath home in Todd's Station in Simpsonville offers a flexible layout, multiple living and entertaining spaces, a 2-car garage, and convenient access to I-64. A covered front porch welcomes you inside, where beautiful flooring carries through the main level. Just off the entry, the spacious dining room gives you room for holiday dinners, celebrations, or simply gathering around the table. At the heart of the home, the open great room brings the living room, kitchen, and dining area together, creating an easy flow for everyday life and entertaining. Just beyond, a vaulted sunroom adds the kind of flexible space that can change right along with you, whether it be a home office, playroom, game room, reading space, or additional place to relax. From the sunroom, step directly onto the large back deck, extending your living space outdoors with plenty of room for grilling, dining, entertaining, or unwinding at the end of the day. A half bath and laundry room conveniently located near the kitchen and 2-car garage complete your main level. Upstairs, the primary suite gives you a place to recharge with a spacious walk-in closet and ensuite bath featuring double sinks, a jetted tub, and separate shower. Three additional bedrooms and another full bath provide even more options for bedrooms, guests, hobbies, or work-from-home space. Located in Simpsonville's Todd's Station neighborhood, you're just minutes from I-64 and the Outlet Shoppes of the Bluegrass, making it easy to reach shopping, dining, and destinations throughout Shelby County and the Louisville area. If your next home needs to give you more space, more flexibility, and more ways to enjoy it, this one is ready to fit the way you live.

140 Lincoln Station Dr, Simpsonville

$1,550,000

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 warming drawer, dressing area, and double walk-in closets. The kitchen is a chef's dream, with Thermador gas cooktop and double ovens, Bosch dishwasher, and warming drawer. Upstairs is a large living room, 3 more bedrooms, all with walk-in closets, and two full baths. The basement features a large game and media room, a partial kitchen, bedroom, newly remodeled bath, and second laundry. Stepping outside onto one of the many patios, porches, or decks, you will find a private, lush oasis. The property has a 40,000 gallon heated salt water system pool with waterfall and stately terraced sundeck, a fully landscaped back yard, and a large garden with six Vego raised beds with drip irrigation. About one acre of the property is surrounded by four-board fencing with a sprinkler system. Additionally, the property includes extensive storage, a security system, 3 separate HVAC units (2 with humidifiers), and 2 water heaters. Adding even more versatility, there is a detached three-car garage connected by a covered breezeway, and an unfinished apartment/studio with a separate entrance is above the garage. There is also plenty of open, flat acreage for a barn to be built in the future, and the neighborhood features over 7 miles of horse trails. The current owners have treasured this home for 26 years, and their care and love is evident. This private estate is designed to create unforgettable memories and allow for effortless entertaining on any scale. It is perfectly positioned to capture the surrounding peace and beauty of the rolling countryside of Simpsonville, with breathtaking sunsets in a parklike setting.

5 Beds ⋅ 6 Baths ⋅ 1729331 MLS

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 warming drawer, dressing area, and double walk-in closets. The kitchen is a chef's dream, with Thermador gas cooktop and double ovens, Bosch dishwasher, and warming drawer. Upstairs is a large living room, 3 more bedrooms, all with walk-in closets, and two full baths. The basement features a large game and media room, a partial kitchen, bedroom, newly remodeled bath, and second laundry. Stepping outside onto one of the many patios, porches, or decks, you will find a private, lush oasis. The property has a 40,000 gallon heated salt water system pool with waterfall and stately terraced sundeck, a fully landscaped back yard, and a large garden with six Vego raised beds with drip irrigation. About one acre of the property is surrounded by four-board fencing with a sprinkler system. Additionally, the property includes extensive storage, a security system, 3 separate HVAC units (2 with humidifiers), and 2 water heaters. Adding even more versatility, there is a detached three-car garage connected by a covered breezeway, and an unfinished apartment/studio with a separate entrance is above the garage. There is also plenty of open, flat acreage for a barn to be built in the future, and the neighborhood features over 7 miles of horse trails. The current owners have treasured this home for 26 years, and their care and love is evident. This private estate is designed to create unforgettable memories and allow for effortless entertaining on any scale. It is perfectly positioned to capture the surrounding peace and beauty of the rolling countryside of Simpsonville, with breathtaking sunsets in a parklike setting.

107 My Kentucky Rose Cir, Simpsonville

$999,000

Welcome to a truly one of a kind opportunity in Simpsonville, offering over 4,000 square feet of above grade living space, 4 bedrooms, 4.5 bathrooms, and more than five beautiful acres, all just minutes from I-64. The main residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed floor plan perfect for both everyday living and entertaining. The main level primary suite provides a private retreat, while the great room with gas fireplace flows into a spacious kitchen with granite countertops, generous bar seating, and excellent storage. Upstairs, two additional bedrooms and a full bathroom provide plenty of space for family or guests. What truly sets this property apart is the entirely separate living quarters connected to the main residence by a covered breezeway. This is much more than a traditional mother in law suite. It functions as essentially a second home on the property, complete with its own bedroom, private living room, full kitchen, bathroom, and laundry. It is an incredible setup for multigenerational living, extended family, long term guests, or anyone wanting a completely independent living space while still being just steps from the main residence. Out back, the versatility continues with a large barn offering both finished and unfinished space. The finished, climate controlled area is currently being used as a private office and includes its own full bathroom. For someone who works from home, it offers the rare opportunity to have a dedicated office completely separate from the residence. Or make it your own and create the ultimate man cave, golf simulator room, hobby space, studio, or private retreat. The possibilities for this space are endless. The barn also includes a large open area ready for the next owners to make their own, with plenty of room to add stalls. Combined with the property's three fenced paddocks, the property offers an incredible starting point for someone looking to create their own horse or hobby farm setup. The outdoor setting is every bit as impressive. The 5.07 acres provide a peaceful sense of space and privacy, with a back porch overlooking the acreage and beautifully maintained, well manicured landscaping throughout the property.

4 Beds ⋅ 4 Baths ⋅ 1729102 MLS

Welcome to a truly one of a kind opportunity in Simpsonville, offering over 4,000 square feet of above grade living space, 4 bedrooms, 4.5 bathrooms, and more than five beautiful acres, all just minutes from I-64. The main residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed floor plan perfect for both everyday living and entertaining. The main level primary suite provides a private retreat, while the great room with gas fireplace flows into a spacious kitchen with granite countertops, generous bar seating, and excellent storage. Upstairs, two additional bedrooms and a full bathroom provide plenty of space for family or guests. What truly sets this property apart is the entirely separate living quarters connected to the main residence by a covered breezeway. This is much more than a traditional mother in law suite. It functions as essentially a second home on the property, complete with its own bedroom, private living room, full kitchen, bathroom, and laundry. It is an incredible setup for multigenerational living, extended family, long term guests, or anyone wanting a completely independent living space while still being just steps from the main residence. Out back, the versatility continues with a large barn offering both finished and unfinished space. The finished, climate controlled area is currently being used as a private office and includes its own full bathroom. For someone who works from home, it offers the rare opportunity to have a dedicated office completely separate from the residence. Or make it your own and create the ultimate man cave, golf simulator room, hobby space, studio, or private retreat. The possibilities for this space are endless. The barn also includes a large open area ready for the next owners to make their own, with plenty of room to add stalls. Combined with the property's three fenced paddocks, the property offers an incredible starting point for someone looking to create their own horse or hobby farm setup. The outdoor setting is every bit as impressive. The 5.07 acres provide a peaceful sense of space and privacy, with a back porch overlooking the acreage and beautifully maintained, well manicured landscaping throughout the property.

1799 Veechdale Rd, Simpsonville

$1,590,000

A truly one-of-a-kind property in Simpsonville. Set on 5 beautiful acres within Simpsonville's only gated community, this exceptional 5 bedroom, 5-bath home offers a rare combination of luxury, privacy, and country living. The property features an impressive ¾ of an acre established vineyard that has produced award-winning wine, making this estate truly special. 485 vines. Approximately 50% Noiret, 45% Vidal Blanc and 5% others. In addition to the vineyard, the grounds are dotted with a variety of mature fruit trees, creating a picturesque setting and an opportunity to enjoy your own harvest right at home. A brand- new barn adds incredible versatility to the property, providing space for equipment, hobbies, storage, or whatever your lifestyle requires. Inside the spacious home offers plenty of room for family and guests. The walk-out basement features a full kitchen, along with additional living space, making it ideal for entertaining, extended-stay guests, a private suite, or multi-generational living. There is a temperature controlled wine room in the basement, providing the ideal environment for storing and showcasing a collection. Additional features of the home include a whole house generator, and four working fireplaces. From the beautiful acreage and established vineyard to the new barn, direct access to scenic horse trails from the property, and thoughtfully designed living spaces, this property offers a lifestyle that is rarely found. Private, peaceful, and truly unique- this is Kentucky living at its finest.

5 Beds ⋅ 5 Baths ⋅ 1727770 MLS

A truly one-of-a-kind property in Simpsonville. Set on 5 beautiful acres within Simpsonville's only gated community, this exceptional 5 bedroom, 5-bath home offers a rare combination of luxury, privacy, and country living. The property features an impressive ¾ of an acre established vineyard that has produced award-winning wine, making this estate truly special. 485 vines. Approximately 50% Noiret, 45% Vidal Blanc and 5% others. In addition to the vineyard, the grounds are dotted with a variety of mature fruit trees, creating a picturesque setting and an opportunity to enjoy your own harvest right at home. A brand- new barn adds incredible versatility to the property, providing space for equipment, hobbies, storage, or whatever your lifestyle requires. Inside the spacious home offers plenty of room for family and guests. The walk-out basement features a full kitchen, along with additional living space, making it ideal for entertaining, extended-stay guests, a private suite, or multi-generational living. There is a temperature controlled wine room in the basement, providing the ideal environment for storing and showcasing a collection. Additional features of the home include a whole house generator, and four working fireplaces. From the beautiful acreage and established vineyard to the new barn, direct access to scenic horse trails from the property, and thoughtfully designed living spaces, this property offers a lifestyle that is rarely found. Private, peaceful, and truly unique- this is Kentucky living at its finest.

60 Lizas Cir, Simpsonville

$329,900

Welcome to 220 Rolling Ridge Way, a Charming 2 Story Colonial-style home situated on a corner lot with a white picket fence surrounding the Backyard. This Beautiful home features 3 Bedrooms, 2 full bathrooms upstairs, and 1 half bath on the first floor; an amazing fenced-in backyard with a large, freshly stained deck; a 1 Car Attached garage; and a double-wide driveway. As you step inside, you will find New LVP Flooring installed throughout the entire first floor in August 2026, freshly painted walls & trim on the first floor, built-in bookshelves, and an entertainment center. There is a Formal Dining Room just off the Living Room, with a lovely Bay Window that flows into the Kitchen, which features a New Refrigerator, New Microwave, 2 New Ceiling Lights, and a Newer Backsplash. The Laundry Room is also located just off the Kitchen. Upstairs, you will find 3 Bedrooms that all have New Carpet installed in August 2026, New LVP flooring in the Hallway and Primary Bathroom, a New Ceiling Fan in the front bedroom, freshly painted trim throughout the upstairs, freshly painted hallway, a freshly painted vanity in the Primary Bathroom, a new light in the Primary Bathroom, and a New Light in the Full Hall Bathroom. Out back is your own outdoor Oasis with a Large Backyard, freshly stained deck, freshly painted white picket fence, mature trees, and an attached storage shed. There is plenty of space out back for a garden, a pool, and space for the kids and dogs to run around. This wonderful home is located only 1.5 miles from the Outlet Mall, only 1 mile from I-64, and 10 miles from the Gene Snyder. Also, Beckley Creek Park is only 10 miles away and features picnic areas, fishing lakes, farmers' markets, community gardens, and paved and natural-surface trails that wind along the creek. Come see this wonderful home today!

3 Beds ⋅ 3 Baths ⋅ 1727753 MLS

Welcome to 220 Rolling Ridge Way, a Charming 2 Story Colonial-style home situated on a corner lot with a white picket fence surrounding the Backyard. This Beautiful home features 3 Bedrooms, 2 full bathrooms upstairs, and 1 half bath on the first floor; an amazing fenced-in backyard with a large, freshly stained deck; a 1 Car Attached garage; and a double-wide driveway. As you step inside, you will find New LVP Flooring installed throughout the entire first floor in August 2026, freshly painted walls & trim on the first floor, built-in bookshelves, and an entertainment center. There is a Formal Dining Room just off the Living Room, with a lovely Bay Window that flows into the Kitchen, which features a New Refrigerator, New Microwave, 2 New Ceiling Lights, and a Newer Backsplash. The Laundry Room is also located just off the Kitchen. Upstairs, you will find 3 Bedrooms that all have New Carpet installed in August 2026, New LVP flooring in the Hallway and Primary Bathroom, a New Ceiling Fan in the front bedroom, freshly painted trim throughout the upstairs, freshly painted hallway, a freshly painted vanity in the Primary Bathroom, a new light in the Primary Bathroom, and a New Light in the Full Hall Bathroom. Out back is your own outdoor Oasis with a Large Backyard, freshly stained deck, freshly painted white picket fence, mature trees, and an attached storage shed. There is plenty of space out back for a garden, a pool, and space for the kids and dogs to run around. This wonderful home is located only 1.5 miles from the Outlet Mall, only 1 mile from I-64, and 10 miles from the Gene Snyder. Also, Beckley Creek Park is only 10 miles away and features picnic areas, fishing lakes, farmers' markets, community gardens, and paved and natural-surface trails that wind along the creek. Come see this wonderful home today!

220 Rolling Ridge Way, Simpsonville

$360,000

Welcome to 268 Lang Run Ct in desirable Todds Station in Simpsonville Kentucky! This well appointed all-brick walkout ranch offers 4 bedrooms and 3 full baths on a lot just under 0.5 acres. The main level features an open floor plan with a vaulted great room, 3 bedrooms, and 2 full baths. The primary suite includes a trey ceiling and private bath with double vanity, garden tub, and separate shower. The finished walkout lower level offers the 4th bedroom, full bath, and additional living space and storage. A new fence encloses the spacious backyard, perfect for entertaining, pets, or relaxing. Enjoy the added amenity of the community pool. Conveniently located near I-64!

4 Beds ⋅ 3 Baths ⋅ 1726643 MLS

Welcome to 268 Lang Run Ct in desirable Todds Station in Simpsonville Kentucky! This well appointed all-brick walkout ranch offers 4 bedrooms and 3 full baths on a lot just under 0.5 acres. The main level features an open floor plan with a vaulted great room, 3 bedrooms, and 2 full baths. The primary suite includes a trey ceiling and private bath with double vanity, garden tub, and separate shower. The finished walkout lower level offers the 4th bedroom, full bath, and additional living space and storage. A new fence encloses the spacious backyard, perfect for entertaining, pets, or relaxing. Enjoy the added amenity of the community pool. Conveniently located near I-64!

268 Lang Run Ct, Simpsonville

$245,000

Welcome home to this beautifully updated 3-bedroom, 2-bath property situated on just over half an acre in Simpsonville, Kentucky. The refreshed kitchen and interior create a warm, move-in-ready atmosphere, while major recent improvements include a brand-new roof, brand-new water heater, and an oversized new deck that's perfect for entertaining, grilling, or relaxing outdoors. With generous yard space and plenty of parking, this home offers comfort, convenience, and room to enjoy both inside and out.

3 Beds ⋅ 2 Baths ⋅ 1725643 MLS

Welcome home to this beautifully updated 3-bedroom, 2-bath property situated on just over half an acre in Simpsonville, Kentucky. The refreshed kitchen and interior create a warm, move-in-ready atmosphere, while major recent improvements include a brand-new roof, brand-new water heater, and an oversized new deck that's perfect for entertaining, grilling, or relaxing outdoors. With generous yard space and plenty of parking, this home offers comfort, convenience, and room to enjoy both inside and out.

210 Montclair School Rd, Simpsonville

$744,000

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, while providing the elegance of a formal living room and dining room. The split floor plan takes you to a generously sized primary suite, with double clothing 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 some very nice additional completed space that is conditioned with it's own HVAC unit. The basement is unfinished, but roughed in for a bathroom, and wall framing is complete for TONS of space waiting 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. Of particular excellence in the home is the beautifully crafted millwork and trim, 8-foot tall doors throughout the main level, and the amount of storage space and closets on the main living level. 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 (no maintenance decking and rails!) from the gathering room, living room, and primary suite, and enjoy BEAUTIFUL evenings with expansive views overlooking the UofL Golf Course, and many sightings of wildlife, especially deer. 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, just a couple of miles from the Outlets of the Bluegrass and access to I-64.

4 Beds ⋅ 4 Baths ⋅ 1725347 MLS

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, while providing the elegance of a formal living room and dining room. The split floor plan takes you to a generously sized primary suite, with double clothing 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 some very nice additional completed space that is conditioned with it's own HVAC unit. The basement is unfinished, but roughed in for a bathroom, and wall framing is complete for TONS of space waiting 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. Of particular excellence in the home is the beautifully crafted millwork and trim, 8-foot tall doors throughout the main level, and the amount of storage space and closets on the main living level. 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 (no maintenance decking and rails!) from the gathering room, living room, and primary suite, and enjoy BEAUTIFUL evenings with expansive views overlooking the UofL Golf Course, and many sightings of wildlife, especially deer. 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, just a couple of miles from the Outlets of the Bluegrass and access to I-64.

1051 Champions Cir, Simpsonville

$985,000

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

$228,500

Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that has enough seating for 6 or more for those nights of entertaining. Beautiful brand new kitchen cabinets along with butcherblock countertops and shiplap backsplash, bring a cozy cottage feel while the brushed gold fixtures add a modern element. Follow the new LVP floors down the hall to find 2 bedrooms, 2 closets, and a fully updated full bathroom with marble vanity and gold fixtures. Don't miss out Schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ 1723074 MLS

Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that has enough seating for 6 or more for those nights of entertaining. Beautiful brand new kitchen cabinets along with butcherblock countertops and shiplap backsplash, bring a cozy cottage feel while the brushed gold fixtures add a modern element. Follow the new LVP floors down the hall to find 2 bedrooms, 2 closets, and a fully updated full bathroom with marble vanity and gold fixtures. Don't miss out Schedule your showing today!

3936 Aiken Rd, Simpsonville

$1,900,000

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.

4 Beds ⋅ 4 Baths ⋅ 26012052 MLS

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.

22 Timberwood Dr, Simpsonville

$459,900

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 upstairs offer beautiful views and share a generous full bath with a double vanity. The open-concept design seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and effortless entertaining. A conveniently located powder room is tucked just off the hallway, thoughtfully positioned away from the kitchen--and you should see the premium appliances! Every detail has been carefully considered, from the smart layout to the quality finishes, making this home as practical as it is beautiful. Located in the coveted Villas at Cardinal Club community in Simpsonville, this home is nestled in one of the area's most desirable neighborhoods. This is your opportunity to own a brand-new home without a lengthy build timeline. Don't miss your chance to make this beautiful new home yours.

4 Beds ⋅ 3 Baths ⋅ 1722161 MLS

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 upstairs offer beautiful views and share a generous full bath with a double vanity. The open-concept design seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and effortless entertaining. A conveniently located powder room is tucked just off the hallway, thoughtfully positioned away from the kitchen--and you should see the premium appliances! Every detail has been carefully considered, from the smart layout to the quality finishes, making this home as practical as it is beautiful. Located in the coveted Villas at Cardinal Club community in Simpsonville, this home is nestled in one of the area's most desirable neighborhoods. This is your opportunity to own a brand-new home without a lengthy build timeline. Don't miss your chance to make this beautiful new home yours.

1204 Divot Way, Simpsonville

$1,390,000

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 constructed outbuilding. With plenty of room to add a pool, this is truly an entertainer's dream. Inside, the home offers a desirable split-bedroom floor plan and convenient first-floor living. The spacious primary suite features a vaulted ceiling, large walk-in closet, and an ensuite bath complete with a Jacuzzi tub and separate shower. Seller has prepared the home for immediate occupancy with all freshly painted living areas, laundry room and primary bedroom. Stunning! And be sure to check out the large laundry room conveniently located just outside the primary bedroom. The inviting living room showcases a soaring vaulted ceiling and a beautiful fireplace as its focal point. The large kitchen is designed for both everyday living and entertaining, featuring a cooktop, abundant cabinetry, and numerous windows overlooking the picturesque backyard. Central vacuum adds an extra touch of convenience throughout the home. Two additional bedrooms share a full bath on the main level. The finished walkout basement provides endless possibilities with a large open recreation area, a cozy nook perfect for an office or exercise space, an oversized room currently being used as a bedroom, and a full bath. Outside is where this property truly shines. The newly built outbuilding is much more than a standard metal building, featuring attractive stone accents and exceptional functionality. It includes a 50-amp RV hookup, three overhead doors (one 12' x 14' and two 10' x 10'), heating and air conditioning, a storage loft, and ample space for hobbies, business use, vehicle storage, or workshop needs. Attached to the building is a charming one-room apartment complete with a full bath, tongue-and-groove wood walls, fireplace, covered porch, and its own septic system—perfect for guests, a home office, studio space, or rental potential. A second 40' x 60' barn offers even more versatility with a newer roof, updated lighting, water, electric, and a run-in shed. As you make your way toward the pond, you'll discover a treehouse built approximately five years ago that serves as the perfect children's retreat, hunting blind, or private getaway. The scenic pond is complemented by a pavilion that creates a stunning backdrop for gatherings, celebrations, photos, or even a wedding. Generator connection is already in place for lighting and event needs. Explore the winding acreage and you'll feel like you're touring far more than 10 acres, with beautiful trees, abundant wildlife, and breathtaking views around every turn. Properties offering this combination of acreage, amenities, privacy, and versatility rarely become available. Don't miss your opportunity to own this one-of-a-kind Simpsonville retreat.

3 Beds ⋅ 3 Baths ⋅ 1721287 MLS

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 constructed outbuilding. With plenty of room to add a pool, this is truly an entertainer's dream. Inside, the home offers a desirable split-bedroom floor plan and convenient first-floor living. The spacious primary suite features a vaulted ceiling, large walk-in closet, and an ensuite bath complete with a Jacuzzi tub and separate shower. Seller has prepared the home for immediate occupancy with all freshly painted living areas, laundry room and primary bedroom. Stunning! And be sure to check out the large laundry room conveniently located just outside the primary bedroom. The inviting living room showcases a soaring vaulted ceiling and a beautiful fireplace as its focal point. The large kitchen is designed for both everyday living and entertaining, featuring a cooktop, abundant cabinetry, and numerous windows overlooking the picturesque backyard. Central vacuum adds an extra touch of convenience throughout the home. Two additional bedrooms share a full bath on the main level. The finished walkout basement provides endless possibilities with a large open recreation area, a cozy nook perfect for an office or exercise space, an oversized room currently being used as a bedroom, and a full bath. Outside is where this property truly shines. The newly built outbuilding is much more than a standard metal building, featuring attractive stone accents and exceptional functionality. It includes a 50-amp RV hookup, three overhead doors (one 12' x 14' and two 10' x 10'), heating and air conditioning, a storage loft, and ample space for hobbies, business use, vehicle storage, or workshop needs. Attached to the building is a charming one-room apartment complete with a full bath, tongue-and-groove wood walls, fireplace, covered porch, and its own septic system—perfect for guests, a home office, studio space, or rental potential. A second 40' x 60' barn offers even more versatility with a newer roof, updated lighting, water, electric, and a run-in shed. As you make your way toward the pond, you'll discover a treehouse built approximately five years ago that serves as the perfect children's retreat, hunting blind, or private getaway. The scenic pond is complemented by a pavilion that creates a stunning backdrop for gatherings, celebrations, photos, or even a wedding. Generator connection is already in place for lighting and event needs. Explore the winding acreage and you'll feel like you're touring far more than 10 acres, with beautiful trees, abundant wildlife, and breathtaking views around every turn. Properties offering this combination of acreage, amenities, privacy, and versatility rarely become available. Don't miss your opportunity to own this one-of-a-kind Simpsonville retreat.

37 Timberwood Dr, Simpsonville

$325,000

Built in 2022 in the heart of Simpsonville, this beautifully designed home sits on a quiet street with a wooded lot that offers both privacy and charm. This home is currently used as a furnished short term rental but would also be a great full time residence! Step inside to a completely open first floor where the living room, dining area, and kitchen flow seamlessly together - perfect for entertaining. The kitchen features custom wood cabinetry and granite countertops, while a half bath and mechanical closet complete the main level. Upstairs, you'll find two guest bedrooms, a full bathroom, convenient second-floor laundry, and a spacious primary suite with an en suite bath and two closets. Outside, enjoy a deck overlooking the backyard, creating the perfect space to relax or gather with friends and family.

3 Beds ⋅ 3 Baths ⋅ 1718653 MLS

Built in 2022 in the heart of Simpsonville, this beautifully designed home sits on a quiet street with a wooded lot that offers both privacy and charm. This home is currently used as a furnished short term rental but would also be a great full time residence! Step inside to a completely open first floor where the living room, dining area, and kitchen flow seamlessly together - perfect for entertaining. The kitchen features custom wood cabinetry and granite countertops, while a half bath and mechanical closet complete the main level. Upstairs, you'll find two guest bedrooms, a full bathroom, convenient second-floor laundry, and a spacious primary suite with an en suite bath and two closets. Outside, enjoy a deck overlooking the backyard, creating the perfect space to relax or gather with friends and family.

310 E Main St, Simpsonville

$999,999

Welcome home to this exceptional custom property nestled on 7.42 gorgeous acres in the lush green countryside of Shelby County, complete with a secluded solar panel garden . Enjoy lower electric bills while luxuriating in the comfort and functionality of this stunning home featuring 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 dishwashers, abundant cabinetry, and all appliances included—making it ideal for entertaining, holiday gatherings, or everyday living. Enjoy meals in the formal dining room or relax year-round in the bright and inviting sunroom overlooking the peaceful landscape. The first-floor primary suite offers a private retreat complete with a gorgeous ensuite bathroom, while hardwood floors, fresh paint, and thoughtful updates throughout create a move-in-ready experience. The finished walk-out basement provides incredible flexibility with the potential for a mother-in-law suite or separate apartment, featuring additional living space, a second laundry room, an office or bonus room, full bathroom, family room, and plenty of extra storage. Outside, the expansive acreage offers endless opportunities for recreation, gardening, or simply enjoying the beauty and privacy of country living. A solar panel system helps keep electric costs lower, adding energy efficiency and long-term savings to this remarkable property. With two laundry rooms, abundant storage, versatile living spaces, and breathtaking surroundings, this one-of-a-kind Shelby County home offers the perfect combination of elegance, practicality, and peaceful country living.

5 Beds ⋅ 5 Baths ⋅ 1717809 MLS

Welcome home to this exceptional custom property nestled on 7.42 gorgeous acres in the lush green countryside of Shelby County, complete with a secluded solar panel garden . Enjoy lower electric bills while luxuriating in the comfort and functionality of this stunning home featuring 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 dishwashers, abundant cabinetry, and all appliances included—making it ideal for entertaining, holiday gatherings, or everyday living. Enjoy meals in the formal dining room or relax year-round in the bright and inviting sunroom overlooking the peaceful landscape. The first-floor primary suite offers a private retreat complete with a gorgeous ensuite bathroom, while hardwood floors, fresh paint, and thoughtful updates throughout create a move-in-ready experience. The finished walk-out basement provides incredible flexibility with the potential for a mother-in-law suite or separate apartment, featuring additional living space, a second laundry room, an office or bonus room, full bathroom, family room, and plenty of extra storage. Outside, the expansive acreage offers endless opportunities for recreation, gardening, or simply enjoying the beauty and privacy of country living. A solar panel system helps keep electric costs lower, adding energy efficiency and long-term savings to this remarkable property. With two laundry rooms, abundant storage, versatile living spaces, and breathtaking surroundings, this one-of-a-kind Shelby County home offers the perfect combination of elegance, practicality, and peaceful country living.

401 Old Stone Dr, Simpsonville