Rankinluxerealtygroup.com Search Results

$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 ⋅ 1727868 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

Listing courtesy of Julie Pogue Properties.

$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

Listing courtesy of Covenant Realty LLC.

$340,000

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, 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, 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

Listing courtesy of United Real Estate Louisville.

$875,000

Beautiful 4 bedroom, 3.5 bath Ranch home sits on over 1.5 acres. The entire acreage has been beautifully landscaped complete with an inground saltwater pool , low-maintenance composite decking, fencing around pool area. When you enter the home from the front door you are welcomed in a large foyer which looks directly though the Great Room onto the pool area. The home is full of natural light with the many windows and French doors which lead to the deck and pool area. As you walk through the great room you reach the stunning designer eat-in kitchen with breakfast bar, informal dining area, a large pantry and a cathedral ceiling sunroom which also overlooks the pool. First floor primary suite offers a large walk-in closet and dual vanities. First floor laundry room offers extra storage. Main

3 Beds ⋅ 4 Baths ⋅ 1727052 MLS

Beautiful 4 bedroom, 3.5 bath Ranch home sits on over 1.5 acres. The entire acreage has been beautifully landscaped complete with an inground saltwater pool , low-maintenance composite decking, fencing around pool area. When you enter the home from the front door you are welcomed in a large foyer which looks directly though the Great Room onto the pool area. The home is full of natural light with the many windows and French doors which lead to the deck and pool area. As you walk through the great room you reach the stunning designer eat-in kitchen with breakfast bar, informal dining area, a large pantry and a cathedral ceiling sunroom which also overlooks the pool. First floor primary suite offers a large walk-in closet and dual vanities. First floor laundry room offers extra storage. Main

9929 Shelbyville Rd, Simpsonville

Listing courtesy of Palazzo REALTORS, LLC.

$349,900

Enjoy the peace and privacy of a country setting with no HOA in this well-maintained 3-bedroom, 1.5-bath home on a spacious .36-acre lot. Built and lovingly maintained by the original owner, this move-in-ready property offers comfort, functionality, and plenty of versatile space. The updated kitchen and bathroom provide a fresh, modern feel, while the partially finished basement offers additional room for a family or recreation area, home office, hobbies, or storage. Outside, the large covered deck is perfect for relaxing or entertaining while enjoying the peaceful surroundings. Parking and storage are abundant with a 1-car attached garage and an additional 2-car detached garage, each served by its own driveway. With its peaceful country setting, desirable updates, flexible basement space, multiple garage options, and no HOA, this home is ready for its next owner to move right in and make it their own!

3 Beds ⋅ 2 Baths ⋅ 1726400 MLS

Enjoy the peace and privacy of a country setting with no HOA in this well-maintained 3-bedroom, 1.5-bath home on a spacious .36-acre lot. Built and lovingly maintained by the original owner, this move-in-ready property offers comfort, functionality, and plenty of versatile space. The updated kitchen and bathroom provide a fresh, modern feel, while the partially finished basement offers additional room for a family or recreation area, home office, hobbies, or storage. Outside, the large covered deck is perfect for relaxing or entertaining while enjoying the peaceful surroundings. Parking and storage are abundant with a 1-car attached garage and an additional 2-car detached garage, each served by its own driveway. With its peaceful country setting, desirable updates, flexible basement space, multiple garage options, and no HOA, this home is ready for its next owner to move right in and make it their own!

5648 Fisherville Rd, Simpsonville

Listing courtesy of Keller Williams Collective.

$1,699,000

Welcome to 2259 Taylor Wood Road in Simpsonville, Kentucky. This stunning custom home sits on 6 private acres with no HOA, offering the perfect blend of luxury, privacy, and space in the heart of Shelby County. Built in 2023, this home features 4,731 square feet above grade with 5 bedrooms, a bonus room, 3 full bathrooms and 2 half baths. From the moment you step inside you will notice the soaring ceilings, luxury finishes, and upscale appliances throughout. The builder truly spared no expense when designing this home. A standout feature of the property is the private mother in law suite with its own exterior entrance, creating the perfect setup for extended family, guests, or anyone wanting their own private wing of the home. The walkout basement offers more than 3,000 additional square feet and incredible potential. Once finished, this home could easily offer over 8,000 square feet of total living space. If you are looking for a nearly new luxury home on acreage with privacy, flexibility, and room to grow, 2259 Taylor Wood Road is a rare opportunity.

5 Beds ⋅ 5 Baths ⋅ 1727001 MLS

Welcome to 2259 Taylor Wood Road in Simpsonville, Kentucky. This stunning custom home sits on 6 private acres with no HOA, offering the perfect blend of luxury, privacy, and space in the heart of Shelby County. Built in 2023, this home features 4,731 square feet above grade with 5 bedrooms, a bonus room, 3 full bathrooms and 2 half baths. From the moment you step inside you will notice the soaring ceilings, luxury finishes, and upscale appliances throughout. The builder truly spared no expense when designing this home. A standout feature of the property is the private mother in law suite with its own exterior entrance, creating the perfect setup for extended family, guests, or anyone wanting their own private wing of the home. The walkout basement offers more than 3,000 additional square feet and incredible potential. Once finished, this home could easily offer over 8,000 square feet of total living space. If you are looking for a nearly new luxury home on acreage with privacy, flexibility, and room to grow, 2259 Taylor Wood Road is a rare opportunity.

2259 Taylor Wood Rd, Simpsonville

Listing courtesy of Lenihan Sotheby's Int'l Realty.

$730,000

Beautiful custom-built 1.5-story home in desirable Cardinal Club Estates. This home features an open floor plan great for entertaining, current finishes, and abundant natural light. The spacious kitchen offers beautiful cabinets, huge island, walk-in pantry, additional pantry, and opens to the living and dining areas. The first-floor primary suite includes a private bath, large closet, and access to the partially covered deck.Upstairs are three large bedrooms, two share a Jack and Jill bath and one has an ensuite bath. One bedroom has additional attic storage. The partially finished basement includes lots of natural light, new carpet and LVP flooring, a bar area, flex room, backyard access, and an unfinished area that allows for storage or future expansion. This home provides energy efficiency with a zoned HVAC system. The back yard is bordered by mature evergreen trees and backs up to an open green space. This home enjoys a neighborhood setting with golf course and pool available through membership.

4 Beds ⋅ 5 Baths ⋅ 1726826 MLS

Beautiful custom-built 1.5-story home in desirable Cardinal Club Estates. This home features an open floor plan great for entertaining, current finishes, and abundant natural light. The spacious kitchen offers beautiful cabinets, huge island, walk-in pantry, additional pantry, and opens to the living and dining areas. The first-floor primary suite includes a private bath, large closet, and access to the partially covered deck.Upstairs are three large bedrooms, two share a Jack and Jill bath and one has an ensuite bath. One bedroom has additional attic storage. The partially finished basement includes lots of natural light, new carpet and LVP flooring, a bar area, flex room, backyard access, and an unfinished area that allows for storage or future expansion. This home provides energy efficiency with a zoned HVAC system. The back yard is bordered by mature evergreen trees and backs up to an open green space. This home enjoys a neighborhood setting with golf course and pool available through membership.

201 Champions Way, Simpsonville

Listing courtesy of Covenant Realty LLC.

$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 a 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 a 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

Listing courtesy of Realty Advanced.

$305,000

Welcome to this charming ranch home in the heart of downtown Simpsonville on a quiet cul de sac street. Featuring 3 bedrooms and 2 full baths, this home offers comfortable one-level living with thoughtful updates throughout. The remodeled kitchen provides a fresh, inviting space for cooking and gathering, while newer flooring and updated interior lighting create a bright, modern feel. The spacious primary suite features an updated en-suite bath. Outside, enjoy a large fenced backyard with a deck that's perfect for entertaining, relaxing, or enjoying your morning coffee. Additional highlights include a 2-car garage and a roof replaced in 2024. Conveniently located close to the shops, restaurants, and charm of downtown Simpsonville, this move-in-ready home is one you won't want to miss!

3 Beds ⋅ 2 Baths ⋅ 1726090 MLS

Welcome to this charming ranch home in the heart of downtown Simpsonville on a quiet cul de sac street. Featuring 3 bedrooms and 2 full baths, this home offers comfortable one-level living with thoughtful updates throughout. The remodeled kitchen provides a fresh, inviting space for cooking and gathering, while newer flooring and updated interior lighting create a bright, modern feel. The spacious primary suite features an updated en-suite bath. Outside, enjoy a large fenced backyard with a deck that's perfect for entertaining, relaxing, or enjoying your morning coffee. Additional highlights include a 2-car garage and a roof replaced in 2024. Conveniently located close to the shops, restaurants, and charm of downtown Simpsonville, this move-in-ready home is one you won't want to miss!

504 Garden Ct, Simpsonville

Listing courtesy of First Saturday Real Estate.

$249,900

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

Listing courtesy of 3C Property Management LLC.

$749,000

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

Listing courtesy of Keller Williams Collective.

$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

Listing courtesy of Segrest Flaherty Realtors LLC.

$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

Listing courtesy of EXP Realty LLC.

$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

Listing courtesy of Torrey Smith Realty Co., LLC.

$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

Listing courtesy of Weichert Realtors-H. Barry Smith Co..

$14,000,000

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.

7 Beds ⋅ 3 Baths ⋅ 1719199 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

Listing courtesy of Fathom Realty Ky LLC.

$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

Listing courtesy of Lenihan Sotheby's Int'l Realty.

$1,100,000

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

Listing courtesy of Keller Williams Collective.