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$1,650,000
5 Beds ⋅ 6 Baths ⋅ 1724741 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.

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

1219 Taylor Wood Rd, Simpsonville

Listing courtesy of Segrest Flaherty Realtors LLC.

$1,650,000
5 Beds ⋅ 6 Baths ⋅ 1723681 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.

$205,000
2 Beds ⋅ 2 Baths ⋅ 1723543 MLS
This 2BR/1.5BA patio home offers 1,004 sq ft of comfortable living in one of Simpsonville's most desirable condo communities. Enjoy resort-style amenities including a clubhouse, fitness center, stocked pond, and picnic areas, all covered by your HOA. Ideally located minutes from I-64, the Outlet Shoppes of the Bluegrass, and award-winning Shelby County schools. Sellers are motivated and eager, bring your offer! Whether you're downsizing or buying your first home, this is the value play in the neighborhood. Schedule your showing today before it's gone!

853 Garden Pointe Dr, Simpsonville

Listing courtesy of Parkside Realty.

$315,000
3 Beds ⋅ 3 Baths ⋅ 1723399 MLS
Some homes simply feel right the moment you pull into the driveway—and this Rolling Ridge beauty is one of them. Thoughtfully updated from top to bottom, this 3-bedroom, 2.5-bath home offers the perfect balance of timeless style and functional living. At the heart of the outdoor space is a brand-new oversized deck that's ready for everything from quiet mornings with a cup of coffee to evenings spent grilling with friends. The fully fenced backyard provides plenty of room for pets, play, or simply enjoying your own private outdoor retreat. Inside, you'll find updates throughout that make this home truly move-in ready, while a brand-new roof offers peace of mind for years to come. The attached two-car garage provides ample storage and convenience, and the home's inviting layout is designed to fit both everyday living and entertaining with ease. Located in the sought-after Rolling Ridge neighborhood, you'll love being just minutes from Simpsonville's local favorites, the Outlet Shoppes of the Bluegrass, I-64, and everything Shelby County has to offer. Homes that combine this level of care, thoughtful updates, and an unbeatable location don't come along often—come see what makes this one so special.

1213 Evergreen Way, Simpsonville

Listing courtesy of Torrey Smith Realty Co., LLC.

$249,500
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.

$449,900
5 Beds ⋅ 3 Baths ⋅ 1722355 MLS
Welcome to 416 Buckman Station Court in Simpsonville, KY, where comfort, space, and outdoor living come together! This beautiful five-bedroom, three full-bath ranch offers a desirable split-bedroom floor plan and a finished walkout basement designed for entertaining. The spacious lower level features soaring ceilings, a custom bar, and a pool table area, creating the perfect space for gatherings. Situated on a peaceful lakefront lot at the end of a cul-de-sac, you'll enjoy beautifully landscaped grounds, wooded views, abundant wildlife, an above-ground pool, and a hot tub—your own private backyard retreat. Imagine spending your days relaxing by the pool, unwinding in the hot tub under the stars, casting a fishing line after dinner, and watching deer and other wildlife right from your backyard. Conveniently located in the heart of Simpsonville, this home offers quick access to the interstate, shopping, dining, and everything this sought-after community has to offer. Don't miss your opportunity to own this exceptional property that offers the perfect balance of everyday comfort and resort-style living. If you're trying to make buyers feel the lifestyle, this version paints that picture while still being appropriate for MLS remarks.

416 Buckman Station Ct, Simpsonville

Listing courtesy of Brown Realty.

$489,900
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. 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. Construction is expected to be completed in approximately 30 days, providing the opportunity to own a brand-new home without a lengthy build timeline. BONUS: $6000 Appliance Allowance! Don't miss your chance to make this beautiful new home yours.

1204 Divot Way, Simpsonville

Listing courtesy of Torrey Smith Realty Co., LLC.

$249,900
3 Beds ⋅ 2 Baths ⋅ 1721636 MLS
Welcome to this 3-bedroom, 2-bath ranch offering convenient one-level living with approximately 1,372 sq ft. The home features a spacious kitchen, dining area, first-floor laundry, and a primary bedroom with private bath. Outside, enjoy a fenced backyard, patio, front porch, and driveway parking. Solar panels add an energy-conscious feature; buyer to verify ownership, lease terms, transfer requirements, and any related obligations. Conveniently located near the heart of Simpsonville with quick access to US-60, local shops, and nearby amenities. A solid opportunity with space, comfort, and small-town charm.

313 E Main St, Simpsonville

Listing courtesy of Re/Max Five Star Properties.

$1,499,900
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..

$218,900
2 Beds ⋅ 2 Baths ⋅ 1721255 MLS
Per the development plan, this is the largest unit in the complex. Custom built as handicapped accessible but these modifications would benefit anyone- wider hallways and door openings, step-in primary tiled shower with very low barrier, no steps into unit, etc. This rear corner unit means privacy for the fenced patio that many units don't have. One owner since new. You will find a very livable floorplan with good closet space and large bedrooms. The kitchen and breakfast area are open with a nice laundry room off the kitchen. Trey ceilings and several builder upgrades. Being sold to settle an estate. Unit is in good condition but estate is selling as-is. There is a clubhouse and fitness room on site. Only 66 garden-style units here. Professionally managed.

850 Garden Pointe Dr, Simpsonville

Listing courtesy of THINK Real Estate LLC.

$214,000
2 Beds ⋅ 2 Baths ⋅ 1721151 MLS
Nice 2 bedroom condo conveniently located in the desirable town of Simpsonville. This condo features 2 bedrooms, Family room with tray ceiling, eat-in Kitchen, laundry room and 1.5 baths. The buyer of this condo unit can enjoy time outside on the covered front porch or the private back yard.

816 Garden Pointe Dr, Simpsonville

Listing courtesy of Coldwell Banker Larry Rogers.

$1,174,500
4 Beds ⋅ 4 Baths ⋅ 1720268 MLS
5 Acres, Two Homes, Zero Compromises: Simpsonville's Most Versatile Estate Some properties check a box. This one checks all of them, and then hands you a barn, a guest house, and a lifestyle nobody else is offering in Shelby County. Set on 5.07 gorgeous acres just minutes from the Outlet Shoppes and downtown Shelbyville, 1799 Veechdale Rd is a rare package: a beautifully updated main home, a fully accessible guest house, and a barn built for real horsepower, all wrapped in blackboard fencing and orchard-grass pastures that would make any hobby farmer's heart skip The Main House Step into a great room warmed by a gas fireplace, flowing into a chef's kitchen with granite counters, a generous bar, and, yes, we're saying it twice, a butler's pantry with walk-in storage. The main-level primary suite offers a true retreat with walk-in closet and private bath, while a formal dining room and flexible den round out a layout made for entertaining and everyday life alike. Upstairs, two more bedrooms and a full bath give family or guests their own space. The Guest House: Built for Real Life Connected by a covered deck, this isn't a converted garage or an afterthought. It's a purpose-built, 840-sq-ft accessible living space with a wide-door ramp entry, zero-entry shower, full kitchen, living room, laundry, and an unfinished second level ready for your vision. Whether it's aging parents, adult kids, a live-in caregiver, or rental income, this home solves the problem most buyers spend years searching for. The Barn & Grounds This is where the property goes from "nice acreage" to "how did we get so lucky." A heated and air-conditioned office with its own full bath, stalls, equipment storage, and a loft ready to be finished into a workshop, studio, or additional living space, all connected by a covered breezeway. Add in the blackboard fencing and orchard-grass pastures (previously home to prize-winning alpacas), and you've got a genuine Kentucky horse property. Why This Home Just Works • 4 separate HVAC systems: 2 for the main house, 1 for the guest house, 1 mini-split for the barn office • Fully encapsulated crawl spaces under both the main house and guest house for serious energy efficiency • Maintenance-free Trex decking connecting both living spaces • Buried propane tank • Dedicated irrigation spigot keeping the front landscaping picture-perfect • Main house/guest house and barn each on their own separate septic systems • Professionally landscaped throughout There's even a 2-page history document detailing the property's updates and improvements over the years, just ask your agent for a copy. Homes like this don't come up twice. Schedule your showing and come see what's possible on 5 acres.

1799 Veechdale Rd, Simpsonville

Listing courtesy of EXP Realty LLC.

$14,000,000
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.

$649,900
5 Beds ⋅ 4 Baths ⋅ 1719127 MLS
Ideally located between Louisville and Lexington, Simpsonville combines small-town charm with convenient access to shopping, dining, and I-64. Nestled in the heart of Kentucky's renowned horse country, you'll enjoy scenic rolling landscapes, beautiful horse farms, and a peaceful setting just minutes from modern conveniences. Situated in the highly desirable Cardinal Club Estates Golf Community, this exceptional 5-bedroom, 3.5-bath home offers luxury living with stunning views overlooking the 13th hole. Relax on the back patio and take in breathtaking sunsets across the fairway. Designed for both comfortable everyday living and effortless entertaining, the open-concept floor plan features hardwood flooring, soaring ceilings in the great room, a cozy fireplace, elegant crown molding, and a formal dining room. The spacious kitchen is a chef's dream with granite countertops, raised-panel maple cabinetry, and abundant workspace. The first-floor primary suite is a private retreat, complete with custom built-ins, a beautiful en-suite bath, and a walk-in closet featuring California Closets. Throughout the home, you'll appreciate the exceptional closet space and abundant storage, offering a place for everything and keeping everyday living organized and clutter-free. Upstairs, you'll find three generously sized bedrooms and a full bath, providing ample space for family and guests. The finished walkout basement offers even more living space with a large family room, fifth bedroom, and full bath—perfect for guests, recreation, a home office, or multi-generational living. Don't miss this opportunity to own a beautiful golf course home in one of Shelby County's premier communities. Schedule your private showing today!

209 Champions Way, Simpsonville

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

$325,000
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.

$259,900
2 Beds ⋅ 2 Baths ⋅ 1718474 MLS
Beautifully Updated Patio Home With Garage In The Gardens Of Station Pointe - Wonderful Low-Maintenance Living In The Heart of Simpsonville! Remodeled Kitchen With White & Gray Cabinetry With Quartz Countertops & Backsplash And Upgraded Stainless Steel Appliances. Luxury Vinyl Plank Flooring Throughout ~ No Carpet. Spacious Living Room Plus A Sunroom Off The Kitchen With Peaceful Wooded Views & Cozy Fireplace. Updated Bathrooms, Including a Walk-In Shower, Modern Vanities & Comfort-Height Commodes. Private Patio With Awning—Perfect For Relaxing Or Entertaining! New Triple Pane Windows. New Storm Doors. Updated HVAC & Water Heater. Garage. Attic Storage W/New Pull-Down Stairs. New Lighting. Non-Slip Epoxy Coat On Garage Floor & Patio. Low Utilies. The Upgrades Are Complete—Just Move In!

801 Garden Pointe Dr, Simpsonville

Listing courtesy of Real Broker, LLC.

$1,100,000
5 Beds ⋅ 5 Baths ⋅ 1717809 MLS
Welcome home to this exceptional custom property nestled on 7.42 picturesque acres in the lush green countryside of Shelby County. Offering the perfect blend of luxury, comfort, and functionality, this stunning home features 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.

$915,000
4 Beds ⋅ 5 Baths ⋅ 1716373 MLS
*NEW PRICE* Welcome to a truly extraordinary estate in Simpsonville, KY where luxury, space, and timeless elegance come together on more than 5 breathtaking acres. From the moment you arrive, the grand scale and stunning curb appeal make an unforgettable impression. This custom home was designed for those who appreciate refined living, exceptional entertaining spaces, and the flexibility for multi-generational living. Inside, the home feels grand at every turn. A dramatic double staircase and soaring entryway set the tone for the incredible craftsmanship and spacious design throughout. The spectacular two-story great room is filled with natural light and offers a striking focal point for gatherings both large and small. Rich flooring, updated lighting, and thoughtfully selected finishes create an elevated yet welcoming atmosphere. The beautifully updated kitchen is a dream for both everyday living and entertaining, featuring stylish cabinetry, modern finishes, generous prep space, and an oversized walk-in pantry that offers exceptional storage and functionality. Multiple dining and gathering areas provide endless possibilities for hosting family holidays, celebrations, and guests with ease. This remarkable home features two luxurious primary suites, including one on the main level and another on the second floor, making it ideal for multi-generational living, extended guests, or those seeking ultimate flexibility and comfort. The finished walkout basement expands the living space even further with an impressive entertainment area and a dedicated media room complete with a newer projector and screen, creating the perfect private theater experience right at home. Step outside and prepare to fall in love with the incredible outdoor living spaces. Expansive patios, decks, and beautifully landscaped green space provide endless opportunities for entertaining, relaxing, gardening, recreation, or simply enjoying the peaceful surroundings. With over five acres, there is room to create the lifestyle you've always imagined. This is more than just a home — it is a private estate designed for making memories, hosting loved ones, and enjoying luxury living at its finest.

451 Todd Dr, Simpsonville

Listing courtesy of Keller Williams Collective.

$949,750
4 Beds ⋅ 4 Baths ⋅ 1714873 MLS
Welcome to one of Simpsonville's most versatile luxury properties, where beautifully renovated living spaces, exceptional craftsmanship, and a rare 30x60 insulated shop come together on a private, beautifully landscaped homesite. This move-in-ready estate offers over 4,500 finished square feet designed for both everyday comfort and entertaining. The completely renovated kitchen features custom cabinetry, granite countertops, double ovens, a prep sink, and an oversized pantry, flowing seamlessly into spacious living areas with refinished and newly installed hardwood flooring throughout. The finished walkout lower level provides incredible flexibility with its own private entrance, kitchenette, full bath, and laundry hookups—ideal for multigenerational living, extended guests, a private office, or future income potential. The detached 1,800-square-foot insulated shop is a standout feature rarely found in this market. Complete with HVAC, plumbing, office space, bathroom, 100-amp electrical service, and a separate driveway, it offers endless possibilities for business owners, car enthusiasts, hobbyists, or anyone needing premium workspace. Outside, you'll enjoy a thoughtfully improved property featuring new fencing, expanded patios, an enclosed rear porch, mature landscaping with 88 evergreen trees, and fruit-bearing plantings that create exceptional privacy without the maintenance of a large farm. Nearly every major surface and system has been updated, including renovated bathrooms, hardwood flooring, lighting, paint, doors, windows, insulation, security enhancements, and countless additional improvements—allowing the next owner to simply move in and enjoy. If you've been searching for a property that combines luxury living, flexible space, and an exceptional workshop in one of Shelby County's most desirable locations, this home deserves your attention. Seller is a licensed real estate broker in Kentucky and Indiana.

1948 Todds Point Rd, Simpsonville

Listing courtesy of Move With Me Realty.

$230,000
2 Beds ⋅ 2 Baths ⋅ 1713711 MLS
Seller offering a $2000 Credit towards Buyers closing and or prepaid!!! Welcome home to this beautifully maintained patio home in the sought-after Gardens of Station Pointe community. Featuring a spacious family room with a cozy fireplace, a separate private living room, and you own private patio retreat. This home offers a lifestyle that's both comfortable and refined. Abundant storage throughout means this home lives much larger than its footprint. Low maintenance living is the theme - enjoy life while the HOA handles the exterior upkeep. Community amenities include a beautiful clubhouse for entertaining and a fully equipped exercise room, all just steps from your door. Located in charming Simpsonville - the heart of Kentucky's celebrated bluegrass horse country - and just minutes the Outlets of the Bluegrass, where name-brand shopping, entertainment, and great dining await.

828 Garden Pointe Dr, Simpsonville

Listing courtesy of Abbot Realty & Auction.

$1,699,000
5 Beds ⋅ 5 Baths ⋅ 1710983 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.

$5,439,000
4 Beds ⋅ 2 Baths ⋅ 1680398 MLS
Located just minutes away from Simpsonville and the Jefferson Co. line, this beautiful pristine farm offers all the amenities of country living along with the convenience of urban benefits. With almost 156 acres of rolling ground, there are limitless opportunities. The historic farm home features 4 BRs and 1.5 baths with almost all original hardwood flooring throughout. Spend the mornings and evenings on the covered porch enjoying the gorgeous views. Currently being used as a short term rental, this property has limitless possibilities. It also has two large ponds, along with over 2300' of frontage on Plum Creek. There are 3 platted five acre tracts included in the total acreage. An equipment barn built in 2018 is the perfect place to store your things. Don't miss this one!

4260 Fisherville Rd, Simpsonville

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