Simpsonville Homes for Sale

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.

$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..

$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..

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