Simpsonville Real Estate

Simpsonville Real Estate

Welcome to Simpsonville, Kentucky – a charming town nestled in the heart of Shelby County, where Southern hospitality meets modern convenience. With its picturesque landscapes and vibrant community spirit, Simpsonville offers a unique blend of small-town charm and accessibility to urban amenities.

Simpsonville is strategically located just off Interstate 64, providing easy access to the bustling city of Louisville, which is only a short drive away. This prime location means residents can enjoy the tranquility of suburban life while still being close to the cultural and entertainment offerings of a major city. Known for its friendly atmosphere, Simpsonville boasts a strong sense of community, making it an ideal place for families, retirees, and young professionals alike.

The town is home to beautiful parks, including the popular Simpsonville Park, where families can enjoy picnics, playgrounds, and walking trails. The local schools are highly regarded, ensuring that children receive a quality education in a nurturing environment. Additionally, the town hosts various community events throughout the year, fostering connections among residents and celebrating the local culture.

With a growing number of shops, restaurants, and services, Simpsonville continues to evolve while maintaining its quaint charm. Whether you’re looking for a cozy home in a friendly neighborhood or a place to start a new chapter, Simpsonville offers a welcoming environment that feels like home. Explore the possibilities in this delightful Kentucky town, where every day is an opportunity to embrace the beauty of life in Shelby County!

Newest Listings in Simpsonville

$305,000
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
$1,550,000
5 Beds ⋅ 6 Baths ⋅ 1725855 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
$875,000
3 Beds ⋅ 4 Baths ⋅ 1725835 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 floor also offers 2 additional bedrooms connected by a jack and jill bathroom. Downstairs, you will find a great family room complete with a gas fireplace, wet bar, build in beverage fridge which is perfect for entertaining. A 4th bedroom and full bath complete the finished portion of the lower level. There is plenty of storage area and unfinished square footage to create any additional spaces you desire.

9929 Shelbyville Rd, Simpsonville
$267,000
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
$749,000
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
$2,950,000
4 Beds ⋅ 5 Baths ⋅ 1722813 MLS
Turning off Chesterfield Way onto the newly sealed blacktop driveway, the pace of life immediately begins to slow. The drive winds through rolling pasture, four-board fencing, and across a picturesque tree-lined stream before arriving at the iron entrance gates. Beyond them, mature trees frame both sides of the lane, creating a beautiful approach that feels like a welcome home every time you arrive. This is more than a home it's a private estate encompassing over 43 acres of peaceful Western Shelby County countryside, where open pasture, eleven acres of mature timber, a winding creek with natural stone banks, a tranquil pond, and miles of natural beauty create a setting that feels far removed from the everyday. Ten acres of woods have recently been cleared and mulched, making it easy to explore the property, enjoy the creek, or simply take in the privacy, all while being just five minutes from Simpsonville and only twenty minutes from Louisville. Meticulously maintained, the home blends timeless design with thoughtful updates. The soaring two-story great room is filled with natural light, while new Andersen doors open to a covered porch and a recently built deck overlooking the backyard. The kitchen has been refreshed with countertops, a backsplash, and a gas cooktop supplied by a newly installed gas line, creating a space equally suited for everyday meals or entertaining a full house. The first-floor primary suite serves as a private retreat with bay windows overlooking the backyard, engineered wood flooring, motorized blinds, a spa-inspired bath, and a dressing room centered around a custom island. Upstairs are two additional bedrooms and a loft, while the finished walkout basement offers a spacious family room, wet bar, game room with pool table, fitness room, and a fourth bedroom tucked behind sliding barn doors. French doors lead directly to the backyard, seamlessly connecting indoor and outdoor living. The outdoor amenities rival those of a private resort. The in-ground pool features a tanning shelf and four elegant fountains, while the nearby timber pavilion with its impressive stone fireplace provides the perfect gathering place long after the sun goes down. Guests can enjoy complete privacy in the carriage house, which includes a one-bedroom apartment with its own kitchen, bathroom, laundry, and covered veranda. Attached is a 43-foot climate-controlled show garage with durable polyurea flooring. The property also includes a 36x60 tool shed, farm and 4-board fencing, and deed restrictions that allow horses and barns. Major improvements have already been completed, including geothermal heating with a new exchanger and coils, a 2019 roof, new windows and Andersen doors, resurfaced pool deck and porches, a repaved entrance and driveway, an 18-foot automatic front gate with a sensor, and a pond aerator. Public water, septic service, and no HOA dues complete this truly exceptional property. Plat and restrictions are attached.

486 Chesterfield Way, Simpsonville
$174,900
2 Beds ⋅ 2 Baths ⋅ 1724743 MLS
Come check out this cute 2 Bedroom/1 Full and 1 Half Bath Condo in The Gardens of Station Pointe. Home consists of a Living Room, Eat-in Kitchen, 1 Full Bath and 1 Half Bath/Laundry Room Combo. Nice privacy fenced patio off the Kitchen for your outdoor enjoyment. Stop by today before this one is SOLD!

799 Garden Pointe Dr, Simpsonville
$985,000
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
$235,000
2 Beds ⋅ 1 Baths ⋅ 1723074 MLS
Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that has enough seating for 6 or more for those nights of entertaining. Beautiful brand new kitchen cabinets along with butcherblock countertops and shiplap backsplash, bring a cozy cottage feel while the brushed gold fixtures add a modern element. Follow the new LVP floors down the hall to find 2 bedrooms, 2 closets, and a fully updated full bathroom with marble vanity and gold fixtures. Don't miss out Schedule your showing today!

3936 Aiken Rd, Simpsonville
$1,900,000
4 Beds ⋅ 4 Baths ⋅ 26012052 MLS
Exceptional opportunity in desirable Timberwood Farms. Situated on approx. 10 acres, this impressive property offers space, privacy, and a prime Simpsonville location with convenient access to I-64, Shelbyville, and Louisville.

22 Timberwood Dr, Simpsonville
$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
$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
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