30 - Shelby County Homes with Outside Entry Basement

30 - Shelby County Homes with Outside Entry Basement

Welcome to Shelby County, Kentucky! Located in the heart of the Bluegrass State, Shelby County offers a unique blend of small-town charm and modern amenities. With its picturesque landscapes, rich history, and friendly community, it's no wonder why so many people are choosing to call this region home.

One of the standout features of Shelby County's real estate market is the abundance of homes with outside entry basements. Whether you're looking for additional living space, a home office, or a place to entertain guests, these homes provide the perfect solution. With an outside entry basement, you have the flexibility to use the space in a way that suits your needs, making it a popular choice among homeowners.

Aside from its impressive housing options, Shelby County boasts a variety of recreational activities for residents to enjoy. From exploring the scenic trails at Red Orchard Park to tee-ing off at the Shelbyville Country Club, there's something for everyone here. The Shelby County Fair, held annually, is a highlight of the community, offering fun rides, delicious food, and entertaining shows for all ages.

In terms of education, Shelby County is home to excellent schools, providing a top-notch learning environment for students of all ages. The county also offers convenient access to healthcare facilities, ensuring that residents have access to quality medical care when needed.

Whether you're a first-time homebuyer or looking to upgrade to a larger property, Shelby County has a diverse range of real estate options to suit every taste and budget. With its charming atmosphere, beautiful landscapes, and welcoming community, Shelby County is a fantastic place to call home.

Newest 30 - Shelby County Homes with Outside Entry Basement

2 Beds ⋅ 1 Baths ⋅ 1724164 MLS

Move right in and enjoy the updates, space, and possibilities offered at 203 Cardinal Drive. Situated on a mostly private half-acre lot in Simpsonville, this charming Bedford stone ranch features 2 bedrooms, 1 full bathroom, 1,038 square feet of main-level living, and a full unfinished walkout basement ready for future expansion. Inside, the home has been refreshed with new LVP flooring and updated lighting throughout. The remodeled kitchen features new cabinetry, countertops, and appliances, while the removal of a wall created an open and inviting connection between the kitchen and living room. The result is a bright, comfortable layout that works well for both everyday living and entertaining. A new HVAC system was installed in December 2025, adding even more peace of mind. The full unfinished walkout basement provides an abundance of storage and offers plenty of room to create additional living space in the future. Whether you envision a family room, home office, fitness area, hobby space, or one or two potential additional bedrooms, the possibilities are endless. One of the home's most unique features is the large glass-enclosed carport. Use it for covered parking, a relaxing sunroom, an entertaining area, or a bright space for plants and hobbies. Outside, the spacious yard offers mature shade trees, room for a garden, space to play or entertain, and a large shed for tools, equipment, and additional storage. Combining recent updates, classic Bedford stone character, a flexible walkout basement, and a beautiful lot with room to grow, this home is ready for its next chapter.

203 Cardinal Dr, 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

2 Beds ⋅ 1 Baths ⋅ 1723664 MLS

Are you ready to get away from a busy lifestyle for a while, slow down and appreciate nature? Kick back and enjoy a slow morning on the deck with your coffee and the wildlife wakes up around you. Here is your chance to own 78 acres of seclusion in the peace and quiet of country living in Shelby County. As you enter the property you'll drive over a beautiful creek. The property is mostly wooded with a few open fields. There are ravines and streams throughout. Nestled toward the top of the hill you have a wonderful log cabin. This is a lovely country setting with all the conveniences of home. This can easily be a full time residence or a weekend retreat. This property is in 4 separate tracts with a shared entrance. This cabin is 1.5 stories, 2 bedrooms, 1 bath on a basement with outside entrance. Inside has an open Kitchen and Family Rm with wood-burning stove. Kitchen has nice granite countertop, bar area for additional seating. A loft great for office or additional living space. Kitchen appliances and washer/dryer can remain. A metal 24x32 pole barn is also located on the property. All this and just 3 miles from Waddy/Peytona exit #43 on Bardstown Trail.

5191 Bardstown Trail, Waddy

3 Beds ⋅ 3 Baths ⋅ 1723591 MLS

329 Comanche Road - where classic brick architecture, generous space, and easy living come together in one of Shelbyville's most desirable neighborhoods: Town N Country. Set on a beautifully landscaped lot, this all-brick 3 bedroom, 3 bath home offers impressive style and flexibility. Much of the interior has just been painted in a fresh, neutral palette, and several new light fixtures give the home an updated, move-in-ready feel from the moment you walk in. You're welcomed by a formal entry with gleaming hardwood floors. To the left, the living room feels bright and airy with its vaulted ceiling and striking palladium window overlooking the manicured front yard. The living room flows directly into the formal dining room—also with hardwood floors—creating a great setup for gatherings, holidays, or quiet dinners at home. The kitchen is built for real life and real cooking: generous cabinet space, sizeable pantry, granite countertops, travertine backsplash, center island, eat-in area, under-cabinet and recessed lighting, and ceramic tile floors. A large bay window overlooks the beautifully landscaped back yard and fills the space with natural light, making it a comfortable spot for everyday meals. Just off the kitchen is a spacious family room that manages to feel both polished and relaxed. It features a tray ceiling, built-in bookcases, wainscoting, and a brick fireplace with gas logs. The hardwood floors continue from this room into the hallway and primary suite, adding warmth and continuity to the main level. The primary suite is a true retreat with a tray ceiling, generous bedroom space, and an en-suite bath that includes a double-bowl vanity, ceramic tile floor, oversized shower, and a large walk-in closet. The overall layout offers a smart balance of privacy and convenience. The finished lower level significantly expands your options. There's a large family room that can easily be divided into multiple zones or rooms, plus a brick fireplace with a wood-burning heatilator insert. A full second kitchen and third full bath make this level ideal for multi-generational living, an in-law or guest suite, a teen space or game room, home gym, hobby area, or a roomy home office setup. It's flexible square footage that can grow and shift with your needs. Outside, a large deck off the kitchen creates an easy indoor-outdoor flow for entertaining or everyday living. It overlooks the beautifully landscaped back yard—a great spot for grilling, relaxing with a book, container gardening, or hosting friends and family. The oversized 2+ car garage is another standout feature. It's heated and cooled, and includes a workbench area, ample storage, and a cedar closet for seasonal clothing and extras. Whether you're into projects, need space for gear, or just like an organized garage, this one goes beyond the basics. Town N Country is one of Shelbyville's most sought-after neighborhoods for good reason: established homes with character, mature trees, manicured lawns, sidewalks, and quiet streets that are perfect for evening walks or kids on bikes. There's a genuine neighborhood feel here, while still being conveniently close to schools, shopping, dining, and everyday essentials. And as a serious bonus, Shelbyville Country Club is just a quick golf cart ride away. It's easy to picture rolling over for a weekend round of golf, grabbing burgers at the club grill, or spending a sunny afternoon by the pool. Early riser? Enjoy a peaceful walk along the course before golfers head out or cast a line from the bridge. Whether you're a frequent golfer, an occasional swimmer, or just someone who likes having those options close by, having a beautiful course, pool, and grill in your orbit is a major perk of this address. 329 Comanche Road delivers a spacious, all-brick home with a finished lower level, fresh neutral decor, thoughtful updates, and a prime Town N Country location—with the added advantage of country club amenities just around the corner when you want them.

329 Comanche Rd, Shelbyville

2 Beds ⋅ 1 Baths ⋅ 1722460 MLS

2 Bedroom, 1 Bath home in beautiful neighborhood with original hardwood floors, new windows on the main floor, the basement is a blank canvas and a nice yard. Home is being sold as-is but with a little TLC this house could be a BEAUTIFUL home. Call today for your own private showing! **Interior Pictures Coming Soon**

704 Greenwood Ct, Shelbyville

4 Beds ⋅ 4 Baths ⋅ 1718997 MLS

Custom built builder"s home, located in highly desired Town "n Country subdivision. Main floor consists of an open floor plan with 3 BRs, 2 full baths, 1 half bath, large entry, Dining Rm, GR, Kitchen w/snack bar and Breakfast Rm. Main floor has 10 ft ceilings, 8 ft solid core interior doors, upgraded Poplar interior trim package. Lower level consists of another BR and a full bath. Basement walls are 10" poured concrete with 9 ft ceiling height. Plenty of additional space for future expansion. All this with 3 car garage. Must see, executive home across from Shelbyville Country Club. Drive your golf cart to golf course!

212 Cherokee Dr, Shelbyville

1 Beds ⋅ 2 Baths ⋅ 1712655 MLS

Great Investment opportunity. Previously used as a bakery with efficiency living quarters upstairs. Please see repair list for complete details of the work that has been completed on this property.

1023 Main St, Shelbyville

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