Shepherdsville Homes with Detached Parking

Shepherdsville Homes with Detached Parking

Welcome to Shepherdsville, Kentucky, a charming city nestled in the heart of Bullitt County. Known for its friendly atmosphere and rich history, Shepherdsville offers a delightful blend of small-town charm and modern conveniences. With its picturesque landscapes and vibrant community, it’s no wonder that many families and individuals are drawn to this wonderful area.

Shepherdsville boasts a variety of homes that cater to diverse lifestyles, including those with detached parking. These properties not only provide ample space for your vehicles but also offer the flexibility of extra storage or even a workshop. Imagine having the convenience of a dedicated space for your car, boat, or recreational vehicle, all while enjoying the comfort of your own home.

The city is well-connected, making commuting a breeze whether you’re heading to nearby Louisville or exploring the beautiful surrounding areas. Residents can enjoy local parks, shopping, and dining options that add to the appeal of living in Shepherdsville. The community is also known for its excellent schools and family-friendly events, making it a perfect place to raise children or settle down.

If you’re looking for a home with detached parking in a welcoming city that combines the charm of rural living with the benefits of urban accessibility, Shepherdsville is the ideal choice. Explore the real estate options available and discover your dream home in this delightful Kentucky town. Your new life in Shepherdsville awaits!

Newest Shepherdsville Homes with Detached Parking

369 Jackie Way, Shepherdsville
$265,000
3 Beds ⋅ 1 Baths ⋅ 1732955 MLS
Well-maintained brick ranch, conveniently located near I-65, schools, dining, and shopping! The main level features an updated kitchen open to the living room, 3 bedrooms, and a full bath. An enclosed front porch adds 125 SF of versatile space. Two outbuildings offer exceptional flexibility: a former hair salon ideal for a studio apartment, gym, or game room, plus a spacious garage perfect for a workshop, man-cave, or extra storage. All roofs were replaced in 2024! The full unfinished basement offers room to expand and includes a lifetime transferable waterproofing warranty. Outside, enjoy a fully fenced backyard with two level grassy areas and a large patio for entertaining or relaxing. With abundant space inside and out, this property offers endless possibilities to make it your own!

369 Jackie Way, Shepherdsville
1140 Rams Run, Shepherdsville
$699,000
3 Beds ⋅ 3 Baths ⋅ 1732928 MLS
Hidden away at the end of a peaceful cul-de-sac, 1140 Rams Run offers the rare opportunity to enjoy a private, self-reliant lifestyle surrounded by nature—without sacrificing convenience. Tucked off the beaten path, this exceptional property provides quick access to I-65 for easy travel to Shepherdsville and Elizabethtown, as well as nearby Hwy 245 for a direct route to Bardstown. Whether you're seeking a private country retreat, a homestead, a recreational paradise, or a property designed with preparedness in mind, this one-of-a-kind estate delivers. The location is ideal for outdoor enthusiasts. Nearby attractions include Bernheim Forest, Pine Creek Barrens Nature Preserve, Forest Edge Winery, and the world-famous Jim Beam Distillery. Multiple lakes, parks, campgrounds, off-roading destinations, hiking opportunities, and trail-riding areas are all within easy reach. Sportsmen will appreciate the ability to enjoy target shooting on the property, with the Kentucky Gun Club and Knob Creek Gun Range also located nearby. The home is nestled among beautiful wooded acreage featuring established hiking and biking trails that wind through your own backyard. Here, nature isn't something you visit—it's part of everyday life. Outdoor living is a centerpiece of the property. Four tiered aggregate patios, including two covered areas, create distinct spaces for entertaining and relaxation. Enjoy family cookouts, grilling, barbecuing, relaxing beneath the gazebo, gathering around the pool area, or simply taking in the peaceful surroundings. The circular driveway provides abundant parking and easy maneuverability for RVs, boats, campers, and trailers. For homesteaders and preppers, this property is exceptionally well-equipped. The chemical- and pesticide-free garden plot is ready for growing your own food, while established asparagus beds provide annual harvests. A plant map will be available for the new owner. The property also features a 15,000-gallon cistern that continues to collect rainwater, offering an additional layer of self-sufficiency. Combined with the whole-house Generac generator and a second chimney flue available for a future wood stove installation, the home is well-positioned for off-grid or emergency preparedness living. Inside, the meticulously maintained residence combines comfort, functionality, and timeless design. The spacious living room features soaring vaulted ceilings, hardwood flooring, custom shutters, and a striking creekstone fireplace highlighted by a unique Kentucky-shaped stone feature and double-flue chimney. The expansive kitchen was designed for both everyday living and large gatherings, offering abundant cabinetry, a large center island, generous dining space, and dual workstations that are ideal for meal preparation, remote work, or homeschooling. The oversized primary suite offers a peaceful retreat with dual closets and a spacious ensuite bath featuring a skylight and jetted tub/shower combination. Two additional bedrooms are larger than typical secondary bedrooms and feature new carpeting and generous closet space. The walkout basement expands the home's living space while providing peace of mind. Filled with natural light, it includes large rooms, extensive storage, a full bathroom, and dedicated storm- and tornado-safe rooms, making it an ideal refuge during severe weather. Accessibility considerations have also been thoughtfully incorporated throughout the home. Additional recent improvements include: New HVAC system New water heater New basement pump Newer roof with gutter guards Generac whole-house generator Custom shutters A charming guest cottage adds tremendous flexibility for guests, hobbies, home office use, or recreational space. Well insulated and climate controlled for year-round comfort, the cottage is connected to the generator system and features a dog door leading directly to an enclosed pen area, making it perfect for pet owners. The impressive "double barn" is truly a standout feature. One side serves as an insulated six-bay workshop with concrete floors, water service, fan, air hose system, two large workbenches, and a wood stove—an ideal setup for mechanics, craftsmen, hobbyists, or small business owners. The large bays measure approximately 50 feet deep with 18-foot clear height, providing exceptional versatility. The second side offers massive storage capacity for multiple RVs, boats, campers, ATVs, equipment, tractors, and recreational vehicles. With no HOA restrictions, abundant storage, established trails, room for chickens or kennels, recreational opportunities at your doorstep, and infrastructure designed for both comfort and preparedness, 1140 Rams Run is far more than a home—it's a lifestyle. Private yet connected. Peaceful yet prepared. A place where adventure, self-sufficiency, and everyday comfort come together in one extraordinary Kentucky property.

1140 Rams Run, Shepherdsville
240 Brennan Ct, Shepherdsville
$527,555
4 Beds ⋅ 2 Baths ⋅ 1732600 MLS
Refined comfort awaits at 240 Brennan Ct in Shepherdsville's desirable Maplehurst community. Built in 2022, this beautifully maintained 4-bedroom, 2-bath home offers 2,248 sq ft on a level .75-acre lot. Soaring ceilings, hardwood floors, and a welcoming fireplace enhance the open layout. The elegant kitchen features white cabinetry, granite countertops, stainless steel appliances, a generous island, and custom pantries. The first-floor primary suite includes a walk-in closet, double vanity, and tiled shower. A second-floor loft adds versatility. Enjoy a covered porch and patio, attached and detached garages, and solar panels. Convenient to I-65, Louisville, and UofL Health-South Hospital.

240 Brennan Ct, Shepherdsville
361 Valley Ln, Shepherdsville
$339,000
3 Beds ⋅ 2 Baths ⋅ 1732491 MLS
Welcome to 531 Valley Lane in Shepherdsville Kentucky. Less than 5 minutes to I65 at exit 116 and less than 30 Minutes to Staniford Field Airport and Louisville. Professional Photos coming soon.. Country living, Great Location and walking distance to Heritage Hills Golf Course. This 3 bed 1.5 bath Bedford Stone home with basement, carport, Large concrete floored Pole Barn Garage is all situated beautifully on 3.3 acres. Home has a B-Dry system and Leaf Filter system on gutters. Home needs some updating but is move in ready. Great Investment and close by dining, shopping, interstates, school and the Beautiful Heritage Hills Golf Course. Motivated Seller and immediate Possession. Priced to sell.

361 Valley Ln, Shepherdsville
2375 Pumpkin Rd, Shepherdsville
$450,000
3 Beds ⋅ 1 Baths ⋅ 1732043 MLS
THE GREAT PUMPKIN ROAD PROPERTY! Fall in love with 15 acres of country possibilities in Shepherdsville, KY! Offered at $450,000, this unique property features a 3-bedroom, 1-bath home situated on three 5-acre lots with an impressive collection of barns, garages, machinery storage, dog kennels and chicken coops! Dreaming of a homestead, hobby farm, mini farm or horse property? Imagine fresh eggs, homegrown vegetables, orchards, vineyards and room for livestock, horses and more! With expansive open acreage and exceptional agricultural improvements already in place, this property offers an exciting opportunity to create your own country lifestyle. Bring your animals, your equipment and your imagination! Don't let this Pumpkin Road opportunity get away! MORE THAN A HOME — IT'S 15 ACRES OF OPPORTUNITY!Welcome to 2375 Pumpkin Road in Shepherdsville, Kentucky, where country living meets extraordinary versatility! Whether you're an aspiring homesteader, hobby farmer, horse enthusiast, gardener, animal lover or simply looking for room to spread out, this Bullitt County property offers the space and improvements to make your vision a reality. OUTBUILDINGS & EQUIPMENT STORAGE: This property is exceptionally well-equipped with two barns featuring gravel and concrete surfaces, a substantial 4-bay concrete machinery shed with an attached 27' x 30' concrete-floored room featuring walk-through and double-door access, plus a large garage with bay-door and walk-through access and an additional spacious expansion with its own walk-through and double doors. From tractors and farm machinery to recreational equipment, workshops and storage, there's room for it all! ANIMAL LOVERS, TAKE NOTICE! Seven 10' x 30' partially covered dog kennels provide dedicated animal housing, while established chicken coops offer an excellent start for raising your own flock and enjoying farm-fresh eggs. The wide-open acreage offers exciting possibilities for horses, livestock and other farm animals. GROW YOUR OWN FUTURE! Imagine rows of vegetables, fruit trees, berry bushes, a beautiful orchard or even a small vineyard. With approximately 15 acres divided into three 5-acre lots, this property provides tremendous flexibility for gardening, farming, outdoor recreation and exploring a more self-sufficient lifestyle. THE HOMESTEADING DREAM STARTS HERE! Instead of starting with vacant land and building every agricultural improvement from scratch, discover a property with substantial existing infrastructure. Whether you're interested in a small-scale farm, country retreat, agricultural venture or simply peaceful rural living, the possibilities are limited only by your imagination and applicable land-use requirements. OFFERED AT $450,000! This is your opportunity to own a distinctive 15-acre property with a home, multiple agricultural buildings, animal facilities and room to grow. DON'T WAIT FOR THE GREAT PUMPKIN - YOUR COUNTRY DREAM IS ALREADY HERE! Schedule your private tour of 2375 Pumpkin Road today!

2375 Pumpkin Rd, Shepherdsville
2240 Raymond Rd, Shepherdsville
$425,000
3 Beds ⋅ 3 Baths ⋅ 1731978 MLS
**5.26 ACRES, GATED ENTRANCE, DETACHED GARAGE & A ONE-OF-A-KIND TINY CABIN!** Welcome to 2240 Raymond Road, where privacy, space, and unique amenities come together to create a property unlike most others! Nestled on 5.26 beautiful acres, this 3-bedroom, 3-bath home offers plenty of room to spread out, both inside and out. The finished basement provides additional living and entertaining space, including a room currently used as a 4th bedroom. Inside, you'll find multiple gathering areas, fireplaces, and a spacious kitchen, offering flexibility for everyday living and hosting guests. Step outside to enjoy the expansive deck with a covered gazebo, perfect for relaxing, grilling, or entertaining while overlooking the peaceful surroundings. Need room for vehicles, hobbies, or equipment? The oversized 3.5-car detached garage, additional storage bays beneath the home, and separate storage shed provide exceptional versatility. But perhaps the most memorable feature is the charming TINY CABIN, built in 2020! Tucked away among the trees, this rustic retreat features beautiful wood finishes, soaring ceilings, a cozy living area, kitchenette, and sleeping loft. Whether used as a guest getaway, creative retreat, or simply a peaceful escape without ever leaving your property, it's a truly special addition that's hard to put a price on! From the gated entrance and scenic acreage to the abundance of storage and incredible outdoor spaces, this property offers a rare combination of privacy, functionality, and character. Come experience everything 2240 Raymond Road has to offer!

2240 Raymond Rd, Shepherdsville
1239 Pitts Point Rd, Shepherdsville
$848,500
6 Beds ⋅ 5 Baths ⋅ 1731863 MLS
Experience the perfect blend of grandeur and versatility in this stunning home situated on over 6.5 acres, complete with a beautiful pond and an impressive 30' x 80' pole barn. Step inside to a grand entryway featuring elegant columns, soaring ceilings, and a majestic staircase. The main level offers a formal dining room, a charming sitting room, and an inviting living room with a fireplace and mini-bar. The open-concept kitchen features an additional dining area, bar seating, a center island with cooktop, and double built-in ovens—perfect for everyday living and entertaining. The expansive primary suite is a true retreat, boasting a fireplace, a regal private bath with a columned soaking tub and walk-in shower, an attached dressing room, and direct access to the covered rear porch. An additional bedroom, full bathroom, and convenient main-level laundry complete the first floor. Upstairs, you'll find two generously sized bedrooms and two additional full bathrooms, providing plenty of space and privacy for family and guests. The walkout basement offers exceptional additional living space, featuring two more bedrooms, bonus rooms, a family room with fireplace, a second full kitchen, a laundry area, and a full bathroom. Glass doors open to the covered rear porch and patio, creating a seamless connection to the outdoors and even more room to relax or entertain. Additional highlights include an attached two-car garage and an impressive 30' x 80' pole barn equipped with office space, water, electricity, and a mini-split system. With ample room to accommodate multiple vehicles, the barn is ideal for hobbyists, collectors, workshop space, or additional storage. Enjoy the beauty and privacy of the expansive grounds, complete with a picturesque pond and over 6.5 acres to explore. With its spacious layout, multiple living areas, abundant bedrooms and bathrooms, and exceptional outbuildings, this remarkable property offers endless possibilities for comfortable living, entertaining, and more!

1239 Pitts Point Rd, Shepherdsville
226 S Shore Dr, Shepherdsville
$262,000
3 Beds ⋅ 2 Baths ⋅ 1731797 MLS
This well-maintained 3-bedroom, 2-bath ranch offers comfortable living with plenty of extra space, including an unfinished basement and a large 24 x 36 detached garage. The primary bedroom comes with an attached private full bathroom. Enjoy relaxing on the back deck overlooking the fenced-in backyard, perfect for pets or outdoor gatherings. The detached garage offers endless possibilities for storage, workspace, or entertaining. Conveniently located near Shepherdsville Park, the new aquatic center, and Bernheim Forest, this home is close to plenty of opportunities for recreation and outdoor fun! Call today for your private showing!

226 S Shore Dr, Shepherdsville
265 Drake Dr, Shepherdsville
$249,500
3 Beds ⋅ 2 Baths ⋅ 1731657 MLS
Welcome to this charming ranch offering comfortable one-level living with three bedrooms, two full baths and approximately 1,170 square feet. The functional floor plan provides inviting living spaces, while the primary bedroom and everyday essentials are conveniently located on the main level. Outside, the privacy-fenced backyard, deck and porch create plenty of space for relaxing or entertaining. A detached two-car garage adds valuable parking, storage and workspace options. With no HOA and convenient access to Shepherdsville shopping, dining and major roadways, this home combines practicality, outdoor enjoyment and everyday convenience. Schedule your private showing today!

265 Drake Dr, Shepherdsville
288 Deatsville Rd, Shepherdsville
$519,900
3 Beds ⋅ 2 Baths ⋅ 1731575 MLS
Spacious One-Story On 7.6 Acres With Large Outbuilding, Covered Front & Back Porches, Remodeled Inside & Out ... Less Than 5 Miles From I-65 Off Cedar Grove Rd. Absolutely Adorable Home Set Back Off The Road With A Long, Circular Driveway ~ Great Potential For A Mini Farm (Horses, Goats, Chickens), Large Garden, Second Home, More Garage Or Barn Space - Many Options! Front & Back Porches Stretch Across The Full Width Of The House, Offering Superb Sunrise & Sunset Views! New Siding, Heat, Air, Water Heater, Flooring, Paint, Bathrooms, Remodeled Kitchen & Soo Much More. Expansive Kitchen With Lots Of Cabinets, Quartz Counters, Breakfast Bar, New Appliances, Coffee Bar .... The Kitchen & Living Room Flow Together With Lots Of Room For Family Gatherings! Designer Bathrooms. Beautiful Home!!!

288 Deatsville Rd, Shepherdsville
914 Big Springs Rd, Shepherdsville
$585,000
3 Beds ⋅ 3 Baths ⋅ 1731524 MLS
WOW! Privacy, panoramic views, and room to live, work, and entertain—this exceptional 5.1-acre property truly has it all! Nestled among mature trees and rolling terrain, this updated, move-in-ready, all-brick ranch offers the kind of peaceful, panoramic setting that feels more like a Gatlinburg getaway than home. Inside, the open and split-bedroom floor plan is designed for both everyday living and entertaining. Beautiful hardwood floors, beamed and vaulted ceilings, a striking stone wood-burning fireplace, and a wall of windows and doors across the rear of the home immediately draw your attention to the spectacular outdoors. A covered front porch spans both sides of the home, providing the perfect place to enjoy morning coffee, warm summer days, or crisp autumn evenings. The spacious kitchen features beautiful maple cabinetry, a center island, abundant counter space, and an effortless flow into the open dining and family room areas. Just off the kitchen, the oversized primary suite offers plenty of room for large furnishings and features a luxurious ensuite bath with a jetted tub, separate walk-in shower, and walk-in closet. Conveniently, the closet connects directly to the laundry room. The primary bedroom also offers direct access to the covered rear deck, where you can relax and take in the peaceful surroundings and creek below. On the opposite side of the main level, two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for family and guests. An open staircase leads to the finished walkout basement—an entertainer's dream! The lower level features a second family room with another wood-burning fireplace, a bar area with sink, game room with billiards table that remains, a third full bathroom with standalone shower, finished sleeping quarters, and additional unfinished storage. A one-car attached garage provides convenient access to the lower level, along with direct access to the patio and yard. Outside, the property truly shines. New black aluminum fencing and a recently fortified and capped retaining wall creates another level, usable yard area—ideal for a pool, trampoline, fire pit, outdoor entertaining space, or play equipment. The newly paved and widened driveway improves accessibility while providing abundant additional parking for guests, large vehicles, boats, or recreational equipment. And then there's the 30' x 40' detached outbuilding, offering an incredible amount of flexibility for the hobbyist, craftsman, collector, or small-business owner. Featuring concrete floors, electric, 10' walls, a 9' x 9' garage door, and an additional carport sized for a camper, this space provides exceptional workshop, storage, and parking options. With 5.1 wooded acres, expansive views, a creek, multiple outdoor living spaces, a finished walkout basement, attached garage, and a substantial detached outbuilding, this property offers a rare combination of privacy, functionality, and convenience. Located just minutes from I-65, area distilleries and the Bourbon Trail, and Bernheim Forest, with easy access to Louisville, Bardstown, Fort Knox, and Elizabethtown, this is country living without sacrificing convenience. Newer mechanicals & roof, and a recently inspected & pumped septic tank provide added peace of mind. Come experience the views, explore the acreage, and see everything this one-of-a-kind property has to offer. Schedule your private showing today!

914 Big Springs Rd, Shepherdsville
289 Douglas Ln, Shepherdsville
$225,000
3 Beds ⋅ 1 Baths ⋅ 1731483 MLS
Welcome to this all-brick ranch in Shepherdsville! Featuring 3 bedrooms, 1 full bath, and a charming front porch, this home offers comfortable one-level living with timeless appeal. The living room, dining area, and bedrooms feature hardwood floors, adding warmth and character to the space. The kitchen overlooks the large backyard, providing a great view. Additional highlights include a full-sized, unfinished basement offering plenty of storage or potential for future customization. Outside, you'll find a 2-car detached garage, a wide driveway for additional parking, and a covered patio. With its classic brick exterior, functional layout, and room to make it your own, this home is full of possibilities!

289 Douglas Ln, Shepherdsville
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