Shelbyville Homes with Entry Side Parking

Shelbyville Homes with Entry Side Parking

Welcome to Shelbyville, Kentucky – a charming city that perfectly blends small-town warmth with modern conveniences. Nestled in the heart of Shelby County, Shelbyville is renowned for its rich history, vibrant community spirit, and picturesque landscapes. Just a short drive from Louisville, this idyllic locale offers residents the tranquility of suburban life while remaining close to the bustling city.

One of the standout features of Shelbyville is its diverse range of homes, particularly those with entry side parking. This thoughtful architectural design not only enhances the curb appeal of the properties but also provides practical convenience for homeowners. Imagine coming home after a long day, pulling into your driveway, and enjoying easy access to your front door without the hassle of navigating tight spaces. Homes with entry side parking are perfect for families, offering ample space for multiple vehicles, guests, or even a recreational vehicle.

Living in Shelbyville means you’ll have access to top-rated schools, beautiful parks, and a welcoming community filled with friendly neighbors. The local economy is thriving, with a variety of shops, restaurants, and recreational activities to explore. Whether you’re strolling through the historic downtown district or enjoying a weekend at one of the nearby equestrian events, there’s always something to see and do.

With its unique blend of convenience, charm, and community spirit, Shelbyville is the perfect place to call home. Explore the wonderful homes with entry side parking and discover the lifestyle that awaits you in this delightful Kentucky city!

Newest Shelbyville Homes with Entry Side Parking

527 1st St, Shelbyville
$389,000
6 Beds ⋅ 4 Baths ⋅ 1733443 MLS

527 1st St, Shelbyville
820 South Stallard Dr, Shelbyville
$1,150,000
5 Beds ⋅ 4 Baths ⋅ 1733278 MLS
Situated on 6.64 beautifully maintained acres, this nearly new residence enjoys a picturesque setting with mature trees, expansive lawns, thoughtful landscaping, and a creek bordering the rear of the property. Located within the highly desirable Stallard Springs community, 820 S Stallard Drive offers an exceptional combination of quality, acreage, and refined country living. Its timeless architecture, inviting covered front porch, and impressive approach establish a strong first impression. Built just 3 years ago, the home offers nearly 2,600 square feet above grade, plus a finished walkout basement, with 5 bedrooms and 3.5 baths. The vaulted Great Room features a floor-to-ceiling stone fireplace and opens to a well-appointed kitchen with custom cabinetry, granite countertops, tiled backsplash, a generous center island, and views of the surrounding property. The primary suite includes a spacious bath with soaking tub, tiled walk-in shower, and oversized walk-in closet with custom shelving. The finished walkout basement provides substantial additional living and entertaining space, including a family room, recreation area, mini kitchen, large workshop, and utility garage. Outdoors, the inground pool serves as the centerpiece of a beautifully landscaped backyard, complemented by a covered screened deck overlooking the grounds. The expansive front porch offers additional outdoor living space with views of the surrounding countryside and evening sunsets. Beyond the property itself, Stallard Springs has become one of Shelby County's most sought-after estate communities, recognized for its generous acreage, attractive homes, scenic surroundings, and thoughtful development. Underground utilities, high-speed internet availability, community walking trails, and natural waterways provide modern convenience while preserving the character of the Kentucky countryside. 820 S Stallard Drive represents a compelling opportunity to own a nearly new home on substantial acreage within an established and highly regarded community. A property where the quality of the home, the land, and the neighborhood come together to offer lasting appeal.

820 South Stallard Dr, Shelbyville
5762 Frankfort Rd, Shelbyville
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 1732016 MLS
Just in time for the holidays, your new home and horse farm await! Situated on approximately 42.5 beautiful acres in Shelbyville, this turnkey equestrian property offers a custom-built, energy-efficient ICF home, exceptional horse facilities, and picturesque Kentucky countryside. The thoughtfully designed home features insulated concrete form (ICF) construction with reinforced concrete walls, substantial insulation, passive-solar elements, and storm-resistant construction. Inside, beautiful hardwood floors, detailed woodwork, graceful arches, and expansive countryside views create a warm and inviting atmosphere. The unfinished walkout lower level offers excellent potential for additional living space, with a bedroom already framed, plumbing roughed in for a full bathroom, and space planned for a future bar area. The three-car garage includes a convenient dog washing station with hot and cold running water. A paved driveway approximately 0.4 miles long winds through beautiful four-board-fenced pastures, leading past the riding arena and four-stall barn to the home. The barn features a spacious drive-through aisle accommodating a truck and trailer, rubber-matted stalls, water, electricity, and an exterior lean-to for equipment storage or additional stalls. Two large paddocks are located near the barn, with additional paddocks near the arena. The fenced 150' x 240' sand riding arena features all-weather footing, making this property ready for horses from day one. Rolling pastures, mature woods, abundant wildlife, and scenic views of Jeptha Knob provide a private setting with opportunities for riding, recreation, and hunting. The home is also pre-wired for a whole-house generator. Conveniently situated with access to I-64, the farm offers proximity to Keeneland, Churchill Downs, the Kentucky Horse Park, and Lakeside Arena, and is approximately 35 minutes from Louisville International Airport. Enjoy peaceful country living without sacrificing accessibility.

5762 Frankfort Rd, Shelbyville
1458 St Andrews Dr, Shelbyville
$584,900
4 Beds ⋅ 3 Baths ⋅ 1731564 MLS
Welcome to Brentwood, one of Shelby County's most sought after neighborhoods! Tucked away toward the back of this beautiful, established community, this spacious 4-bedroom, 3-full-bath home offers a wonderful sense of privacy and a peaceful setting away from the main neighborhood entrance. Located next to Shelbyville Country Club, and minutes from local schools, parks, and downtown Shelbyville, this property offers an incredible combination of location, comfort, and opportunity. With approximately 2,800 square feet of finished living space above grade, this home features a desirable main-level layout with a spacious family room, separate living room/library, large eat in kitchen, laundry room, and two bedrooms, including the primary suite. Upstairs, you'll find two additional generously sized bedrooms, a full bathroom, and convenient walk-in attic storage. Major updates have already been completed! Enjoy a brand-new roof, new HVAC system, beautiful new hardwood flooring throughout the main level, updated flooring in every bedroom, and fresh interior paint throughout the entire home. These improvements provide a fresh, modern feel while maintaining the character and charm of this established neighborhood. Need more room? The expansive 2,200-square-foot unfinished basement offers endless possibilities! Whether you envision additional living space, a home theater, recreation room, home gym, or simply an abundance of storage, the opportunity to make this space your own is already there. Outside, enjoy a beautiful lot offering privacy, mature surroundings, and plenty of room to relax. An oversized two-car garage provides additional convenience and storage. Homes in Brentwood are highly desirable, and opportunities to purchase in this established neighborhood don't come along every day. With its generous square footage, extensive updates, incredible basement potential, and attractive price point, this home offers a fantastic opportunity to enjoy everything Brentwood has to offer. Schedule your private showing today and discover the possibilities!

1458 St Andrews Dr, Shelbyville
132 Winners Cir, Shelbyville
$644,000
6 Beds ⋅ 4 Baths ⋅ 1730080 MLS
Welcome to 132 Winners Circle in Shelbyville's Triple Crown Estates, where generous living space meets lake views. This six-bedroom, four-bath home offers approximately 3,805 square feet, hardwood flooring throughout, and a layout designed for flexibility. The kitchen features quartz countertops, while the dining room and great room provide inviting places to gather. Enjoy views of the lake from the great room, then step onto the covered porch to take in the setting outdoors. The main-floor primary suite offers everyday convenience. Upstairs, two bedrooms share a full bath. The finished walkout level adds a bedroom, full bath, and large family room, creating space for guests, extended family, or multigenerational living. A two-car garage and approximately 0.28-acre lot complete the property. With room to come together and space for different routines, 132 Winners Circle is ready for its next chapter. Schedule your showing and experience the layout and lake views in person.

132 Winners Cir, Shelbyville
44 Cherokee Dr, Shelbyville
$375,000
3 Beds ⋅ 3 Baths ⋅ 1730042 MLS
Welcome home to this charming 3 bed, 2.5 bath home in the HIGHLY sought after Town N Country neighborhood in Shelbyville, KY. Located across the street from the Shelbyville Country Club, this cozy Cape Cod style home boasts over 2200+ sq ft of finished living space and a tranquil backyard that's perfect for entertaining or relaxing. The interior of the home features an eat-in kitchen, brick gas-burning fireplace, natural light galore, a private dining room, a den, large primary suite with en-suite, attached two-car garage with outside access and the list goes on and on. This home has been meticulously maintained and thoughtfully updated. The main floor features farmhouse style LVT throughout. The furnace and AC unit are less than 5 years old. An oversized deck and a beautifully designed stone patio highlight the partially wooded and fully fenced backyard. This home is a must see!

44 Cherokee Dr, Shelbyville
238 Forest View Ridge, Shelbyville
$924,900
3 Beds ⋅ 2 Baths ⋅ 1730004 MLS
Perched on 2.5 acres along the ridgeline of The Views at Southville, 238 Forest View Ridge is a nearly new custom ranch where exceptional craftsmanship, thoughtful design, and expansive Kentucky views come together beautifully. Built less than two years ago by Unbridled Homes, this residence makes an immediate impression with its striking elevation, wraparound front porch, and commanding setting. Inside, soaring 12-foot ceilings define the main living spaces, with 10-foot ceilings throughout the remainder of the home, 8-foot doors, beautiful Craftsman-inspired trimwork, and an abundance of natural light. Engineered hardwood flooring extends throughout the home with no carpet anywhere. The centerpiece is an extraordinary gourmet kitchen designed as much for entertaining as everyday living. Quartz countertops, Vittitow custom cabinetry, soft-close doors and drawers, and a Wolf range are complemented by an incredible butler's pantry that dramatically expands the kitchen's storage and workspace. A substantial wood beam provides architectural definition between the kitchen, dining area, and great room while preserving the open-concept design. The great room is anchored by a dramatic floor-to-ceiling stone fireplace with custom built-ins, creating a spectacular focal point for the home's central gathering space. An adjoining office features custom built-in desks and cabinetry and integrates beautifully into the floor plan. The private primary suite occupies its own wing of the home. The spa-inspired bath features an oversized tiled shower with dual shower heads and a large double vanity. The custom Closet Factory dressing room is exceptional in both scale and organization, with extensive built-in shelving and a center island with drawer storage. Even the laundry room was designed to impress, with quartz countertops, a sink, and extensive cabinetry. Its convenient pass-through design connects directly to the primary closet, creating an exceptionally functional owner's suite. On the opposite side of this split-bedroom ranch, two generously sized bedrooms provide privacy for family or guests. One features a built-in desk area and direct access to the full bath. Outdoor living is equally impressive. The wraparound front porch and covered rear porch provide multiple places to enjoy the property's elevated setting and the wide-open, big-sky views that distinguish this unique neighborhood. The unfinished walkout lower level encompasses essentially the same footprint as the home above, offering tremendous potential for future living and entertaining space. Tall ceilings and expansive open areas provide a blank canvas for a theater, recreation room, fitness space, additional bedroom, or guest suite. The septic system has already been sized to accommodate an additional bedroom. Perhaps the most unique feature downstairs is the substantial concrete safe room, constructed with concrete on all sides and designed to accommodate a Fort Knox vault door, with rough-ins already in place for ventilation and electricity. An extra-deep three-car garage with tall ceilings provides abundant space for vehicles, storage, a workshop, or recreational equipment. The Views at Southville is one of Shelby County's hidden gems, offering the tranquility and scenery of country living while remaining convenient to Shelbyville, Taylorsville, Frankfort, and Louisville. The neighborhood sits near the intersection of Highways 44 and 53 and the beloved Carriss's Grocery, a local institution known for its breakfasts and burgers. Louisville International Airport is just over 30 minutes away, with Frankfort approximately 30 minutes from the property. Nearly new construction. 2.5 acres. Exceptional craftsmanship. Remarkable outdoor views. And one of the most thoughtfully designed ranch floor plans you'll find. 238 Forest View Ridge isn't simply a beautiful home—it is a property that needs to be experienced in person. Schedule your private showing today.

238 Forest View Ridge, Shelbyville
98 Plantation Dr, Shelbyville
$585,500
4 Beds ⋅ 4 Baths ⋅ 1729949 MLS
Highly Motivated Seller! This house comes with a REDUCED RATE as low as 6.625% (APR 7.142%) as of 10/23/2026 through List & Lock™. This is a seller paid rate-buydown that reduces the buyer's interest rate and monthly payment. Terms apply. Space, privacy, and golf-community living come together in desirable Weissinger Estates! Situated on a beautiful 1.27-acre lot in picturesque Shelby County, this spacious four-bedroom walkout two-story offers multiple living areas, a finished basement, and a peaceful setting just minutes from I-64 giving you direct access to Louisville, Frankfort, and Lexington. Inside, a two-story foyer with hardwood floors opens to a formal dining room and a bright eat-in kitchen featuring classic white cabinetry, quartz countertops, mosaic tile backsplash, breakfast bar, and hardwood flooring. Inside, a two-story foyer with hardwood floors opens to a formal dining room and a bright eat-in kitchen featuring classic white cabinetry, quartz countertops, mosaic tile backsplash, breakfast bar, and hardwood flooring. The spacious great room offers vaulted ceilings, skylights, a gas fireplace, and access to an elevated deck overlooking the well-manicured back lawn. The first-floor primary suite includes a double vanity, whirlpool tub, separate walk-in shower, water closet, and walk-in closet. A conveniently located laundry room near the garage entry completes the main level. Central vacuum access on both the first and second floors adds everyday convenience. Upstairs are three generously sized bedrooms, a full bath with a linen closet, and an open landing overlooking the foyer and great room. An additional insulated storage room with flooring and lighting provides the perfect space for holiday décor and seasonal belongings. The finished walkout basement adds even more versatility with a family room, dining area, full bathroom with a walk-in shower, and direct access to the backyard—perfect for entertaining, guests, recreation, or additional outdoor space. The home also has an unfinished workshop and additional storage area offering plenty of room for projects, tools, and household items. The backyard is one of the property's standout features. The expansive, flat yard offers a rare combination of privacy and usable space, with endless possibilities for a pool, garden, fire pit area, play space, outdoor kitchen, room for pets, or simply wide-open green space to enjoy. Mature trees and flowering shrubs add privacy and seasonal beauty while preserving the yard's flexibility. Located in a golf-cart-friendly community, Weissinger Estates also features sidewalks throughout the neighborhood, allowing residents to travel throughout the community without having to use Highway 53 to access the golf course. With four bedrooms, a finished walkout basement, a workshop and storage area, a two-car attached garage, central vacuum on two levels, and a private 1.27-acre lot, this home offers a rare combination of space, flexibility, convenience, and peaceful country living.

98 Plantation Dr, Shelbyville
18 Arlington Ct, Shelbyville
$399,900
3 Beds ⋅ 2 Baths ⋅ 1729122 MLS
PROPOSED NEW CONSTRUCTION! Don't miss this exceptional opportunity to build your dream home. Nestled on a quite dead-end street with minimal traffic, this rare 1/3-acre lot offers the perfect combination of privacy, convenience, and timeless design. This elegant Farmhouse style home features 3 bedrooms and 2 bathrooms with 1676 SQ Ft. and a 2-car garage, thoughtfully designed with modern living in mind. Enjoy an ideal location just minutes from schools, shopping, restaurants, and easy access to Interstate 64. The property already includes a newly poured concrete driveway, approximately 100 ft. long, 14.5 ft wide and over 6" thick, adding durability and exceptional value before constructions even begins. One of the greatest advantages of purchasing early is the opportunity to personalize your new home. Buyers will work with the builder to select finishes throughout the construction process and will receive allowances for flooring, lighting, and paint colors, allowing you to create a home that reflects your own style and preferences. This is a rare chance to own a beautiful custom home in a peaceful setting while enjoying all the conveniences of Shelbyville. Secure your lot and make your dream home a reality.

18 Arlington Ct, Shelbyville
453 Erie Ct, Shelbyville
$280,000
3 Beds ⋅ 2 Baths ⋅ 1728902 MLS
Welcome to 453 Erie Ct in Shelbyville! This home offers the perfect combination of comfort, functionality, and space to enjoy every season. Inside, you'll find a warm and inviting layout with plenty of room for everyday living and entertaining. Step outside and you'll quickly see why the outdoor space is a standout—whether Kentucky decides to give you sunshine, rain, or all four seasons in one day, you'll have the perfect place to relax and enjoy it! Located on a quiet cul-de-sac while still convenient to everything Shelbyville has to offer, this home gives you that tucked-away neighborhood feel without sacrificing location. If you've been waiting for a home that feels comfortable, welcoming, and ready for its next chapter, 453 Erie Ct is one you'll want to see in person.

453 Erie Ct, Shelbyville
2280 Anderson Ln, Shelbyville
$1,899,000
5 Beds ⋅ 5 Baths ⋅ 1728798 MLS
Luxury newer construction on 15.01 acres in Shelbyville, KY! This exceptional custom-built 5-bedroom, 4.5-bath Kentucky estate combines modern farmhouse architecture, designer finishes and beautiful Shelby County countryside views. The open-concept interior showcases soaring ceilings, dramatic wood beams, wide-plank flooring and a stunning great room with floor-to-ceiling stone fireplace and custom built-ins. The chef-inspired kitchen features custom cabinetry, stone countertops, oversized island, professional-style gas range, pot filler, designer lighting and walk-in pantry. The luxurious primary suite offers a spa-inspired bath with freestanding soaking tub, oversized glass shower, dual vanities and custom finishes. A massive unfinished walkout basement, already roughed in for 2 additional bathrooms and a wet bar, provides incredible future living and entertainment potential with impressive ceiling height and double-door exterior access. Situated on 15.01 newly platted acres, this rare Shelbyville luxury home with acreage offers privacy, space and Kentucky country living while remaining convenient to Shelbyville, Simpsonville and the greater Louisville area.

2280 Anderson Ln, Shelbyville
5383 Benson Pike, Shelbyville
$680,000
3 Beds ⋅ 3 Baths ⋅ 1727122 MLS
Location, location, location—and this custom-built home on Benson Pike has it all. Just 2 miles from Guist Creek Lake, 4 miles from schools, 5 miles from shopping, and minutes from I-64, this property offers the country living you have been hoping to find. This all-brick ranch provides 2,300 square feet of comfortable living space, featuring beautiful hardwood floors, custom cherry cabinets, granite countertops, a split three-bedroom floor plan, 2½ baths, and an office or craft room. The open, airy great room flows into the kitchen and dining area, creating a welcoming space for family activities. The service island doubles as an eating bar, and built-in cabinets surround the fireplace for a cozy feel. A double-hip vaulted ceiling adds character to the great room. The primary suite includes double vanities, a tile walk-in shower, his-and-her closets, a whirlpool tub, and a sliding door to the patio. Enjoy morning coffee on the covered front porch overlooking the stocked pond, or gather with family and friends on the covered back patio. The home also includes a laundry room with a sink and half bath, plus a two-car garage with pull-down attic stairs for storage. For extra vehicles, tools, or toys, the property offers a detached two-car garage with a workshop, plus a 30-by-30 barn with a 10-by-30 shed and a tall overhead door for an RV or boat, all accessible by the fully concrete driveway and parking area. The home sits on 5 acres with four-board and woven-wire fencing. The back 3 acres are fenced for cattle or horses, and the small run-in shed attached to the large barn includes a couple of stalls. The possibilities are endless—come see it and picture yourself living here. The sellers are downsizing and moving out of state, and they believe you will love this home as much as they have. Please note that sellers have an accepted contract on this property with a first right of refusal and those buyers have a home to sell that is currently on the market

5383 Benson Pike, Shelbyville
Start Your Search

How much is your home worth?

Get instant property value now!