Midway Homes with Garage Faces Side Parking Features

Midway Homes with Garage Faces Side Parking Features

Welcome to Midway, Kentucky—a charming city nestled in the heart of Woodford County, where small-town charm meets modern convenience. Known for its picturesque landscapes and friendly community, Midway is a delightful place to call home. The city boasts a rich history, with its roots dating back to the 19th century, and it continues to thrive as a vibrant hub for residents and visitors alike.

One of the standout features of homes in Midway is their thoughtful design, particularly those with side-facing garages. These homes not only enhance the curb appeal of the property but also provide practical benefits. With garage doors positioned on the side, homeowners enjoy a cleaner, more aesthetic front view, allowing for beautifully landscaped yards and inviting entries. This feature is particularly appealing for families who value outdoor space and a welcoming atmosphere.

In addition to their striking appearance, homes with side-facing garages often come with ample driveway space, making parking a breeze for guests and family gatherings. This design maximizes the use of space, providing room for additional vehicles while maintaining a tidy street scene.

Midway's real estate market offers a variety of options, ensuring there’s something for everyone. From charming historic homes to modern builds, the community's diverse architecture reflects its rich heritage and forward-thinking spirit. With its friendly atmosphere, excellent schools, and proximity to Lexington, Midway is not just a place to live; it’s a place to thrive. Come explore what makes Midway, KY, the perfect backdrop for your next chapter!

Newest Midway Homes with Garage Faces Side Parking Features

405 Merrywood Dr, Midway
$629,000
3 Beds ⋅ 2 Baths ⋅ 26029624 MLS
Enjoy the best of Bluegrass living in this custom-built, all-brick ranch home, offered for the first time on the market in 48 years! Beautifully situated on over half an acre with gorgeous views overlooking the surrounding horse farms of Midway, this property offers a special opportunity to own a home with a long history and a beautiful setting. Inside, the home features an updated kitchen and bathrooms, newer appliances, and updated flooring, offering comfortable, move-in-ready living. A newer roof adds peace of mind, while the attached two-car garage provides everyday convenience. One of the standout features is the approximately 400-square-foot detached garage, complete with heating and air conditioning. Whether you envision a workshop, home office, fitness room, hobby space, or additional flex space, the possibilities are endless. Outside, the beautifully landscaped grounds and brick patio create a wonderful setting for relaxing, entertaining, or simply enjoying the scenic surroundings. Located in the heart of Kentucky horse country, Midway offers a charming historic downtown filled with locally owned restaurants, unique boutiques, and inviting places to gather. Enjoy the character of historic Main Street while being just approximately 15 minutes from Versailles, Lexington, and Frankfort. Truly Midway! With its custom-built quality, thoughtful updates, versatile additional space, and picturesque Bluegrass setting, this is a rare opportunity to make a special property your own.

405 Merrywood Dr, Midway
130 Lighthouse Way, Midway
$869,900
5 Beds ⋅ 5 Baths ⋅ 26029134 MLS
Set on 2.38 private acres in Fishers Mill Landing, this 5-bedroom, 4.5-bath brick two-story pairs a quiet country setting and views of the surrounding horse farms with an easy drive to Midway, Lexington, Georgetown and Frankfort. Special features include: Two-story foyer * Step-down family room with a cozy raised mantel wood-burning fireplace * Kitchen with center island, walk-in pantry and breakfast nook opening to the deck * Wraparound covered deck with new Trex decking and roof * Primary suite with sitting room, walk-in closet, soaking tub, separate shower and double vanities * All bedrooms upstairs, one with a private bath * Upper-level laundry * Walk-out lower level opening to a brick patio, with 31x19 recreation room, full bath, flex room and second fireplace * 3-car side-entry garage * Upgraded upstairs furnace in 2024 * New gutters and expanded driveway in 2026. Plenty of room to spread out inside and out, just minutes from the shops and restaurants of downtown Midway.

130 Lighthouse Way, Midway
3200 Fishers Mill Rd, Midway
$2,420,000
5 Beds ⋅ 5 Baths ⋅ 26028502 MLS
Exceptional 34-Acre Equestrian Estate in Charming Midway, Kentucky Discover the perfect blend of luxury living and premier equestrian amenities on this exceptional 34-acre farm in the heart of picturesque Midway, Kentucky. Thoughtfully designed for both the serious equestrian and those seeking a peaceful Bluegrass lifestyle, this remarkable property offers outstanding facilities, a custom-built residence, and endless possibilities. The equestrian amenities are truly impressive, beginning with a 19-stall barn featuring a heated tack room, feed room, half bath, and both indoor and outdoor wash stalls. A spectacular 80' x 160' indoor arena with premium TruTek footing provides an exceptional year-round training environment, while the expansive 100' x 200' outdoor arena, completely redone in 2025 with upgraded footing and drainage, offers an equally impressive space for riding and training. An additional equipment barn provides ample storage and the potential for six additional stalls, ideal for quarantine. There are six fully fenced paddocks with automatic waterers. There is also a 50 AMP RV Hookup and ample space for visiting trailers. Equally impressive is the custom-designed residence, thoughtfully created with multigenerational living in mind. The main level features a spacious primary suite, two additional bedrooms connected by a Jack-and-Jill bath, and a beautifully appointed chef's kitchen. An upper-level guest suite provides additional privacy and comfort. The bright, expansive walkout lower level is a retreat of its own, complete with a second full chef's kitchen, bedroom, full bath, and generous living, dining, and entertaining spaces. With its own private entrance, this beautifully designed space is ideal for extended family, guests, or farm staff, offering independence without sacrificing connection. A theatre room completes this amazing family home! Whether your vision includes a private equestrian retreat, a professional training operation, or a multigenerational family estate, this extraordinary Midway property offers the rare opportunity to enjoy sophisticated country living alongside exceptional equestrian infrastructure. A truly special offering in the heart of Kentucky's celebrated horse country, where luxury, lifestyle, and functionality come together. Priced well below recent appraisal!

3200 Fishers Mill Rd, Midway
120 Elkhorn Bend Dr, Midway
$825,000
2 Beds ⋅ 3 Baths ⋅ 26027774 MLS
Spacious, well-maintained home situated on the bank of the South Elkhorn Creek just outside of historic Midway, KY. Enjoy the convenience of being located 20 minutes +/- from downtown Lexington, Georgetown, Frankfort, Versailles, Keeneland, and the Bluegrass airport. The entrance to South Elkhorn Bend subdivision winds through an active horse farm, leading to the end of a Cul-de-sac where you will find 120 Elkhorn Bend Drive, a beautiful, 4800 sq ft plus brick home. The main floor features spectacular views of the creek and surrounding farmland from the primary bedroom, living room, and a large eat-in kitchen that leads to a partially covered deck, perfect for entertaining and enjoying sunset family meals. The primary suite includes two walk-in closets, a large bathroom with double bowl vanities, linen closet, jacuzzi tub, and a walk-in shower with two shower heads. Also located on the first floor is a secondary bedroom, adjoining full bathroom, first floor laundry room, and an impressive 2.5+ car garage with ample storage, perfect for the car enthusiast. The walkout basement features a generous open floor plan with lots of natural light highlighted by a stunning stone fireplace, and a large patio accessed by two separate entrances. Other features include a finished half bathroom that could easily be converted into a full bathroom, mechanical room (with a built in safe), and a fully roughed in secondary bathroom, making the entire package a plug and play canvas to add an in-law suite, additional bedroom/rooms, or the perfect entertaining space. Whether you enjoy fishing, kayaking, or birdwatching, this property offers amazing private access to one of the best smallmouth fisheries in Central Kentucky mere steps from the back door. Houses in this lovely neighborhood and incredible location do not come available very often. Make an appointment to view this truly special listing today! New roof as of 2023, and new HVAC system as of 2022. * Exact square footage and property lines to be verified by buyer or buyer's agent. Property to be sold in as is condition, with inspections welcome.

120 Elkhorn Bend Dr, Midway
136 Seahawk Trl, Midway
$1,250,000
5 Beds ⋅ 5 Baths ⋅ 26024375 MLS
Welcome to 136 Seahawk Trail, where refined living meets the unmistakable beauty of Kentucky's Bluegrass. Perfectly positioned between the historic downtowns of Midway and Georgetown, with Lexington and Frankfort just a short drive away, this beautifully reimagined residence offers the rare combination of privacy, convenience and resort-inspired living. Recently and extensively remodeled, the home showcases a gorgeous new kitchen designed to become the heart of everyday living and entertaining. The coveted main-level primary suite provides a private retreat, highlighted by a beautifully remodeled ensuite bath. Upstairs, three additional bedrooms and two full baths provide generous accommodations, while the finished lower level offers the flexibility of a fifth bedroom with an additional full bath. Yet it may be what lies beyond the walls that truly sets this property apart. Situated on a private two-acre setting with a wooded backdrop adjoining picturesque horse country, the views deliver a quintessential Kentucky experience. The sellers thoughtfully expanded the outdoor living spaces to create a private resort of their own, anchored by a luxurious pool with a striking modern waterfall feature and sun shelf—perfect for relaxing in the water while soaking up a little Kentucky sunshine. The finished walkout basement was made for entertaining, featuring a spacious gathering area and wet bar with full-size refrigerator that transitions effortlessly to the covered patio. Step outside to the hot tub, catch the game on the outdoor TV, lounge poolside, or simply enjoy an evening overlooking the surrounding countryside. From summer afternoons by the pool to cool evenings under the covered patio, this is a home designed to be enjoyed in every season. Two private acres. Horse-country views. Beautifully remodeled interiors. Exceptional outdoor living. And a location that puts some of Central Kentucky's most beloved communities within easy reach. 136 Seahawk Trail isn't simply a place to come home to, t's a place you'll rarely want to leave.

136 Seahawk Trl, Midway
122 Lighthouse Way, Midway
$875,000
4 Beds ⋅ 5 Baths ⋅ 26022643 MLS
Welcome to Fishers Mill Landing, where rural Kentucky charm meets everyday convenience — large lots, horse farms, and the beauty of Elkhorn Creek, yet just minutes to Midway's quaint downtown shops and restaurants. Easy access to Georgetown, Frankfort, and Lexington via I-64, US 421, and US 460. This 4 BR, 4.5 BA home offers over 4,500 finished sq ft plus 1,600+ sq ft of garage and basement storage. The main floor features tall ceilings, a huge primary suite with bath featuring heated tile floors, soaking tub and tile shower, a second en-suite bedroom, separate office with French doors for privacy, formal dining, and an eat-in kitchen that opens to a covered patio overlooking the beautiful backyard. Upstairs, a spacious rec room with window seat joins two more bedrooms and full bath. The basement adds a bar area, fireplace, full bath also with heated tile floors, a clever Murphy bed, and abundant storage. With living rooms on all three levels, there is room for fun and togetherness no matter where you are in this home. Amenities like a 500 gallon buried propane tank, central vac, whole house water filtration, built-ins and upgraded trim are here as expected in a home this well planned. Outside, enjoy fruit trees, a raised bed garden, a play set, and room to relax by the koi pond, under the covered front or back porches, or on the patio by the firepit. A rare blend of space, character, and unbeatable location.

122 Lighthouse Way, Midway
1599 Woodlake Rd, Midway
$1,420,000
4 Beds ⋅ 4 Baths ⋅ 26012411 MLS
Exceptional Brick Ranch with Expansive Walk-Out Basement on 11.14 Private Acres — Just Minutes from Downtown Midway, KY! Welcome to your private retreat — a rare opportunity to own a beautifully constructed, approximately 5,000 SF custom brick ranch home situated on over 11 tranquil acres located just 4 miles from the vibrant and historic downtown Midway. This estate with its panoramic views offers the perfect blend of timeless charm, privacy, and flexible living spaces — including potential for multi-generational living, equestrian use, and future expansion. Step through the front door into an expansive, light-filled open floor plan designed for both comfortable living and elegant entertaining. At the heart of the home is a truly breathtaking two-story natural stone fireplace, serving as both a visual centerpiece and cozy gathering spot in the vaulted great room. One of the most exciting and valuable aspects of this property is the approx. 5,700 square ft walk-out basement. It is already partially finished with drywall, electrical, roughed-in plumbing for 2 full baths & kitchenette, also has a functioning laundry room. The basement is a blank canvas for you to make it your own! Some photos are VIRTUALLY STAGED for inspiration purposes only. Note: Sellers require 48 hours notice for showings and a preapproval letter, please.

1599 Woodlake Rd, Midway
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