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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.

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

$785,000

A grand dame of historic Midway, this stately 1888 Victorian/Queen Anne residence offers beautiful architectural details along with elegant proportions of the era. Distinguished by its Blue Grass Trust designation, this four-bedroom, two-and-a-half-bath home features stained glass windows & doors throughout, generously sized bedrooms, two staircases—including a beautifully refinished formal staircase—and an exceptional abundance of closets and storage rarely found in a historic home. All windows have been replaced with custom-fitted storm windows and screens throughout, improving energy efficiency, reducing outside noise, and providing a tighter seal against drafts. Formal living and dining rooms offer space for entertaining, while a comfortable den with a gas fireplace just off the kitchen provides a welcoming spot for everyday gathering. Two additional flex spaces on the first floor offer possibilities for home offices, guest accommodations, or additional bedrooms. The large primary suite boasts two cedar-lined closets and a spacious bath with a soaring ceiling, soaking tub, double vanity, and walk-in shower. A convenient second-floor laundry room with utility sink adds everyday practicality, while a generous attic with pull-down stairs provides additional storage and houses a second HVAC unit. Expansive covered porches at the front and rear invite a slower pace—morning coffee overlooking the garden, a quiet afternoon with a book, or evening conversations as the landscape lighting illuminates the grounds. The rear patio incorporates salvaged brick from renowned Dixiana Farm, adding another distinctive connection to the Bluegrass. The backyard, fully enclosed by iron fencing, features lush, established plantings of hydrangeas, holly, clematis, viburnum, and magnolia, complemented by dry-stacked raised stone planting beds and an irrigation system on a separate water meter. Freshly painted siding, predominantly made of durable Hardie board, copper gutters and downspouts, a detached one-car garage, and a Ring security system complete this remarkable residence—a gracious setting for enjoying the charm and rhythms of a beautiful life lived in historic Midway.

4 Beds ⋅ 3 Baths ⋅ 26028276 MLS

A grand dame of historic Midway, this stately 1888 Victorian/Queen Anne residence offers beautiful architectural details along with elegant proportions of the era. Distinguished by its Blue Grass Trust designation, this four-bedroom, two-and-a-half-bath home features stained glass windows & doors throughout, generously sized bedrooms, two staircases—including a beautifully refinished formal staircase—and an exceptional abundance of closets and storage rarely found in a historic home. All windows have been replaced with custom-fitted storm windows and screens throughout, improving energy efficiency, reducing outside noise, and providing a tighter seal against drafts. Formal living and dining rooms offer space for entertaining, while a comfortable den with a gas fireplace just off the kitchen provides a welcoming spot for everyday gathering. Two additional flex spaces on the first floor offer possibilities for home offices, guest accommodations, or additional bedrooms. The large primary suite boasts two cedar-lined closets and a spacious bath with a soaring ceiling, soaking tub, double vanity, and walk-in shower. A convenient second-floor laundry room with utility sink adds everyday practicality, while a generous attic with pull-down stairs provides additional storage and houses a second HVAC unit. Expansive covered porches at the front and rear invite a slower pace—morning coffee overlooking the garden, a quiet afternoon with a book, or evening conversations as the landscape lighting illuminates the grounds. The rear patio incorporates salvaged brick from renowned Dixiana Farm, adding another distinctive connection to the Bluegrass. The backyard, fully enclosed by iron fencing, features lush, established plantings of hydrangeas, holly, clematis, viburnum, and magnolia, complemented by dry-stacked raised stone planting beds and an irrigation system on a separate water meter. Freshly painted siding, predominantly made of durable Hardie board, copper gutters and downspouts, a detached one-car garage, and a Ring security system complete this remarkable residence—a gracious setting for enjoying the charm and rhythms of a beautiful life lived in historic Midway.

304 S Winter St, Midway

$869,900

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.

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

$825,000

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.

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

$1,250,000

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.

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

$1,420,000

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.

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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