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101 Sand Piper Ct, Midway
$990,000
5 Beds ⋅ 5 Baths ⋅ 26004651 MLS
Situated on 2.41 breathtaking acres just minutes from Georgetown, Frankfort and Lexington, 101 Sandpiper Court offers over 5,500 square feet of beautifully appointed living space in a setting that captures the very best of the Bluegrass. Backing to an Elkhorn Creek tributary and located just a mile from Elkhorn Creek itself, this property blends privacy, recreation and natural beauty. The main level features a generously sized kitchen with cherry cabinetry, granite and GE Profile appliances, spacious living and formal dining rooms, an executive-style primary suite, with heated tile floors and a private office complete with its own bar. Upstairs, three well-designed bedrooms and two baths provide ideal guest accommodations. The finished lower level expands the home's versatility with a bar, kitchenette, home theater, abundant storage, a fifth bedroom and full bath - perfect for in-law or extended guest living. Thoughtful upgrades include newer systems, a two-year-old roof, central vacuum, new garage doors, custom closet systems, plantation shutters and three gas fireplaces. Outdoors, this spectacular lot is the true showpiece with views to be enjoyed from the covered porch or lower level patio. The back yard is completed with an expansive garden space, a fire pit and a scenic creek, with the rare opportunity to enjoy acreage living while remaining conveniently close to town. Do not hesitate on this gorgeous home!

101 Sand Piper Ct, Midway

425 N Winter St, Midway
$820,000
4 Beds ⋅ 3 Baths ⋅ 26016428 MLS
American Gothic beauty in the heart of horse country in storybook, Midway Kentucky. This ICONIC home on 2acres sits across from the Holly Hill Inn and 2mins from Hallmark Movie quaint downtown Midway. Updated for modern living blending the historic with thoughtful updating. Open floor plan with spacious great room, gourmet kitchen and butler's pantry. Soaring ceilings with floor to ceiling windows that flood the space with soft natural light filtered through the old growth trees. Original heart pine floors beautifully preserved and many original features remain throughout the home. Full bath and a bedroom on the 1st floor. Primary suite on the 2nd floor with tile shower and large bath. Second en-suite bedroom on the 2nd floor. Copper gutters and copper roof on the seamless side porch addition. The barn is converted to a 3-car garage with tons of extra storage above. Tucked behind the garage is an 1800 sq. ft auxiliary building currently used as a wood shop. The building with covered porch and full bathroom offers enormous upside potential for whatever your dreams or hobbies are made of. Don't miss this rare opportunity to own a piece of Midway's history.

425 N Winter St, Midway

314 N Winter St, Midway
$814,800
4 Beds ⋅ 2 Baths ⋅ 26008044 MLS
3.52 acres, fully renovated home - A rare find indeed with - usable land, updated living space and walkable access to everything Midway has to offer. The main home offers over 3200 sq ft with a layout designed for both everyday living and gathering. The updated kitchen includes granite countertops, gas range, pot filler, built in dishwasher and refrigerator, opening into a comfortable fireside sitting area. Multiple living spaces create a natural flow, making the home feel both connected and functional. The home includes 4 bedroom and 2 full bathrooms and an office, providing flexibility based on your level needs. A main-level bedroom and full bath offer added convenience for guests or single level living. Above the detached three-bay garage is a fully equipped 878 sq ft apartment with its own kitchen and laundry - ideal for guests, extended family or additional living space. ( not included in listing sq ft ) One garage bay is currently used an a workshop. The 3.52 acre property is partially wooded, with many native trees planted and landscaping designed to support pollinators and local bird population. A large front porch provides a place to take in the sunset, while outdoor spaces - including the fire pit area - offer opportunities to enjoy the property throughout the seasons. A well maintained chicken coop adds to the usability of the land. No roosters allowed per City Ordinances. Located just across from Walter Bradley walking trail, this home provides direct access to Midway's trail system, connecting you to local restaurants, shops, the dog park and nearby school. The home was fully renovated 3 years ago, bringing together modern updates with a setting that is increasingly difficult to find. Shown by appointment only. Security and cameras on site. OPEN HOUSE SAT MAY 23rd 2026 NOON to 3 PM

314 N Winter St, Midway

119 Seahawk Trl, Midway
$760,000
5 Beds ⋅ 4 Baths ⋅ 26022885 MLS
Set on 2.88 acres—one of the largest lots in Fisher Mill, 119 Seahawk Trail offers the space, setting and floor plan that are increasingly hard to find. Built in 2003, this well-established home is ready for its next owner to bring a fresh perspective and make it their own. The main level features both the primary suite and a guest suite, offering flexibility for everyday living, guests or multigenerational needs. Upstairs, you'll find two additional bedrooms connected by a Jack-and-Jill bath, along with a generously sized bonus room. The basement adds even more versatility with an additional bedroom and bath, living and flex space plus a storm shelter. With nearly three acres, there's plenty of room to enjoy the outdoors, create gardens, entertain or simply appreciate a little more privacy between neighbors. Fisher Mill is known for its large homesites, executive feel and convenient location between Midway, Georgetown and Lexington. For the buyer willing to add their own updates and style, this property offers an exceptional opportunity to create something special in a setting worth investing in.

119 Seahawk Trl, Midway

208 S Winter St, Midway
$470,000
2 Beds ⋅ 2 Baths ⋅ 26020088 MLS
The newly renovated Nave-Werhle House is available for purchase. This charming cottage dates to 1877 and is beautifully situated on S. Winter Street in Midway Kentucky. The location is superb, just steps from the Downtown Midway and all of the amenities offered there. The home has been tastefully renovated recently with a new Kitchen and high quality appliances, new primary bathroom with large walk in shower, and newly painted inside and out! Other features include very nice hardwood floors, 10ft ceilings, vaulted ceiling in the primary bedroom, large walk in closet, built in cabinetry in the family room, a charming front porch and side deck/porch, a 1 car detached garage with carport and basement storage area. While technically a two bedroom, two bath residence, it is currently configured as three bedrooms. Take your pick...either way this a great house in an awesome location.

208 S Winter St, Midway

2722 Leestown Rd, Midway
$452,500
4 Beds ⋅ 2 Baths ⋅ 26006418 MLS
Spacious 4-bedroom, 2-bath home on 1.98 acres in Frankfort, KY, offering the perfect blend of privacy and convenience. Located only minutes from Frankfort dining/shopping/recreation or downtown Lexington, this property provides easy access to city amenities while maintaining a peaceful, country setting. The home features a functional layout with multiple living areas and a Murphy bed in the basement, ideal for guests or flexible use of space. Make sure and ask your showing agent about the flooring allowance that is included, giving buyers the opportunity to personalize the interior to your taste. Outdoor amenities make this property stand out. Enjoy warm-weather fun in the above ground pool, host gatherings on the sand volleyball court, or take advantage of the large utility building, perfect for entertaining, storage, or recreational use. A rare opportunity to own a versatile property with exceptional outdoor amenities and room to grow, all in a convenient location to where life takes you each day. Franklin County location (not city of Frankfort) allows for fewer restrictions on land usage.

2722 Leestown Rd, Midway

301 S Turner St, Midway
$425,000
3 Beds ⋅ 3 Baths ⋅ 26004565 MLS
This Midway home has a story to tell - it's a joy to show. It is a beautifully cared-for home that is more than a century old yet has updates for modern living. Definitely rich with character and detail, let it tell you it's story when you visit. There are 3 well sized bedrooms, and 2 1/2 baths. The primary and a full bath are on the first level - with the ability for someone to live all on one floor if needed, only limited steps to garage. The primary en-suite even has a walk-in closet, rare for a home of this era. You will also find a delightful cozy library nook that invites quiet reading or a cozy workspace, along with a generously sized living room and dining room (both with fireplaces) perfectly suited for memorable dinners and gatherings. The kitchen truly speaks to the period of origin —featuring an original butler's pantry with second farmhouse sink. This kitchen has handcrafted cabinetry rarely found today, complete with thoughtful details like a flour sifter and built-in cabinet pull-out organizers. A charming pass-through connects the space to the finished keeping area, while a newer gas vintage stove compliments the home's historic vibe. Enjoy peaceful mornings on the screened side porch with a cup of coffee while listening to the sounds of the neighborhood waking up. Outside, a serene patio tucked behind a privacy fence creates the perfect setting for relaxing evenings or entertaining in the quiet backyard. Location is everything with this one, it is just a short stroll from the heart of downtown Midway and Midway University, this historic gem offers the rare opportunity to enjoy small-town charm, walkability, and a home filled with authentic character too. Don't miss a chance to take a look and add your chapter to the story of this home.

301 S Turner St, Midway

419 Mill Rd, Midway
$410,000
4 Beds ⋅ 3 Baths ⋅ 26018990 MLS
Welcome to 419 Mill Street, where the charm of Midway meets the peaceful beauty of Kentucky farm country. Nestled on a quiet cul-de-sac and backing to picturesque farmland, this thoughtfully built home offers the perfect blend of small-town character, quality craftsmanship, and everyday comfort. Designed for convenient one-level living, the home features a first-floor primary suite and first-floor laundry, making daily life effortless. Upstairs, you'll find three additional bedrooms and a full bath, providing plenty of room for family and guests. A spacious unfinished bonus room offers abundant storage or the opportunity to create a home office, media room, playroom, or additional living space tailored to your needs. Well maintained and built with lasting quality, this home provides an exceptional foundation while offering the opportunity to add your own personal style over time. Step outside to enjoy peaceful farm views, quiet evenings, and the kind of setting that reminds you why so many people dream of living in Midway. Just minutes from Midway's historic downtown, you'll enjoy locally owned restaurants, charming boutiques, and the welcoming community that has made this one of Central Kentucky's most beloved small towns. Conveniently located between Lexington, Georgetown, and Frankfort, 419 Mill Street offers the best of Kentucky living—where life feels a little slower, a little quieter, and a little more connected to what matters most. Property is under contract with contingency and 24 hour kickout.

419 Mill Rd, Midway

250 N Winter St, Midway
$389,000
2 Beds ⋅ 2 Baths ⋅ 26015702 MLS
Beautifully restored while preserving its original character, this charming cottage seamlessly blends timeless appeal with modern conveniences. The inviting interior features vaulted ceilings, beautiful hardwood floors, and abundant natural light throughout. The Chef's Kitchen is equipped with a gas range, Carrara marble countertops, and an adjoining dining area that opens to the spacious family room highlighted by a stunning stone fireplace. The thoughtfully designed floor plan also offers a spacious primary bedroom suite with a walk-in closet and spa-inspired bath, a welcoming living room, guest bedroom, hallway full bath, and a convenient laundry room. Enjoy relaxing on the wonderful screened porch overlooking the deep backyard, which offers direct access to the city walking trail. Two custom-built sheds provide exceptional space for storage and a workshop. Don't miss this rare opportunity to own a beautifully restored cottage in the heart of downtown Midway, just steps from shopping, dining, and everything this charming Kentucky town has to offer.

250 N Winter St, Midway

130 Carriage Ln, Midway
$375,000
3 Beds ⋅ 3 Baths ⋅ 26017279 MLS
Rare opportunity to own a charming home in the highly sought-after town of Midway, KY! This beautiful home is nestled against picturesque farmland, and offers peaceful views where you can relax and watch the cows graze from your own backyard. Step inside the entry to discover beautiful new engineered hardwood flooring throughout the main level & a new front storm door that welcomes you home. Fresh new carpet has been installed in all 3 bedrooms, creating a warm and comfortable retreat. The beautifully renovated primary bathroom on the first level, features a stunning new tiled walk-in shower, stylish vanity w/granite countertop, faucets, fixtures, and toilet, as well as new wallpaper. Enjoy entertaining in the open vaulted living and kitchen area. Upstairs, you'll find a bonus room that's perfect for a home office, fitness, playroom or flex space to fit your lifestyle. The second floor bath has also been tastefully updated with new tile flooring, vanity, countertop, faucet and towel fixtures. New water heater and garage door replaced , along with a fairly new HV/AC to give a new owner peace of mind. If you have been searching for small town charm with modern updates and serene countryside views, this exceptional home is one you won't want to miss.!!! Call for a showing today.

130 Carriage Ln, Midway

129 S Gratz St, Midway
$300,000
2 Beds ⋅ 1 Baths ⋅ 26011261 MLS
Step into a piece of history with this charming, well-maintained shotgun-style cottage, circa 1835, nestled in the heart of Midway, Kentucky. Rich in character and timeless appeal, this one- story home offers a rare opportunity to own a slice of local heritage just steps from everything this vibrant town has to offer. Enjoy the convenience of being located in the heart of downtown Midway, where you'll find beloved local restaurants, unique shops, a pharmacy, soda shop, medical offices, Midway Bakery, Midway University, and several nearby parks. Let the iconic church bells of Midway Christian gently mark the passing of time, adding to the home's storybook charm. Inside, you'll find beautiful heart pine hardwood floors throughout, complemented by a tiled kitchen. The home features two comfortable bedrooms, a full bath, and a dedicated laundry room, offering both functionality and ease of living. Outdoors, relax or entertain on the inviting flagstone back patio, surrounded by a quaint yard space. The property also includes a garden shed and brand-new off-street asphalt parking for added convenience. Original refinished hinged shutters complete the home's historic character with thoughtful updates. Whether you're looking for a full-time residence, weekend retreat, or investment opportunity, this unique Midway gem is truly one-of-a-kind. *Chandelier located in the dining room will not convey with the property. Property to be sold in "as is" condition, inspections welcome.

129 S Gratz St, Midway

403 Newton St, Midway
$295,000
3 Beds ⋅ 2 Baths ⋅ 26021103 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bath raised ranch offering the perfect blend of modern updates, nature, and convenience. All living space is located on the second level above a spacious first-floor garage with installed flood vents. The updated eat-in kitchen features newer granite countertops, dishwasher, sink & faucet, backsplash, and refinished cabinetry. This space is open to the living room with a cozy gas log fireplace. The primary suite offers a relaxing retreat with double vanities and soaking tub as well as a walk-in closet. The hallway bathroom was recently remodeled with a new shower, vanity, fixtures, and paint. Major updates include a new roof (2023) and new hot water heater (2026). Step outside to enjoy a private backyard oasis with newly stained decks, a back patio, fire pit, and thoughtfully designed landscaping featuring beneficial native plants. The property overlooks a wetland area connected to Lee's Branch Creek, creating a peaceful setting where butterflies, deer, foxes, herons, screech owls, and other wildlife are frequent visitors. Bordering the scenic 28-acre Walter Bradley Park, you'll have direct access to approximately 4 miles of walking trails, a dog park, and a community flower-cutting garden. Enjoy the feeling of secluded country living while being just a short walk from Midway's charming Main Street shops, restaurants, and elementary school, with convenient access to Lexington, Georgetown, Frankfort, and Versailles. A one-year home warranty is included with an accepted offer.

403 Newton St, Midway

327 Smith St, Midway
$257,000
2 Beds ⋅ 2 Baths ⋅ 26010193 MLS
Just got a brand new ROOF! Priced below the recent appraised value. Downtown in the beautiful, historic Midway! Picture this... It's Saturday night, you can hear the live music from your porch, so you grab the dog, a beverage and you take a stroll to the charming downtown streets to sit under the stars and huge trees for the perfect evening with friends and neighbors. Heaven. This home is everything we all love about Midway. From its location to its charm, it really is just special. The home's 2 bedrooms and 2 full baths have been updated. There is also a bonus/flex space that could be used as a third bedroom. A huge backyard and detached garage are an added bonus as well. This home is ready for new memories, just in time for spring and summer.

327 Smith St, Midway

103 Richardson St, Midway
$250,000
3 Beds ⋅ 1 Baths ⋅ 26010398 MLS
Charming fully updated brick ranch located directly across the street from Midway University in the highly desirable Campus Gate subdivision. This 3 bedroom, 1 bath home blends classic character with modern updates and an unbeatable location. Inside, you'll find beautiful hardwood floors, a spacious living area filled with natural light, an updated kitchen with modern finishes, and a renovated bath. The full basement provides excellent storage, workshop space, or future expansion potential. Bonus room in basement providing even more space to expand. Outside, enjoy a large yard perfect for entertaining, gardening, or relaxing evenings at home. Whether you're looking for a primary residence, investment opportunity, or housing convenient to the university, this move-in ready home offers comfort, charm, and exceptional convenience in the heart of Midway.

103 Richardson St, Midway

224 E Cross St, Midway
$230,000
3 Beds ⋅ 2 Baths ⋅ 26022040 MLS
Charming Midway Ranch Within Walking Distance to Downtown! Don't miss this opportunity to own a piece of historic Midway! This inviting ranch is conveniently located within walking distance of downtown & Midway University, putting shopping, dining, campus activities, festivals, & community events right at your doorstep. With the popular Midway Fall Festival & college activities just around the corner, the location offers the best of small-town living with plenty to enjoy. Featuring 3 bedrooms, 2 full baths, and a bonus room at the back of the home with heat (no air), there is plenty of flexibility for your needs. The bonus room could make a great recreation space, home office, or potentially a 4th bedroom with a full bath nearby. Whether you're an investor looking for an opportunity in a desirable location, a parent seeking a convenient home for students, or a family ready to make it your own, this property offers plenty of possibilities. Bring your vision and updates while enjoying everything charming Midway has to offer. Estate sale, Inspections welcome; property is being sold as-is. Square feet is approximate, buyer to verify. Call today to schedule your private showing!

224 E Cross St, Midway

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