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$248,800
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
$319,900
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
$1,295,000
26021296 MLS
Beautiful 52± acres just minutes from downtown Midway with 9 stall horse barn, new fencing, auto waterers, and a spring fed pond. The barn has been recently renovated from top to bottom with new roof, metal siding, steel doors, stamped concrete aisle, 14x13 stalls with custom stall fronts, wash rack, 13x12 feed room, and 40x15 tack room with roughed-in bathroom. The barn loft could be converted to a barn apartment or there are several great build sites for a residence on the property. There is also a brand new 32x72 hoop barn perfect for hay or equipment storage. Just 5 minutes from Downtown Midway, 15 minutes from Frankfort, 20 minutes to the Kentucky Horse Park, and 25 minutes to Lexington. Don't miss out on this wonderful equestrian property!

1625 Woodlake Rd, Midway
$840,000
26019967 MLS
A once in a lifetime opportunity to own 20 acres of prime land in the heart of the bluegrass awaits! Nestled between downtown Lexington, Midway, and Georgetown, this ideal location boasts incredible views for your home or farm... all tucked down a shared paved driveway. This premier land offering backs up to the Elkhorn Creek, but is high enough ground to have no water concerns. Surrounded by boutique horse farms, hay fields, and beautiful new residences, this land has not been available for public purchase in over 100 years! * Water and electric are available.

2639 Weisenberger Mill Rd Unit -001, Midway
$897,900
3 Beds ⋅ 2 Baths ⋅ 26019997 MLS
Coming home never felt so good! This beautiful 10 acre parcel with an open concept 3 bed 2 bath ranch home is yours to love as is or customize to suit. With privacy at its heart, this prime location offering is only minutes from Midway, Lexington, Georgetown, and the highway, making it the ideal blend of accessibility and seclusion. Boasting rich bluegrass soils, flat open spaces, treelined boarders, and paved driveway, this acreage is ready to become the boutique farm of your dreams. Move in and change nothing, or develop it into the estate you never thought you could find! A 2680 sq foot unfishished basement, with 9 foot ceilings is already plumbed for a bathroom and could double your square footage. Additional acreage possible.

2639 Weisenberger Mill Rd, Midway
$4,999,999
3 Beds ⋅ 4 Baths ⋅ 26020214 MLS
A thoughtfully designed, gated, turnkey horse farm w 121 immaculate, lush acres, with 17, V mesh fenced paddocks and 5 fields, large run in sheds, and automatic waterers. Updated farm managers house and 2 updated tenant houses, 3 barns with a total 54 stalls. Tobacco barn converted into 18 (14 x 14) stalls, covered hay storage, attached office, breeding shed, lab, studio apartment, and additional storage. 2 other barns with 12x12 stalls, and 4 foaling stalls totaling another 36 stalls, large storage barn. Kraft covered euro-cisor, round pen and brand new state of the art, 110 x 220, GGT footing, Fully insulated Indoor arena w/ large viewing room and roll up windows and big ass fans for awesome ventilation. This farm is incredibly well updated from housing to barns to fencing. For history buffs, this farm has ties to Thomas Jefferson and Benjamin Franklin. Indoor arena completed in July, Main house, farm managers house and tenant houses updated 2020, roads paved and over coated in 2019, best soils-double seeded and treated for virtually weed free fields.Barn #1 updated w new stain powder coated stall doors and windows. Kraft covered equicisor 2019. Large barn #3 has a studio apartment connected to the insemination breeding complex. There is ample room to include more apartments, if needed, in this space. Farm is completely move in ready and immaculate.

3945 W Leestown Rd, Midway
$495,000
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
$415,000
2 Beds ⋅ 2 Baths ⋅ 26019469 MLS
One of Midway's oldest homes has been updated throughout and features a new porch overlooking a private garden area with lots of landscaping. The updated, chef's kitchen is open to the living room with French doors onto the large private deck. There is also a 1st floor primary bedroom and bathroom. The second floor features a bedroom, full bathroom, and an office or third bedroom area. The private yard is fenced and has a large storage building with room for a workshop and storage. The house has plenty of it's own off-street parking.

212 W Main St, Midway
$425,000
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
$417,000
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
$99,900
25507441 MLS
Build your dream home on this prime lot in Midway! Connected to water and sewer with a convenient location that is just a short drive into Lexington. (Lot 8)

275 Northside Dr, Midway
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 26012123 MLS
This expansive, private country farm property covers, 35.8 acres, divided into four distinct pastures of varying size. Property is well-suited for agricultural use, equestrian activities and rural living. Prime, secluded location, 11 miles from Lexington, 12 miles from Frankfort, 1.5 miles from Midway. Immediately adjacent to world-class thoroughbred foaling/boarding/breaking/training facility, Margaux Farm. The house has had a spectacular remodel done by Crawford Builders. It features a gourmet kitchen, with high-end appliances, open to the great room and 18 foot ceilings to complete the effect. The master suite is impeccable, including his and hers closets, fabulous bathroom, private sitting area, and exercise room. The home also features another first floor en suite bedroom. the two bedrooms upstairs are also en suite. There is a fabulous private Office, Butler's pantry, laundry room, covered porch, entertainment room and full bar with a game room. There are 15 deluxe stalls in 2 barns, hay storage, manager's house, run-in sheds, and gated and treelined driveway. Property entrance gate with advanced telephone entry and live streaming video. Whole house emergency generator fueled from underground propane storage. The house is completely integrated with remotely controlled audio/visual/heating control/security camera system!

595 Moores Mill Rd, Midway
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 26012105 MLS
This expansive, private country farm property covers, 35.8 acres, divided into four distinct pastures of varying size. Property is well-suited for agricultural use, equestrian activities and rural living. Prime, secluded location, 11 miles from Lexington, 12 miles from Frankfort, 1.5 miles from Midway. Immediately adjacent to world-class thoroughbred foaling/boarding/breaking/training facility, Margaux Farm. The house has had a spectacular remodel done by Crawford Builders. It features a gourmet kitchen, with high-end appliances, open to the great room and 18 foot ceilings to complete the effect. The master suite is impeccable, including his and hers closets, fabulous bathroom, private sitting area, and exercise room. The home also features another first floor en suite bedroom. the two bedrooms upstairs are also en suite. There is a fabulous private Office, Butler's pantry, laundry room, covered porch, entertainment room and full bar with a game room. There are 15 deluxe stalls in 2 barns, hay storage, manager's house, run-in sheds, and gated and treelined driveway.

595 Moores Mill Rd, Midway
$2,680,000
5 Beds ⋅ 5 Baths ⋅ 26008218 MLS
Minutes from the charming town of Midway and conveniently positioned for easy access to the Kentucky Horse Park, this 34-acre equine facility — complete with a custom five-bedroom home, a 19-stall barn and both indoor and outdoor arenas — is built for the serious equestrian. The farm infrastructure is extensive and well-appointed. The barn is finished to a high standard with quality stalls, a heated tack room and bathroom, and indoor and outdoor wash bays. The outdoor arena was completely rebuilt in 2025 with upgraded footing for exceptional performance in any weather, and the indoor arena is equipped with premium Trutek footing and designed to ride comfortably year-round. Six paddocks each have individual automatic waterers. Additional support facilities include a run-in shed, an oversized equipment barn with water and electric, and a full RV hookup. The custom home is designed for livability, with the primary suite, two additional bedrooms with a jack-and-jill bath, and a dedicated office all on the main floor. The lower level can function as a fully independent suite with its own living area, full kitchen, bedroom suite, home theater, and walk-out access — ideal for farm management, extended family, or guest accommodations. The home and farm are on separate utilities for easy management.

3200 Fishers Mill Rd, Midway
$900,000
26009053 MLS
A nice opportunity for investors and developers for 8.04 acres in the heart of Midway. Property is currently zone R-1B and has access via 2nd Street. This land is within walking distance to downtown Midway and close to I-64 and only 15 minutes to Frankfort or Lexington. This is a prime location with lots of possibilities.

6888-A Midway 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
$614,500
2 Beds ⋅ 1 Baths ⋅ 26015758 MLS
This property has been in the same family since 1948. Beautiful setting in Franklin County near Versailles, Georgetown and Lexington. Enjoy the large country kitchen, the quiet and the spacious rooms. The house has stairs to a second-floor attic which could be converted into more than storage space. The basement could also be converted into living space. You will find new windows, new HVAC system, new hot water heater and new bathroom fixtures. On the property is a second building that was an apartment at one time and still has a septic tank connected and could have water connected. The home comes with a 1-year home warranty from America's Preferred Home Warranty, Inc which allows the new owner to pick their preferred repair companies. Selling the property AS IS. Inspections welcome.

1116 Duckers Rd, Midway