Courtesy: CENTURY 21 Simpson & Associates
502-223-1600
Historic Midway Charm located in the heart of Midway. This 3 bedroom 2 bath home offers 1726 sq ft with original hardwood floors, a brick fireplace, and spacious room sizes throughout. The solid brick construction and classic layout provides excellent potential for updates and added value. Ideal for local buyers, first-time homeowners looking to build sweat equity or investors seeking a strong long-term or short-term rental opportunity in a highly desirable location. This is a chance to own in one of Woodford County's most sought-after areas.
Courtesy: McCallie Real Estate
859-312-7599
CLASSIC.......MIDWAY.....KENTUCKY describes this lovely property and neighborhood....quiet, simple Shaker like character that is immediately comfortable and attractive, very useable, not fussy or ostentatious, very livable and affordable, and with a bit of a Kentucky farmhouse vibe, all describe 217 West Stephens Street. This sweet house has had little alteration from it's original iteration and several of the light fixtures appear to be original but it is ready to be refreshed and reinvigorated for your imprint and lifestyle. The bones of this Kentucky classic seem strong but there are some updates and repairs that will springboard this structure well into this century while still embracing Midway charm. A new furnace and AC were recently installed for the first floor and beautiful pine floors throughout the first floor give the house immense character. Outside a generously sized one vehicle garage sits at the back right. And if flower or vegetable gardening is your passion a large, left side wide yard provides plenty of space to create your own natural paradise. The basics are all here just waiting for your imagination and recreation. Come see for yourself what a charmer it is now and imagine the touches you can provide to make it a Midway Delight! This property is in an estate and the listing agent is also the executor of the estate. The property is being sold 'As Is' and we fully welcome general and specific inspections. Due to our harsh winter weather in the area we are extending the view and offer to purchase period until February 10th and any follow up inspections until Saturday February 14th. On Monday February 16, the winning offer will be selected. It is imperative that any offer be accompanied with verification of funds or full qualification for financing.
Courtesy: DIY Flat Fee.com
888-601-3771
Priced below recent appraisal! Beautifully maintained and extensively updated ranch home in highly desirable Midway. Major 2022 upgrades include a new roof, full interior and exterior paint, engineered wood flooring throughout, remodeled kitchen and bathrooms, updated fireplace, smooth drywall ceilings, 5 base molding, all new lighting and ceiling fans, and custom closet organizers in every bedroom. Enjoy outdoor living on the 12x28 covered and screened back patio with pavers and blackout shades, plus custom blinds on rear windows. Curb appeal shines with a new front door, paver-lined driveway and walkway, and refreshed front landscaping with additional landscaping along the backyard fence. Additional highlights include a split-bedroom floor plan for privacy, vaulted living room ceiling, and a new (2025) drop-down aluminum attic ladder with added attic flooring. Located just minutes from the elementary school. Move-in ready schedule your showing today.
Courtesy: Real Broker LLC
855-450-0442
Set across 34 picturesque acres in the heart of Kentucky Horse Country, this exquisite equestrian estate offers the perfect fusion of world-class facilities and refined country living. Located minutes from the Kentucky Horse Park, this facility is designed for professional-level training and competition across disciplines. The centerpiece of the farm is a 19-stall barn featuring 12' x 12' rubber-matted stalls, tongue-and-groove wood finishes, indoor and outdoor wash bays, a heated tack room and bathroom, washer/dryer hookups, and a fully guttered drainage system. The 80' x 160' indoor arena is outfitted with premium Trutek footing and large windows that provide natural light and cross ventilation. The 100' x 200' outdoor arena was completely rebuilt in 2025 with a 7-inch crushed limestone base and 3 inches of mortar sand for exceptional drainage and rideability. Six fenced paddocks, each with individual automatic waterers, are laid out for efficient turnout and easy access to the barn. Additional facilities include a 24' x 60' equipment barn with water and electric, a run-in shed, full RV hookup, and separate utilities for the home and farm—ideal for flexible management or future expansion. Beyond the equestrian facilities, the property's custom five-bedroom home features a walk-out basement, home theater, and expansive living spaces with sweeping views of the pastures, offering the perfect blend of comfort and functionality. Located in one of the most desirable equestrian regions in the country, this property is perfectly suited for professionals, competitors, or discerning enthusiasts seeking a turnkey facility with close proximity to top-tier events, veterinary services, and training circuits.
Courtesy: Bentley & Co., REALTORS
859-231-5366
Beautifully remodeled three-bedroom, two-bathroom home in Historic Midway, KY. Conveniently located in the middle of horse country, enjoy the luxury of being within a 20+/- minute drive of Keenland, Fasig-Tipton, Lexington, the Bluegrass airport, Frankfort, Georgetown and Versailles. The home itself was fully remodeled in 2020, with a new roof, floors, ceilings, plumbing, drywall, electric, closed cell spray foam insulation, appliances, HVAC, water heater, fixtures, and flooring. Windows were replaced in 2017, and all appliances do convey with the property. The property features a sizeable lot (just over 1/4 of an acre,) detached single car garage, and is located within walking distance of Downtown Midway, numerous restaurants, shopping, and several public parks. Make an appointment and come by to see this thoughtfully remodeled home yourself! Property to be sold as is, inspections welcome.
Courtesy: Real Broker LLC
855-450-0442
Set across 34 picturesque acres in the heart of Kentucky Horse Country, this exquisite equestrian estate offers the perfect fusion of world-class facilities and refined country living. Located minutes from the Kentucky Horse Park, this facility is designed for professional-level training and competition across disciplines. The centerpiece of the farm is a 19-stall barn featuring 12' x 12' rubber-matted stalls, tongue-and-groove wood finishes, indoor and outdoor wash bays, a heated tack room and bathroom, washer/dryer hookups, and a fully guttered drainage system. The 80' x 160' indoor arena is outfitted with premium Trutek footing and large windows that provide natural light and cross ventilation. The 100' x 200' outdoor arena was completely rebuilt in 2025 with a 7-inch crushed limestone base and 3 inches of mortar sand for exceptional drainage and rideability. Six fenced paddocks, each with individual automatic waterers, are laid out for efficient turnout and easy access to the barn. Additional facilities include a 24' x 60' equipment barn with water and electric, a run-in shed, full RV hookup, and separate utilities for the home and farm ideal for flexible management or future expansion. Beyond the equestrian facilities, is a beautifully designed custom five-bedroom home featuring expansive living areas, a walk-out basement, home theater, and sweeping views of the surrounding landscape. Large windows flood the interior with natural light, creating a warm and inviting atmosphere throughout. Thoughtfully designed for both everyday living and entertaining, the home balances comfort with elegance. Located in one of the most desirable equestrian regions in the country, this property is perfectly suited for professionals, competitors, or discerning enthusiasts seeking a turnkey facility with close proximity to top-tier events, veterinary services, and training circuits.
Courtesy: Bluegrass Sotheby's International Realty
859-268-0099
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.
Courtesy: RO&CO Real Estate
859-487-5670
Welcome to 170 Davistown Rd — where timeless country charm meets everyday convenience! Nestled on just under 2+/- acres in the heart of Kentucky's famed horse country, this inviting home offers the best of both worlds: peaceful, scenic living just 5 minutes from historic downtown Midway and only 15 minutes to Lexington via I-64. Imagine hosting dinner parties in your open-concept kitchen, gathering around the fire pit with friends, or simply enjoying the expansive backyard with plenty of room to roam. Whether you're sipping coffee on the porch or entertaining loved ones under the stars, this home is made for connection and comfort. Here, you get the serenity of the countryside with quick access to all the shopping, dining, and amenities the city has to offer. Functional, stylish, and perfectly located—this is Midway living at its finest. Your big ticket items are already done! HVAC and water heater are all five years old, new roof in November 2024, detached garage that can fit all your outdoor equipment - with water and electric already there (Water needs to be connected). There is a cellar that can be used as a storm shelter or additional storage.
Courtesy: Four Seasons Realty
859-396-7295
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!
Courtesy: Keller Williams Bluegrass Realty
859-260-1444
Turnkey Equestrian Facility 16 Stalls 2 Arenas Eurociser 20 Min to KY Horse Park. Exceptional 12.59-acre equestrian farm in Midway, KY, designed for high-level training and year-round use. Features a 100x180 outdoor arena with glacier-sand footing and a fully insulated 80x180 indoor arena with low-dust polytrack. Equine amenities include a 10-stall pony/yearling barn, six 14x14 stalls in the main barn with surveillance, two 80-ft lunge pens, and a 4-bay Eurociser. A spacious 2-bedroom apartment above the barn offers comfortable on-site living or income potential. Additional highlights: fowl barn, stocked pond, 32x70 hoop barn, two 20x30 storage barns, four run-in sheds, 3-bay equipment shed, and pool house with above-ground pool. The property is fenced with 4-board and wire/top board, serviced by two wells, Bar Bar A field waterers, and offers top-grade soils. Zoned A-1 with no HOA. Additional acreage available.
Courtesy: Keller Williams Bluegrass Realty
859-260-1444
Coming in at just under 24 acres total, this Midway farm has it all! Thoughtfully designed by it's present owners, it is ready for some new love! Improvements on it's two parcels include: a 100x180 outdoor arena w/glacier sand, a 10 stall pony/yearling barn, (2) 80 ft lunge pins, a 4 bay Eurociser, a fowl barn, stocked pond, an 32x70 hoop barn, (2) 20x30 storage barns, an 80x180 indoor arena w/ polytrack footing, 6 run in sheds, and the main barn offers (6) 14x14 stalls equipped with surveillance cameras, and an ample two bedroom apartment living quarters up top. Rounding out the farm is a pool house and above ground pool and a 3 bay equipment shed. The property has varying top grade soils on it and combinations of wire/top board fencing to 4 board plank along with Bar Bar A field waterers. Lots of natural elements and is a current working farm. This is the best the Bluegrass has to offer and you owe it to yourself to put your stamp here!
Midway is located in Kentucky. Midway, Kentucky 40347has a population of 1,786. Midway 40347 is less family-centric than the surrounding county with 24.95% of the households containing married families with children. The county average for households married with children is 30.26%.
The median household income in Midway, Kentucky 40347 is $69,464. The median household income for the surrounding county is $72,765 compared to the national median of $69,021. The median age of people living in Midway 40347 is 38.3 years.
The average high temperature in July is 86.2 degrees, with an average low temperature in January of 24.1 degrees. The average rainfall is approximately 45.3 inches per year, with 8.2 inches of snow per year.
