Midway, KY Homes

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  /78

  $1,450,000

  • 4 Beds
  • 3.5 Baths
  • 5,033 Sq Ft

  1599 Woodlake Rd, Midway, KY 40347

  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

  Christal Browning Four Seasons Realty

  1599 Woodlake Rd, Midway, KY 40347
• Explore Midway

• 

  

  

  /20

  $3,500 per month

  • 4 Beds
  • 3 Baths
  • 2,076 Sq Ft
  • House for Rent

  109 Lantern Trail, Midway, KY 40347

  Luxurious Craftsman-Style Home for Rent in Fisher's Mill Landing, Midway, KentuckyWelcome to your new home, a flawless, one-of-a-kind Craftsman-style house nestled on nearly 2.5 acres in the tranquil neighborhood of Fisher's Mill Landing, Midway, Kentucky. This is a 4 bedroom, 3 bathroom, 3082 square foot home in Midway, Kentucky. The property has a 2 car garage, up to 8 additional

  109 Lantern Trail, Midway, KY 40347
• 

  

  

  /18

  $320,000 Sold Nov 21, 2025

  112 Richardson St, Midway, KY 40347

  • 3 Beds
  • 1 Bath
  • 1,530 Sq Ft
  • Built 1888

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Last Listing Agent Brett Franklin EXP Realty, LLC

  112 Richardson St, Midway, KY 40347
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  /52

  Est $386,140 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,760 Sq Ft

  106 Cottage Grove, Midway, KY 40347

  106 Cottage Grove, Midway, KY 40347
• 

  

  

  /23

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  103 Highview Dr, Midway, KY 40347

  Beautifully updated and move-in ready, this charming brick ranch offers the perfect blend of classic character and modern convenience — all nestled in the heart of picturesque Midway. This home is less than a half mile from downtown Midway with all the shops and restaurants it has to offer. Featuring 3 bedrooms, 2 full baths, and a full basement. New roof, HVAC, and water heater! This home

  Miranda Hinchman Keller Williams Bluegrass Realty

  103 Highview Dr, Midway, KY 40347
• 

  

  /10

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  101 N Brand St Unit 6, Midway, KY 40347

  Welcome to 101 Brand Street — a charming 2-bedroom, 1-bathroom apartment offering 800 square feet of comfortable living space right in downtown Midway. Enjoy being steps away from local shops, restaurants, and everything this vibrant community has to offer. This cozy apartment features an open living area, a well-appointed kitchen, and plenty of natural light. Perfect for anyone looking for

  Walker Mack Bluegrass Property Exchange

  101 N Brand St Unit 6, Midway, KY 40347
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  /32

  $370,000 Sold Jul 11, 2025

  107 Highview Dr, Midway, KY 40347

  • 3 Beds
  • 2 Baths
  • 2,118 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $175/SF
  • 27 Days On Market

  Current Estimated Value $362,846

  Last Listing Agent David Humes Christies International Real Estate Bluegrass

  107 Highview Dr, Midway, KY 40347
• 

  

  /28

  Est $227,494 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,083 Sq Ft

  334 2nd St, Midway, KY 40347

  334 2nd St, Midway, KY 40347
• 

  

  /15

  $864,000

  2639 Weisenberger Mill Rd, Midway, KY 40347

  A once in a lifetime opportunity to own prime farm land with an incredible homesite awaits. Nestled between downtown Lexington and Midway, this Lot boasts soil of statewide importance, as well as incredible views for your home... all tucked down a private (soon to be paved) driveway. This premier land offering backs up to the Elkhorn Creek, but is high enough ground to have no concerns.

  Sarah MacHarg Kentucky Land and Home

  2639 Weisenberger Mill Rd, Midway, KY 40347
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  /8

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  121 N North Brand St Unit 11, Midway, KY 40347

  Welcome to 121 Brand Street — a charming 2-bedroom, 1-bathroom apartment offering 800 square feet of comfortable living space right in downtown Midway. Enjoy being steps away from local shops, restaurants, and everything this vibrant community has to offer. This cozy apartment features an open living area, a well-appointed kitchen, and plenty of natural light. Perfect for anyone looking for

  Jared Gadd Bluegrass Property Exchange

  121 N North Brand St Unit 11, Midway, KY 40347
• 

  

  /23

  $273,500 Sold Apr 25, 2025

  318 2nd St, Midway, KY 40347

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $193/SF
  • 115 Days On Market

  Current Estimated Value $279,225

  Last Listing Agent David Montgomery Lifstyl Real Estate

  318 2nd St, Midway, KY 40347
• 

  

  /75

  Est $765,472 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,689 Sq Ft

  134 King Fisher Way, Midway, KY 40347

  134 King Fisher Way, Midway, KY 40347
• 

  

  /5

  $98,500

  • Land
  • 0.33 Acre
  • $298,485 per Acre

  2 Northside Dr, Midway, KY 40347

  Come and visit this rare opportunity to build your dream home in Historical Midway. These lots front on Northside Dr, just steps to the library, Walter Bradley Park, and Northside elementary school. This building site will have access to water, sewer, electric(underground) and gas. Mike Bradley is a licensed realtor in Ky and a partner in the Northside Homes LLC. Please do not drive up the

  E Missy Bradley KY Local

  2 Northside Dr, Midway, KY 40347
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  /66

  $975,000 Sold Sep 19, 2025

  321 S Turner St, Midway, KY 40347

  • 4 Beds
  • 3.5 Baths
  • 4,808 Sq Ft
  • Built 1968

  Last Sold Summary

  • 11% Below List Price
  • $203/SF
  • 34 Days On Market

  Current Estimated Value $1,013,460

  Last Listing Agent Hill Parker Turf Town Properties

  321 S Turner St, Midway, KY 40347
• 

  

  /98

  Est $923,744 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,873 Sq Ft

  136 Seahawk Trail, Midway, KY 40347

  136 Seahawk Trail, Midway, KY 40347
• 

  

  /94

  $1,550,000

  • 2 Beds
  • 1.5 Baths
  • 1,914 Sq Ft

  106 Sand Piper Ct, Midway, KY 40347

  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

  Mohamed Mahmoud Keller Williams Bluegrass Realty

  106 Sand Piper Ct, Midway, KY 40347
• 

  /2

  $725,000 Sold Aug 08, 2025

  143 Lighthouse Way, Midway, KY 40347

  • 4 Beds
  • 3.5 Baths
  • 3,532 Sq Ft
  • Built 2010

  Last Sold Summary

  • 3% Below List Price
  • $205/SF
  • 1 Day On Market

  Current Estimated Value $729,015

  Last Listing Agent Amy Barron LPT Realty

  143 Lighthouse Way, Midway, KY 40347
• 

  

  /76

  Est $899,451 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,616 Sq Ft

  393 Roaring Springs Ln, Midway, KY 40347

  393 Roaring Springs Ln, Midway, KY 40347
• 

  

  /13

  $465,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  280 Browns Mill Rd, Midway, KY 40347

  This beautifully remodeled property is currently undergoing the final phases of renovation. This secluded one-acre lot is surrounded by some of Central Kentucky's most prestigious horse farms. This rare offering combines privacy, potential, and location — a true hidden gem in the heart of horse country. Completion estimation around 60 days. Active Construction site call 859-825-8719 for agent

  Jessica Bach Lifstyl Real Estate

  280 Browns Mill Rd, Midway, KY 40347
• 

  

  /82

  $670,000 Sold Aug 15, 2025

  2004 E Leestown Rd, Midway, KY 40347

  • 5 Beds
  • 4.5 Baths
  • 3,733 Sq Ft

  Last Sold Summary

  • 17% Below List Price
  • $179/SF
  • 2 Days On Market

  Current Estimated Value $700,016

  Last Listing Agent E Missy Bradley KY Local

  2004 E Leestown Rd, Midway, KY 40347
• 

  

  /45

  Est $412,946 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,971 Sq Ft

  419 Mill Rd, Midway, KY 40347

  419 Mill Rd, Midway, KY 40347
• 

  

  /5

  $98,500

  • Land
  • 0.33 Acre
  • $298,485 per Acre

  Lot 3 Northside Dr, Midway, KY 40347

  Come and visit this rare opportunity to build your dream home in Historical Midway. These lots front on Northside Dr, just steps to the library, Walter Bradley Park, and Northside elementary school. This building site will have access to water, sewer, electric(underground) and gas. Mike Bradley is a licensed realtor in Ky and a partner in the Northside Homes LLC. Please do not drive up the

  E Missy Bradley KY Local

  Lot 3 Northside Dr, Midway, KY 40347
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  /53

  $460,000 Sold Mar 07, 2025

  121 W Bruen St, Midway, KY 40347

  • 2 Beds
  • 2 Baths
  • 2,214 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $208/SF
  • 22 Days On Market

  Current Estimated Value $473,639

  Last Listing Agent Kristol Yeager Bluegrass Sotheby's International Realty

  121 W Bruen St, Midway, KY 40347
• 

  

  /73

  Est $568,129 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,891 Sq Ft

  412 Mill Rd, Midway, KY 40347

  412 Mill Rd, Midway, KY 40347
• 

  

  /79

  $2,825,000

  • 5 Beds
  • 6 Baths
  • 6,152 Sq Ft

  3200 Fishers Mill Rd, Midway, KY 40347

  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'

  Kenny Whalen Real Broker LLC

  3200 Fishers Mill Rd, Midway, KY 40347
• 

  

  /86

  $5,400,000 Sold Jul 21, 2025

  1782 W Leestown Rd, Midway, KY 40347

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft
  • Built 2019

  Last Sold Summary

  • 32% Below List Price
  • $1,080/SF
  • 0 Days On Market

  Current Estimated Value $7,196,000

  Last Listing Agent Hill Parker Turf Town Properties

  1782 W Leestown Rd, Midway, KY 40347
• 

  

  /41

  Est $262,069 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  108 Ann St, Midway, KY 40347

  108 Ann St, Midway, KY 40347
• 

  

  /45

  $803,000 Pending

  • 5 Beds
  • 3 Baths
  • 4,202 Sq Ft

  136 King Fisher Way, Midway, KY 40347

  When only the best will do... From the moment you step from the front porch into the inviting foyer you will be amazed the space as well as the amenities this home brings. At the heart of the home a spacious great room with masonry fireplace and gas logs, flows seamlessly into a massive kitchen, an abundance of tall white cabinets, highlighted by an oversized island, plus bar quartz countertops.

  Diana Roark Rector Hayden Realtors

  136 King Fisher Way, Midway, KY 40347
• 

  

  /14

  $216,500 Sold Oct 02, 2025

  224 E Higgins St, Midway, KY 40347

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $197/SF
  • 67 Days On Market

  Last Listing Agent Alex Doyle Torrey Smith Realty Co., LLC

  224 E Higgins St, Midway, KY 40347
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  /38

  Est $300,468 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  105 Oak St, Midway, KY 40347

  105 Oak St, Midway, KY 40347
• 

  

  /50

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  255 W Higgins St, Midway, KY 40347

  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,

  Nicholas Bentley Bentley & Co., REALTORS

  255 W Higgins St, Midway, KY 40347
• 

  

  /25

  $254,000 Sold Jan 03, 2025

  107 Oak St, Midway, KY 40347

  • 3 Beds
  • 1 Bath
  • 1,125 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $226/SF
  • 47 Days On Market

  Current Estimated Value $258,203

  Last Listing Agent Jenifer Sweet The Agency

  107 Oak St, Midway, KY 40347
• 

  

  /21

  Est $349,132 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,746 Sq Ft

  105 Cottage Garden Ln, Midway, KY 40347

  105 Cottage Garden Ln, Midway, KY 40347
• 

  

  /128

  $860,000

  • 4 Beds
  • 3 Baths
  • 3,166 Sq Ft

  425 N Winter St, Midway, KY 40347

  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

  Meredith Walker Bluegrass Sotheby's International Realty

  425 N Winter St, Midway, KY 40347
• 

  

  /5

  $95,000 Sold Oct 10, 2025

  Lot 5 Northside Dr, Midway, KY 40347

  • Land
  • 0.33 Acre
  • $287,879 per Acre

  Last Sold Summary

  • 725 Days On Market

  Last Listing Agent E Missy Bradley KY Local

  Lot 5 Northside Dr, Midway, KY 40347
• 

  

  /13

  Est $328,284 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /5

  $98,500 Pending

  • Land
  • 0.33 Acre
  • $298,485 per Acre

  6 Northside Dr, Midway, KY 40347

  Come and visit this rare opportunity to build your dream home in Historical Midway. These lots front on Northside Dr, just steps to the library, Walter Bradley Park, and Northside elementary school. This building site will have access to water, sewer, electric(underground) and gas. Mike Bradley is a licensed realtor in Ky and a partner in the Northside Homes LLC. Please do not drive up the

  E Missy Bradley KY Local

  6 Northside Dr, Midway, KY 40347
• 

  

  /28

  $330,000 Sold Mar 17, 2025

  105 Coach Station Rd, Midway, KY 40347

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $202/SF
  • 11 Days On Market

  Current Estimated Value $326,538

  Last Listing Agent Carlos Elliott Tru Life Real Estate

  105 Coach Station Rd, Midway, KY 40347
• 

  

  /31

  Est $319,616 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,524 Sq Ft

  208 Cottage Grove, Midway, KY 40347

  208 Cottage Grove, Midway, KY 40347
• 

  

  /3

  $209,999

  • Land
  • 1.5 Acres
  • $139,999 per Acre

  1120 Duckers Rd, Midway, KY 40347

  Perfect location near Frankfort, Scott County, Woodford County and Lexington. Build a home that meets your needs. Property at one time had a business on it. It is currently zoned residential. Seller is working to change the zoning back to commercial.

  Elizabeth Betty White Keller Williams Bluegrass Realty

  1120 Duckers Rd, Midway, KY 40347

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