Midway, KY Homes

• 

  

  

  /23

  $300,000 Pending

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

  103 Highview Dr, Midway, KY 40347

  ** OPEN SUNDAY 1-3 ** 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

  Miranda Hinchman Keller Williams Bluegrass Realty

  103 Highview Dr, Midway, KY 40347
• Explore Midway

• 

  

  

  /20

  $1,600 per month

  • 2 Beds
  • 1.5 Baths
  • House for Rent

  302 S Gratz St, Midway, KY 40347

  Property Id: 1120836This no-pet property is a recently renovated corner lot home in Historic Midway. It has restored original hardwood floors in the living room and bedrooms adding warmth to this home. The newly ceramic tiled kitchen and bonus room offer easy cleaning. It has newly installed HVAC, energy-efficient windows, new blinds, and curtain hardware. This spacious 2

  302 S Gratz St, 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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  /76

  Est $871,182 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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 $368,383

  Last Listing Agent David Humes Christies International Real Estate Bluegrass

  107 Highview Dr, Midway, KY 40347
• 

  

  /33

  Est $326,091 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft

  900 Duckers Rd, Midway, KY 40347

  900 Duckers Rd, Midway, KY 40347
• 

  

  /44

  $699,000

  • 6 Beds
  • 3 Baths
  • 2,604 Sq Ft

  170 Davistown Rd, Midway, KY 40347

  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,

  Katherine Jackson RO&CO Real Estate

  170 Davistown Rd, Midway, KY 40347
• 

  

  /8

  $1,200 per month

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

  101 N Brand St Unit 2, 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

  101 N Brand St Unit 2, 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 $271,333

  Last Listing Agent David Montgomery Lifstyl Real Estate

  318 2nd St, Midway, KY 40347
• 

  

  /45

  Est $430,781 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
• 

  

  /35

  $465,000 Pending

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

  280 Browns Mill Rd, Midway, KY 40347

  This beautifully remodeled property at 280 Browns Mill is a rare opportunity to own a fully renovated home on a secluded one-acre lot, just minutes from Lexington. Surrounded by some of Central Kentucky's most prestigious horse farms, the setting offers exceptional privacy while remaining close to shopping, dining, and major conveniences. Thoughtfully updated throughout, this home blends modern

  Jessica Bach Lifstyl Real Estate

  280 Browns Mill Rd, Midway, KY 40347
• 

  

  /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
• 

  

  /73

  Est $601,760 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
• 

  

  /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
• 

  /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 $730,228

  Last Listing Agent Amy Barron LPT Realty

  143 Lighthouse Way, Midway, KY 40347
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  /41

  Est $281,715 Not Listed For Sale

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

  108 Ann St, Midway, KY 40347

  108 Ann St, 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
• 

  

  /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 $700,735

  Last Listing Agent E Missy Bradley KY Local

  2004 E Leestown Rd, Midway, KY 40347
• 

  

  /25

  Est $261,581 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,125 Sq Ft

  107 Oak St, Midway, KY 40347

  107 Oak St, 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
• 

  

  /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 $477,957

  Last Listing Agent Kristol Yeager Bluegrass Sotheby's International Realty

  121 W Bruen St, Midway, KY 40347
• 

  

  /38

  Est $307,783 Not Listed For Sale

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

  105 Oak St, Midway, KY 40347

  105 Oak St, Midway, KY 40347
• 

  

  /21

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,349 Sq Ft

  131 Carriage Ln, Midway, KY 40347

  Beautifully maintained and updated ranch home in highly desired Midway .Many updates done in 2022 to include roof replaced, entire inside and outside of home painted, engineered wood floors throughout, kitchen and bathrooms remodeled, built-in closet organizers in all bedrooms, all lighting and ceiling fans replaced, fireplace remodel, ceilings refinished with smooth drywall, 5 1/4" base molding

  Darrell Lewis DIY Flat Fee.com

  131 Carriage Ln, 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
• 

  

  /21

  Est $342,845 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
• 

  

  /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
• 

  

  /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

  Current Estimated Value $213,553

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

  224 E Higgins St, Midway, KY 40347
• 

  

  /13

  Est $331,105 Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
• 

  

  /34

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,681 Sq Ft

  122 Old Towne Walk, Midway, KY 40347

  Move-in ready 3-bedroom, 2-bath ranch located in an HOA subdivision on approximately 0.31 acres. This well-maintained home offers comfortable single-level living with numerous updates throughout. The kitchen features suede granite countertops, a motion-sensor smart faucet, and updated cabinetry hardware. Major improvements include a newer roof, refreshed bathrooms, commercial-grade water heater,

  Jennifer Hazelrigg 606 Real Estate & Auctions

  122 Old Towne Walk, 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
• 

  

  /31

  Est $325,412 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
• 

  

  /79

  $2,725,000

  • 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
• 

  

  /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 $331,077

  Last Listing Agent Carlos Elliott Tru Life Real Estate

  105 Coach Station Rd, Midway, KY 40347
• 

  

  /40

  Est $376,343 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft

  104 Cottage Garden Ln, Midway, KY 40347

  104 Cottage Garden Ln, 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
• 

  

  /70

  $625,000 Sold Jun 27, 2025

  242 W Stephens St, Midway, KY 40347

  • 4 Beds
  • 3.5 Baths
  • 2,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $213/SF
  • 46 Days On Market

  Current Estimated Value $611,328

  Last Listing Agent Maxine Reyburn RO&CO Real Estate

  242 W Stephens St, Midway, KY 40347
• 

  

  /30

  Est $293,657 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  107 Coach Station Rd, Midway, KY 40347

  107 Coach Station Rd, 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

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