Midway, KY Homes

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  /62

  $460,000

  • 4 Beds
  • 2 Baths
  • 2,078 Sq Ft

  119 E Stephens St, Midway, KY 40347

  Built in 1872, this property features period characteristics including detailed gingerbread style trim, distinctive exterior color combinations, and architectural elements consistent with homes of its era. The rear of the property includes a deck with an attached potting shed, a greenhouse, and raised garden beds. Additional outdoor features include yard art, a garage/workshop structure that can

  

  David Humes

  Christies International Real Estate Bluegrass

  (859) 696-6492

  119 E Stephens St, Midway, KY 40347
• Explore Midway

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  /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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  /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 $280,606

  Last Listing Agent David Montgomery Lifstyl Real Estate

  318 2nd St, Midway, KY 40347
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  /76

  Est $889,999 Not Listed For Sale

  393 Roaring Springs Ln, Midway, KY 40347

  • 4 Beds
  • 4 Baths
  • 4,616 Sq Ft
  • Built 2004

  393 Roaring Springs Ln, Midway, KY 40347

  Last Sold Summary

  • 10% Above List Price
  • $175/SF
  • 62 Days On Market

  Last Sold Price $810,000

  Last Listing Agent Tess Utterback RE/MAX
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  $1,045,000

  • 5 Beds
  • 4.5 Baths
  • 5,542 Sq Ft

  101 Sand Piper Ct, Midway, KY 40347

  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

  

  Kristine Cassata

  Indigo & Co

  (859) 659-7872

  101 Sand Piper Ct, Midway, KY 40347
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  /8

  $1,095 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
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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 $1,024,641

  Last Listing Agent Hill Parker Turf Town Properties

  321 S Turner St, Midway, KY 40347
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  /33

  Est $366,229 Not Listed For Sale

  900 Duckers Rd, Midway, KY 40347

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft
  • Built 1975

  900 Duckers Rd, Midway, KY 40347

  Last Sold Summary

  • 9% Above List Price
  • $162/SF
  • 68 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Bonnie Fint CENTURY 21 Simpson & Associates
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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
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  /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

  Current Estimated Value $331,614

  Last Listing Agent Brett Franklin EXP Realty, LLC

  112 Richardson St, Midway, KY 40347
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  /45

  Est $414,304 Not Listed For Sale

  419 Mill Rd, Midway, KY 40347

  • 4 Beds
  • 2.5 Baths
  • 1,971 Sq Ft
  • Built 1985

  419 Mill Rd, Midway, KY 40347

  Last Sold Summary

  • 14% Above List Price
  • $185/SF
  • 3 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Steve Moore Bluegrass Sotheby's International Realty
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  /52

  $489,000

  • 4 Beds
  • 2 Baths
  • 2,829 Sq Ft

  2722 Leestown Rd, Midway, KY 40347

  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

  David Dooley CENTURY 21 Simpson & Associates

  2722 Leestown Rd, Midway, KY 40347
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  /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 $755,193

  Last Listing Agent Amy Barron LPT Realty

  143 Lighthouse Way, Midway, KY 40347
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  /73

  Est $527,880 Not Listed For Sale

  412 Mill Rd, Midway, KY 40347

  • 4 Beds
  • 3.5 Baths
  • 2,891 Sq Ft
  • Built 1987

  412 Mill Rd, Midway, KY 40347

  Last Sold Summary

  • 6% Above List Price
  • $173/SF
  • 6 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Ryan Smith Rector Hayden Realtors
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  /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
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  /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 $696,866

  Last Listing Agent E Missy Bradley KY Local

  2004 E Leestown Rd, Midway, KY 40347
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  /41

  Est $275,366 Not Listed For Sale

  108 Ann St, Midway, KY 40347

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • Built 1964

  108 Ann St, Midway, KY 40347

  Last Sold Summary

  • 8% Above List Price
  • $158/SF
  • 1 Day On Market

  Last Sold Price $255,750

  Last Listing Agent Bradley Warford Century 21 Pinnacle
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  /37

  $460,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  301 S Turner St, Midway, KY 40347

  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

  Diane K Scott The Brokerage

  301 S Turner St, Midway, KY 40347
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  /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 $6,039,830

  Last Listing Agent Hill Parker Turf Town Properties

  1782 W Leestown Rd, Midway, KY 40347
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  /20

  Est $226,313 Not Listed For Sale

  101 Richardson St, Midway, KY 40347

  • 3 Beds
  • 1 Bath
  • 1,090 Sq Ft
  • Built 1959

  101 Richardson St, Midway, KY 40347

  Last Sold Summary

  • 10% Above List Price
  • $188/SF
  • 1 Day On Market

  Last Sold Price $205,000

  Last Listing Agent Raegen Cox-Lowe Coldwell Banker McMahan
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  /5

  $98,500 Pending

  • 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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  /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 $224,575

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

  224 E Higgins St, Midway, KY 40347
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  /25

  Est $254,598 Not Listed For Sale

  107 Oak St, Midway, KY 40347

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

  107 Oak St, Midway, KY 40347

  Last Sold Summary

  • $226/SF
  • 47 Days On Market

  Last Sold Price $254,000

  Last Listing Agent Jenifer Sweet The Agency
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  /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
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  /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
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  /38

  Est $310,350 Not Listed For Sale

  105 Oak St, Midway, KY 40347

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

  105 Oak St, Midway, KY 40347

  Last Sold Summary

  • 38% Above List Price
  • $141/SF
  • 47 Days On Market

  Last Sold Price $225,000

  Last Listing Agent E Anthony Phillips RE/MAX
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  /24

  $260,000

  • 3 Beds
  • 1 Bath

  421 Elkton Place, Midway, KY 40347

  Welcome to 421 Elkton Place in Midway, KY - a beautifully renovated 3-bedroom, 1-bath home offering 1,056 square feet of modern, move-in-ready living space. Recently relisted with a brand new HVAC system, this home now offers even greater value and long-term peace of mind for its next owner. Inside, you'll find stylish modern updates throughout, including updated flooring, fresh paint,

  Hunter Miller GSP Homes

  421 Elkton Place, Midway, KY 40347
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  /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 $583,450

  Last Listing Agent Maxine Reyburn RO&CO Real Estate

  242 W Stephens St, Midway, KY 40347
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  /21

  Est $329,894 Not Listed For Sale

  105 Cottage Garden Ln, Midway, KY 40347

  • 3 Beds
  • 2.5 Baths
  • 1,746 Sq Ft
  • Built 1999

  105 Cottage Garden Ln, Midway, KY 40347

  Last Sold Summary

  • 5% Above List Price
  • $179/SF
  • 0 Days On Market

  Last Sold Price $313,000

  Last Listing Agent Jessica Johnson Pinnacle Real Estate Group
• 

  

  /21

  $355,000 Pending

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

  131 Carriage Ln, Midway, KY 40347

  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

  Darrell Lewis DIY Flat Fee.com

  131 Carriage Ln, Midway, KY 40347
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  /63

  $419,000 Sold Sep 18, 2025

  102 Cottage Garden Ln, Midway, KY 40347

  • 4 Beds
  • 2.5 Baths
  • 2,332 Sq Ft
  • Built 1999

  Last Sold Summary

  • $180/SF
  • 6 Days On Market

  Current Estimated Value $434,995

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  102 Cottage Garden Ln, Midway, KY 40347
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  /13

  Est $334,650 Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1999

  Unlisted Address

  Last Sold Summary

  • 1% Above List Price
  • $209/SF

  Last Sold Price $330,000

  Last Listing Agent Lauren Back The Brokerage
• 

  

  /5

  $98,500 Pending

  • 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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  /52

  $1,090,000 Sold Dec 12, 2025

  401 Shady Ln, Midway, KY 40347

  • 4 Beds
  • 3 Baths
  • 3,778 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Below List Price
  • $289/SF
  • 83 Days On Market

  Current Estimated Value $1,104,632

  Last Listing Agent Tom Biederman Biederman Real Estate

  401 Shady Ln, Midway, KY 40347
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  /31

  Est $315,228 Not Listed For Sale

  208 Cottage Grove, Midway, KY 40347

  • 3 Beds
  • 2.5 Baths
  • 1,524 Sq Ft
  • Built 1998

  208 Cottage Grove, Midway, KY 40347

  Last Sold Summary

  • 1% Above List Price
  • $206/SF
  • 6 Days On Market

  Last Sold Price $313,650

  Last Listing Agent Hope Hedden EXP Realty, LLC
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  /34

  $340,000 Pending

  • 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
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  /12

  $355,000 Sold Nov 06, 2025

  2772 Weisenberger Mill Rd, Midway, KY 40347

  • Land
  • 5.36 Acres
  • $66,231 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 40 Days On Market

  Current Estimated Value $354,011

  Last Listing Agent Adam Boardman Block + Lot Real Estate

  2772 Weisenberger Mill Rd, Midway, KY 40347
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  /40

  Est $356,965 Not Listed For Sale

  104 Cottage Garden Ln, Midway, KY 40347

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft
  • Built 1999

  104 Cottage Garden Ln, Midway, KY 40347

  Last Sold Summary

  • 17% Above List Price
  • $157/SF
  • 6 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Cynthia Hubbard RE/MAX
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  /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
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  /4

  $590,000 Sold Jul 08, 2025

  1605 Woodlake Rd, Midway, KY 40347

  Last Sold Summary

  • 15% Below List Price
  • 467 Days On Market

  Last Listing Agent Tom Biederman Biederman Real Estate

  1605 Woodlake Rd, Midway, KY 40347

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