MidwayRailroad TownHistoric Main StreetHorse CountryWalkable Downtown
~$325K–$375Kmedian sale price · 2025
Kentucky's Oldest Railroad Town
Midway is Kentucky's oldest railroad town, laid out in 1835 by the Lexington & Ohio Railroad at the geographic midpoint between Lexington and Frankfort. With a population of roughly 1,770 and active rail tracks running straight down Main Street, the town packs a James Beard-recognized restaurant (Holly Hill Inn), boutique shopping, Midway University, and a direct 20-minute I-64 commute to downtown Lexington into a few walkable blocks.
Schools
Woodford County Public Schools (A). Midway University (private liberal arts college) ()
Grocery
Midway Bakery & Cafe (artisan bakery, Main Street), Kroger Marketplace in Versailles (~10 min south), Walmart Supercenter in Versailles, Save-A-Lot in Versailles
Parks
Walter Bradley Park (Midway), Walkable downtown Main Street (active rail line running through center of street)