| Name | Styles | Significance | Periods |
|---|
Abell House (12210 Old Shelbyville Rd.) | Federal | architecture, exploration, settlement | 1800-1824 |
Bank of Middletown (11615 Main St.) | No Style Listed | architecture, commerce | 1900-1924 |
Beynroth House (11503 Main St.) | Federal | architecture | 1800-1824, 1750-1799 |
Davis Tavern (11180 Shelbyville Rd.) | Federal | commerce, architecture | 1800-1824, 1825-1849, 1875-1899, 1850-1874, 1750-1799 |
George B. Yenowine House (1021 Watterson Trail) | No Style Listed | exploration, settlement, architecture | 1825-1849 |
Head House (Main St.) | No Style Listed | architecture, commerce | 1800-1824 |
Henry Frank House (Madison Ave.) | Colonial Revival | architecture | 1900-1924 |
Jefferson Marders House (211 Madison Ave.) | No Style Listed | architecture | 1800-1824, 1850-1874, 1825-1849 |
Middletown Inn (11705 Main St.) | No Style Listed | commerce | 1875-1899, 1800-1824 |
Middletown United Methodist Church (Madison and Main Sts.) | Gothic | architecture | 1875-1899 |
William Bull House (11918 Old Shelbyville Rd.) | Greek Revival | architecture | 1850-1874 |