| Name | Styles | Significance | Periods |
|---|
Achilles Eubank House
(Elkin Rd.) | Federal | exploration, settlement, architecture, politics, government | 1800-1824 |
Alpheus Lewis House
(Off Wades Mill Rd.) | | architecture, military, industry | 1800-1824, 1825-1849 |
Antioch Christian Church
(Off Muddy Creek Rd. at Four Mile Creek and Stone Branch) | | architecture | 1825-1849 |
Brown- Proctoria Hotel
(Main St. and Lexington Ave.) | Beaux Arts, Colonial Revival | commerce, architecture | 1900-1924 |
Bybee House
(Bybee Rd.) | | architecture | 1750-1799 |
Clark County Courthouse
(Main St.) | Greek Revival | architecture, politics, government | 1850-1874 |
Colby Tavern
(Jct. of Colby and Becknerville Rds.) | | architecture | 1800-1824 |
Couchman House
(Off Old Boonesboro Rd.) | | architecture, exploration, settlement | 1800-1824 |
David Gist House
(Stoner Rd.) | | architecture, exploration, settlement | 1750-1799 |
Elkin House
(Off US 227) | | architecture, exploration, settlement | 1750-1799 |
| F. Taylor Mill | | industry, historic - non-aboriginal, exploration, settlement | 1800-1824 |
Frances Cullom Jr. House
(Muddy Creek Rd.) | | architecture, exploration, settlement | 1750-1799, 1800-1824 |
Gen. Thomas Hart House
(Ecton Rd.) | | architecture, politics, government | 1800-1824 |
Goshen Primitive Baptist Church
(Goshen Rd.) | | exploration, settlement | 1850-1874 |
Gov. James A. Clark Mansion
(Burns Ave. and Belmont St.) | Georgian, Federal | politics, government, architecture | 1800-1824, 1825-1849 |
Henry W. Calmes House
(US 227) | | architecture, politics, government, exploration, settlement | 1800-1824 |
Hodgkins House
(Old Boonesborough Rd.) | Greek Revival | architecture | 1875-1899 |
Jesse Hampton House
(Bybee Rd.) | | architecture | 1800-1824 |
Joel Quisenberry House
(Flanagan Station Rd.) | | architecture | 1800-1824 |
Lampton House
(Muddy Creek Rd.) | | architecture | 1800-1824 |
| Martin- Holder- Bush- Hampton Mill | | historic - non-aboriginal, exploration, settlement, industry | 1750-1799 |
Nathaniel Haggard House
(Off New Boonesborough Rd.) | | architecture, exploration, settlement | 1750-1799 |
Providence Baptist Church
(6 mi. SW of Winchester off KY 627) | | architecture, exploration, settlement, religion | 1800-1824, 1825-1849, 1750-1799 |
Redmond House
(Off US 60) | | architecture | 1750-1799 |
Robert Scobee House
(Off SR 60) | | architecture, exploration, settlement | 1800-1824, 1825-1849 |
Stipp House
(Van Meter Rd.) | | architecture | 1800-1824 |
Strauder Goff House
(Off Van Meter Rd.) | | agriculture, architecture | 1825-1849 |
Van Meter Distillery
(Van Meter Rd.) | | agriculture, industry | 1875-1899, 1850-1874 |
Vinewood
(4 mi. NE of Winchester on U.S. 60) | Italianate | architecture, agriculture | 1850-1874 |
W. Pruett House
(Ecton Rd.) | | architecture | 1850-1874 |
Wade Farmstead
(Donaldson Rd.) | | architecture | 1800-1824, 1875-1899, 1850-1874, 1825-1849 |
William Clinkenbeard House
(Old Paris Pike) | | exploration, settlement, architecture | 1800-1824 |
Winchester Downtown Commercial District
(Roughly bounded by RR tracks, KY 627, Maple and Highland Sts.) | Mixed (More Than 2 Styles From Different Periods) | commerce, architecture | 1825-1849, 1875-1899, 1850-1874, 1900-1924 |
