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| B&G Sandwich Shop | 1949 | 11 First Street North | |
| Western Oil & Burner Company Building | 1947 | 15 First Street North | |
| Lithia Springs Garage | 1925 | 30 First Street South | Industrial |
| Enders House | 1896 | 31 Second Street North | Queen Anne |
| Frideger House | 1910 | 36 Second Street North | Craftsman |
| Trinity Episcopal Church (National Register Listing #84003015) | 1894 | 44 Second Street North | Gothic Revival |
| Beach-Good House | 1895 | 66 Second Street North | Queen Anne |
| Roper (Fordyce and Julia) House (National Register Listing #85003075) | 1886 | 35 Second Street South | Stick Eastlake |
| Shaw-Sanderson Annex | 1911 | 37 Third Street North | American Renaissance |
| Nininger's Drive In Market | 1945 | 180 C Street | Streamlined Art Moderne |
| First Baptist Church (National Register Listing #79002066) | 1911 | 241 Hargadine Street | California Mission Revival |
| Goldsby-Bryan House | 1907 | 353 Hargadine Street | Vernacular |
| Carnegie Library | 1912 | 0 Main Street East | American Renaissance |
| Carter Memorial Fountain | 1910 | 0 Main Street East | |
| Lithia Water Fountain | 1927 | 0 Main Street East | |
| Mickelson-Chapman Fountain | 1929 | 0 Main Street East | |
| Veteran's Memorial Flag Pole & Marker | 1949 | 0 Main Street East | |
| City Hall | 1891 | 20 Main Street East | |
| Knox Building | 1946 | 33 Main Street East and 75-77 Oak Street | Art Moderne/Streamlined |
| Pioneer Building | 1880 | 38-42 Main Street East | Vernacular storefront commercial |
| Chautauqua Walk | 1898 | 42-50 Main Street East | The walk is between the buildings at 42 and 50 Main Street East |
| Flatiron Building-Claycomb Block | 1920 | 40 Main Street East | Vernacular storefront concrete. Substantially remodeled in 1946. |
| Camps Building | 1904 | 50 Main Street East | Vernacular storefront commercial |
| Vaupel Store/Oregon Hotel Building (National Register Listing #80003319) | 1910 | 68 Main Street East | American Renaissance |
| First National Bank Building (National Register Listing #80003319) | 1909 | 100 Main Street East | American Renaissance |
| Dodge Building | 1904 | 125 Main Street East | Vernacular storefront commercial |
| First Southern Oregon Spiritualist Society Building | 1905 | 131 Main Street East | American Renaissance |
| McGee-Fortmiller Building | 1925 | 142 Main Street East | American Renaissance |
| Weber (George) Building | 1904 | 145 Main Street East | The original brick façade was updated to streamlined art moderne, probably in the 1930' |
| Ashland Daily Tidings Building | 1938 | 154 Main Street East | Vernacular storefront commercial. |
| Varsity Theater | 1937 | 166 Main Street East | Art Moderne/Streamlined |
| Jordon Electric Building | 1911 | 180 Main Street East | Vernacular storefront commercial. The brick potion probably was built before 1911 and the concrete portion was built in 1925. |
| Lithia Springs Hotel (National Register Listing #78002289) | 1925 | 212 Main Street East | Gothic Revival |
| Citizen's Banking & Trust Company Building (National Register Listing #85000364) | 1910 | 232-236 Main Street East | Chicago School |
| Ashland | 1910 | 247-255 Main Street East | American Renaissance |
| Enders Building and Annex (National Register Listing #86002902) | 1910 | 264-266 Main Street East | Chicago School |
| Peterson Furniture (Hershey Building) | 1907 | 281 Main Street East | Vernacular storefront commercial |
| Swedenburg Building | 1909 | 283 Main Street East | American Renaissance |
| Paulson-Drue Rental Building | 1910 | 341 Main Street East | Vernacular storefront concrete |
| Drue-Miller Building | 1928 | 343 Main Street East | Vernacular storefront concrete |
| Stoner Building | 1904 | 345 Main Street East | Vernacular storefront concrete |
| Sanderson Building | 1909 | 349 Main Street East | Vernacular storefront concrete |
| Rundell Building | 1909 | 357 Main Street East | Vernacular storefront brick |
| Shook Isaac Building/White House Grocery | 1910 | 372-374 Main Street East | American Renaissance |
| General Petroleum Service Station | 1931 | 376 Main Street East | Colonial Revival |
| Shaw-Sanderson Building | 1911 | 393-399 Main Street East | American Renaissance |
| Bank of Ashland | 1884 | 11-15 Main Street North | Beaux Arts Classicism. The vernacular brick extension was built in 1906. The first floor of the main building has been repeatedly remodeled and bears no resemblance to the original classical façade. |
| Masonic Lodge (National Register Listing #92000663) | 1879 | 25 Main Street North | Colonial Revival |
| Ashland Improvement Company Building | 1904 | 27-29 Main Street North | Classical Revival |
| Mills-McCall Building | 1904 | 31-35 Main Street North | American Renaissance |
| Johnson-Simpson Building | 1886 | 37 Main Street North | Vernacular storefront commercial. Remodeled in 1928. |
| Avery Johnson Building | 1886 | 41-45 Main Street North | Vernacular storefront commercial. |
| Henry Judge Building | 1886 | 47 Main Street North | Vernacular storefront brick |
| IOOF Building (National Register Listing #78002288) | 1879 | 49 Main Street North | Italianate Victorian |
| Werth (Louis) Building | 1909 | 82 Main Street North | Vernacular storefront concrete |
| Stock (Herman) Building | 1909 | 88 Main Street North | Vernacular storefront concrete |
| Crocker (Josephine) Building | 1889 | 89 Main Street North | Vernacular storefront brick |
| Cullen Building | 1946 | 99 Main Street North | Vernacular storefront concrete |
| Wietzel's Department Store | 1947 | 115 Main Street North | Art Moderne/Streamlined |
| Paulson Building | 1905 | 89-93 Oak Street | Vernacular storefront brick |
| Whittle Garage Building (National Register Listing #97000142) | 1925 | 101 Oak Street | Vernacular storefront concrete |
| Paulson-Freeburg Building | 1909 | 107 Oak Street | Vernacular storefront concrete |
| Dodge and Sons Funeral Home | 1923 | 90 Pioneer Street North | California Mission Revival |
| Chautauqua Dome Foundation | 1916 | 0 Pioneer Street South | |
| Selby Chevrolet Garage | 1947 | 0 Pioneer Street South | Utilitarian |
| Christian Science Church | 1923 | 15 Pioneer Street South | Colonial Revival |
| Star Steam Laundry Building | 1911 | 31 Water Street | American Renaissance |
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