The Dearing Street Historic District is the area roughly bounded on the west by South Milledge Avenue, on the north by Broad Street, on the east by Finley street, and on the south by Henderson Avenue.

This fairly level area, which occupies part of a broad ridge west of the University of Georgia campus, is almost square. Streets form a north-south gridiron except for South Milledge Avenue, which bends westward to stay on the center of the ridge. The district features Finley Street as Athens's only surviving street paved with belgian block. Constructed mostly between 1810 and 1910, the majority of the homes are of frame construction typical of the Georgia Piedmont. Buildings range in size from cottages to two-story houses. Originally occupying substantial lots or entire city blocks, the larger dwellings are interspersed among the cottages, which date from the 1880s through the first decade of this century and feature high hipped roofs. Offering a sampler of styles in domestic architecture, the district also contains three large Italianate style houses. South Milledge Avenue, preferred for mansions by the wealthy, possesses several monumental residences, primarily of the Greek Revival and Neoclassical Revival styles. The distinctive character of the district derives partly from its narrow streets, old hardwood trees, and upper middle-class residences. Some apartment complexes and condominiums have intruded, yet the interior of the district remains residential, confining encroaching office and multiple unit use to South Milledge Avenue and commercial use to Broad and Baxter streets.

Originally part of the 633 acres donated for the site of the University, the area was laid off in three successive surveys. In 1830 Major James Meriwether platted a section west of Pulaski Street, including Finley, Pope, Dearing, Waddell, and Church streets. Each block formed by the intersecting streets was designated as a lot, four acres in size, minus the amount taken for the streets; smaller lots were designated fraction lots. In 1833 W. L. Thomas laid out streets and lots from Church Street on across South Milledge as far west as Rocksprings Street. The last tier of lots fronted the south side of Waddell Street, the southernmost street in this era. In 1844 William L. Mitchell completed a plat that would extend the town's southern and southwestern residential area. The survey added no new streets, but divided the remaining land into large lots of about 16 acres each, which resulted in triple-long blocks from Waddell Street to Bass, now Baxter, Street.

Within the Dearing Street Historic District reside two sites of individual distinction, the Anderson Cottage and the Tree That Owns Itself (see Inventory: Part I). Other buildings of individual merit include the Barrow-Tate Cottage, Bloomfield-Talmadge House, Bond-Kelly House, Carr-Nicholson-Galis House, Chase-Yancey House, Cobb-Ward-Erwin House, Crane-Harris-Coleman House, Descamps Cottage, Durham Cottage, Hartman Cottage, Hutchins-Paddock Cottage, Lehmann-Bancroft-Land House, Meeker-Barrow House, Mell-McAdams House, Morris-Miller-Kelley House, and Rucker-Teague House (see Inventory: Part II). The western boundary of the Dearing district incorporates an area along the east side of South Milledge Avenue between Broad Street and the south side of Henderson Avenue, which overlaps the Milledge Avenue Historic District; because the larger scale properties within this section front South Milledge Avenue, they are reviewed therein (see Inventory: Part I).

The Dearing Street Historic District is listed on the National Register of Historic Places (September 5, 1975).