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Built within the original 1818 plat surveyed by James Borland, the four hundred block of East Fourth Street contains several large and substantial homes dating from the late 19th century and early 20th century. The east, west and north sides of the district are anchored by structures listed in the 1986 historic sites survey or in the Indian University survey.

The oldest structure is a restored brick, federal style I-house (322 East Fourth Street) built c. 1850 by Augustus Holtzman, who also owned a woolen mill at what is now Third and Lincoln Streets. Before the end of the century, the house passed to W.D. Dill, who owned a mill on the West Side of Bloomington.

To the north of the Holtzman-Dill house is a turreted Dutch Revival House (114 S. Grant Street, C. 1907) with a curved limestone porch that currently houses a law office. The house resembles many of those built by architect J.L. Nichols, who also built the structure to the immediate north, now known as 'Kirkwood Manor.' Both buildings are listed in the 1986 survey as in the Trinity Episcopal Church across the street at 111 S. Grant. Designed by architect Alfred Grindle, Trinity Church was built in 1909 in the English Country Church Style.

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To the east, the district is anchored by the Henry A. Lee House (502 East Fourth Street), which is a Stick Style house with Arts and Crafts elements built c. 1913. The University gave it an "outstanding" rating in its survey. Lee was a prominent attorney active in local Republican Party politics.

The structure is now vacant, but in the past Indiana University has used it as an Annex to the Law Department and most recently the Mathematics Department. Immediately to the south (209 S. Dunn), is a locally designated vernacular Gable-Ell with Italianate and Greek Revival detailing that for a time was occupied by Henry Lee's son, also a prominent attorney.

Between the Lee and Holtzman houses on Fourth Street are several substantial two-story houses and a couple of one-story cottages built between 1890 and 1927. At the turn of the century, city directories indicate a large number of transient residents, often seven or more students. After WW II medical professionals increasingly occupied the block. By 1990, the block was known locally as "Restaurant Row" due to the proliferation of new restaurants. Today these restaurants are the core of a successful, bustling commercial district.

It should be emphasized the basic historical integrity of these structures is sound, and it is their historical character that has attracted so many restaurants and patrons to the area.