Ocala became the first town and a commercial, educational, and religious center in what would become Marion County. The town first experienced some settlement within its commercial center in the 1840s. The city and its downtown section continued steady growth into the last part of the twentieth century. This was in part due to a major downtown fire in 1883 that required a considerable portion of downtown to be rebuilt, thus resulting in and constituting downtown Ocala's second major period of development. Both archival and field data indicate that the Florida Land Boom years of the 1920s were not of great impact to construction in the downtown area as in most other cities in Florida during the same period. The city's third substantial period of downtown development took place in the last part of the 1930s and early 1940s at the close of the Great Depression. Although downtown Ocala did see the completion of some commercial and industrial construction projects during this period and a substantial increase in new construction following World War II, a number of period buildings dating from the town's earlier settlement survive.

In the early development of Ocala, as in most towns in America, the downtown business district represented more than just a collection of buildings in which to purchase necessary goods and services. It served as the center for informal socializing, for participating in special events, and as a symbol of a community's achievements and potential. Essential to the downtown, were mercantile and grocery stores that provided the necessities of life to a growing community not dependent on farming. Patrons could not only purchase needed supplies, but also catch up on gossip, news, and matters of importance in the town.

Evidence of Ocala's downtown commercial center's original historic architectural character can still be seen within a few blocks of downtown in a number of Masonry Vernacular Style and/or Commercial Vernacular Style buildings that continue to relay their original historic setting, character, and use. In some other areas, a great deal of non-historic construction has taken place. In addition, in all areas of downtown, a number of historic downtown buildings have undergone considerable non-historic and/or non-sympathetic modification. From a physical examination and comparison to available Sanborn Fire Insurance Maps, bearing dates of 1884-1930, and available aerial photos and copies of historic postcards, a concentration of the earliest commercial activity began its development in the city by extending from the Public Square at center to the railroad depot, along and proximate to NE First Avenue, formerly Main Street. Additional early commercial buildings were constructed to the east, generally along E and W Broadway Street, at various times bearing street names of South and Exposition Streets. Subsequently, later commercial development took place along Pine Avenue and more recently to the southwest. Many of Ocala's earliest commercial buildings constructed within the historic commercial center of the city in the early development of the town no longer exist. An 1883 fire destroyed several of the town's early downtown landmarks, although many were replaced within a short time with masonry structures that have survived. Several other early downtown buildings, and in some cases blocks of buildings, have been demolished, leaving their former sites vacant, although more were demolished to make way for modern commercial buildings. In some instances, surviving historic commercial structures were extensively modified with the application of contemporary facades. Generally, this occurred in two time periods. The first replacement facade applications took place in the late 1930s and early 1940s and were generally executed in the Art Moderne Style. Based on the fifty year criteria for historic significance, these replacement facades have gained historic merit in their own right. More recent facade applications, dating from the 1950s to the present, for the most part bear no identifiable architectural style. Furthermore, they cannot be considered to have any historic distinction at this time.

The use of Masonry Vernacular construction dominated commercial architecture in Ocala following the fire of 1883, during the later part of the nineteenth century and the first 45 years of this century. Masonry Vernacular construction responded to a desire for its fireproof properties which understandably would be desirable for Ocala businessmen rebuilding after the major downtown fire of 1883. Vernacular architecture responded to the local environment, local accessibility to milled lumber, and was not based on technical or academic training. Such buildings were executed by local builders, usually without the use of an architect, but influenced by dominant architectural trends of the time. Fenestration is usually regular, but not always symmetrical. Original windows are frame double-hung sash and doors are wood. Most roofs are obscured by parapet walls on the primary facades. The original brick exteriors of a number of facades or entire buildings have been surfaced with stucco. One such example is the former Masonic Hall at 18 S Magnolia Avenue. The existing historic commercial architecture in the survey project area of downtown Ocala is predominantly one or two-stories in character and constructed between 1884 and c.1946.

Although a number of pre-1948 commercial buildings have survived within the downtown core surveyed in this project, commercial activity has moved away from the original business district. Subsequent to 1948 and until the 1970s, Pine Avenue underwent the most extensive commercial development in Ocala. In more recent years, considerable commercial activity has taken place southwest of the city. However, the historic downtown core does continue to maintain commercial activity resulting from local patronage, although a few historic buildings are presently vacant and, a number are in need of sensitive and appropriate historical rehabilitation. The historic commercial structures that continue to survive within the historic downtown Ocala area surveyed are all of masonry load bearing construction. These buildings were generally two-story, two-part commercial blocks, the majority of the remaining buildings are single story, although 3 three-story buildings, 1 four-story, and 1 five-story building survive and were documented.

In general, the historic building stock included in this Phase I of a Downtown Ocala Historic Building Survey resulted in the classification of most buildings in good condition. Of the total of 47 buildings surveyed, 4 were classified as in excellent condition, 36 in good condition, 6 in fair condition, and only 1 was classified as deteriorated.

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