EWF Stirrup-Ebenezer Woodbury Franklin Stirrup Sr. made the transition from immigrant to a successful Coconut Grove landholder. Stirrup came to Florida with nothing, but through his entrepreneurial talent, became a substantial landholder in Coconut Grove. His is an amazing legacy, as his success is all the more incredible in that his accomplishments took place in an overwhelmingly segregated and discriminatory environment. When Stirrup died in 1957 at the age of 84, he was one of the largest landholders in Coconut Grove, and also had done much to improve housing conditions of the African-American community. Stirrup was born on Governors Harbor Island off Eleuthera in the Bahamas in 1873. A nine -year old Stirrup was left in the care of relatives when his mother died. Determined to advance, Stirrup saved his meager earnings and in 1888, at the age of 15, immigrated to Key West to live with an uncle. He became a carpenter apprentice to his uncle, and learned the skills of woodworking and construction. Stirrup would remain in Key West for 10 years. Once he felt sufficiently prosperous, he returned to the Bahamas to marry his childhood sweetheart, Charlotte Jane Sawyer and they settled in Cutler, then a settlement 14 miles south of the Miami River. There he worked in the pineapple fields by day and cleared land for home sites in the evening. In lieu of cash, Stirrup was sometimes paid in land, the nucleus of what would become a vast accumulation of valuable real estate. In 1899, when he was 25, Stirrup moved the family to Coconut Grove, where he was employed by James Peering as both a chauffeur and a farm worker on Deering's magnificent estate, Villa Vizcaya. Bahamian immigrants played an integral role in the development of Coconut Grove, which was the heart of the Bahamian community. The Bahamas had the same coral rock and climate, so Stirrup and others knew how to use this soil to plant tropical trees, vegetables, and fruits. Furthermore, they knew how to use the local limestone to make lime mortar used in stone foundations for houses. Stirrup built his own home in Coconut Grove in 1897, a two-story frame vernacular house close to the present day Coconut Grove Playhouse at the head of Charles Avenue. This house served as Stirrup's residence for 58 years and has been the residence of some of Stirrup's descendants.

The Stirrup house is one of a few wood-frame residences from the late nineteenth century remaining in Miami-Dade County. The house's narrow proportions, the size and shape of its doors and windows, and its L-shape plan are characteristics frequently associated with the era's residential architecture. The house contains materials of outstanding quality that are native and unique to South Florida, including Dade County slash pine. Though the building has been altered over the years, it retains much of its overall integrity, and is a remarkable example of architecture associated with the Bahamian experience in South Florida. The existence of this wooden building from the late nineteenth century is remarkable and is a rarity in South Florida, and serves as a reminder of the achievement of these early pioneers and a legacy to its builder. The historic Stirrup house is being restored as a Bed and Breakfast Inn. Stirrup knew people of color from the Bahamas, the West Indies, and the southern states would be moving to Miami to seek jobs in the booming new area. He anticipated that most of these people would need temporary shelter upon their arrival. Stirrup's land holdings increased and Stirrup invested most of his earning in land, and when Coconut Grove pioneer John Frow offered to sell land in Coconut Grove. Stirrup was in a position to purchase a significant number of lots. Stirrup with his wife's assistance began to construct approximately 100 small frame houses on his property to rent to other Bahamians and African Americans in the region who were immigrating to South Florida and provided an opportunity for the newly arrived Bahamians and other Blacks to own their first home. The houses were built of sturdy Dade County pine, and were simple structures based on Bahamian housing types. Stirrup believed that people would be better citizens if they owned their own home, thus he allowed many of his tenants to purchase their first home in which they lived once they had saved the necessary funds.

Through his entrepreneurial talent, Stirrup became one of the largest landowners in the area. In addition to real estate, Stirrup owned a grocery store, bicycle repair shop, tailor shop, and meat market. He jointly owned land with William Burdine, the patriarch of the white pioneer family. One of their ventures was a dry goods store, located in the Grove, Another successful Stirrup venture was a horse, mule, and buggy business, which was developed in anticipation that newly arriving blacks would need transportation for work and for convenience purposes. Stirrup was as generous as he was successful. A noted philanthropist, he donated the land on which Coconut Grove's Christ Episcopal Church was built. Stirrup enjoyed success, wealth, and communitywide recognition until his death in 1957 at the age of 84.