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Originally called the Hunting Ground due to its long use for that purpose by Native American tribes, the area was part of the 36-square-mile survey township granted to Henry Perrine by the United States Congress in 1838. In 1864, John and Mary Addison arrived at the Hunting Ground from Manatee County and built a home. By the 1870s, the area was being called Addison’s Landing. In the early 1880s, Dr. William C. Cutler visited the area and subsequently purchased 600 acres. In 1882, Cutler persuaded his friend, William Fuzzard, to settle in the area, and in 1883, Fuzzard built a wooden two-story home. In 1884, Fuzzard, along with several other settlers, cut a path from his homestead to Coconut Grove, which eventually became Old Cutler Road. By the end of the year, the population had reached 75, and a post-office with the name “Cutler” was established near a wharf built at the northeastern part of the settlement.

In 1896, residents built the Cutler Schoolhouse. That same year, Samuel H. Richmond built a large, two-story balloon frame home known as the Richmond Cottage, which in 1899 was transformed into the area’s only inn. A factory, stores, and other buildings were located around the intersection of what is now S.W. 168th Street (Richmond Drive) and S.W. 72nd Avenue (then the location of Old Cutler Road). The post office was moved to the Brown & Moody General Store. However, after the Florida East Coast Railway bypassed Cutler in 1903 for the new railroad town of Perrine 2 1/2 miles west, the town fell into a decline as farmers and settlers left to be closer to the railroad. From 1914 to 1917, Charles Deering purchased most of the land in the area, subsuming it within his estate. Except for the Richmond Cottage, which Deering incorporated into his estate, all of the buildings in the town were torn down.

Suburban development slowly began to approach the boundaries of the Deering Estate in the 1960s. By the end of the 1970s, the area west of the Estate was almost fully developed and became the Cutler CDP. In 1986, after Charles Deering’s last surviving daughter died, the Estate was purchased by the State of Florida.