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The Nelmar Terrace area has been the site of portions of a Timucuan Indian village, a plantation under British Governor James Grant in the 1770s, and parcels of Spanish land grants after 1784. From 1844-1869 the area was the southern part of the plantation owned by Florida Supreme Court Justice Thomas Douglas. During St. Augustine's Henry Flagler era, Dr. J.K. Rainey, a preeminent physician, acquired the Douglas Plantation and platted it in 1886. It was re-platted in 1913 following its purchase by C.M. Fuller and L. Orin Larson, who were among the most prominent developers in St. Augustine. They named the area Nelmar Terrace after Fuller's two daughters, Nellie and Mary. Marketed as an exclusive, upscale, suburban neighborhood, lots were among the largest in the city with deed restrictions and subdivision regulations, which controlled the design and quality of construction. By 1914 a trolley line ran up San Marco Avenue from downtown to the Florida School for the Deaf and Blind and served as a catalyst for development of this prestigious subdivision in the North City area during World War I and the 1920s Florida land boom.
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Between 1914 and 1930 the quality of design and construction was among the best in the
city. Construction receded during the Great Depression, but renewed after World War II. "Los Robles" at 24 Nelmar Avenue, designed by California architect Wallace Neff, is an outstanding example of Spanish Revival style. On the water are two excellent examples of Mediterranean Revival architecture: "Los Cedros," built for L.O. Larson at 30 Nelmar Avenue; and 27 Milton Street, built for Sidney Harrison, the secretary/treasurer of the Flagler's Model Land Tract. Larson's house became the home of composer Sidney Homer and opera diva Louise Homer, and then of Adjutant General Vivian Collins. Harrison's house became the home of St. Augustine Mayor O.D. Wolfe, and then of the president of the Florida School for the Deaf and Blind. The Moorish Revival castle at 16 May Street was the home and studio to sculptor C. Adrian Pillars. Fine examples of Georgian and Dutch Colonial Revival, Spanish Revival, Tudor, Craftsman, and Bungalow style are located throughout the neighborhood. The Nelmar Terrace Historic District was listed on the National Register of Historic Places in 2011 for architecture and its role in St. Augustine's development.