As Sarasota's population surged in the early 1920s, land that became the nucleus of San Remo Estates was assembled by business partners Edith Atkinson, the first female judge in Dade County, and John Kerns of Duval County, who bought two parcels in October 1923 from Hattie Campbell, Charlie Collins Lanier, W.C. Lanier, and former Sarasota mayor and prominent landowner A.B. Edwards. The more than 20 acres then drew Chicago real estate developer Michael Schiavone, who bought the property, formed the San Remo Improvement Corporation in 1926, and proposed a subdivision named after the Italian resort of San Remo, with three fill acres retained by seawalls and residential and business sections including an apartment hotel designed by Alfred C. Clas, but the end of the Florida Land Boom halted those plans. After several later sales, Raymond J. Roy of Roy Construction Company acquired the property in 1952 and advanced its development during Sarasota's renewed post-World War II growth, adding 30 acres of submerged land to the original 20-plus-acre tract by 1953; once filled, about 50 acres were available for development, with Roy Construction Co. acting as developer, sales promoter, and builder. San Remo Estates followed the 1950s national trend toward ranch-style detached single-family houses, and Roy also allowed other builders to work there to encourage varied designs; at least one house was designed by Victor Lundy of the Sarasota School of Architecture movement, and although many original houses have since been replaced or altered, remnants of the ranch-style homes remain visible.