A 1960s community transformed into an inviting retreat. Welcome inside Old Cutler Bay, one of the top addresses in South Florida. Centrally located one block south of Kendall Drive on Old Cutler Road in the southernmost tip of Coral Gables, this private gated community is situated nearby award-winning public and private schools, five-star restaurants and high-end shopping malls. Overlooking 136 homes on Biscayne Bay, including new construction mansions and charming estates, Old Cutler Bay offers residents an architectural time capsule into the City Beautiful Movement. From tree-lined streets to Mediterranean Revival-style homes, this balmy tropical community speaks to the character that Coral Gables was originally built on. But what makes this historic neighborhood unique to others is its wide winding canals. An aquatic roadmap encircling the neighborhood, these tranquil canals offer residents direct access to the Atlantic Ocean, making Old Cutler Bay idyllic for boat and yacht enthusiasts.