The Vias — Winter Park

The Vias are the most storied addresses in Winter Park — a collection of streets whose names end in Via: Via Tuscany, Via Lugano, Via Capri, Via Bella, and others radiating from the shores of the Winter Park Chain of Lakes. The streets were platted in the 1920s during Winter Park's first great land boom, inspired by the Italian lakeside villages that the city's founders — many of them wealthy Northerners — had visited on grand tours of Europe. The street names, the brick pavers, and the canopy of live oaks were intentional from the beginning: this was designed to be the finest residential district in Central Florida.

The homes built in the 1920s and 1930s range from Mediterranean Revival to English Tudor to Colonial, and many of the originals survive — lovingly maintained or carefully restored by successive generations of owners. The 1940s and 1950s added a handful of mid-century estates, and the past three decades have brought a wave of custom new construction on lots where older homes were torn down, some reaching 8,000 to 12,000 square feet.

The Vias have remained essentially immune to the cycles that affect other luxury markets. Lakefront lots on Lakes Maitland, Osceola, and Virginia are finite and non-reproducible, and the brick-street historic district designation has prevented the kind of commercial encroachment that eroded similar neighborhoods elsewhere in Orlando.