Windsong

Windsong is a private, gated lakefront community developed on the western shore of Lake Maitland in Winter Park, with a smaller presence on adjoining lakes in the chain. The community was developed beginning in the early 2000s on land that had previously been a combination of estate parcels and undeveloped lakefront — one of the last large tracts of prime lake frontage in Winter Park proper. The developer, recognizing the finite nature of the land, positioned Windsong as a true custom-home enclave rather than a production community; lots were sold to individual buyers who then selected their own architects and builders.

The result is a neighborhood of significant architectural variety — Mediterranean villas, French Country estates, Contemporary lake houses, and Traditional colonials — unified by lakefront orientation and the private, gated setting. The community built out across roughly a decade, with the last lots filling in during the 2010s. Because every home is custom, Windsong never had the look of a subdivision; it reads more like a curated collection of estates.

In the years since buildout, several original homes have been torn down and replaced with even larger contemporary builds as the market for ultra-luxury Winter Park lakefront has continued to appreciate. Windsong today represents roughly 100 homes, many of them in the $3 to $8 million range, making it one of the most valuable residential enclaves in Central Florida.