Get to know Windermere

Windermere was, not so long ago, agricultural land, and there were more cow noses than golf balls dipping into these lakes. But it doesn't take a developer long to spot beauty, and shoreline after shoreline was soon lined with estate homes where tractor sheds once stood. Genteel golf-club living may have led the way, but there’s a real party-boat vibe to the area, and it's a rare evening that a backyard barbecue (or twelve) doesn’t echo across the choppy lake waters. The country club lifestyle is still at the core of Windermere, though in that distinctly laid-back Florida way. Patio parties serve great wine and cheap beer, local barbecue, and imported cigars, and the dress code is flip-flop formal.

Windermere and immediate surrounds have a few restaurants with local charm, as well as some nicer chains (even the burger joints are nicer chains), but the central location gives this crowd easy access to wonderful culinary options in Metro West and Doctor Phillips, most notably a strip called “Restaurant Row.” That area offers an amazing array of options, from fine dining to small, chef-driven cafes. It’s the best concentration of great dining in Central Florida, and people from Windermere treat it like their dining room. For shopping, the central location means a short drive to dozens of great shops and boutiques in any of the town centers and suburban shopping districts on the south side of Orlando. Designer retail is due east at the Mall at Millenia, and those same brands are discounted at the gigantic outlet malls just south of there.