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Get to know Windermere

As a place, Windermere is tiny: a quaint little town of live oaks and clapboard on a spit of land between two beautiful lakes. As a mindset, Windermere is huge, representing the area surrounding both of those lakes, where sleek boats are tied up to long piers running to gracious homes of significant square footage. To have a Windermere address is to say that one has arrived. Outside of the city proper, lots run from large to estate-sized, and always seem to be in riotous bloom. Gated communities — sometimes rather heavily gated — secret away the homes of CEOs, famous athletes, international bankers, and those who have been lucky either in the market or in inheritance. A chain of lakes spreads out to the south, where big-name golf courses anchor winding avenues of big homes.
Nearby Neighborhoods:
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History & Culture

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.

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Dine & Shop

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 chef-driven cafes, to cocktail bars and inventive ethnic cuisine. 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.