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Dexter’s of Windermere

Written By Scott Joseph On April 22, 2016

dexter pie

Dexter’s is certainly one of the area’s most enduring concepts. And one of the more adaptable ones, too.

It started with a single location on Fairbanks Avenue in Winter Park, a cramped-quarters operation that was one half wine bar and one half wine shop. It was always my guess that founder Dexter Richardson preferred to focus more on the retail side than the bar side. But the patrons preferred it the other way around, and it became known more as a place for young professionals to hang out. (And make no mistake, no one cared about how tightly packed the bar area was.)

When Dexter’s opened it Thornton Park location, just over 20 years ago (!), it was still keen on being known as a wine retailer. And even more, the Washington Street space attempted to offer produce and some grocery items to the neighborhood, which had no easily accessed grocery store at the time. That didn’t work.

And in fact the wine shop concept was eventually scrapped for all Dexter’s.

In 1999 he original Winter Park Dexter’s moved to the then-emerging Hannibal Square neighborhood west of Park Avenue. (In fact, in the early days of regentrification, the city was branding the area as the West End.) The wine shop didn’t move with it.

(By the way, the building that now sits on the lot where the original Dexter’s used to be, the place where other restaurants have tried to make a go of it and failed miserably, appears to be headed to be a new bookstore for Rollins College.)

In 2004, Dexter’s opened a third location, in Lake Mary, in the curiously named Colonial Town Park. The newness of the shopping center made for a different feel of the northernmost Dexter’s, different from the other two, which had their own soul and character. The Lake Mary one was akin to a tract home in a neighborhood of cookie-cutter houses.

So it’s a bit disheartening that the newest Dexter’s, in Windermere, more closely resembles the Lake Mary location. (I wouldn’t be surprised if the two malls had the same builder.)

But I was happy to revisit a Dexter’s — hadn’t been in one for a long time — and see the familiar offerings of the colorful menu.

And to once again order one of my Dexter’s favorites, the Chicken Tortilla Pie, seen at top, a guilty pleasure. It’s constructed with fried flour tortillas layered with sauteed chicken breast meat, with tomatoes and melted cheese, some slices of jalapeno for some heat and a dollop or two of sour cream to cool it a bit.

Dexter dip

A lunch companion had the Uptown French Dip. (I would have gone with the Pressed Duck Sandwich myself.) It had plenty of thinly sliced roast beef on a soft baguette, with white cheddar cheese melted on top. It was served with a nice stack of truffle fries.

Although the view isn’t all that great, it was nice to sit on the sidewalk patio on a balmy Florida afternoon.

I was glad to round out my Dexter’s experiences with the latest location, and I’m pleased that this homegrown restaurant has evolved into such a reliable spot to grab a bite to eat and sip some wine.

Dexter’s of Windermere is at 4747 The Grove, Windermere. It is open for lunch and dinner daily. The phone number is 407-258-7028.

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