Lakeside, Winter Park

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Orlando, FL
Lakeside, Winter Park
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Lakeside is a small shopping plaza on Lake Killarney in the heart of Winter Park, a university town. It has a gorgeous round white dock where you can stand and feel the breeze through your hair. Total paradise is to get a crispy hot dog from Shake Shack and sit outside on the adirondack chairs or picnic tables. It reminds me of one of my favorite spots in California, Padaro Beach Grill. Too bad they have awful music- Hawaiian music, like Iz, would be better!

There is a lovely fountain with statues of children and a frog. Further down in the shopping center is a sculpture of a woman surrounded by water vessels of all different sizes.
Pop into Trader Joe's market to buy some healthy groceries and interesting treats. There is also a frozen yogurt place called Yogen Fruz, and a cupcake shop called Jillycakes.
For more formal dining on the lake, have the Kale Salad at Hillstone's, on the southern border of this shopping plaza.
I found Lakeside and the seating behind Shake Shack by accident while shopping at Trader Joe's. I saw glimpses of the glittering lake and wandered over for a better view. Then I found it! My new place to hang out! You can get into a dreamy mood just sitting on the adirondack chairs and staring out at the lake. Where else in a big, congested city is that possible?
Cross Orlando Ave and you will come to Lakeside Crossing, a new development with chic restaurants, and a coffee shop called San Julian's. At night it's lovely here with the many fountains, sculptures, and elegant lights.
Just a short walk along Morse Blvd leads you to Castle Playground (or Community Playground) at Martin Luther King Jr Park where you'll find a great workout station, wooden castle playground, and walking path around a pond.
Or drive to Azalea Lane Playground, an adorable playground that you won't forget!

Continue to directions...

Peeking between the buildings at the lake on a blissful March day.

A sweet older couple sitting by the lake. He said, "I'd love a backyard like this!"

Sunny spot to sit and eat your hot dog or burger.

A little girl looks out on the dock and fountain.

This is the life!

Fountain with statues on the lake.

The fountain and the seating behind Shake Shack.

The dock!

Looking out on Paddleboard Orlando from the dock.

Jillycakes and Yogen Fruz! And beautiful sculpture with water vessels.

Giraffe sculpture beside the water.

Gorgeous water on a sunny day.

Dock at Lakeside.

Roses and ducks at Lakeside.

Two young women paddle on the lake.

Colorful adirondack chairs and paddle boards!

Palm trees in the parking lot.

Glassy lake and picnic tables outside Shake Shack.

Duck, outside Shake Shack.

Cute sculpture of boy and girl on an arched tree trunk.

I love this place!

You can hear the water flowing over the rocks.

View of dock.

View of flowers and dock.

Frog sculpture and banana trees.

Cute sculpture and duck.

Adorable sculpture of a garden fairy.

Stained glass lamppost.

Clock and palm tree.

Flowers and fountain, with lake in distance.

Turtle sculpture- it looks like he's eating the plant!

Hands sculpture.

Lovely lakefront.`

Lamppost, tower, and palm, with bird flying by, in early morning.

Gardenia, pampas grass, and bougainvillea, at the lake, behind Shake Shack.

Little tower.

Purple bougainvillea and nice architecture.

Purple flowers.

San Julian's Coffee, across the street.

Fountain outside Bulla Gastrobar, across Orlando Ave.

Banana fronds and windmill-style sculpture, at Lakeside Crossing, across Orlando Ave from Lakeside.

Sculpture at Lakeside Crossing.

Blue pots, white chair, and elegant lighting, at Lakeside Crossing.

Bliss Nail Spa.

Evening at the lake.

Canoeing on the lake.

Grasses by the fountain and lake.

Chairs and tables behind Shake Shack.

Frog sculpture.

Mommy and baby duck!

Little ducklings.

Purple flowers by the fountain.

Little duckling by the waterfall fountain.

Looking between buildings toward the lake.

Hilton Garden Inn, nearby, is the newest hotel in Winter Park, and has Spanish arches.

It's pretty fancy inside Hilton Garden Inn, nearby.


Lakeside is a lakefront shopping plaza. To find it, use one of these two addresses in your GPS:
Trader Joe's Market, 131 N. Orlando Ave, Winter Park FL 32789, call (407) 622-0874.
Shake Shack, 119 N. Orlando Ave, Winter Park FL 32789, call (321) 203-5130.
Another great lakefront restaurant is just south of Lakeside Shopping Plaza: Hillstone's, 215 S. Orlando Ave, Winter Park FL 32789, call (407) 740-4005.


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Last Updated: Sun, 05 Apr 2020 18:28:05 GMT

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