Winter Park was chosen as one of Apartment Therapy’s Coolest Suburbs in America 2019. We showcased the burbs nationwide that offer the most when it comes to cultural activities, a sense of community, and simply a good quality of life. For more on how we define “cool” and what exactly counts as a suburb, check out our methodology here. To view Apartment Therapy’s other Coolest Suburbs in America 2019, head here.
Stylish Park Avenue is the epicenter, with Rollins College on the north end. Just a few blocks west is hip, historic Hannibal Square, with more restaurants, shops, and galleries. There’s a sense of history, and many of the original homes and bungalows still stand, built back when wealthy industrialists came in search of sunshine in the late 1800s. They left a legacy of arts and culture, like the Charles Hosmer Morse Museum of American Art, now home to the most comprehensive collection of Tiffany glass.
For the most exceptional view of Winter Park, get out on the water—a chain of six lakes all are connected by narrow, man-made canals where water-skiers, kayakers, and paddle boarders share the water year-round with pontoons and sailboats. It’s a remarkable snapshot of a suburb of stately trees, abundant parks, and spectacular homes.
Median rent price:
$1,265 for 875 square feet, according to rentcafe.com.
Median house price:
$421,600, according to Zillow.
43, according to Walk Score.
Median household income:
$68,078, according to Census.
30,132, according to the city government.
What the suburb is known for:
Charles Hosmer Morse Museum of American Art states it has the world’s most comprehensive collection of the works of Louis Comfort Tiffany, including art and architectural objects from Laurelton Hall, Tiffany’s Long Island country estate.
Place that makes you happy to live there:
Favorite activity for families:
The Saturday Winter Park Farmers Market in the old train depot, and boasts local produce, artisans, and plenty of food vendors. Get a crêpe or bagel to go, and nosh in Central Park, directly across the street.
Favorite hangout for young professionals:
Favorite place to catch a movie:
Favorite teen hangout:
Favorite outdoor lounge spot:
Luma on Park, which has sliding doors that open onto Park Avenue, is perfect for people watching. Ask for the truffle popcorn with your craft cocktail.
Favorite date spot:
Instead of dinner, try an interactive, DIY wine tasting at The Wine Room. Sample more than 150 different types of wine with the touch of a button. Load up a wine-tasting card with any amount of money, and sample until your balance runs out. Pair your sips with small bites, like flatbreads, cheese flights, and salads.
Average commute/traffic report:
Mostly cars, since public transportation is limited. There’s a reliable SunRail train and buses, but neither is popular. Central Florida is known for its car culture, not public transportation.
Favorite local bookstore:
Writer’s Block Bookstore, an independent bookstore in Winter Park, is a true gem.
Favorite place to get coffee:
Quirky Austin’s Coffee might be a hole in the wall on busy West Fairbanks Avenue, but it serves up organic, fair-trade beans, roasted right in the shop. Austin’s also hosts live bands, art shows, independent films, live comedy, and poetry readings.
Favorite bar for when you want to be around people:
Head to the Ravenous Pig for barrel-aged cocktails and solid eats from 2015 James Beard Award semi-finalists James and Julie Petrakis.
Favorite alone spot:
Favorite free cultural thing to take part in:
Anytime the Charles Hosmer Morse Museum of American Art is open for free, and especially when they bring the gorgeous Tiffany glass windows out of the museum and into Central Park at Christmastime.
The brisket at 4 Rivers Smokehouse (multiple locations). Choose your own sides and order your brisket to go.
Frank, just off Park Avenue, is filled with eclectic eye candy, including everything from jewelry, to linen shirts, to leather handbags. We want everything in the shop.
Most walkable area:
Favorite bike trails/parks/outdoor activities:
Mead Botanical Garden is a 50-acre urban oasis showcasing Florida ecosystems in a natural environment, with a butterfly garden, boardwalk, and bike trail.
Favorite spot for an Instagram:
Husband-and-wife team Alexia and Rhys Gawlak turn out fine, yet simple fare at Swine & Sons. Try the cheddar-chive biscuit with country ham; black pepper-sorghum gravy and a fried egg; or a grit bowl, with brisket burnt ends, cheese grits, chow chow, fried egg, avocado, and pork rinds. It’s Southern breakfast at its best.
Favorite free activity:
Popcorn Flicks in the Park offers free family films in Central Park on the second Thursday of each month, starting around 8 p.m.
Favorite grocery store:
Lucky’s Market, which is new in town, offers beer, vegetarian and vegan options, lots of Florida artisanal goodies, an indoor café, and more.
Favorite place for a workout:
At Club Pilates, you can work your core with TRX and cardio classes, in addition to traditional Pilates classes.
Favorite place to take an out-of-towner:
Take a slow and scenic boat tour of three of the seven lakes in the Winter Park chain on an 18-passenger pontoon boat. Gawk at the mansions during the tour, which has been a Winter Park classic since the ‘60s, and keep an eye out for the occasional gator. The tour only accepts cash, and it’s nice to tip the drivers, who are mostly retired guys who love storytelling.
Worst place to find parking and easiest place to find parking:
Park Avenue Winter/Park Village. Park Avenue has parking garages at both ends of the avenue. There’s a parking lot on Lyman Avenue and additional street parking, but it’s often congested. Winter Park Village has a parking lot, and there’s always an open space, although you may have a short walk to your destination.
What the neighbors say:
“I love Winter Park for [its] proximity to exceptional food and beautiful parks. It is truly is a hidden Florida gem.” —Allie Miller, second-generation Winter Park resident
“We eat, work, and play in a two-mile radius. Within minutes from our home, with no traffic at all, I can be at my kids’ schools; on a date-night at our favorite local restaurant; meeting a friend at the gym for a workout class; or even shopping at a little boutique.” —Ashley Fraxedas, 10-year Winter Park resident
“Tonight I went on a run and remembered just how beautiful Winter Park is… the smell of gardenias in the spring, the sound of college kids laughing on Lake Virginia, and families riding bikes through the quaint neighborhoods are just a few of the reasons why I love living here.” —Morgan Claytor, lifelong Winter Park resident
“Winter Park is the epicenter of dining in Central Florida, with creative, young chefs breathing new life into the city.” —Katie Farmand, editor of Edible Orlando magazine
“We have four world-class art museums, all within walking distance of Park Avenue: The Albin Polasek Museum on the lake; the Morse Museum, with incredible Tiffany glass; the Cornell at Rollins College and Hannibal Square Heritage Center. What a treat!” —Kara McKean, local artist
Favorite annual event:
The prestigious Winter Park Sidewalk Art Festival has been held in Central Park each spring for the past 60 years. Come for the concerts, the parties, and the amazing art.
What I miss about the city living in a suburb:
Walkability. Many of the neighborhoods don’t have sidewalks.
What I never miss about the city:
Favorite local home store:
Miller’s Hardware, a fixture on West Fairbanks Avenue, has got it all–grills, greeting cards, plungers, paint, and a helpful staff who can find anything.
Favorite local garden store:
The Heavy (also my favorite Instagram spot).
Favorite local diner:
Linda’s Winter Park Diner, which has been a local meet-up spot for decades, is open for breakfast and lunch, and includes a bottomless cup of coffee and waitresses who call you “hun.” Keep it simple and order two eggs over easy or a tuna melt. It’s filling, not fancy.
Favorite neighborhood for yard sales:
Winter Park Pines is for everyone: families, old-timers, and new gen, alike.
Favorite house/garden walk:
The Albin Polasek Museum & Sculpture Garden is Czech-American sculptor Albin Polasek’s Mediterranean-style residence, which is open to the public. The museum showcases the artist’s paintings and sculptures in his home and gardens on the shore of Lake Virginia.
Tipsy Salonbar. Easy in, easy out. Best of all, wine is served with your pedicure, manicure, or blowout.
Favorite resale and antique store:
Head to Avalon Exchange for contemporary, vintage, and designer pieces, at great prices. Avalon’s ethos: We’re like a thrift store, but better.
Why do you think your suburb is cool?:
It’s Old Florida, mixed with arts and culture, quality eats, a liberal arts college, and convenience—and just far enough from Orlando.