Winter Park – Orlando, FL

Winter Park, one of the wealthiest cities in the metro Orlando area, sits nestled among the Winter Park Chain of Lakes, a series of picturesque lakes connected by navigable canals. Located just a 15-minute drive north of downtown Orlando, Winter Park is known for winding brick streets and canopies of old live oak trees dripping with Spanish moss. Home to a thriving arts scene, upscale shopping and dining, and plenty of outdoor activities, Winter Park remains a popular choice for those wishing to escape downtown yet still feel connected to a cultural center.

Schools in Winter Park

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Restaurants & Nightlife

With zoning ordinances requiring wait staff to serve patrons, Winter Park's dining options are primarily fine dining, with few counter-service options. This does not mean that Winter Park residents are left wanting; from Turkish and Japanese to Cuban or Creole, unique eateries of all kinds dot the main shopping areas of Winter Park. Ethos Vegan Kitchen, situated on S. New York Avenue near Fairbanks, features a family-friendly, comfortable ambiance with a hearty, homestyle all-vegan menu. Try the Sheep's Pie (a meat-free version of traditional shepherd's pie covered in gravy and mashed potatoes) or the Bay Cakes (vegan crab cakes with basmati rice), and wash it down with one of the rotating draft beers. Check out the Cask and Larder nearby on Fairbanks. This self-proclaimed "Southern Public House" offers a changing menu of classic Southern fare made with seasonal, local ingredients. With an oyster bar and entrées such as Nashville hot chicken, served with broccoli mac and cheese and cornbread, trying a new dish on every visit has never been so fun. The Cask and Larder brews its own beers in-house and also provides an impressive menu of distinctive cocktails. Try the jealous monk made with gin, green chartreuse, lime juice, celery bitters and champagne vinegar. Toasted, an artisanal grilled cheese and burger joint, sources local ingredients and focuses on made-from-scratch high quality cooking. Try the truffle melt grilled cheese with havarti, truffle oil, arugula, fresh ground black pepper and an optional fried egg, or go for the vegan bahn mi burger with Vietnamese veggies and flavored with cilantro, jalapeño and sriracha. Night time entertainment in Winter Park primarily consists of upscale wine bars and tapas bars, but there are a handful of dive bars, hookah lounges and sports bars around. The Wine Room on Park Avenue showcases over 150 wines, which guests can sample in 1-ounce, 2.5-ounce or 5-ounce sizes from wine-dispensing machines. Sample fine cheeses or a mezze platter with roasted peppers, olives and focaccia bread to accompany your wine, champagne or the all-day $3 mimosas.

History & Culture

Winter Park, as the name suggests, was founded as a fashionable winter resort community for wealthy businessmen from the north during the late 19th and early 20th centuries. Chester A. Arthur, the first president to visit the city, remarked that Winter Park was "the prettiest place I have seen in Florida." Now known for its arts and culture, Winter Park houses a surprising number of museums, including the Albin Polasek Museum and Sculpture Gardens, the Charles Hosmer Morse Museum of American Art and the Cornell Fine Arts Museum. The city also holds several well-known festivals, such as the Bach Festival, a good portion of the Florida Film Festival, the Winter Park Autumn Art Festival, and the Winter Park Sidewalk Art Festival, one of the nation's oldest and most prestigious juried outdoor art festivals.


You can best explore Winter Park, like the rest of the Orlando area, via car, but alternative methods of transportation are still viable. The Lynx bus system operates in Winter Park, and Uber is an option, as well. With an official Pedestrian and Bicycle Advisory Board, the city seeks to improving the infrastructure for these modes of transportation by further linking neighborhoods with bike and pedestrian-friendly pathways. Sidewalks shaded from the harsh Florida sun with mature trees in both the commercial and residential areas make walking a pleasurable activity. SunRail operates a commuter train line running north/south through the greater Orlando metro area, with a station in the heart of Winter Park. With bike racks on all of the trains, one could conceivably use a combination of bicycle and train to access many parts of the metro area from Winter Park. Several parking garages toward the southern end of Park Avenue charge during peak times, but you can get your ticket validated at any of the local shops. On-street parking remains free, but only for three hours during normal business hours. Residential parking rarely poses a problem. Winter Park's location next to Interstate 14, the main artery in Orlando, gives you access to the entire Orlando area. .


As a wealthy suburb, the cost of living in Winter Park sits at 19 percent greater than the national average. Fortunately amenities do not seem quite as steep, with the average cost of a cup of coffee costing 10 percent less than the national average, a beer costing around $3.50, and the city's gasoline prices average very close to the national average. The median rental rate in Winter Park is 17 percent greater than the national average, with a standard one-bedroom apartment running around $850 per month.


Park Avenue, the focal point of downtown, serves as the primary high-end shopping district in Winter Park. Visit Tugboat and the Bird on Park Avenue for locally handmade baby blankets and bibs. Check out the store's bedding, diaper bags, shoes and toys for kids of all ages. The little shop represents the perfect place to pick up a gift for a baby shower. Find hidden treasures at Orange Tree Antiques Mall, including vintage selections of glassware, furniture, jewelry, lighting and art. Browse through hundreds of vinyl records from old-time recording artists. Scroll through vintage holiday items, classic Disney characters and plenty of fine China porcelain to augment your home's decor. Grocery shoppers have a number of options in Winter Park. The neighborhood contains large chains such as Publix, Trader Joe's, and Whole Foods. The Winter Park Farmers' Market opens its doors every Saturday morning from 7 a.m. to 1 p.m. at the old train depot on West New England Avenue. The market serves as a popular community gathering place, providing fresh produce, plants, baked goods, and a variety of food booths.


Winter Park houses a large number of city and neighborhood parks to enjoy. Central Park, however, prides itself on being the crown jewel of Winter Park. Located in the heart of the downtown shopping district, this park hosts the Winter Park Sidewalk Art Festival, as well as other events throughout the year. Every winter an ice skating rink sets up in Central Park's West Meadow, allowing residents to pretend they live in a real winter wonderland. Although dogs are not allowed, the park's beautiful fountains, shady oak tree canopy and rose gardens make it the perfect spot for a stroll. Lake Baldwin Park, in comparison, represents the city's only real dog-friendly park in that dogs can run off leash during posted hours. With a sandy beach and boat ramp, Lake Baldwin Park works great for outdoor enthusiasts.
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Bishop Park
3250 Bishop Park Dr, Winter Park, FL 32792
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2890 Red Lion Sq, Winter Park, FL 32792
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