Orlando Neighborhood Guide: Living in Winter Park, FL

Situated 5 miles north of downtown Orlando, Winter Park, Florida has been a popular retreat since its founding in the late 19th century, thanks to its beautiful lakeside setting. While it continues to attract many tourists, this city of about 30,000 has established itself as one of the best places to live in Central Florida. It’s an ideal place for people who want the countryside feel of a small town while having easy access to the modern conveniences found in a big city. There’s a reason it topped our list of the best neighborhoods in Orlando. 

The epicenter of Winter Park is Park Avenue, a charming tree-lined, brick-paved street with European-style buildings, Gothic arches, and intricate ironwork. You’ll also find a wide range of shopping, dining, and entertainment options, including chain stores, boutiques, jewelry shops, cafes, restaurants, art galleries, and museums. Additionally, the city has a robust park system and a magnificent chain of lakes that provide virtually endless outdoor activities (plus a secret boat tour).

Commuting in Winter Park

When it comes to transportation, there are many options to choose from in Winter Park, Florida. If you’re traveling to another town, you can take a train from Winter Park Station. This station has SunRail commuter trains that travel throughout the Greater Orlando area and Amtrak trains on the Silver Meteor and Silver Star routes.

If you’re looking for an affordable way to get around, hop on one of the LYNX buses operating on numerous routes around Winter Park. These buses serve many nearby towns and cities, including Altamonte Springs, Fern Park, Rosemont, Orlando, Kissimmee, and St. Cloud.

Winter Park also has a well-connected road network. It takes about five minutes to drive from the city to Winter Park Village, about 15 minutes to get t downtown Orlando, and between 20 and 30 minutes to reach Orlando’s top theme parks. Additionally, you’ll have easy access to U.S. Route 17, which runs from Punta Gorda to Jacksonville.

Where to eat while living in Winter Park

Winter Park is home to some of the finest restaurants in the Orlando area, so it attracts many food enthusiasts from near and far. Here are some of the most popular restaurants in Winter Park:

• The Parkview: The Parkview has an eclectic menu with an emphasis on American and continental dishes. It’s one of the best restaurants in Winter Park for Sunday brunch, offering a variety of delectable and nutritious dishes.
• Prato: Prato serves crispy wood-fired pizza, homemade pasta, paninis, and other classic Italian dishes with a modern flair. With a cosmopolitan setting and a large patio, Prato is upscale enough for celebrating a special occasion but casual enough for a meal with your family.
• Tako Cheena: Tako Cheena offers delicious tacos, burritos, empanadas, and hot dogs with influences from around the world. Open until 11 p.m. on Friday and Saturday, it’s the perfect place to grab a bite after a night out with friends.
• Mediterranean Deli: Mediterranean Deli is one of the most sought-after takeout restaurants in Winter Park because of its tasty food and quick service. So, stop by for some amazing gyros and falafel sandwiches when you’re in a hurry or don’t feel like cooking.
• Foxtail Coffee: With its warm and relaxing environment, Foxtail Coffee is a great place to hang out with friends or work remotely while enjoying a delicious cup of craft coffee. It also serves a wide range of snacks and pastries.

Where to drink while living in Orlando

Besides great restaurants, Winter Park also has numerous bars, pubs, and lounges where you can unwind with your friends or enjoy a romantic date. Check out some of the best places to get a drink around Winter Park, Florida.

• The Hideaway Bar: The Hideaway Bar is a great place to mingle with the locals and make new friends, thanks to its warm and friendly atmosphere. This dive bar also offers mouthwatering burgers, subs, sandwiches, and chicken wings, as well as a long list of beers.

• Enzian Theater: Tucked amidst lush foliage and ancient oak trees, this outdoor garden bar features a wide range of classic American dishes and an extensive drink menu. With its beautiful surroundings, relaxing atmosphere, and movie screenings, Enzian Theater is the perfect place to enjoy cocktails with a date.
• Howl at the Moon Orlando: Howl at the Moon Orlando is a high-energy nightclub in the Winter Park area. They frequently host cover bands and boast a large dance floor.

Things to Do in Winter Park

Whether you’re an avid shopper or an outdoor lover, you won’t run out of things to do in Winter Park. Here are some of the places you’ll soon recognize as local favorites.

Boutiques

• Tuni’s: A contemporary boutique offering trendy clothes, footwear, and accessories for women from accomplished and emerging designers.
• The Lovely Boutique Market: A vintage apparel store selling unique and eclectic clothing, furniture, and handmade gifts.
• Max and Marley: This upscale resale boutique offers high-quality children’s clothes, shoes, and accessories.

Theaters

• Winter Park Playhouse: An intimate theater featuring musical productions like comedies, revues, and cabarets.
• Enzian Theater: This indie theater hosts art-house movie screenings, film festivals, and special events. Grab drinks at Eden Bar before or after a show.
• Aloma Cinema Grill: A unique theater where you can watch movies while servers bring food and drinks to your table.

Farmers’ Markets

• Winter Park Farmers’ Market: Located outside an old train depot, this bustling farmers market offers a wide range of produce, baked goods, and plants.
• Audubon Park Community Market: A weekly market featuring produce, handicrafts, food stalls, and live entertainment.

Parks

• Ward Park: A 66-acre sports-oriented park with a wetland trail and facilities for jogging, football, baseball, and soccer.
• Phelps Park: A local park with a playground, picnic facilities, pavilions, and basketball and tennis courts.
• Kraft Azalea Park: This scenic lakefront public park features massive cypress trees and the Exedra Monument, which is the perfect spot for weddings.

Attractions

• The Charles Hosmer Morse Museum of American Art: As one of the most visited attractions in Winter Park, this family-friendly, historic museum features the world’s most comprehensive Tiffany collection.
• Hannibal Square Heritage Center: This museum showcases oral histories and photos with an emphasis on African-American experiences.
• Casa Feliz Historic Home Museum: A restored Spanish farmhouse with a permanent exhibit about the life and works of renowned architect James Gamble Rogers II.

Renting in Winter Park

Rental prices in Winter Park vary, depending on the number of bedrooms and the specific amenities you choose. Here is what you can expect to pay for rent in Winter Park:

• Average cost of a studio rental: $1,300 per month
• Average cost of a one-bedroom rental: $1,588 per month
• Average cost of a two-bedroom rental: $1,900 per month

Short-term rentals are another possibility in Winter Park. If you plan on living in Orlando temporarily, a short-term rental may be a better investment since most of them are already furnished. It’s also a good option if you’re deciding whether or not living in Winter Park is right for you. You’ll be able to explore different parts of town, check out local attractions, and really get to know the area before committing to a long-term lease.

Relocating to a new place can be challenging when you don’t know what to expect. Search thousands of Winter Park apartments for rent on Zumper and find your new home in this charming neighborhood.