Winter Park, Florida is a historic and very quaint city with unique architecture. The natural feel and historic setting makes way for many one-of-a-kind shops, restaurants, and bars. The area is rich with happenings as several family friendly events are constantly taking place. The old brick roads that line the beautiful business’s structures in Winter Park have roots influenced from its very early New England investors and founders in the 1880s, that required stylistic and architectural standards for buildings to be built. In addition to the city’s allure, Rollins College, Florida’s oldest university is at the southern end of Winter Park’s historic main road Park Avenue.

What to See

Winter Park’s Central Park – In the epicenter of winter park and lining the popular Park Avenue is the 11-acre, beautifully groomed Central Park. Central Park consists of winding sidewalks with numerous heavily shaded cast iron benches that line the whole park and walk ways. Some of the walk ways encompass fountains or at the south end where the very popular rose garden is located, which blooms with several colors of roses.

Rollins College  – Established in 1885, Florida’s oldest university is Rollins College and it is right at the south end of Park Avenue. The campus is open to walk through and to enjoy the very attractive architecture of Annie Russell Theatre, Knowles Memorial Chapel, or the Cornell Fine Arts Museum, which contains objects from antiquity to the 21st century.

Dinky Dock – Dinky Dock is a small 1.5 acre public park that neighbors Rollins College. Dinky Dock has a swimming area, grills, picnic tables, two wood docks, and restrooms. Also, the park has access to two a boat ramps for a very small fee.

What to Do

Annual Art Events -There are several artistic events like the Autumn Art Festival, Sidewalk Art Festival, and the Florida Film Festival that allows local to national artists to display and sell their works. Go to one of these events and enjoy the culture that the events bring to Winter Park.

Winter Park City happenings – From youth dance classes, “Popcorn Flicks in the Park”, and adult “Sip & Strolls” which is a wine tour of all the unique restaurants and bars on the historic Park Avenue.

Austin’s Coffee – A coffee house and small venue with lots of charm. Every brick on the interior is painted by a different artist and the stage holds some of the best local talent with Austin’s open mic nights. Besides serving stealer coffee, they also serve alcoholic beverages so you can kick back and enjoy a comedy act, some nice music, or poetry within one of Winter Park’s coolest locations.

The Wine Room – A local hot spot for not only Winter Park, but Orlando too, with a state of the art dispensing system that allows customers to load money on to a card and then use the card to dispense an amount of wine in one once, two and a half ounce, or five ounce portions. Want to try a $100 bottle? One ounce might be all you need to make up your mind. Want to pair it with imported cheeses? They have a true variety of artisan cheeses from the USA and most of Europe.

Where to Shop

Winter Park has a nice collection of unique high end boutiques and shops right on Park Avenue, but if you venture just outside the down town area, there is the Winter Park Village a more traditional town center mall, with businesses like movie theatres, home goods, clothing, and dinning.

Local Businesses, Restaurants & Employers

Where to Eat

Winter Park is full of many restaurants and eateries and many of those restaurants are located right on the Park Ave strip. The list of restaurants is vast; from a true French cuisine at Café de France to local casual hang out at Park Avenue Pizza. If you are looking for more restaurants outside of the immediate down town Winter Park are there is Tijuana Flats and the Winter Park Miller’s Ale House.

Café de France – originally opened in Winter Park in 1982 and has always been operated by the same French family. It is an anchor in the line of restaurants that make up the Park Avenue’s cuisine.

Park Avenue Pizza – Local chill spot and they don’t just serve pizza, they have baked dishes and gourmet entrees, and they are all very reasonably priced. They also have a nice beer and wine list in addition to their regular beverage list.

Tijuana Flats – This Mexican short order restaurant is always busy and it doesn’t matter which location you go to in Orlando. Provided to you inside is a sauce bar with a full line of unique sauces to put some heat on your dishes. There is a lot of pride with the locals as it was started from a student from the University of Central Florida.


Winter Park has a connection to the whole network of Lynx’s ‎bus lines in the Orlando area for the daily commuter or for errands or use the Sun Rail that stretches from Sand Lake Road to the City of DeBary, but for a person that would like to go further, Winter Park has an Amtrak train stop (code WPK) right in the heart of the city which goes from Miami Station all the way up to New York’s Penn Station. Amtrak also has an Auto Line, where you can make a short drive to Sanford, Florida and load your car on the Auto Train and ride it to its only other destination, Washington, DC.


In addition to the neighboring city of Orlando and all the jobs that are created there, Winter Park’s main employers include the Winter Park Memorial Hospital , Rollins College, Orange County Public Schools, and the City of Winter Park.

Places to Live Near Winter Park

Bainbridge Winter Park

  • Winter Park, Florida

Apartment Homes Coming Summer 2019!

More information coming soon!

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Bishop Park

  • 3250 Bishop Park Dr.
  • Winter Park, Florida 32792

Bishop Park Apartments is centrally located to both Rollins College and Full Sail, and just minutes from downtown Orlando and exclusive Park Avenue. Bishop Park offers a convenient lifestyle like no other apartments for rent in Winter Park!


Mon - Fri: 10 am - 6 pm
Sat: 10 am - 5 pm
Sun: Closed

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