
Winter Park
Winter Park is home to several unique shopping areas. First, there is Park Avenue, the main shopping district with boutiques and national brands sharing the avenue with restaurants offering out-door dining. The side streets of Morse, Welbourne and Canton are included in this district. At the North end of Park Avenue don’t miss the Hidden Garden Courtyard, where you will find more restaurants, more shopping and even a coy pond.
Moving to the West, is Hannibal Square, a historic district which could remind one of New Orleans, with it’s multi-use building, retail at the street level, apartments above. Bridal shops, restaurants, and The Rifle Paper Company all make their home there.
Orange Avenue as it splits off from Fairbanks as you are going west is another specific shopping and dining area.
Winter Park Village, on N. Orlando Avenue between Canton and Webster roads, is an outdoor, walkable shopping complex with nationally known brand stores, restaurants and the Regal Movie Theater.
All along Orlando Avenue on the west and Aloma Avenue on the east are strip shopping centers with large retailers, grocery stores, local, regional and nationally known restaurant brands.
The Mall at Millenia
The Mall at Millenia is located at 4200 Conroy Road, just six miles south of Downtown Orlando. This upscale mall houses over 150 stores and in anchored by Macy’s, Bloomingdales and Neiman Marcus. This indoor shopping mall also provides 30 great restaurants.
The Mall at Millenia
Outlet Shopping

While not in Winter Park, the Orlando area boasts many upscale outlet shopping centers. These centers are south of Downtown Orlando, in an area commonly known as the Attractions. The area is so named because it is in close proximity to Universal Resort Orlando and Walt Disney World, and several other smaller attractions.
- Bealls Outlet –
- Orlando International Premium Outlets –
- Orlando Outlet Market Place –
- Orlando Vineland Premium Outlet –
Disney Springs
And way farther to the south, at the north side of Walt Disney World, is Disney Springs. This is a shopping and dining district completely separate from the Theme Park. You do not need a pass to get in, it is very much like it’s own little town. The restaurants are very good, the grounds are scenic, as only Disney can make them, and of course the shops are filled with Disney items. Spending an afternoon or evening at Disney Springs is definitely something fun to do!
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