An aerial view of the stores and brick-paved streets in the city of Winter Park.

Explore Upscale Shopping in Winter Park

Luxury malls and designer outlets aren’t the only factors that make Orlando a shopper’s paradise. Many unforgettable retail opportunities are waiting for you in eclectic, walkable neighborhoods throughout the destination — including charming Winter Park!

Shopping on Park Avenue

A warmly lit storefront corner shop on Park Avenue in Winter Park
City of Winter Park

Located 20 minutes north of downtown Orlando, Winter Park is home to acclaimed dining, a robust cultural scene — and some of the most sophisticated shopping in Central Florida. On Winter Park’s tree-lined, cobblestoned central thoroughfare, Park Avenue, and adjacent streets, you can shop more than 60 upscale retailers offering everything from clothing, jewelry, footwear, gifts, wine, books and other lines.

Situated in the heart of Park Avenue, Shops on Park is a great place to start. Boasting more than 20,000 square feet of retail space, this elegant, indoor center is anchored by world-famous brands such as J. McLaughlin, Lilly Pulitzer, lululemon athletica, and more, plus local favorites offering wares you won’t find anywhere else.

Not that Winter Park’s excellent shopping is limited to one retail center: the entire district is an outdoor shopping mecca! Homegrown clothiers like Tuni and John Craig are known for making grownups look their best, and the professionals at Bebe’s & Liz’s and Tugboat & The Bird can do the same for your children.

You can buy a lot more than clothes in Winter Park, too. Discover melt-in-your-mouth confections at Peterbrooke Chocolatier. Stock up on unique vintages — and try before you buy — at The Wine Room. Build your dream kitchen at Williams-Sonoma. Find timeless treasures at Goldsmith Jewelers and Be on Park. The fact is, you’ll find everything and anything you’re looking for while shopping on Park Avenue.

When you’re ready for a break from the shopping, keep in mind that Park Avenue’s acclaimed restaurants provide a perfect place to rest and regroup — or just obsess over your new possessions during a leisurely, gourmet dinner.

Shopping at Winter Park Village

Winter Park Village fountain with shops in the background
Winter Park Village

Although a majority of Winter Park’s best shopping can be found on and along Park Avenue, the city has more in store at Winter Park Village. Less than 10 minutes from the city’s core, this chic, outdoor venue has its own collection of best-of-brand retailers, salons and restaurants, as well as one of the area’s most comfortable movie theaters.

Fashionistas won’t want to miss Winter Park Village’s mix of nationally famous and regional clothing boutiques, including Francesca’s, Jos. A. Bank, LOFT, Soma, Versona, White House Black Market, and others. But as with Park Avenue, Winter Park Village offers many other shopping opportunities, such as Adjectives Market, Calvet Couture Bridal, Guitar Center, Pier 1 Imports, Ulta Beauty and more.

Paired with Winter Park Village’s salons, service providers, restaurants and bars, it’s easy to spend a day unlocking everything this unique shopping destination has to offer!