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Moving to Orlando Neighborhood Highlight: Winter Park

Beyond its reputation for tourism and hospitality, Orlando is a cool city with so much to offer. It’s diverse with a collection of unique neighborhoods. It has a good mix of city and suburban areas. Are you thinking of moving to Orlando? In this series, we will be highlighting different neighborhoods in Orlando and what makes them unique. We’ll explore things to do, places to eat, and sights to see in each neighborhood. For today’s neighborhood highlight, we’re featuring the Winter Park neighborhood.

A young couple holding boxes in front of a home.

Winter Park isn’t technically an Orlando neighborhood, but it’s considered part of the Orlando metro area. It is an affluent neighborhood rich in history, arts, and culture. It’s also home to the private research university, Cornell. There is a lot to enjoy from chains of lakes to gardens and museums.

Things to Do

Stroll Through Park Ave.

The exterior of some restaurants and shops on Park Ave.

Winter Park is well known for its popular cobblestoned street that’s filled with delicious eateries, upscale boutiques, and unique shops. Along the street sits Central Park, a large open lawn area with pathways, benches, and fountains. Every month, they host “Popcorn Flicks in the Park”, where family and friends can set up on the lawn with a blanket, picnic, or snacks to enjoy a movie.

Take a Scenic Boat Tour

Cruise through Winter Park’s chain of lakes on an 18 passenger boat tour. They hold tours every day on the hour from 10 am-4 pm. This scenic boat tour will give you views of swaying palms, towering cypress trees, lush ferns, and sub-tropical flowers. You’ll also get to see breathtaking views, beautiful homes, and estates along the shores.

Sample a Variety of Wines at The Wine Room

A woman smelling a glass of wine at Wine Room.

Enjoy a unique wine experience at The Wine Room. At the Wine Room, you’ll have access to 156 hand-selected wines to sample from all over the world. Their special wine tasting system allows you to choose from 1oz, 2.5 oz or 5oz pour sizes. This makes it easy to find your next favorite wine. They also have a wonderful selection of small plates, flatbreads, cheese flights, and charcuterie.

Places to Eat

Briar Patch

A close-up of eggs bennedict.

Briar Patch is a popular breakfast spot amongst locals in Winter Park. Using only the freshest local ingredients, Briar Patch serves contemporary American cuisine in a warm and inviting atmosphere. Along with delicious food, they also serve homemade pastries, cakes, and ice cream.


Financier is one of the newest additions to Park Ave. It is an elegant bistro, bar, and French Patisserie. Their lunch menu has offerings like the Croque Monsieur or Madame, Saumon Fumée, and Quiche Lorraine. On the dinner menu, they have seared salmon, steak frites, and more. In addition, they have quality pastries, desserts, and wines.


The bar area of Prato in Winter Park.

Another local favorite is the stylish Italian eatery, Prato. Enjoy modern takes of classic Italian dishes in a beautiful rustic-chic ambiance. They have a wide variety of dishes including inventive pizzas and pasta.

Sights to See

Mead Garden

A variety of plants at Mead Garden.

Recharge in nature by visiting Mead Garden. This tranquil garden is 47 acres complete with a greenhouse and butterfly garden. It also has hiking trails, a creek, and a boardwalk. Stroll through the tall pine trees or sit by the pond to observe turtles, fish, and wading birds.


Morse Museum of American Art

The Morse Museum houses the world’s most comprehensive collection of works by artist and designer Louis Comfort Tiffany. The collection includes her jewelry, pottery, art glass, and more. There are also a few other collections on display. They include American Decorative Art and Sculpture, Painting and Graphic Arts, and European and Miscellaneous Collections.

Hannibal Square Heritage Center

The inside of the Hannibal Square Heritage Center with framed photos on the wall.

Get educated on Black History at the Hannibal Square Heritage Center. This site is a tribute to the past, present, and future contributions of Winter Park’s historic African-American community. It hosts an award-winning, museum-quality exhibition and The Hannibal Square Timeline which, according to their website, documents significant local and national events in African-American history since the Emancipation Proclamation.

Ready to Move to Winter Park?

The Winter Park neighborhood is a pleasant place to move, especially if you’re looking for a luxurious lifestyle or an Old World charm. Once you’ve decided on your dream neighborhood, it’s time to start planning your move. Consider hiring a white-glove moving company, like Megan’s Moving. We take extra measures to move your belongings safely and efficiently. Schedule a consultation with one of our moving experts today!

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