Welcome to Winter Park
An affluent community near Orlando with gorgeous luxury homes and upscale shopping
Winter Park, Florida, is an affluent community known for its unique charm and beauty. Located near Orlando, it is the ideal destination for those looking to experience a small-town feel with all the amenities of a big city. Residents love the vibrant community, diverse population, and great restaurants. Winter Park is also home to some of the state’s most beautiful homes and architecture.
As one of the most desirable communities in the region, Winter Park offers its residents a lifestyle of both convenience and beauty. With plenty of outdoor activities and stunning architectural details, it is no wonder why so many people flock to the area. The community has been around since 1885 and has seen many new developments and progressions since its inception. Though new developments and high-end homes and shops are found throughout the community, Winter Park still maintains an old-world charm and character that attracts locals and visitors.
What to Love
- Upscale shopping and dining
- Stunning luxury homes and amenities
- Walkable town center with nightlife
- Close to downtown Orlando
Local Lifestyle
Winter Park is renowned for its beauty, with its rolling hills, magnificent lakes, and lush greenery, as well as its unique lifestyle. Residents of this affluent community enjoy the perfect balance of leisure and luxury; with its grand architecture, historic landmarks, and exquisite culture, all while in proximity to the downtown Orlando area.
It is easy to see why many choose to call Winter Park home. Furthermore, because of its unique location and history, the city of Winter Park has become a unique microcosm of American culture. With its mix of traditions and beliefs, it is a place like no other.
Dining, Entertainment & Shopping
Park Avenue in downtown Winter Park is an upscale shopping and dining area with many high-end options. Prato is a modern dining space that serves Italian cuisine in a rustic and communal atmosphere. The Parkview is a sophisticated neighborhood bar with an elevated menu and rare wines. It serves fresh, artisan dishes from local farms and vendors. AVA MediterrAegean is a refined bar and restaurant that celebrates Greek food, hospitality, and service to transport guests to the Mediterranean coast.
There are also many high-end stores and boutiques in the community. Winter Park Village is a common shopping spot with upscale fashion brands and beautiful landscaping with water features and outdoor games. The Ancient Olive is a gourmet grocery store with imported oils, vinegar, and quality meats and cheeses. Lombardi’s Seafood is an upscale seafood supplier that aims to provide the finest selection of crab, fish, lobster, and specialty products.
Things to Do
Winter Park Sidewalk Art Festival is an annual event and one of the oldest art festivals in the nation. The celebration of art showcases works across all mediums, vendors, and local cuisine. The Winter Park Christmas Parade and Winter on the Avenue are back-to-back holiday events in Downtown Winter Park. The parade includes marching bands, local businesses, scouts, and local police and fire departments. Winter on the Avenue is a tree-lighting ceremony with smores, photos with Santa, and live music.
Winter Park Farmers Market is a weekly market for produce, specialty items, plants, and baked goods. Taste of Winter Park is a yearly event that gathers the top chefs and bakers in the region for locals to sample dishes, try new drinks, and find new favorites. Cows N’ Cabs is a local food and drink charity event to support children in need. The event features live performances, regional cuisine, an auction, and vendors.
Find Your Dream Home in Winter Park
Search Winter Park Homes for Sale
