Welcome to Winter Park
A lavish haven designed with resort living in mind, primed with high-end estates and bountiful nature
Surrounded by sweeping lakes and engulfed with the sweet aromas of flowering orange blossoms, it’s not hard to understand why many locals refer to the city of Winter Park as the Venice of Florida. Winter Park delights its visitors with palm-lined, cobblestoned streets, and a pervasive elegance, while its position as a northeast suburb of Orlando allows for plenty of nearby entertainment.
Winter Park was established in the 1880s as a resort community, and its reputation for excellence has continued ever since. The area is well-known for its abundance of arts and culture and is home to a plethora of museums and galleries. Additionally, Winter Park houses the elite, private liberal arts college — Rollins University.
A luxury market through and through, Winter Park abounds in spectacular lakeside estates with waterfront views and mature landscaping that create a perfect paradise escape. Among the sprawling, multimillion-dollar properties — in styles from historic, Tuscan villas to modern Mediterranean abodes — are a solid number of refined single-family and executive homes.
What to Love
- Classy atmosphere and personality
- Overflowing with award-winning eateries
- Culturally rich with many day-to-day opportunities to learn
Winter Park is a place known for its honorable residents, who take great pride in maintaining the city’s verdant natural parks and vibrant arts community. Days here are spent meandering down the charming main street and ducking into independent shops, or relishing the balmy Florida weather in a variety of outdoor activities.
Dining, Entertainment, Shopping
Downtown Winter Park is the undeniable pulse of the city and an effervescent hub of stylish boutiques and top-notch eateries where cuisines range from gourmet bakeries to authentic Thai. Nearby businesses include those such as Marc Michaels Interior Design, a creative luxury designer ready to elevate the already immaculate homes of Winter Park.
There is a bevy of dining options in Winter Park, such as Prato — the modern Italian hotspot decked out in a rustic-chic style. The food at Prato is sumptuous, paying homage to the traditions of the Italian countryside. Briar Patch is Winter Park’s iconic breakfast and brunch must-try, with an expansive menu that includes indulgent ice creams in a wide scope of flavors.
Craving some upscale gastropub fare? The Ravenous Pig dishes up inspiring New American fare, from bourbon-glazed porterhouse steaks to mouthwatering lobster tacos. The restaurant also serves as a beer garden, whose brews are crafted on-site for top-tier taste. An unforgettable stay at the posh Alfond Inn comes with a chance to sample the incredible fare at their Hamilton’s Kitchen restaurant.
Things to Do
More than its exciting commercial scene, Downtown Winter Park is also the location of Central Park, the city’s crown jewel among its more than 70 outdoor recreation areas. Central Park’s 11 acres contain everything from a blushing rose garden to stone fountains and stunning oak tree canopies. The park also hosts many of the city’s events throughout the year, including the annual Winter Park Sidewalk Art Festival. As one of the nation’s oldest and most distinguished outdoor art festivals, this beloved event draws in over 350,000 attendees each year.
On the tranquil shores of Lake Maitland, the Kraft Azalea garden invites visitors in with over five acres of captivating displays. Cypress-shaded walkways and scenic stonework make this lakefront gem a favorite wedding venue. Alternatively, Casa Feliz — a restored Spanish farmhouse turned museum and event venue — provides a historic grandeur to special occasions.
Winter Park is home to a number of excellent schools. Top educational opportunities include:
Rollins College, an exceptional, private liberal arts university founded in 1885, offering graduate and undergraduate studies
Full Sail University, a notable private university offering graduate and undergraduate degrees centered around the arts and entertainment
Winter Park High School, 9-12, highly rated public high school ranked in among the top 50 in the state