A Local’s Guide on Things to Do in Winter Park, FL

Fernanda Negromonte


Situated roughly seven miles north of metro Orlando, Winter Park is one of the area’s most desirable suburbs for upscale living. Originally founded as a resort community, Winter Park continues to cater to a prosperous and discerning clientele.

Despite its proximity to the hustle and bustle of Orlando, this affluent enclave boasts a quiet and relaxing atmosphere with a unique blend of historic charm and modern first-class amenities. Residents love living in Winter Park for various reasons, but the ability to curate an ideal lifestyle is most appealing.

Fernanda Negromonte is an award-winning Realtor and broker specializing in the Winter Park real estate market. If you are considering a move or visit, Fernanda highlights some top things to do in Winter Park, FL.

Bring the Family to the Parks

Winter Park boasts more than 70 area parks, large and small, where residents take pleasure in frequent outings with family and friends. Kraft Azalea Garden and Mead Botanical Garden are among local favorites for a scenic and tranquil stroll.

There are also numerous parks catering to younger and more playful patrons. With facilities like pools, playgrounds, sports fields, and courts, Cady Way Park and Phelps Park are perfect for kids.

Amid the myriad parks sprinkled throughout the community, Central Park is the most beloved. In the heart of the city, nestled alongside downtown, this 11-acre park is a hub for community events and everyday leisure. From annual festivals and regular movie screenings to a local farmer’s market, this park is a community focal point.

Explore Downtown Winter Park

When locals are not gathering in Central Park, they are likely socializing in neighboring downtown. Any day is suited to a relaxing excursion among red brick-paved streets, tree-lined sidewalks, and charming European-style buildings. Picturesque Park Avenue is the quintessential main street with lovely eateries, al fresco cafes, and boutique shopping, among other attractions. Downtown Winter Park is a vibrant and charming area where you are sure to run into a neighbor or two.

Visit the Winter Park Chain of Lakes

Undoubtedly, one of Winter Park’s most unique features is the Winter Park Chain of Lakes. Some of the area’s most luxurious homes are nestled along the shores of one of six interconnected lakes. Casually boating among the lush and peaceful canals is a regular, beloved pastime. From kayaking and paddleboarding to water skiing and fishing, residents love spending time on the water.

Go Sporting

Orlando is a premier golfing destination with championship courses and first-class members-only greens. Among the area’s only courses, Interlachen Country Club is Winter Park’s crown jewel for hitting the links. The golf enthusiasts in your family will appreciate this pristine and secluded 18-hole course. In addition to golf, you can always join a friendly game of other local staples like tennis or croquet.

Delve into the Arts and Culture Scene

Winter Park is a historic city, and residents take pride in preserving and honoring its history. Located in the quaint downtown, the Hannibal Square Heritage Center pays tribute to past and present contributions to the city’s character and identity. Other notable attractions like the Winter Park History Museum and the Casa Feliz Historic Home Museum provide insight into the community’s development since its founding in the 1800s.

In addition to celebrating its local history, Winter Park residents are also champions of the arts. You will find a nearly complete collection of Louis Comfort Tiffany works at the downtown Charles Hosmer Morse Museum of American Art. The Albin Polasek Museum and Sculpture Garden and Rollins Museum of Art are other cherished institutions with unique and engaging exhibits for the whole family.

Aside from visual arts, you can also delight in live performances at the Winter Park Playhouse or relish the outstanding musical talents of the Bach Festival Society. Additionally, with several nationally acclaimed art festivals, you will appreciate the creative and cultured nature of this community.

Treat Your Taste Buds

Winter Park is renowned for its powerhouse culinary scene. With a wide array of independent restaurants ranging from casual cafes and bistros to award-winning fine dining, indulging in exquisite local and international cuisines is the norm.

For an intimate and exclusive dining experience, the Michelin-star Kadence Sushi and Sake Bar offers a multi-course chef’s tasting experience guaranteed to impress the most discerning foodie. Prato is a local favorite for rich and savory Italian, enjoyed in a rustic yet contemporary atmosphere. And the James Beard nominated chefs at The Ravenous Pig serve flavorful gourmet classics in this chic and elevated gastropub.

Whether you are meeting friends for a delectable brunch or hosting a private event at The Wine Room, Winter Park has an establishment to satisfy every taste.

Enjoy Some Retail Therapy

Like many of Winter Park’s treasured activities and attractions, downtown is home to numerous upscale shops and boutiques offering everything from apparel and home furnishings to jewelry and gifts, to mention a few.

From custom made-to-order suits and tuxedos to sophisticated and expertly curated collections of high-end menswear, Leonardo 5th Avenue and John Craig Clothier cater to the distinguished gentlemen in your family.

Meanwhile, posh and chic shops like Louise James Boutique and Tuni specialize in stunning women’s fashion. If jewelry is the adornment of choice, Be On Park provides brilliant and mesmerizing selections from some of the most talented designers worldwide.

On the off chance you have all the apparel you need, there are also elegant boutiques to style your stately luxury home. You can browse handmade custom Brazilian furnishings at Saccaro or enlist the professional design services of the acclaimed Morrone Interiors. Winter Park is also home to the flagship store for the world-famous gift and stationery brand Rifle Paper Co. 

Live Luxuriously

Winter Park is a family-friendly community with an atmosphere of quiet elegance. Locals live a comfortable and relaxed lifestyle while enjoying the high-end and modern conveniences they expect.

Aside from impressive attractions and amenities, locals also appreciate lounging and entertaining in their opulent homes. Homes for sale in Winter Park range from expansive seven-bedroom waterfront estates to modern and majestic Italian-style villas complete with climate-controlled wine cellars.

If finding your dream home and curating your ideal lifestyle is on your Winter Park things to do list, contact Fernanda Negromonte. With more than 15 years of experience and expert knowledge in this coveted market, she will work diligently to help you join this highly sought-after community.

Fernanda Negromonte

Fernanda Negromonte

Real Estate Broker

About The Author

Hi, my name is Fernanda. I am a Real Estate Broker and the owner of Nova Real Estate Services, Inc. I started my Real Estate career in 2008 (great timing, right?) and while everyone was getting out of the game I pressed in. In just a few short months I was hooked! The years to follow provided necessary, difficult, and incredible exposure that led me to fancy myself an expert in the industry. Now with 15 years of experience I’ve worked with first time home-buyers, investors, developers, domestic and international clients, to name a few. Eight years ago I decided it was time to take my career to the next level and got my Brokers license - Nova Real Estate Services was born. It was an immediate challenge; however, the pride felt rising to the occasion and providing a boutique experience in our industry was invaluable and worth the obstacles overcome. It’s humbling to say that even after all these years I am learning every day and continue to adapt the business alongside an evolving market and client need. I work tirelessly to ensure my clients’ goals and best interests are the foundation of my approach to buying and selling Real Estate. If you’re searching for a committed, honest, and personable broker, look no further.


Fernanda works tirelessly to ensure her clients’ goals and best interests are the foundation of her approach to buying and selling Real Estate.

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