The Ultimate Guide to Moving to Winter Park, FL

Moving to Winter Park, FL can be an exciting adventure! The name “Winter” is a bit of a misnomer, as this sunny and warm residential haven is situated in the heart of Central Florida. Winter Park offers a blend of natural beauty, cultural richness, and a vibrant community that makes it a lovely place to live year-round, even though it is close to tourism-driven Orlando.

Whether you’re drawn to its picturesque lakes, charming downtown area, or thriving arts scene, here’s a guide to help you navigate your move to this lovely city:

Step #1. Research the Area

  • Neighborhoods: Explore the different neighborhoods in Winter Park to find the one that best suits your lifestyle and preferences. Consider factors like proximity to amenities, schools, parks, and public transportation or walkability.
  • Understand Local Cost of Living: Familiarize yourself with the cost of living in Winter Park, including housing prices, utilities, groceries, and transportation expenses. This will help you budget accordingly.

Step #2. Find Housing in Your Neighborhood of Choice

  • Real Estate Market: Work with a local real estate agent to find housing options that meet your criteria. Winter Park offers a variety of housing styles, including single-family homes, apartments, and condominiums.
  • Rental Options: If you’re not ready to buy, explore rental properties in the area. Websites like Zillow, Trulia, and can help you find available rentals. You can also post in local groups like NextDoor for word-of-mouth opportunities.

Step #3. Set Up Utilities

  • Electricity: Contact the local utility provider to set up your electricity service.
  • Water and Sewer: Arrange for water and sewer services through the city’s utilities department.
  • Internet and Cable: Research internet and cable providers in the area and schedule installation for your new home.

Step #4. Register for Services

Step #5. Explore Amenities

Step #6. Get Involved

  • Volunteer Opportunities: Consider volunteering with local organizations or nonprofits to make a positive impact in the community and meet new people. There are lots of local groups like the Winter Park Chamber of Commerce and Winter Park Women’s Club that will help you acclimate to your new home and contribute.

Step #7. Embrace the Lifestyle

  • Outdoor Activities: With its sunny weather year-round, Winter Park offers ample opportunities for outdoor recreation. Whether you enjoy golfing, biking, or simply soaking up the sun, there’s something for everyone to enjoy.
  • Day Trips: Take advantage of Winter Park’s central location by exploring nearby attractions like Orlando’s theme parks, the Kennedy Space Center, or the beaches on Florida’s east coast.

Step #8. Connect with Neighbors

  • Join Community Groups: Connect with neighbors and fellow residents by joining local community groups or social clubs. Websites like can help you find like-minded individuals with similar interests.
  • Attend Neighborhood Events: Participate in neighborhood events or block parties to get to know your neighbors and build a sense of community.

Where to Shop in Winter Park, FL

Winter Park, FL is home to a diverse array of local businesses that contribute to the city’s unique charm and vibrant atmosphere. From boutique shops and art galleries to cozy cafes and fine dining restaurants, there’s something for everyone to explore.

Here’s a closer look at some of the notable local businesses in Winter Park:

  • Boutique Shops: Park Avenue is lined with upscale boutiques offering everything from designer clothing and accessories to home decor and gifts. Explore clothing stores like TuniLilly Pulitzer, and Gatorlilly upscale resale for a luxurious shopping experience.
  • Art Galleries: Discover local and international artists at art galleries along Park Avenue. The SoBo Art Gallery showcases contemporary works by emerging artists, while the Winter Park Art Gallery features a diverse collection of paintings, sculptures, and ceramics.
  • Cafes and Bakeries: Hannibal Square is known for its cozy cafes and bakeries, perfect for enjoying a leisurely breakfast or afternoon treat. Visit Croissant Gourmet for authentic French pastries or Axum Coffee for artisanal coffee and light bites. Peterbrooke Chocolatier serves up custom chocolate gifts, famous chocolate covered popcorn and delectable ice cream.
  • Restaurants: Indulge in a culinary adventure at one of Hannibal Square’s acclaimed restaurants. The Ravenous Pig offers modern American cuisine with a focus on locally sourced ingredients, while Bosphorous Turkish Cuisine serves up authentic Turkish dishes in a stylish setting.
  • Shopping and Entertainment: Winter Park Village is a premier shopping and entertainment destination with a mix of national retailers and local boutiques. Browse stores like Anthropologie, Pottery Barn, and Lululemon Athletica, then catch a movie at the Regal Cinemas theater.
  • Dining Options: Enjoy a diverse selection of dining options at Winter Park Village, ranging from casual eateries to upscale restaurants. Grab a slice of pizza at Mellow Mushroom, savor sushi at RA Sushi Bar Restaurant, or dine al fresco at The Cheesecake Factory.

Farmer’s Markets:

  • Winter Park Farmer’s Market: Held every Saturday morning in the heart of Winter Park, the Winter Park Farmer’s Market features a wide variety of locally grown produce, artisanal foods, handmade crafts, and more. It’s the perfect place to support local farmers and artisans while enjoying the vibrant atmosphere.

Local Breweries and Bars:

  • Breweries: Winter Park is home to several craft breweries where you can sample a variety of locally brewed beers. Enjoy a pint at breweries like Ten10 Brewing Company or Deadly Sins Brewing, which offer a rotating selection of creative brews.
  • Bars and Lounges: Whether you’re in the mood for craft cocktails or a laid-back atmosphere, Winter Park has plenty of bars and lounges to choose from. Check out The Wine Room on Park Avenue for an extensive selection of wines by the glass or Enzian Theater’s Eden Bar for cocktails and indie films.

Art and Culture:

  • Galleries and Studios: Explore Winter Park’s thriving arts scene by visiting local galleries and artist studios. The Crealde School of Art offers classes, workshops, and exhibitions showcasing the work of emerging and established artists.
  • Community Events: Stay connected with the community by attending local events and festivals. Winter Park hosts various events throughout the year, including the Winter Park Sidewalk Art Festival and the Bach Festival.

Supporting local businesses is not only a great way to discover unique products and experiences but also helps contribute to the local economy and foster a sense of community in Winter Park. Whether you’re shopping, dining, or exploring the arts, be sure to take advantage of all that the city’s local businesses have to offer!

Winter Park’s Live Music Scene

Winter Park, FL, offers a vibrant live music scene with various venues and events where you can enjoy different genres and performances. Here are some of the top options for experiencing live music in Winter Park:

The Blue Bamboo Center for the Arts: A unique venue dedicated to promoting the arts, including live music performances. This venue offers a variety of music genres such as jazz, classical, blues, and more. The intimate setting provides a great atmosphere for enjoying live performances.

The Wine Room on Park Avenue: A popular wine bar that also features live music. Enjoy live jazz and acoustic performances while sampling from an extensive selection of wines and enjoying small plates.

Hannibal’s Lounge at The Alfond Inn: A sophisticated lounge within The Alfond Inn hotel. Features live jazz music on select evenings, creating a relaxing and elegant atmosphere.

Casa Feliz Historic Home Museum: A beautifully restored Spanish farmhouse that hosts various cultural events. Offers live music events, including their popular “Music at the Casa” series on Sunday afternoons, featuring local musicians in a stunning historic setting.

Park Avenue District: The main street in downtown Winter Park, lined with restaurants and bars. Several venues along Park Avenue offer live music performances regularly. It is a great area to explore for dining and live entertainment.

Central Park: As the aptly named central gathering space in downtown Winter Park, Central Park hosts numerous outdoor concerts and music festivals throughout the year. This includes “Olde Fashioned 4th of July Celebration” and “Winter Park Autumn Art Festival.”

Jazz Tastings: Although technically in Maitland, this cozy restaurant and bar is just outside of Winter Park and specializes in live jazz music. With jazz performances several nights a week, this spot also serves up a stunning menu of tapas, wine, and cocktails.

Best Restaurants in Winter Park

Winter Park, FL, boasts a vibrant dining scene with a variety of restaurants offering diverse cuisines and exceptional dining experiences. Here are some of the best restaurants in Winter Park:

Prato: Known for its wood-fired pizzas, house-made pastas, and contemporary Italian dishes. The rustic-chic atmosphere and a frequently changing menu featuring fresh, local ingredients make it a must-visit. Locals rave about the meatballs, margherita pizza, and the Fiorentina steak.

The Ravenous Pig: A local Winter Park gastropub favorite for its innovative American cuisine with a focus on farm-to-table ingredients. The restaurant also features an on-site brewery so you can find the perfect IPA to pair with your shrimp and grits, or pork porterhouse.

Hillstone: Located on Lake Killarney, Hillstone offers stunning views, a serene ambiance, and a menu featuring high-quality steaks, seafood, and American classics like hickory-smoked ribs, Hawaiian ribeye, and the Hillstone burger.

Bosphorous Turkish Cuisine: Known for its authentic Turkish dishes and warm, inviting atmosphere. The menu includes a variety of flavorful and well-prepared Mediterranean dishes. Do not miss the homemade baklava.

Briarpatch Restaurant: A popular spot for breakfast and brunch, offering a charming atmosphere and a menu filled with hearty, classic American breakfast and lunch items like blueberry pancakes, Southern eggs benedict, and the Briarpatch burger.

Hamilton’s Kitchen at The Alfond Inn: Located in The Alfond Inn, Hamilton’s Kitchen offers a farm-to-table dining experience with a menu that features Southern-inspired dishes.

Ethos Vegan Kitchen: It can be difficult to find a quality vegan spot, and Ethos is that place in Winter Park. It’s a casual eatery that offers a diverse menu of vegan dishes, from comfort food classics to innovative plant-based creations. Favorites are the coconut curry wrap and BBQ tofu sandwich.

Hannibal’s on the Square: Known for its fresh seafood dishes and elegant dining atmosphere, Hannibal’s on the Square is a top choice for seafood lovers. The lobster bisque is a classic!

Winter Park, FL Outdoor Activities

Winter Park, FL, offers a variety of outdoor activities that cater to different interests, from leisurely strolls and water activities to exploring nature trails and participating in community events.

Mead Botanical Garden: This 48-acre garden offers trails, a boardwalk, and a variety of plant species, making it perfect for a peaceful day in nature. If you’re interested in nature walks, bird watching, and exploring the butterfly garden this is a perfect day trip.

Kraft Azalea Garden: Located on the shore of Lake Maitland, this garden is known for its beautiful cypress trees and serene setting.

Winter Park Chain of Lakes: This chain of interconnected lakes offers stunning views and numerous opportunities for water recreation. Boat rentals and guided tours are available.

Winter Park Scenic Boat Tour: A one-hour tour through the lakes and canals, offering views of mansions, wildlife, and the Rollins College campus.

Cady Way Trail: This popular trail spans over 7 miles, connecting Winter Park to Orlando and offering a scenic route through parks and neighborhoods.

West Orange Trail: Although a short drive from Winter Park, passing through nearby Winter Garden, this 22-mile trail is worth the trip for its well-maintained paths and beautiful scenery for biking, hiking, and rollerblading.

Winter Park Golf Course: A historic 9-hole course located near downtown, perfect for a leisurely round of golf.

Winter Park Tennis Center: Offers multiple courts and professional coaching services for players of all levels.

Pickleball Orlando: Provides lessons and rentals for those learning how to play pickleball.

Best Activities for Kids in Winter Park

You’ve heard of Disney World, of course, but what else is there to do with kids living in Winter Park, FL?

Winter Park, FL, offers a variety of activities and attractions that are perfect for kids – and don’t cost the price of an admission ticket. From educational museums and interactive play areas to beautiful parks and family-friendly events, there’s plenty to keep children entertained. Here are some of the best activities for kids in Winter Park:

Central Park: This large park in downtown Winter Park features open green spaces, fountains, and walking paths. It’s a great spot for a family picnic, outdoor games, and enjoying the beautiful surroundings. The park also hosts events like outdoor concerts and festivals that are family-friendly.

Albin Polasek Museum & Sculpture Gardens: The museum features beautiful sculptures and art pieces, and the gardens are a serene place to explore. Kids can enjoy the outdoor sculptures and participate in special events and workshops designed for families.

Rollins College Campus: The beautiful campus of Rollins College is open to the public and offers a picturesque setting for walks. The Cornell Fine Arts Museum is free and often has exhibits that are engaging for children, along with educational programs.

Winter Park Public Library: The library offers a variety of programs for children, including story times, reading challenges, craft workshops, and educational activities. It’s a great place to foster a love of reading and learning.

Orlando Science Center: Located nearby in Orlando, the Science Center is a favorite for families. It features hands-on exhibits, a planetarium, live science shows, and special events. It’s both fun and educational, with interactive exhibits, planetarium shows, and live science demonstrations, making it a great day trip from Winter Park.

Lake Baldwin Park: This park offers a sandy beach on Lake Baldwin, a playground, picnic areas, and a dog park. It’s a great place for the whole family (including fur kids) to play, swim, and enjoy outdoor activities.

Enzian Theater: While Enzian Theater is also a great spot for adults to get away, the venue also hosts family-friendly movie events and has an outdoor seating area where kids can enjoy snacks and beverages. It’s a unique venue for watching movies under the stars as a family.

Cady Way Trail: This trail is perfect for a family bike ride, walk, or rollerblading session. It’s safe and well-maintained, offering a scenic route through Winter Park and into neighboring areas without being too difficult for children.

Ward Park: This park features multiple sports fields, a playground, and picnic areas. It’s a great spot for kids to play sports, enjoy the playground, and have a family picnic.

Schools in Winter Park

Winter Park, FL is part of the Orange County School System, and boasts a range of excellent educational institutions, from public schools to private academies, and higher education options.

Elementary Schools:

  1. Brookshire Elementary School:
    • Known for its strong academic programs and supportive learning environment.
    • Offers various extracurricular activities and enrichment programs.
  2. Lakemont Elementary School:
    • Focuses on academic excellence and character development.
    • Provides a range of extracurricular activities, including music, art, and sports.
  3. Dommerich Elementary School:
    • Recognized for its dedicated staff and engaging curriculum.
    • Offers programs to support both gifted and special education students.

Middle Schools:

  1. Maitland Middle School:
    • Provides a rigorous academic curriculum with opportunities for advanced coursework.
    • Offers numerous extracurricular activities, including sports, arts, and clubs.
  2. Glenridge Middle School:
    • Known for its strong academic programs and diverse student body.
    • Offers a variety of electives and extracurricular activities.

High Schools:

  1. Winter Park High School:
    • Offers a comprehensive academic program with Advanced Placement (AP) and International Baccalaureate (IB) courses.
    • Known for its strong athletic programs, arts, and extracurricular activities.
    • Home to the Winter Park High School Band, which has a national reputation.

Private School Options:

  1. Lake Highland Preparatory School:
    • A private, co-educational school in Orlando offering grades Pre-K through 12.
    • Known for its strong academic programs, including AP courses, and a wide range of extracurricular activities.
    • Emphasizes character education and community service.
  2. Trinity Preparatory School:
    • Offers grades 6 through 12 with a focus on college preparatory education.
    • The No.1-ranked private school and STEM school in the Orlando area.
    • Strong emphasis on leadership development and community involvement.
  3. The Geneva School:
    • A private Christian school in Casselberry, FL offering grades Pre-K through 12.
    • Focuses on classical education and integrating faith with learning.
    • Offers various extracurricular activities, including athletics and fine arts.

Higher Education:

  1. Rollins College:
    • A private liberal arts college located in Winter Park.
    • Offers undergraduate and graduate programs in a wide range of disciplines.
    • Known for its beautiful campus, rigorous academic programs, and strong emphasis on global citizenship and leadership.

Special Programs and Charter Schools in Winter Park

  1. Orlando Science Schools:
    • A charter school with a strong emphasis on STEM (Science, Technology, Engineering, and Mathematics) education.
  2. Fern Creek Elementary School:
    • Provides various programs to meet the needs of diverse learners, including gifted and talented programs.

Key considerations when choosing a new school would mean looking into:

  • School ratings and performance: Research school ratings and performance metrics through resources like or the Florida Department of Education website to get a sense of each school’s academic standing.
  • School visits and tours: Schedule visits or tours to get a firsthand look at the schools and their facilities. This can help you get a feel for the environment and meet with faculty and staff.
  • Community and parental involvement: Consider the level of community and parental involvement in the schools, as this can greatly impact the overall educational experience.

Winter Park’s schools, with their commitment to academic excellence and diverse extracurricular offerings, provide a solid foundation for students to grow and succeed. Whether you’re looking for public, private, or specialized education, Winter Park offers a range of options to meet your needs.

Day Care Centers in Winter Park

Finding the right daycare for your child is crucial when moving to a new location, and Winter Park, FL, offers several excellent options known for their quality care and educational programs.

Park Maitland School

Offering early childhood programs starting from 1 year to pre-K, this school provides a nurturing environment that promotes both social and cognitive development.

Bright Horizons at Baldwin Park

Offering infant care, toddler care, preschool, and pre-kindergarten, Bright Horizons touts a focus on individualized learning experiences tailored to each child’s needs.

Kids R Kids Learning Academy of Oviedo

With infant care, toddler care, preschool, pre-kindergarten, and before/after school programs, this innovative curriculum combines educational excellence with fun. A high-tech, secure facility with live-streaming cameras for parents.

Primrose School of Winter Springs

Programs offered includes infant care, toddler care, preschool, pre-kindergarten, and after-school programs. A Balanced Learning® approach that combines teacher-directed and child-initiated activities.

Winter Park Community and Social Clubs

Winter Park Chamber of Commerce: Support local businesses and promotes economic growth in the area through monthly networking events, business development workshops, and community initiatives.

Winter Park Garden Club: A club for gardening enthusiasts interested in horticulture, conservation, and beautification projects. Take part in community garden tours, educational programs, and community gardening projects.

Winter Park Women’s Club: A historic social club that engages in charitable activities and provides a platform for women to connect and support each other.

Crealdé School of Art: A community-based arts organization offering classes and workshops in visual arts.

Winter Park Playhouse: A professional musical theatre dedicated to producing year-round musical theatre programming.

Winter Park Racquet Club: A private club offering tennis, swimming, and social activities.

Winter Park Writers Group at Writer’s Block Bookstore: A group for writers to share their work, receive feedback, and support each other’s writing endeavors.

YMCA of Central Florida – Winter Park Branch: Offers programs for all ages focusing on healthy living, youth development, and social responsibility. Here you’ll find fitness classes, youth sports, swimming lessons, and family events.


Suddath offers comprehensive moving services, whether you’re making a local, international or long-distance residential move to Winter Park. Our professional moving coordinators are ready to take care of everything from packing, loading, storage and transportation. Get a free, no-obligation moving quote today.

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