Want to live in a charming city with picturesque, shaded oak trees? Winter Park, Florida, is known for its nature parks, vibrant lakes, brick-lined shopping streets and spectacular homes. With bright sunshine and warm weather, you can feel like you’re on vacation daily.

Whether you want to spend your weekends hiking on trails or riding roller coasters, you’ll love living in Winter Park, Florida. Discover why this place is perfect for students, families, professionals and retirees.

Is Winter Park, FL, a Good Place to Live? 

Winter Park is an excellent place to live in Orange County, Florida. In 1881, a New Englander named Oliver Chapman bought a large tract of land there. He wanted to create a resort community for northerners who wished for a warm place to live throughout winter. 

Over the next few years, his dream came to life with a town hall, post office, shopping plaza and Rollins College. Today, the town offers a unique blend of historical architecture and modern amenities. Residents can enjoy quick access to major cities, including Orlando, Florida, about 30 minutes away. 

Demographics and Population

Winter Park’s population is around 30,000 people. The median age is about 42 years old for males and 46 years old for females. According to the latest racial composition surveys, about 80% of residents identify as white, about 9% identify as two or more races, about 6% identify as Asian and about 4% identify as Black or African American. The rest identify as Native American, Native Hawaiian, Pacific Islander or Other. 

Cost of Living

Want all the attractions of a major city with more affordable prices? Winter Park is the perfect place for you. While the cost of living is about 2% higher than the national average, you get what you pay for with paradise in your own backyard and waterfront views everywhere you go. Plus, this city is less expensive and crowded than tourist spots like Miami, Florida. 

Individuals who live here can expect to pay about $1,600 on rent and utilities. Families of four people can expect to pay around $2,650 on their rent and utilities. If you plan to move here, you can use a cost of living calculator to estimate how much your housing, transportation and food expenses could cost. 


Get ready to feel like you’re in paradise — Winter Park, Florida, offers sunshine all year round. To dress comfortably, you can wear hats, sunglasses, tank tops, shorts and sandals.

The best times for warm-weather activities are from March to May and October to December. During these times, the temperatures range from 50 to 90 degrees Fahrenheit. In winter, the temperatures range from 58 to 74 degrees Fahrenheit. You can enjoy your holidays on the beach if you’d like!

Best Places to Live in Winter Park, FL 

The most beautiful and family-friendly neighborhoods in the area include:

  • Cypress Reserve: Enjoy lakefront views in the Cypress Reserve neighborhood. The gated community has a clubhouse, resort-style pool and playground with parks and nature trails only a few miles away. 
  • Windsong: Live in the heart of the city while surrounded by three scenic lakes. The upscale Windsong neighborhood features luxurious homes with community amenities, including playgrounds, Olympic-style pools and walkable streets. 
  • Winter Park Woods: Choose from various home styles, sizes and prices. The Winter Park Woods Condominiums provide a cozy and affordable neighborhood with pools, tennis courts, playgrounds and picnic table areas. 

Schools and Education

Winter Park, Florida, offers short commutes to several schools in the Orange County Public School district. Some top-ranked options include Killarney Elementary SchoolTrinity Preparatory School and Aloma High School where you’ll find excellent academics, extracurricular activities, sports and after-school clubs.


You’ll find many industries to work for here, including education, health care, construction and technology. Some top employers in the area are the Rollins Liberal Arts CollegeThe Geneva SchoolRuth’s Hospitality Group, the Hubbard Construction Company and the Sonobi technology advertising agency. 


There are many safe, comfortable places to live and work in Winter Park, Florida. The city offers significantly lower crime rates than the nation’s average, which can give you peace of mind. 

Things to Do in Winter Park

Here are some fun and exciting activities for you to enjoy in the area:

  • Shop at the farmers market: Visit the Winter Park Farmers’ Market on Saturdays. Discover seasonal produce, fresh bread, flavorful sauces and unique houseplants from local vendors.
  • Explore a botanical garden: Walk through the Mead Botanical Garden, an oasis tucked away from the hustle and bustle of city life. Explore the winding trails and boardwalks to find an extensive collection of orchids, a butterfly garden with colorful plants and wetlands with towering trees. 
  • Go on a scenic boat tour: Have a relaxing time on the Winter Park Scenic Boat Tour, which travels through three lakes with lush landscapes and wildlife. Learn about the history and ecology of the area with information from a local guide.
  • Stroll along Park Avenue: Walk through the city’s charming and cultural Park Avenue District, a brick-paved area with beautiful oak trees. The tree-canopied blocks include over 140 specialty boutiques, cafes and coffee shops to explore.
  • Visit an art museum: Wander through the Charles Hosmer Morse Museum of American Art to see the most comprehensive collection of work by Louis Comfort Tiffany. Tour the exhibits to marvel at magnificent creations, including stainless glass windows and lamps with intricate designs. 
  • Play a round of golf: Take in the breathtaking scenery at Winter Park Golf Course, a historic golf course dating back to 1914. Play a nine-hole, par-35 game that’s enjoyable and challenging for golfers of all skill levels. 
  • Kayak through lakes: Navigate through picturesque lakes. Get half or full-day kayak rentals from Peace of Mind Kayak for the freedom to plan your own journey or book adventurous tours with outfitters who lead the way. 

Get a Free Estimate From David McCarthy Moving

Are you planning on moving to Winter Park, Florida? Trust the experts at David McCarthy Moving to provide residential moving servicescommercial moving servicescustomized packing services and storage unit solutions for you. 

To get started, get in touch with our team today!


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