Winter Park or Winter Garden: An Interesting Debate

Winter Park or Winter Garden: A Delightful Debate

Img: Downtown Winter Park

Two absolute hotspots in Orlando.

Amazing communities, rich in culture, landscape, and attractions.

From the West Orange trail to historic homes.


Are you thinking of moving to Florida? You're not alone. In fact, Florida's population has expanded by nearly 15% since 2010. And as of 2020 this is approximately an additional 2.8 million new Florida residents.

There are a lot of great reasons to move to Florida. There's the great weather, of course. There's a healthy economy, with stable employment rates and low levels of unemployment.

There's a dream home for nearly everybody in The Sunshine State. No matter who you are or what you're into, there's a community where your dreams will be able to flourish like a botanical garden.

Whatever you're looking for, if you're considering moving to Florida, we're here to help you decide where to put down stakes. Today, we'll be looking at two popular Florida areas in the Orlando region - Winter Park and Winter Garden.

Winter Park Vs Winter Garden: Which One's Right for You?

Winter Park and Winter Garden have a lot in common. More than just their names.

They're both located in Orange County, for one thing. They're both Orlando suburbs that are quite popular for raising families.

Despite having such similar names and locations, both Winter Park and Winter Garden have their own unique identities. Let's delve into each to help you decide on your dream home.

Winter Garden, Florida: All You Need to Know

Winter Garden, Florida is located in Orange County. It's got a population of roughly 45,000 residents as of 2020, so it's not enormous.

It is rather affluent, however. The median household income in Winter Garden was last reported in 2020 at: $85,352. The cost of the average 3 bedroom 2 bath home is $217,900.

You can score a 3 bedroom house in Winter Garden for an average price of $521,000. (as of 6/1/2023)

The History of Winter Garden, Florida

Winter Garden started out as a farming community, like many areas of Florida. Farmers settled the shores of Lake Apopka, using its fertile soil to cultivate citrus and vegetables.

The area continued to grow and expand, with a healthy downtown commercial area popping up in conjunction with two railroad lines. The original downtown burned but was rebuilt with stone and concrete, much of which is still standing today.

Winter Garden's development stalled out in the mid-1960s, as Lake Apopka's nutrients began to run dry. The area would experience a renaissance in the '90s, becoming the cultural hub that we know and love today.

Winter Garden's an older community than Winter Park. Those looking for the newest, latest, flashiest trends might do better living in Winter Park. Those who love a sense of history and tradition will delight in exploring Winter Garden's historic architecture.

Winter Garden's still evolving, however. They've just announced a plan to develop their Parks and Recreation Department. They're building a soccer field and a new park alongside Lake Apopka.

Winter Garden is still developing. How it shapes up remains to be seen but it seems likely that it'll stay more of a suburb. Those looking for a quieter, more idyllic existence would do well to settle in Winter Garden.

Here are a few reasons you should consider moving to Winter Garden if you haven't already.

Reasons To Move To Winter Garden, Florida

Winter Garden is blowing up fast! If you're thinking of moving to this quickly-expanding modern area of Florida, here are a few reasons to consider doing so.

West Orange Trail

If you're a fitness fanatic or an outdoor lover, Winter Garden's network of hiking and biking trails is going to give you fits! The West Orange Trail is a 22-mile network of paved trails. This makes it suitable for just about anybody, no matter how in-shape or experienced you might.

The West Orange Trail starts at the Kilkarney Station in Winter Garden. It winds through the downtown area, ending up at the Rock Springs Road in nearby Apopka. It takes you past some of the area's newest developments as well as some of the traditional bungalow homes Winter Garden is known for.

The West Orange Trail isn't just good for fitness lovers. It's also a favorite spot of photographers, bird watchers, and nature lovers. It's part of why many people consider proximity to the trail to be a major selling point for buying a house.

Restaurants In Winter Garden

If you like to go out to eat, you're going to love Winter Garden! There's every kind of chain restaurant you can think of, for one thing. From Starbucks to Five Guys, you won't have to travel far to find the dinners and drinks you desire.

The local eateries are the real reason to get excited about Winter Garden, however. Walk down Plant Street in downtown Winter Garden to glimpse the charm of its local cafes and patios.

Schools In Winter Garden

If you've got kids, or are planning on having some in the near future, Winter Garden's school system is definitely a reason to consider moving there. Winter Park's schools are excellent. There are also a lot of them, so you'll have a range to choose from.

For elementary schools, Winter Garden has Whispering Oak Elementary and Lake Whitney Elementary. For Middle and High School, there's Sunridge and West Orange High.

Those are just the public schooling options, however. There's also the Innovation Montessori School, Hope Charter, and Legacy High School.

There's even a faith-based school if you're looking for your children to receive a religious education. The Foundation Academy provides a faith-based education for hundreds of Winter Garden families.

There are over 60 public schools serving Winter Garden.

The Top 5 School Serving Winter Garden
  • Orlando Middle/High Charter School: 571 Students; Grades 6 - 12
  • Whispering Oak Elementary School: 937 Students; Grades K - 5
  • Orlando Science Elementary Charter School: 495 Students; Grades K - 5
  • Lake Whitney Elementary School: 544 Students; Grades K - 5
  • West Orange High School: 4338 Students; Grades 9 - 12

Farmer's Market In Winter Garden

Winter Garden's farmer's market is regularly voted as the best in the region. Take a stroll through its booths on a busy Saturday afternoon and you'll see why.

Winter Garden's farmer's market is home to countless vendors of all kinds. There are the local farmers, of course, providing guests with an array of their locally-grown organic produce. There are also copious amounts of vendors, ranging from local artisans to regional restaurants.

There's lots of entertainment to be had at the farmer's market, as well. Local musicians provide a soundtrack to inspire and soothe.

That's entertainment for everybody, as well. Winter Garden's farmer's market is very family-friendly. It's even welcoming to the furry members of your family, as four-legged friends are quite welcome at the market, as well.

Winter Park, Florida: What You Need to Know

Winter Park is also a popular choice for people moving to Florida. It's similar to Winter Garden in a lot of ways. It's just a little smaller with slightly different demographics.

Winter Park has a population of 29,182. The median income is $80,500.
The median cost of a house is $632,000 (04/2023).

You can find a 3 bedroom 2 bath house in Winter Park for around $550,000 in Spring 2023

Winter Park's a tiny bit older than Winter Garden, as well. 

The History of Winter Park, Florida

Winter Park started out on only 8 acres, back in 1858. Six hundred additional acres were incorporated in 1881, and the area we now know as Winter Park was born.

Winter Park continued to blossom with the introduction of the railroad into the area. Tourism was largely responsible for Winter Park's earliest popularity. The area has since grown and diversified extensively, being home to numerous different industries.

Winter Park's focusing more on the future while remaining rooted in their rich history. Town officials announced an ambitious plan at the end of 2018, detailing the future of Winter Park.

Winter Park's overhauling everything from infrastructure to connectivity to culture and recreation in the foreseeable future. Winter Park looks likely to expand into a proper city as time rolls on.

For those looking to get in on the ground floor of a new urban environment, Winter Park would be a fine final destination to make home.  

Reasons to Move to Winter Park

Winter Park is less than 15 minutes from downtown Orlando. Despite its proximity to a major city, it's a vibrantly beautiful place with a lot of natural beauty as part of its charm.

Parks In Winter Park

The ability to do outdoor activities year-round is one of Florida's biggest charms. You'll have plenty of options to do so if you relocate to Winter Park.

Central Park is one of Winter Park's most iconic attractions. Its ornate gardens are a regular favorite of joggers and dog walkers. It's also the site for numerous high-profile outdoor arts events, including the Winter Park Sidewalk Arts Festival.

The Winter Park Sidewalk Arts Festival is one of the oldest in the country. Running for over 50 years, the Arts Festival is now home to over 1,000 artists and artisans. It regularly draws in hundreds of thousands of visitors each year.

Central Park is also near to Lake Baldwin Dog Park for those with canine companions. There's a playground for your two-legged children, as well.

Finally, for the flower lovers, Kraft Azalea Gardens is an opportunity to tour the local flora and fauna. You'll see epic, towering examples of the local trees, and the birds that call them home, while you hike around beautiful Lake Maitland.

Museums & Galleries In Winter Park

You won't be restricted to viewing inspiring fine art to the Sidewalk Arts Festival if you transplant to Winter Park. There's plenty of year-round museums and art galleries for the aesthetes!

The Charles Hosmer Morse Museum of American Art is a popular local attraction. The Morse Museum is dedicated to showcasing the works of Louis Comfort Tiffany. Not only will you be able to Tiffany's paintings, but you'll also see examples of her pottery, jewelry, and other related crafts.

The Cornell Fine Arts Museum and Albin Polasek Museum and Sculpture Garden are both popular destinations for local art lovers, also. If you're moving to Florida to inspire your visual art, Winter Park offers plenty of opportunities for you.

Schools In Winter Park

Winter Park has an excellent school system as well. While it doesn't have as many schools as Winter Garden, there are still 59 schools serving Winter Park. Many of them are some of the finest in the state.

Winter Park High School is considered the best in the area, comparable to Orlando's Dr. Phillips in size and quality of education. If you're looking for an Orlando suburb with the same high-quality education and resources you'd find in a major city, you'd do well to consider Winter Park as a home.

Top 5 Schools Serving Winter Park
  • Orlando Science Middle/High Charter School: 571 Students; Grades 9 - 12
  • Winter Park High School: 3,330 Students; Grades 9 - 12
  • Orlando Science Elementary Charter School: 495 Students; Grades K - 5
  • Audobon Park Elementary School: 622 Students; Grades K - 5
  • Dommerich Elementary School: 622 Students; Grades K - 5

Food & Shopping In Winter Park

Winter Park boasts fine dining for every taste palate, making it a fine choice if you're a foodie in search of a flourishing food culture!

Winter Park has all the traditional dining you could ever hope for, for one thing. The 4 Rivers Smokehouse has been causing quite a stir since their founding in 2009. They've moved up from a food cart to a lavish dining room on Winter Park's Fairbanks Ave.

If you're looking for a chance to get your hands on some authentic southern BBQ, 4 Rivers is going to send your taste buds to heaven.

There's more new age fare in Winter Park, as well. There are numerous top-rated vegan restaurants in Winter Park. Proper & Wild on E. Morse Avenue isn't just for vegans. Anyone interested in investigating what a plant-based menu has to offer will find something to drool over in Proper & Wild's rustic boho dining room.

Finally, there's all the shopping you could ever hope for in Winter Park. You'll find all of your favorite chains, from DSW to Nordstrom Rack. You'll also find plenty of local businesses, giving you a flavor of Florida's unique regional culture.

Looking for a Home Near Downtown Orlando?

The Choice is Yours:

Ultimately, the decision between Winter Park and Winter Garden comes down to personal preferences and lifestyle choices. Whether you seek the historical charm and cultural heritage of Winter Park or the modern amenities and community development of Winter Garden, both suburbs offer unique qualities that make them attractive places to call home. Whichever community you choose, you can expect a fulfilling Florida experience filled with natural beauty, cultural experiences, and a strong sense of community.

Contact us today if you're thinking of buying a home in Orlando, Florida!

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