A Magical Guide to Living in Winter Garden, Florida

Iconic Winter Garden downtown in Florida.
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Iconic Winter Garden downtown in Florida with outdoor dining, and cobblestones on the roads.

A detailed guide of great family-friendly things to do in Winter Garden, Florida.

My husband was drawn to Winter Garden. Specifically, he loved Oakland Park. It has houses that are similar to those that are built in Celebration, Florida, with a much lower price tag.

I didn’t fall in love with Oakland Park like he did, as I like the community feel of Celebration. That said there were a lot of small-town community vibes that are quite charming in Winter Garden.

One of the closest towns to Disney’s Magic Kingdom, Winter Garden, Florida, is well known for its lively downtown and southern charm. This former citrus town takes pride in its rich history.

Read Also: Best Places to Live Near Disney World

The Heritage Museum is an excellent place for visitors to stop and learn about the history of Winter Garden. The Historic Downtown is on the National Registry of Historic Places and is full of fun things to do for residents and visitors. 

A view from under the
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Downtown Winter Garden, located on Plant Street, has friendly locals, shops, restaurants with live music, and one of the best farmer’s markets in Central Florida. The small town is also well known for the arts and has the SoBo Art Gallery.

The Garden Theater features live performances and movies. The West Orange Trail runs through downtown and is a 22-mile bike trail families can use to get outdoors. 

Winter Garden Village is a large outdoor shopping mall that is a perfect way to spend the afternoon. The outdoor mall has a variety of great stores, including Target, Best Buy, Forever 21, Victoria’s Secret, and many more.

Harrells dogs on main street in Winter Garden.
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Harrell’s Dogs on the main street in Winter Garden offer custom hotdogs and fresh-cut french fries.

If you’re downtown of Winter Garden, check out Harrell’s Dogs tasty options. It’s a small walkup that my husband and I checked out along with Woofgang Bakery.

We love to visit small non-chain places when we are considering this place to live. It was also nice that our dog Walt, was right down the road at Pet Paradise.

They also have a variety of restaurants, including Cracker Barrel, Panera, AJI, Bonefish, and Macaroni Grill. You will find precisely what you are looking for in Winter Garden Village. 

Where is Winter Garden, Florida?

Winter Garden, Florida, is located just west of Orlando and north of Walt Disney World. Located in Central Florida, Winter Garden is easily accessible by many highways and is close to many great Orlando theme parks and attractions.

The city borders the south side of beautiful Lake Apopka, with many beautiful parks overlooking the lake. 

What county in Florida is Winter Garden?

Winter Garden is located in Orange County, Florida. This is the same county that has Orlando, Universal Studios, Sea World, and part of Walt Disney World. Orange County is the fifth most populated county in Florida.

Read Also: The Best Way To Get To Universal Studios From Disney World

Orange County has various family-friendly things to do for families, such as theme parks, the Dr. Phillips Performing Arts Center, The Amway Arena, bike trails, natural springs, and more. 

Is Winter Garden a suburb of Orlando?

Yes, Winter Garden is a suburb of Orlando. Winter Garden is just outside of Orlando and is ranked as one of the “Best Suburbs to Raise a Family in Orlando Area,” according to Niche.com. The schools in Winter Garden are also some of the best schools in the Orlando area, attracting many families. 

How far is Winter Garden Florida from Disney World and other Theme Parks?

Winter Garden is close to many of the Central Florida theme parks. Many major Central Florida highways run through the city, making it easy to travel across Orange County. Winter Garden is less than 20 miles north of Walt Disney World and about a 20-minute drive.

Winter Garden is just about 30 minutes from the Disney parks.
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Winter Garden is just about 30 minutes from the Disney parks.

Universal Studios is about 15 miles from Winter Garden but about half an hour’s drive because you will travel closer to Downtown Orlando and may have more traffic. SeaWorld Orlando is about 20 miles southwest of Winter Garden and about half an hour’s drive. 

What is the closest or easiest way to get to Walt Disney World?

The closest and easiest way to get to Walt Disney World from Winter Garden is by the 429 Highway. This highway will take you straight to Walt Disney World, which has an exit directly off the highway.

The 429 is less busy than many other Central Florida highways but gets busy during morning and evening traffic hours.  

Is Winter Garden Safe?

One of the biggest draws to families moving to Winter Garden is that it is a safe city. Regarding crime, Winter Garden ranks below the national average on all types of crimes. 

How far is Winter Garden Florida from the beach?

If you want to live in the Sunshine State, you will surely visit the beautiful Florida beaches often. Winter Garden is located almost directly in the center of the state of Florida, making it easily accessible to both the West Coast beaches and East Coast beaches of Florida.

Read Also: What is the closet beach to Disney World in Orlando?

Winter Garden is slightly closer to the east coast of Florida, making the nearest beach the famous Cocoa Beach. Cocoa Beach is approximately 62 miles from Winter Garden and just over an hour’s drive. New Smyrna Beach is also very close to Winter Garden and slightly over an hour’s drive from Winter Garden. 

Is Winter Garden Florida an excellent place to retire?

Winter Garden is the ideal place to retire if you want to retire in Florida. The city has a small-town feel, where you can meet new friends at their many community events.

When you visit downtown, you will surely see a friendly face. The charming city also has a golf cart district and is perfect for a drive to grab a pizza at Winter Garden Pizza Co. or coffee at Axium Coffee.

The West Orange Trail head at Killarney Station.
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The West Orange Trail head at Killarney Station.

Want to make sure to exercise? The West Orange Trail is perfect for an afternoon stroll or a morning bike ride. Winter Garden has many great neighborhoods to choose from and many new homes being built in the area. 

Is Winter Garden expensive to live?

If you are looking at moving to Winter Garden, Florida, and wondering if this city is expensive, it depends on where you are comparing it to. If you are comparing Winter Garden to the rest of the United States, it is about average on the cost of living compared to the rest of America.

The mortgage rates, rent, and gas prices will cost you slightly less than the United States Average. The median home value is $349,700, the median rent is $1,360 in Winter Garden, and the average household income is $90,157.

Read Also: A Look To The Town Disney Built: Celebration, FL

If you are comparing Winter Garden to the Central Florida area, it is one of the most expensive suburbs of Orlando. Winter Garden has gorgeous real estate and many neighborhoods, so you can choose exactly what you want.

There are many older homes with charm and character and many new builds if you want something more modern. 

What types of events happen in Winter Garden Downtown area?

Winter Garden has many great family-friendly events to enjoy throughout the year. Most community events happen in Downtown Winter Garden, though some are held at Newton Park on Lake Apopka. Winter Garden has weekly events, including the Winter Garden Farmers Market and the Fridays on the Plaza. 

The Annual Seasonal Winter Garden Events include:

  • Martin Luther King, Jr. Celebration
  • Winter Garden Heritage & Music Festival
  • Shop, Dine, & Stroll
  • Spring Fever in the Garden 
  • Winter Garden Memorial Day Service
  • Red, White, & Blue on the Plaza
  • All American Kids Parade & Pancake Breakfast
  • Winter Garden Halloween Experience
  • Small Business Saturday Sidewalk Sale
  • Light Up Winter Garden 
  • Winter Garden Christmas Parade

When does the Winter Garden Farmers Market happen?

Winter Garden Farmer's Market
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Winter Garden Farmer’s Market happens every Saturday in downtown Winter Garden. Don’t miss it!

You will want to take advantage of the Winter Garden Farmers Market when visiting the city. The market is held every Saturday from 8:00 am to 1:00 pm.

The Winter Garden Farmers Market has been voted one of the best farmer’s markets in Central Florida time and time again. The market is located in the Historic Downtown Winter Garden and has many vendors selling everything, including fresh produce, homemade soaps, fresh flowers, delicious foods, and more.

They have live entertainment, and small field kids can run around and have fun. 

Have you had the chance to visit Winter Garden? Let us know what you love about the beautiful “Old Florida” city!

Whether looking for a charming place to visit on your Orlando vacation or a friendly small town to retire to, stop by and see why locals love Winter Garden. 

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