Winter Garden

There are four different cities in Central Florida that start with the word “Winter,” and they’re all within 50 miles of each other. It’s confusing, even for us locals. Most people know Winter Park — it’s the popular, successful older sibling that every parent wished their kid would be. This article is not about Winter Park. This article is about the just-as-lovable Winter Garden. Winter Garden feels welcoming. The homes are beautiful. The downtown was lively. The traffic was light. The coffee shop was excellent. (I’m a tough coffee critic.) The city was a pleasant surprise.

LOCATION & HISTORY

Winter Garden is located in the most western part of Orange County, sitting between Lake Apopka and Lake County. Lake Apopka is the second largest lake in Florida, and picturesque. As one of the highest elevation points in Orlando and Central Florida, that very characteristic is what gives Winter Garden a drastically different feel when compared with the majority of Orlando. Orlando is really flat. Really, really flat. But Winter Garden isn’t. It doesn’t feel like swampland, because there are so many hills! The easiest way for me to describe Winter Garden is that it feels like a city up north. I even spotted several homes with basements, which I didn’t know existed in Florida. Clermont is the only other city in Central Florida with lots of hills, and a similar vibe, if that’s your thing.

The city of Winter Garden is also 21 minutes away from Disney property, which is amazing. The west side of Central Florida where Winter Garden is located is not as built up as areas on the east side of Disney like Dr. PhillipsCelebration, and Kissimmee. Like many cities in our region, Winter Garden has an agricultural past specialized in citrus. However, not many orange groves remain today due to the occasional hard freeze in winter every couple of years. Because it is one of the last semi-rural areas, home developers have also taken to the area. This area is set for major expansion, and home construction has taken off in recent years.

A shot of the Downtown Winter Garden area with brick paver streets. The sidewalk in the middle is apart of the 21-mile West Orange Trail, one of the most popular in Orlando!


Map and relative location to theme parks


Things To Do

Local shops are bustling along the brick-paved roads lined with huge live oaks. One of the most popular biking trails in Florida, the 22-mile West Orange Trail also cuts through the middle of downtown Winter Garden. I really like the downtown area because it felt like a destination, albeit small, rather than an area you pass through on your daily commute. Even during one of the hottest weekday afternoons in summer, the downtown area had a much larger turnout than I was expecting. The historic downtown section was clean, and the people who live there take pride in their community. There’s a weekly farmer’s market in the town center every Sunday from 9 am-2 pm, and concerts every Friday from 7-9 pm by local musicians.

HOMES

The average sale price for a single-family residence in 2019 was $426,000. The neighborhoods were beautiful. I noticed a theme of quiet homes in great condition. The selected neighborhoods listed below were ones we drove through and found really appealing:

Winter Oaks was a neighborhood that really took me by surprise. This subdivision featured an ornamental water tower at the entrance, which was both unique and charming. Homes were neo-traditional, with columns, covered porches, and great architectural details. The average sale price for a single-family residence (for 2020) in this neighborhood was $415,000.

WHY MOVE HERE

Winter Garden is a great place to live if you like small-town charm that’s 20 minutes away from Disney without feeling like you’re 20 minutes from Disney. It very much feels like “Small Town America” rather than an annex of Orlando theme parks.  The locals are invested in their community.

Homes for sale in Winter Garden

If you have questions about moving to Central Florida and would like to speak with a real estate professional, please contact us.

Price Change - 11 hours ago
$36,100
Land For Sale
Active
0.09
ACRES
ORANGE, FL
COUNTY
734 Magnolia Avenue
Winter Garden, FL 34787
Merchants Sub Subdivision
$50,000
Land For Sale
Active
0.09
ACRES
ORANGE, FL
COUNTY
727 Magnolia Avenue
Winter Garden, FL 34787
Merchants Sub Subdivision
$89,900
Land For Sale
Active
0.23
ACRES
ORANGE, FL
COUNTY
N West Crown Point Road
Winter Garden, FL 34787
Acreage Subdivision
$89,900
Land For Sale
Active
0.23
ACRES
ORANGE, FL
COUNTY
104 Massey Avenue
Winter Garden, FL 34787
Black Lake Subdivision
New Listing - 2 weeks online
$139,000
Single Family Home For Sale
Active
3
BEDS
1
TOTAL BATH
845
SQFT
921 Palm Avenue
Winter Garden, FL 34787
Winter Garden Manor Subdivision
New Listing - 4 weeks online
$149,000
Single Family Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,316
SQFT
14839 Ticknor Street
Winter Garden, FL 34787
Black Lake Subdivision
$149,900
Land For Sale
Active
0.3
ACRES
ORANGE, FL
COUNTY
14708 Micah Street
Winter Garden, FL 34787
Acreage Subdivision
New Listing - 7 hours online
$155,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
918
SQFT
103 Windtree Lane #103
Winter Garden, FL 34787
Windtree Gardens Condo Ph 03 Subdivision
$187,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,203
SQFT
14200 Avalon Road #225
Winter Garden, FL 34787
Palisades Subdivision
$198,000
Land For Sale
Active
0.83
ACRES
ORANGE, FL
COUNTY
1404 Avalon Road
Winter Garden, FL 34787
Acreage Subdivision
$199,000
Condo For Sale
Active
3
BEDS
2
TOTAL BATHS
1,288
SQFT
14200 Avalon Road #224
Winter Garden, FL 34787
Palisades Subdivision
$199,000
Condo For Sale
Active
3
BEDS
2
TOTAL BATHS
1,288
SQFT
14200 Avalon Road #227
Winter Garden, FL 34787
Palisades Condo Subdivision
$225,000
Land For Sale
Active
0.21
ACRES
ORANGE, FL
COUNTY
809 Burch Avenue
Winter Garden, FL 34787
Burchshire Subdivision
$235,000
Land For Sale
Active
0.5
ACRES
ORANGE, FL
COUNTY
1288 N West Crown Point Road
Winter Garden, FL 34787
Crown Point Town Subdivision
New Listing - 8 hours online
$249,900
Single Family Home For Sale
Active
2
BEDS
1
TOTAL BATH
768
SQFT
213 4th Street
Winter Garden, FL 34787
Twin City Dev Co Sub Subdivision
$255,000
Land For Sale
Active
0.46
ACRES
ORANGE, FL
COUNTY
14718 Micah Street
Winter Garden, FL 34787
Acreage Subdivision
Price Change - 2 weeks ago
$289,999
Single Family Home For Sale
Active
4
BEDS
2
TOTAL BATHS
1,104
SQFT
1025 Maxey Drive
Winter Garden, FL 34787
Bay St Park Subdivision
Price Change - 4 weeks ago
$299,990
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,265
SQFT
14501 Grove Resort Avenue #3503
Winter Garden, FL 34787
Grove Residence & Spa Hotel Condo 3 Subdivision
$300,000
Land For Sale
Active
4
ACRES
ORANGE, FL
COUNTY
Windermere Road
Winter Garden, FL 34787
 
$315,000
Multi-Family For Sale
Active
1,316
SQFT
102 W Story Road
Winter Garden, FL 34787
Overstreet Crate Subdivision

Pete Werner

I'm an Orlando local and owner of The DIS (wdwinfo.com), DVCfan.com, DCLfan.com, and host of the DIS Unplugged podcast.

2 thoughts on “Winter Garden

  • I do not see anyone wearing masks anywhere. Is this an older video, like BEFORE this corolla toyota virus crap started??

    Reply

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