Neighborhood · Ocoee, Florida
The Trails Of Winter Garden
Quiet West Orange living near everything Orlando
The Trails of Winter Garden sits on the west side of Ocoee, close enough to downtown Orlando (about 23 minutes) and Universal (roughly 24 minutes) to make a daily commute painless, while keeping the low-key, residential feel that draws families to this corner of Orange County. It's a pocket surrounded by established communities like Wesmere, Westyn Bay, and Windsor Landing, with kids zoned to Ocoee High, Lakeview Middle, and William S Maxey Elementary.
The market reality here is simple: inventory is tight. There are currently no active listings in the neighborhood, and only 4 homes changed hands over the last 12 months at a median sold price of $485,000. When homes do come up they move fast and sellers are getting about 101% of asking on average, so a prepared buyer with financing lined up has the real advantage. Browse nearby Ocoee homes for sale while you wait for the right listing to surface.
The Trails Of Winter Garden is a community in Ocoee, Florida.
Quick facts
4 sold in 12 months
Drive times
On the market now
Homes for sale in The Trails Of Winter Garden
Nothing active right now.
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Every active listing inside the The Trails Of Winter Garden boundary
Open full map search →The numbers that matter
The The Trails Of Winter Garden market
4
Sold, last 12 months
$485,000
Median sold price
101%
Sale-to-list ratio
What sellers actually get vs asking
29 days
Median time to sell
The Trails Of Winter Garden vs Ocoee
Live Stellar MLS data — every listing and closed sale inside the The Trails Of Winter Garden boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools The Trails Of Winter Garden is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
807
Median age
33
Median income
$84,943
Median home value
$412,200
Beyond the listings
Living in The Trails Of Winter Garden
Hobbies & Interests
Top 1% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Hobbies & Interests
Top 8% in the U.S.Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
Active
Top 8% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Active
Top 11% in the U.S.Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
Culture
Top 11% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Entertainment
Top 16% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Straight answers
The Trails Of Winter Garden FAQs
Is The Trails of Winter Garden a good place to live?+
It's a quiet, residential pocket on the west side of Ocoee with easy access to the wider Orlando metro — downtown is about 23 minutes and Universal roughly 24. Families are drawn to the settled feel and the Ocoee school assignments: Ocoee High, Lakeview Middle, and William S Maxey Elementary.
Is it expensive to buy here?+
Homes here recently sold at a median of $485,000, which places the neighborhood in the mid-$400s range typical of family-oriented West Orange communities. It's not entry-level, but it's a reasonable step below the luxury end of the market.
What do homes cost in The Trails of Winter Garden?+
Over the last 12 months, 4 homes sold at a median price of $485,000. There are no active listings right now, so pricing on the next home to hit the market will hinge on its size, condition, and how quickly it draws offers.
How is the market right now?+
It's tight and competitive. With zero active listings and just 4 sales in the past year, supply is thin — and sellers averaged about 101% of asking, meaning buyers should expect to move quickly and come in strong. Keeping an eye on nearby Silver Glen and other Ocoee communities widens your options while you wait.
What should I know about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available for the neighborhood at the moment, which is common when inventory is this limited. Once a home is listed, your agent can pull the exact HOA dues and tax history for that address so there are no surprises.
Keep exploring
More Ocoee neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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