Neighborhood · Ocoee, Florida
The Trails Of Winter Garden
Established West Orange living close to everything
The Trails Of Winter Garden sits in Ocoee, in the fast-growing West Orange corridor where mature neighborhoods meet easy access to the region's biggest job and entertainment hubs. It's the kind of established, family-oriented pocket that draws people who want space and quiet without giving up a short commute, and it neighbors well-known communities like Wesmere, Westyn Bay and Silver Bend. Downtown Orlando is about 23 minutes out, Universal roughly 24, and Walt Disney World around 35 — close enough to make the theme-park-adjacent lifestyle genuinely practical.
For buyers, this is a tight, low-turnover market: just four homes sold here over the last 12 months, at a median sold price of $485,000. That scarcity shows up in the numbers — sellers have been getting about 101% of asking on average — so when something does list, it tends to move. Keeping an eye on nearby Ocoee homes for sale and neighboring pockets like Towns Of Westyn Bay is a smart way to widen your options while you wait for the right fit.
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.
People who close here
Our Ocoee experts
Straight answers
The Trails Of Winter Garden FAQs
Is The Trails Of Winter Garden a good place to live?+
It's an established West Orange neighborhood with quick access to Orlando's job centers and attractions — about 23 minutes to downtown and 31 to the airport. Assigned schools are William S Maxey Elementary, Lakeview Middle and Ocoee High. It sits near several recognizable communities, so buyers who like this area often also look at nearby Ocoee homes for sale.
Is it expensive to buy here?+
Recent sales point to a median sold price of $485,000 over the last 12 months. That puts it in solid middle-of-the-market territory for West Orange County, and demand has kept pricing firm.
What do homes cost in The Trails Of Winter Garden?+
With only four sales in the past year, the median sold price landed at $485,000. There are currently no active listings, so buyers may need patience or should watch adjacent communities like Silver Bend for comparable options.
How is the market right now?+
It's a low-inventory, seller-favored market — just four homes traded hands over the last 12 months, and sellers averaged about 101% of asking. When a home does hit the market here, expect it to draw quick interest, so it helps to be pre-approved and ready to act.
What about HOA fees and property taxes?+
Specific HOA and tax figures for this neighborhood aren't currently available in the MLS data, which is common for pockets with very few recent sales. Because The Trails Of Winter Garden neighbors HOA communities like Westyn Bay, it's worth confirming exact dues and tax amounts on any individual property before you write an offer.
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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