Neighborhood · Oakland, Florida
Trailside Station
Small-town Oakland living just off the West Orange Trail
1
Homes for sale
$525,000
Median list price
$259
Avg price / sqft
3
Median days on market
Trailside Station sits in Oakland, one of Orange County's quieter historic towns on the edge of Winter Garden, where the West Orange Trail and old oak canopies set the pace. It's an easy fit for buyers who want a neighborhood scale of life with real proximity to the metro — nearby communities like Johns Landing, Johns Cove, and Oak Park Of Winter Garden share the same relaxed character. Families here are zoned for West Orange High, and the commute lands you in Downtown Orlando in about 24 minutes.
The market here is tight and small — a common story in a neighborhood this size. There's currently a single active listing at $525,000, and over the last 12 months just two homes sold, at a median of $492,000. When homes do trade, sellers are getting roughly 99% of asking, so pricing has stayed disciplined; browse Oakland homes for sale or watch the live map to catch new inventory early.
Trailside Station is a community in Oakland, Florida.
Quick facts
$525,000 – $525K price range
2,028 sqft median home
$29/mo median HOA
2 sold in 12 months
Drive times
On the market now
Homes for sale in Trailside Station
Every active listing inside the Trailside Station boundary
Open full map search →The numbers that matter
The Trailside Station market
2
Sold, last 12 months
$492,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
64 days
Median time to sell
Trailside Station vs Oakland
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 1.2% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Trailside Station boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Trailside Station is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Trailside Station home
≈ $3,200/mo
$525,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$29/mo
Median HOA
From current listings inside the boundary
Population
273
Median age
38
Median income
$92,361
Median home value
$396,400
Beyond the listings
Living in Trailside Station
Hobbies & Interests
Top 2% in the U.S.Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
Hobbies & Interests
Top 2% 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.
Beliefs
Top 6% in the U.S.Conservation
Good stewards of the earth, this population advocates for a cleaner environment and responsible use of resources. They often encourage others to recycle and use clean energy.
Hobbies & Interests
Top 7% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Beliefs
Top 8% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Active
Top 9% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
Straight answers
Trailside Station FAQs
Is Trailside Station a good place to live?+
It suits buyers who want small-town Oakland calm with metro reach — Downtown Orlando is about 24 minutes and Universal roughly 26. Families are drawn to the West Orange High zoning and the walkable feel around the West Orange Trail. It's a quiet, established pocket rather than a busy new-build corridor.
Is it expensive to buy here?+
Prices sit in the mid-$500s at list, with the current active listing at $525,000 and an average of about $259 per square foot. That lands it in a comfortable mid-market range for the West Orange area — not entry-level, but well below the county's luxury tier.
What do homes cost in Trailside Station?+
The one active home is listed at $525,000 for around 2,028 square feet, and homes that sold over the past year came in at a median of $492,000. Inventory is thin, so pricing tracks closely to recent sales rather than a wide spread. Nearby Oakland Pointe can give you a sense of comparable options.
How is the market right now?+
It's a very low-volume market — one active listing today and just two homes sold in the last 12 months. Sellers averaged about 99% of asking price and the median days on market was effectively 0, so well-priced homes move fast. Setting up alerts on the live map is the smartest way to catch a listing here.
What about HOA fees and property taxes?+
HOA dues are modest at around $29 a month, and the median property tax runs about $2,334 a year. Those low carrying costs help keep the total monthly picture reasonable relative to the home price.
Keep exploring
More Oakland 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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