Homes on the West Orange Trail: 7 Winter Garden Neighborhoods to Know

Posted by Jeffrey G. Funk P.A. on Friday, August 15th, 2025  3:05pm.

Why the West Orange Trail is a Winter Garden Favorite

West Orange Trail in Downtown Winter Garden Widely known both locally and by visitors as a top recreation trail, the West Orange Trail is a haven for bikers and pedestrians, skaters, and even horseback riders. If you've been seeking to live closer to the trail, there are some great communities that are directly on or adjacent, perfect to hop on and hop off any time. A central hub for the West Orange Trail is Winter Garden. Running directly through the historic downtown, the draw for residents to access the weekly farmers market, local restaurants, and shops is highly sought after. Small town charm meets active lifestyle at its best.

Winter Garden Communities Along the West Orange Trail

The Funk Collection has compiled seven communities that are located along the West Orange Trail. For the ultimate trail fan, these communities are a top choice for those seeking Winter Garden real estate. Starting from west to east in downtown Winter Garden to the border of Ocoee, let's explore these communities.

  1. Park Place Townhomes, located in the heart of Winter Garden, these luxury townhomes offer the ultimate in downtown living directly on the West Orange trail.
  2. 30 North Park, positioned across Plant Street from Park Place Townhomes, 30 North Park also offers luxury townhomes with direct access and views of the trail, including a rooftop oasis.
  3. Heading east and north of downtown Winter Garden, Oakglen Estates, a cozy community of just over 60 single-family homes, is surrounded by trails, including the West Orange Trail and the Lulu Creek Trail, leading to Newton Park and Lake Apopka.
  4. Neighbors to Oakglen Estates, Covington Chase is a sprawling community of over 300 homes with direct access to the West Orange Trail. The community also offers residents a community pool and playground.
  5. Located a bit further north on the trail, Chapin Station is home to just under 130 homes and is ideally located across from Chapin Station, the main park office for the West Orange Trail. Playgrounds, tennis, and basketball courts are located on-site in addition to the trail.
  6. Crown Point Springs, a 275-home community, is located across from Chapin Station and accesses the trail via E. Fullers Road.
  7. Rounding out these 7 West Orange Trail communities is Fullers Crossing, a 206-home community located directly across from Crown Point Spring, also accessing the trail via E. Fullers Cross Road.

Must-Know FAQs About the West Orange Trail

How long is the West Orange Trail?

The West Orange Trail spans 22.32 miles that spans from Oakland, Winter Garden, Ocoee, and Apopka

What activities are permitted on the West Orange Trail?

As a multi-use trail, bicycles, mobility devices, pedestrians, skates, skateboards, horse, electronic bikes (some restrictions apply)

Are there facilities along The West Orange Trail?

There are multiple outposts/stations along the way including Killarney Station, Winter Garden Station, Chapin Station, Clarcona Outpost, Apopka-Vineland Outpost, Tildenville Outpost, McCormick Outpost, Ingram Outpost, and Apopka Station each offering amenities varying from picnic tables, parking, restrooms, and more.

When can you access The West Orange Trail?

The trail is open from Sunrise to Sunset.

Are pets permitted on The West Orange Trail?

Leashed Pets are permitted on the West Orange Traill

Tips for Buying along the West Orange Trail

Letting your Realtor know that being close to a trail system early is key. The Funk Collection team's local area experts who have experience connecting buyers with the best community and home that will maximize their time on the trail. Using a resource like RealtyInOrlando.com, where you can view all of the local Winter Garden communities in depth, will give you a great idea of the neighborhood details that will meet your family's needs. A top tip is to get out and explore by bike! There's no better way to discover the vibe of a community than by visiting.

Ready to explore Winter Garden's Trail-side Living?

If you're ready to start visiting homes along the trail, connect with the team to start a conversation. You'll be ready to hit the trail in no time! Call the team at 407-930-9829.