West Orange Trail Communities

Living on the West Orange Trail

The West Orange Trail passes through four Orlando area communities: Oakland, Winter Garden, Ocoee, and Apopka. The 22-mile paved trail connects each one, and the neighborhoods along it range from smaller, more intimate neighborhoods to move active, sprawling communities. For buyers who want trail access as a feature of daily life as well as a weekend detour, this resource was built specifically for that search. It's one of the only places online where homes near the West Orange Trail are organized by community, so finding the right fit is actually as specific as the lifestyle itself.

West Orange Trail Information

Highlighted West Orange Trail Communities

Oakland Park

Oakland Park is located between Oakland and Winter Garden and has direct access to the West Orange Trail. Community amenities include a pool, fitness center, lakeside trails, and playground.

Visit Oakland Park

Covington Chase

Covington Chase, a single-family home community, located just north of downtown Winter Garden has the West Orange Trail running directly through the community, given direct access to hop on and hop off.

Visit Covington Chase

Heritage at Plant Street

Heritage at Plant Street is a Winter Garden community along the West Orange Trail, offering convenient access to downtown Winter Garden for nearby shopping, dining, and recreation via the trail.

Visit Heritage at Plant Street

Homes for Sale Along the West Orange Trail

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New

$709,000

1083 Dusty Pine Drive, APOPKA

5 Beds 3 Baths 3,384 SqFt Residential MLS® # O6429753

New

$469,900

1463 Sourwood Drive, OCOEE

3 Beds 2 Baths 1,849 SqFt Residential MLS® # O6431550

New

$468,000

665 Stevelynn Circle, WINTER GARDEN

3 Beds 2 Baths 1,540 SqFt Residential MLS® # O6430182

New

$775,995

644 Autumn Oaks Loop, WINTER GARDEN

5 Beds 3 Baths 3,102 SqFt Residential MLS® # O6429028

New

$985,000

1234 Canyon Creek Trail, WINTER GARDEN

4 Beds 4 Baths 2,681 SqFt Residential MLS® # O6427609

New

$620,000

918 Blackthorn Drive, APOPKA

4 Beds 4 Baths 3,039 SqFt Residential MLS® # O6430516

New

$425,000

1188 Foxforrest Circle, APOPKA

4 Beds 3 Baths 2,810 SqFt Residential MLS® # O6430467

New

$585,000

1452 Sourwood Drive, OCOEE

4 Beds 3 Baths 2,642 SqFt Residential MLS® # O6430336

New

$499,990

3057 Timber Hawk Circle, OCOEE

5 Beds 3 Baths 2,447 SqFt Residential MLS® # S5154856

New

$519,900

3432 Islewood Court, OCOEE

4 Beds 2 Baths 1,828 SqFt Residential MLS® # A4701539

New

$365,000

97 Abbey Hollow Drive, APOPKA

4 Beds 2 Baths 1,528 SqFt Residential MLS® # O6429689

$409,900

1268 Foxforrest Circle, APOPKA

5 Beds 4 Baths 3,876 SqFt Residential MLS® # O6421768

$349,999

6 E Thrush Street, APOPKA

3 Beds 2 Baths 1,130 SqFt Residential MLS® # O6429542

$3,295,000

312 Briley Avenue, OAKLAND

6 Beds 7 Baths 5,144 SqFt Residential MLS® # O6429415

$524,900

1889 Pomegranate Court, OCOEE

5 Beds 4 Baths 3,856 SqFt Residential MLS® # O6427129

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What Is the West Orange Trail?

The West Orange Trail is one of Florida's most celebrated rail trails and a defining feature of life in West Orange County. Spanning 22 miles from Killarney Station in Oakland to Lester Road in Apopka, this fully paved, 14-foot-wide multi-use trail runs through the heart of some of Central Florida's most desirable communities, including Oakland, Winter Garden, Ocoee, and Apopka.

Built on the former alignment of the Orange Belt Railway, the trail follows the same corridors that once connected these small farming towns in the late 1800s. Today, it serves hundreds of thousands of cyclists, joggers, walkers, inline skaters, and families each year. It is managed by Orange County Parks and Recreation and is open daily from sunrise to sunset. Dogs on leashes are welcome, and bike rentals are available at Killarney Station and the Winter Garden Station.

The trail is not just a recreational amenity. For buyers focused on lifestyle, walkability, and long-term community investment, proximity to the West Orange Trail is one of the most consistent factors driving real estate desirability in this corridor.

Explore living local on the West Orange Trail, including some of the trail stops highlighted along the trail from Oakland, Winter Garden, Ocoee, and Apopka.

Why Trail Access Matters for Buyers

Real estate research consistently shows that proximity to trails and greenways increases property values and speeds resale timelines. For buyers in West Orange County, the trail functions as permanent open space that will never be developed, a lifestyle amenity that attracts long-term residents, and a community connector that makes the surrounding towns feel integrated rather than isolated.

The addition of the Florida Coast-to-Coast Connector context adds another layer. As the C2C nears completion and gains national recognition as a destination trail, the communities anchoring its central Orange County segment, Winter Garden, Oakland, Ocoee, and Apopka, stand to benefit from the trail tourism, property value appreciation, and civic investment that follow a world-class trail system. For buyers who want trail access now with infrastructure upside ahead, the West Orange Trail corridor is one of the most compelling lifestyle real estate stories in the Orlando metro market.