West Orange Trail Living

Living near the West Orange Trail means having 22 miles of paved trail connecting Oakland, Winter Garden, Ocoee, and Apopka. For buyers comparing homes near the West Orange Trail, this guide organizes nearby communities in one place and makes it easier to see where trail access fits into everyday life.

West Orange Trail Information

Communities along the West Orange Trail

Looking for a curated list of communities located on the West Orange Trail? Explore these neighborhoods for the closest access to the trail.

Highlighted West Orange Trail Communities

Oakland Park Community

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 Community

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 Community

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

Sort by:
New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530

What Is the West Orange Trail?

West Orange Trail Bridge over Florida Turnpike in Oakland, FloridaThe 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.