Oakland Trail Communities | Homes Along the West Orange Trail

Oakland Real Estate On the West Orange Trail

The town of Oakland is one of Central Florida's best-kept secrets and one of the most charming entry points to the West Orange Trail. Small in size but rich in character, Oakland's historic downtown and Lake Apopka waterfront views make it a distinctive place to live. Communities along the West Orange Trail in Oakland include a mix of newer construction and established neighborhoods, offering options for a variety of lifestyles. Downtown Oakland hosts a weekly farmers market and is home to the Oakland Arts & Heritage Center, known for local events, including Yoga on the Porch. Nearby Oakland Nature Preserve and Lake Apopka give residents even more opportunities to get outside and explore.

West Orange Trail Information

Featured Oakland Trail Communities

Oakland Trails

Oakland Trails is located on the border of Oakland and Winter Garden, right along the West Orange Trail. This single-family community features a pool and playground.

Visit Oakland Trails

Longleaf at Oakland

Longleaf at Oakland has direct access West Orange Trail and is located across from the Oakland Nature Preserve. This neighborhood has a pool with cabana and tot lot.

Visit Longleaf at Oakland

Briley Farm

Briley Farm, located on the shores of Lake Apopka, is adjacent to the West Orange Trail and features custom-built homes with a community pool and sports courts.

Visit Briley Farm

Available Oakland Homes near The West Orange Trail

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$3,295,000

312 Briley Avenue, OAKLAND

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

$2,615,320

1152 Prado Lane, OAKLAND

6 Beds 7 Baths 4,658 SqFt Residential MLS® # O6413825

$2,595,000

1134 Prado Lane, OAKLAND

5 Beds 8 Baths 4,433 SqFt Residential MLS® # O6413035

$2,575,000

1155 Prado Lane, OAKLAND

5 Beds 7 Baths 4,210 SqFt Residential MLS® # O6415007

$2,380,160

↑ $142,040

1173 Prado Lane, OAKLAND

5 Beds 6 Baths 4,204 SqFt Residential MLS® # O6359359

$2,310,600

↑ $179,840

1146 Prado Lane, OAKLAND

5 Beds 6 Baths 3,992 SqFt Residential MLS® # O6359354

$2,199,000

↓ $51,000

811 Civitas Way, WINTER GARDEN

4 Beds 5 Baths 5,138 SqFt Residential MLS® # O6403760

$2,098,000

↑ $100,000

1258 Ridge Lake Way, OAKLAND

4 Beds 4 Baths 4,557 SqFt Residential MLS® # O6373776

$1,975,000

1106 Sarah Mathews Drive, OAKLAND

5 Beds 6 Baths 3,596 SqFt Residential MLS® # O6375487

$1,765,000

906 Allendale Lane, WINTER GARDEN

5 Beds 4 Baths 3,784 SqFt Residential MLS® # G5107489

$1,699,000

↓ $50,000

1144 Hull Island Drive, WINTER GARDEN

5 Beds 5 Baths 4,102 SqFt Residential MLS® # O6418306

$1,649,999

↓ $25,000

1101 Eagles Pass Way, WINTER GARDEN

6 Beds 5 Baths 4,104 SqFt Residential MLS® # O6408835

$1,500,000

2010 Boss Hewett Street, WINTER GARDEN

5 Beds 4 Baths 3,781 SqFt Residential MLS® # O6423216

$1,195,000

↓ $30,000

844 Oakland Park Boulevard, WINTER GARDEN

5 Beds 4 Baths 3,525 SqFt Residential MLS® # O6419976

$1,125,000

↓ $40,000

925 Easley Avenue, WINTER GARDEN

4 Beds 4 Baths 2,667 SqFt Residential MLS® # O6412977

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Oakland: The Quieter Side of the West Orange Trail

If Winter Garden is the energetic heart of the West Orange Trail, Oakland is its quieter, more natural neighbor.

Located just west of downtown Winter Garden, Oakland offers a different kind of trail lifestyle. The pace slows down, the tree canopy gets heavier, and the trail begins to feel even more connected to nature. For buyers who want access to the West Orange Trail without being directly in the middle of downtown activity, Oakland can be one of the most appealing options along the corridor.

The West Orange Trail runs directly through Oakland, connecting residents to downtown Winter Garden in one direction and Killarney Station in the other. That means weekends can include a bike ride into Plant Street for coffee, lunch, or the farmers market, then a quieter ride back through one of the most scenic portions of the trail.

A Local's Guide To The West Orange Trail

A local look at what to see, where to stop, and how to enjoy the West Orange Trail through Winter Garden and beyond.

Explore the West Orange Trail

What Surrounds the Trail in Oakland

Oakland Nature Preserve | One of Oakland’s biggest trail-area anchors is Oakland Nature Preserve, a 150-acre preserve located off W. Oakland Avenue at Machete Trail on the westside of town. The preserve is knonw for their boardwalks, nature trails, wildlife viewing, and access to the Lake Apopka shoreline. Be sure to explore their many events like their Yoga on the Lake and Firefly Self-Guided Hikes in the Spring.

Historic Downtown Oakland | Oakland has maintained its small-town character, with historic homes, civic buildings, local gathering spaces, and a quieter village feel. It is close to downtown Winter Garden, but the atmosphere is noticeably different.

Arts & Heritage Center of Oakland | Located directly in downtown Oakland at 126 W. Petris Avenue, the Arts and Heritage Center is home to the West Orange Trail's Oakland Outpost. This stop on the trail features restrooms, picnic area, parking, benches, and air station. Home of local events, including weekly Yoga on the Porch and bi-weekly farmers market, the center is a destination itself.

Killarney Station | Heading west, the trail continues toward Killarney Station, a key West Orange Trail access point near the Lake County line. This gives Oakland residents access to longer rides and a more recreational trail experience as the West Orange Trail ends and the South Lake Trail begins, heading into Clermont, FL.

For even more hidden gems and must-see stops along the West Orange Trail, check out the full blog post linked above.