Winter Garden · Near West Orange Trail · 34787
Oakland Park — Winter Garden's Best-Kept Secret
A beloved, shady community just south of Downtown Winter Garden. Walking distance to Oakland Avenue Charter School and the West Orange Trail. 28 sub-communities, $129K to $2.9M in range — something for every stage of life.
Real numbers from Stellar MLS — not estimates. Based on closed sales data from your MLS report.
Oakland Park is one of Winter Garden's most consistent luxury markets — with 7+ closed sales in 60 days and prices ranging from $845K to $1.7M. Buyers are drawn to the mature landscaping, trail access, and proximity to Downtown Winter Garden.
Everything that makes this community one of Winter Garden's most sought-after addresses.
The 22-mile West Orange Trail runs right alongside Oakland Park — ideal for cyclists, joggers, and families enjoying Florida's outdoor lifestyle.
A highly regarded charter school is within walking distance — one of the most significant advantages for families with school-age children.
Unlike newer developments, Oakland Park features established, shaded streets with mature oak trees — a rare and sought-after feature in Central Florida.
Multiple sections offer community pools, tennis courts, and recreation facilities within the 28 distinct sub-communities.
Minutes from Plant Street's restaurants, boutiques, Axum Coffee, the Farmers Market, and the Garden Theatre.
Several sub-communities within Oakland Park offer private, gated access for added security and exclusivity.
Oakland Park offers a range of home types and price points to fit different lifestyles and budgets.
Zoned for some of Orange County's highest-rated public schools, with private options nearby.
Pre-K–Grade 8. One of the most sought-after charter schools in Orange County, located right within the community.
Highly rated OCPS elementary within minutes of Oakland Park.
Grades 6–8 serving the Oakland Park community.
Home of the Warriors — strong academics, athletics, and arts programs.
Convenient access to everything Winter Garden and greater Orlando has to offer.
Oakland Park residents enjoy one of the most strategically located addresses in the Winter Garden area — close to major employment corridors, top-rated schools, world-class entertainment, and everyday conveniences.
Search Oakland Park Homes →Patricia Hernandez is a licensed Florida REALTOR® with Century 21 BE3. She is ready to assist you with any home in Oakland Park or anywhere in the Winter Garden area — from your first inquiry to closing.