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About Oakland, Florida

Oakland, Florida: A Hidden Gem in Central Florida

Discover small-town charm, lakeside living, and easy Orlando access.

A Charming Town with Deep Roots

Founded in the late 1800s, Oakland, FL preserves its historic character—brick streets, heritage trees, and a close-knit feel—while embracing thoughtful growth. You’ll find a quiet, residential vibe minutes from Winter Garden and the best of Central Florida.

A Nature Lover’s Paradise

Oakland is built for the outdoors. Walk, bike, or jog the 22-mile West Orange Trail. Explore the Oakland Nature Preserve—boardwalks through native habitat leading to Lake Apopka—for birding, kayaking views, and family-friendly programs.

Real Estate Snapshot

Demand is steady and inventory is tight, with options ranging from historic cottages to new construction in master-planned communities. Popular spots include Oakland Trails and Hull Island, plus coveted lakefront and waterfront homes. Proximity to Winter Garden and Orlando keeps property values rising, appealing to both buyers and investors.

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Broker, Founder & CEO of Dream Finders

Angela Rodriguez
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Looking for a Central Florida REALTOR®?

List or buy with Angela Rodriguez for precise pricing, powerful exposure, and expert negotiation.

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A Community That Cares

Oakland’s calendar features farmer’s markets, holiday events, and neighborhood gatherings that build lasting connections. Families appreciate access to Orange County Public Schools (OCPS) and a strong community focus on safety, parks, and local stewardship.Dining & Shopping at Your Fingertips Welcome to Orlando’s famous Restaurant Row along Sand Lake Road—international cuisine, fine dining, and casual favorites just minutes from home. Nearby shopping centers, boutiques, and specialty markets make daily errands easy, while premium retail and entertainment are a short drive away.

Easy Access to Orlando and Beyond

Minutes to SR-429, the Florida Turnpike, and SR-50 means quick trips to downtown Orlando, Walt Disney World, and job centers. Enjoy suburban tranquility without sacrificing big-city convenience.

Why Choose Oakland?

  • Historic charm with modern amenities

  • West Orange Trail + Oakland Nature Preserve at your doorstep

  • Mix of established neighborhoods, gated enclaves, and new builds

  • Strong long-term value thanks to location and demand

Ready to explore homes in Oakland?

Get curated listings, private showings, and strategy that wins in competitive neighborhoods like Oakland Trails and Hull Island.

Angela Rodriguez | Dream Finders Realty Group
Top Oakland Realtor for buying, selling, and investing.
Call/Text: +1 (407) 873-8379 • dfrealty.net