Oakland
Historic Heart, Modern Soul
Oakland is one of those places that people drive through on the way to Winter Garden and suddenly think — wait, what is this? It's a small, historic town tucked along the shores of Lake Apopka and the West Orange Trail, and it has a character that's entirely its own.
The town was incorporated in 1887 and has managed to hold onto its historic identity even as the surrounding area has grown dramatically. The homes here range from lovingly restored historic cottages to newer builds that respect the town's architectural heritage. It's a place where people genuinely care about where they live.
The West Orange Trail runs right through town, connecting Oakland to Winter Garden and beyond — making it a favorite for cyclists, walkers, and anyone who wants to live an active lifestyle without getting in a car. And with Winter Garden's Plant Street just minutes away, you're never far from great food and community events.
Life in Oakland
West Orange Trail Access
The trail runs directly through Oakland, offering miles of paved path for cycling, walking, and jogging — connecting you to Winter Garden, Clermont, and beyond.
Historic Downtown District
A small but charming historic district with original architecture, a community park, and a genuine sense of place that newer communities simply can't replicate.
Lake Apopka Frontage
Florida's fourth-largest lake borders the town, offering natural beauty, wildlife, and a connection to the outdoors that's rare this close to the metro area.
Tight-Knit Community
Oakland is small enough that neighbors know each other. Community events, local pride, and a genuine small-town atmosphere define life here.
Minutes from Winter Garden
Plant Street's restaurants, farmers market, and events are just a short drive or bike ride away — giving you the best of both worlds.
Architectural Character
From historic bungalows to craftsman-style newer builds, Oakland's homes have a character and quality that stands apart from standard Florida subdivisions.
"Oakland doesn't have a lot of inventory — which means when something comes up here, you need to move fast. If this community is on your radar, let me know now so we're ready when the right home appears."
— Karen Tefft, Karen & Co Realty
Interested in Oakland?
Homes here are rare and go quickly. Let's connect so you're first in line when the right one comes up.