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Entry
$450K - $600K
Townhomes and smaller homes in Oakland Park and surrounding areas. Some older resale homes closer to the historic core.
Oakland
A hidden gem nestled among the oaks on the West Orange Trail
NatureHistoricTrail AccessSmall Town
$500K - $1M+
Price Range
25-35 minutes
Downtown
35-45 minutes
Airport
20-25 minutes
Disney
“Oakland is the kind of place people stumble onto and then never want to leave.”
The Lifestyle
You bike the West Orange Trail to Winter Garden for coffee, hike the boardwalk at the Nature Preserve before work, and wave to your neighbors from your front porch. The town has managed to maintain its small-town feel despite the growth exploding around it. There are no major commercial strips – your daily life connects to Winter Garden's downtown for dining and shopping. It's quiet, green, and genuinely charming.
The Highlights
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Oakland Nature Preserve – 150 acres with 13+ miles of free trails
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Direct access to the 22-mile West Orange Trail
- 03
Oakland Park master-planned community by Crescent Communities
- 04
Small-town character with Winter Garden's amenities minutes away
Best For
- Nature lovers who want trail access and preserve hiking as part of daily life
- Families who want a tight-knit small-town community
- Buyers who want to be near Winter Garden's downtown without paying Winter Garden's highest prices
- Cyclists and runners who will use the West Orange Trail regularly
Not Ideal For
- Buyers who want dining, retail, and entertainment within their own town
- Those who need a large selection of housing inventory – Oakland is small
- Buyers who need quick access to I-4 or the attractions corridor
Price Points
$500K - $1M+
What it costs to live in Oakland, from entry-level to premium.
02
Mid-Range
$600K - $850K
Single-family homes in Oakland Park and Oakland Trails. Front-porch architecture with community amenities, trail access, and lake proximity.
03
Premium
$850K - $1M+
Larger custom homes in Oakland Park, lakefront properties, and premium lots. Some waterfront homes on Lake Apopka or Johns Lake.
New Construction
Building new in Oakland
Oakland's new construction centers on the Oakland Park master-planned community developed by Crescent Communities, with homes by Ashton Woods and David Weekley Homes. The community features front-porch architecture, Live Oak-lined streets, and direct access to the West Orange Trail. Outside of Oakland Park, inventory is limited to individual lot builds.
Builders
Ashton WoodsDavid Weekley HomesElement Home BuildersPioneer BuildersCastleworks Custom BuildersJ & J BuildingRockwell HomesD.R. Horton
Active Communities
- Oakland Park
- Briley Farm
Schools
Education in Oakland
Oakland Avenue Charter School
(Niche B+, GreatSchools 10/10, K-5)
West Orange High School
(serves area, Niche rated)
Bridgewater Middle School
(Winter Garden, serves Oakland students)
Foundation Academy
(private, PreK-12, nearby in Winter Garden)
Dining
Where to eat
Winter Garden's Plant Street
dining, breweries, and cafes, 5 minutes away
Local Tips
Nicole's Oakland notes
Nicole Mickle
30 years in Orlando
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The Oakland Nature Preserve is free and open 365 days a year – the boardwalk to Lake Apopka is the highlight
02
Oakland Park's community design emphasizes front porches and Live Oak-lined streets – it's one of the most architecturally intentional communities in the corridor
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The West Orange Trail is the spine of outdoor life here – it connects you all the way to Apopka in one direction and downtown Winter Garden in the other
04
Oakland is technically in Orange County while its neighbors Clermont and Minneola are in Lake County – school districts and taxes differ accordingly
Interested in Oakland?
I can tell you what it's really like to live here, what the market looks like right now, and whether it's the right fit for your lifestyle.