SCOPE | HISTORY AMONGST THE TREES
If you think Winter Garden sounds charming, try Oakland on for size. A brief and beautiful bridge between the borders of Downtown Winter Garden and the rolling (subtle, Florida-style) hills of Clermont, this town provides a picturesque drive through oak-lined streets along with plantation-style homes. Once a thriving center of commerce for the citrus plantations and vegetable farms of old Central Florida, this now mellow, family-friendly community remains one of the oldest municipalities in Orange County.
FEEL | GREEN
A day in the life could look like. . .
Take the dog for a walk on the West Orange Trail. Drink a cup of coffee on the front porch swing. Spend the afternoon set up in your home-office (windows open, of course). Wrap things up in the early evening with plenty of time to help with the day’s homework assignments • race to beat the sun during a golden hour bike ride to downtown Winter Garden.
ARCHITECTURE | OLD-FLORIDA STYLE (WITH SOME MODERN REIMAGINING)
With mid-range to multi-acre lots, the homes of Oakland are a mix of colonial, two-story Florida farmhouses, single-story bungalows, and contemporary blends of the two. Their interiors vary as many were built in the last quarter-century, but were designed with homages to the past. While the bungalows tend to be long and narrow with mid-mod tile and wood floors, cozy kitchens, and windows with the original glass; the larger homes have open floor plans, deep front porches and high ceilings in a more Magnolia Market vein.
MARKET | TBD
WHAT TO EXPECT | A HIDEAWAY
It’s fairly easy to step over into the more urban downtown Winter Garden or
even cross to the east side of Orlando via the interstate. Yet, the more natural landscape of moss-covered trees, dirt roads, and spacious yards will inspire you to slow down and breathe a little deeper—even if you’re just driving through. In fact, we suggest taking advantage of that if you live in the borderlands of Winter Garden or Clermont.
WHAT MAKES IT UNIQUE | THE LIGHT
A certified Tree City, Oakland locals live under a cultivated canopy of green that backs up to the south shore of Lake Apopka. This filter of foliage, mixed with the water’s reflection of Florida sunshine, creates photo-worthy lighting year-round.
PRACTICALLY SPEAKING | CLAY ROADS, SPEED LIMITS & STORM HAZARDS
Clay Roads
While not all, several of the neighborhoods near the town center are intentionally
rustic and ready to threaten the underside of your white car.
Speed Limits
Residential roads and a charter school in the center of town make for slower speed
limits.
Storm Hazards
The delicate balance between power lines and tree limbs can cause some extra
power outages during storm season.
NEIGHBORHOOD LANDMARKS | HISTORY PRESERVED
Town Hall
Built in 1911 in the Colonial Revival Style
Friday Night Jazz
Every 4th Friday of the month at the Oakland Town Center
Arguably, the most beautiful section of the 22 mile-long, multi-use trail
Side Note: This trail was built on top of the old railroad that ran through town
EATS | DONUTS & DRIVES
Breakfast & Coffee
Bites, Beverages & The Finer Side
Plant Street in Downtown Winter Garden
8 min drive
15 min ride
30 - 45 min walk
11 min drive
Downtown Clermont
17 min drive
SHOPPING | BEYOND TOWN LIMITS
Plant Street in Downtown Winter Garden
Plant Street Market, The Farmacy, Adjectives Market, Tri & Run.
8 min drive
15 min ride
30 - 45 min walk
Target, Clermont
9 min drive
Winter Garden Village
12 min drive
Downtown Clermont
17 min drive
Mall at Millenia
23 min drive
29 min drive
PARKS & REC | TRAILS & NATURE PRESERVE
Speer Park
Tennis courts, playground, picnic + grill area, gazebo
Oakland Nature Preserve
128-acre nature preserve with trails + boardwalk to Lake Apopka
Killarney Station
Bike rentals, playground + picnic area on the West Orange Trail
SCHOOLS | ELEMENTARY CHARTER
Oakland Avenue Charter School
K - 5th
COMMUTE TIMES (ISH) | 23 MINUTES
Places to Go
Winter Garden
8 min drive
Downtown Clermont
17 min drive
Windermere
20 min drive
Disney
25 min drive
Apopka
25 min drive
Downtown Orlando
25 min drive
International Drive
26 min drive
Orlando International Airport
29 min drive
Coasts
Tampa (West)
1 hr + 27 min drive
Cocoa Beach (East)
1 hr + 18 min drive
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