Oakland Neighborhood Guide

Updated: Oct 9, 2019


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


West Orange Trail

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

DG Donuts



Bites, Beverages & The Finer Side

Plant Street in Downtown Winter Garden

8 min drive

15 min ride

30 - 45 min walk


Winter Garden Village

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


Disney Springs

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


Orlando International Airport

29 min drive


Coasts


Tampa (West)

1 hr + 27 min drive


Cocoa Beach (East)

1 hr + 18 min drive




Learn more about investing in Oakland, Florida

Contact Us

OUR OFFICE

30 W Smith St.

Winter Garden, FL 34787

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