Oakland Florida Real Estate

Oakland is a historic, naturally beautiful city about 18 miles directly west of Orlando. It lies nestled between the two lakes of Lake Apopka to the North and Johns Lake to the South. Located in the booming southwest region of Orlando, Oakland is a place of majestic oak trees, and small-town charm. Adjacent to the highly sought-after community of Winter Garden, Oakland enjoys convenient shopping, dining, and multiple local community events. To the west lies the fast-growing city of Clermont rich with parks, sports venues, and additional major retailers. The city of Oakland is a quiet gem in this desirable region of Central Florida.

Oakland, FL Homes for Sale

32 Properties Found. Page 1 of 1.
Photo of Listing #O6000187
Pending

Remington Road

$3,100,000
OAKLAND
MLS® # O6000187
8 Acres
Photo of Listing #G5052739
OAKLAND
MLS® # G5052739
4 Acres
Photo of Listing #A4510505
Reduced 23.3%
OAKLAND
MLS® # A4510505
5 Acres
Photo of Listing #A4510544
Reduced 55.3%
OAKLAND
MLS® # A4510544
6 Acres
Photo of Listing #O5858225
Pending
OAKLAND
MLS® # O5858225
3,402 Sf
Photo of Listing #O6028890
Reduced 5.9%
OAKLAND
MLS® # O6028890
5 Beds, 4 Baths, 4,503 Sf
Photo of Listing #O6030431
Reduced 2.5%
OAKLAND
MLS® # O6030431
5 Beds, 4 Baths, 3,562 Sf
Photo of Listing #O6023317
Reduced 2.8%

1364 Foltz Loop

$767,550
OAKLAND
MLS® # O6023317
5 Beds, 4 Baths, 3,562 Sf
Photo of Listing #O6013733
Pending

1024 Catori Road

$717,750
OAKLAND
MLS® # O6013733
5 Beds, 4 Baths, 3,562 Sf
Photo of Listing #O6026687
Reduced 5%

1328 Foltz Loop

$710,260
OAKLAND
MLS® # O6026687
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #O6018559
Reduced 1.4%
OAKLAND
MLS® # O6018559
3 Beds, 3 Baths, 3,829 Sf
Photo of Listing #P4921546
New
OAKLAND
MLS® # P4921546
5 Beds, 4 Baths, 3,290 Sf
Photo of Listing #O6030458
Pending
OAKLAND
MLS® # O6030458
4 Beds, 3 Baths, 3,032 Sf
Photo of Listing #O6037342
New
OAKLAND
MLS® # O6037342
4 Beds, 2 Baths, 2,495 Sf
Photo of Listing #S5066165
Reduced 3.2%
OAKLAND
MLS® # S5066165
5 Beds, 4 Baths, 3,449 Sf
Photo of Listing #O6022859
Pending
OAKLAND
MLS® # O6022859
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #O6013670
Pending

1032 Catori Road

$586,490
OAKLAND
MLS® # O6013670
4 Beds, 2 Baths, 2,277 Sf
Photo of Listing #O6035648
OAKLAND
MLS® # O6035648
3 Beds, 2 Baths, 1,787 Sf
Photo of Listing #O6032385
Reduced 3.5%
OAKLAND
MLS® # O6032385
3 Beds, 3 Baths, 2,000 Sf
Photo of Listing #O6028997
Pending
OAKLAND
MLS® # O6028997
3 Beds, 2 Baths, 1,975 Sf
Photo of Listing #O5999622
Pending

1031 Catori Road

$542,145
OAKLAND
MLS® # O5999622
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #O6034461
Pending
OAKLAND
MLS® # O6034461
4 Beds, 3 Baths, 2,547 Sf
Photo of Listing #O6026371
Pending
OAKLAND
MLS® # O6026371
3 Beds, 3 Baths, 1,992 Sf
Photo of Listing #G5055508
Reduced 2.4%
OAKLAND
MLS® # G5055508
3 Beds, 3 Baths, 1,811 Sf
Photo of Listing #O6037917
New
OAKLAND
MLS® # O6037917
3 Beds, 3 Baths, 1,838 Sf
Photo of Listing #O6032309
Pending
OAKLAND
MLS® # O6032309
2 Beds, 2 Baths, 1,640 Sf
Photo of Listing #O6026062
OAKLAND
MLS® # O6026062
3 Beds, 3 Baths, 1,620 Sf
Photo of Listing #G5051505
Pending
OAKLAND
MLS® # G5051505
4 Beds, 3 Baths, 1,861 Sf
Photo of Listing #S5067992
Pending
OAKLAND
MLS® # S5067992
3 Beds, 2 Baths, 1,308 Sf
Photo of Listing #O6028511
Reduced 2.4%
OAKLAND
MLS® # O6028511
4 Beds, 2 Baths, 1,700 Sf
Photo of Listing #G5049849
Pending
OAKLAND
MLS® # G5049849
2 Beds, 1 Baths, 959 Sf
Photo of Listing #O6035956
Pending
OAKLAND
MLS® # O6035956

Oakland, FL Real Estate

Established in 1887, Oakland grew from a small agricultural village to a thriving local city. In its heyday, it boasted a thriving downtown complete with a newspaper office, hotel, hospital, and even an opera house. Citrus freezes put a halt to the underlying economy, and later a devastating fire leveled the Oakland downtown. For a greater part of the 1900s, Oakland remained a sleepy little village content to move along quietly through the years with little change. More recently, Oakland has been swept up in the wave of dramatic growth in this southwest Orlando region.

Oakland real estate includes a select number of historic homes and a more recent proliferation of contemporary homes constructed within self-contained communities. Many neighborhoods are positioned lakefront, and residences have the benefit of generous lot sizes and spacious interiors. Luxurious trimmings such as executive master suites, walk-in showers, gourmet kitchens, majestic entryways, and professional landscaping are the norm. These modern neighborhoods offer amenities such as gated entrances, water access, community swimming pools, and private playgrounds.

Life in Oakland today is noted for its laid-back lifestyle. The Oakland Nature Reserve on the banks of Lake Apopka is a 128-acre preserve with hiking trails, boardwalk, and ecotourism activities. Parks on both Lake Apopka and Johns Lake provide facilities for picnicking and opportunities for kayaking, canoeing, fishing, hiking, and bird watching. West Orange Trail, passes directly through Oakland, a world-class 22-mile rail-trail popular for walking and cycling.

While Oakland itself is quiet, the location of this historic Central Florida town cannot be beaten. A short drive along West Colonial Drive provides convenient shopping and dining opportunities as well as other commonly looked for necessities. Adjacent Historic Downtown Winter Garden showcases small-town Southern charm with an award-winning farmers market, art gallery, theater, elegant dining, and multiple annual festivals and events. Florida's Turnpike and highways 429 and 408 are nearby, offering direct access to Disney, Universal Studios, SeaWorld, Orlando International Airport, and Downtown Orlando. Studios, SeaWorld, Orlando International Airport, and Downtown Orlando.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 29th, 2022 at 8:49am EDT.