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

31 Properties Found. Page 1 of 1.
Photo of Listing #G5000645
Pending
Oakland
MLS® # G5000645
13 Acres
Photo of Listing #O5898034
Pending

912 Johns Point Dr

$1,749,000
Oakland
MLS® # O5898034
5 Beds, 6 Baths, 6,065 Sf
Photo of Listing #O5917050
Pending

520 Largovista Dr

$1,690,000
Oakland
MLS® # O5917050
5 Beds, 5 Baths, 5,222 Sf
Photo of Listing #G5025317
Pending

15551 W Colonial Dr

$1,500,000
Oakland
MLS® # G5025317
5 Acres
Photo of Listing #O5888880

N/A

$1,444,000
Oakland
MLS® # O5888880
7 Acres
Photo of Listing #O5924846

620 N Tubb St

$929,750
Oakland
MLS® # O5924846
5 Beds, 8 Baths, 5,094 Sf
Photo of Listing #O5858225
Oakland
MLS® # O5858225
3,402 Sf
Photo of Listing #G5025783
Reduced 0.9%
Oakland
MLS® # G5025783
5 Beds, 3 Baths, 2,928 Sf
Photo of Listing #O5937693
New
Oakland
MLS® # O5937693
5 Beds, 4 Baths, 4,044 Sf
Photo of Listing #O5933481
Pending
Oakland
MLS® # O5933481
5 Beds, 3 Baths, 3,467 Sf
Photo of Listing #O5931923
Pending

501 E Gulley Ave

$598,800
Oakland
MLS® # O5931923
5 Beds, 4 Baths, 3,698 Sf
Photo of Listing #G5039972
Pending
Oakland
MLS® # G5039972
4 Beds, 3 Baths, 2,505 Sf
Photo of Listing #O5921963
Reduced 0.8%

119 W Hull Ave

$494,900
Oakland
MLS® # O5921963
4 Beds, 3 Baths, 2,478 Sf
Photo of Listing #G5036483
Reduced 1.9%
Oakland
MLS® # G5036483
4 Beds, 3 Baths, 2,386 Sf
Photo of Listing #O5918261
Oakland
MLS® # O5918261
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #O5925617
Oakland
MLS® # O5925617
4 Beds, 2 Baths, 2,277 Sf
Photo of Listing #O5921935

2101 Bay Line Rd

$413,525
Oakland
MLS® # O5921935
3 Beds, 2 Baths, 1,857 Sf
Photo of Listing #O5937224
New
Oakland
MLS® # O5937224
3 Beds, 2 Baths, 1,992 Sf
Photo of Listing #T3295014
Pending
Oakland
MLS® # T3295014
3 Beds, 3 Baths, 1,877 Sf
Photo of Listing #O5925906
Pending
Oakland
MLS® # O5925906
3 Beds, 3 Baths, 2,069 Sf
Photo of Listing #O5935844
Pending
Oakland
MLS® # O5935844
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O5933764
Pending
Oakland
MLS® # O5933764
4 Beds, 3 Baths, 1,861 Sf
Photo of Listing #O5900039
Pending

408 Postell Ave

$262,000
Oakland
MLS® # O5900039
3 Beds, 3 Baths, 1,489 Sf
Photo of Listing #O5900015
Pending

406 Postell Ave

$262,000
Oakland
MLS® # O5900015
3 Beds, 3 Baths, 1,489 Sf
Photo of Listing #O5900051
Pending

524 W Hull Ave

$262,000
Oakland
MLS® # O5900051
3 Beds, 3 Baths, 1,489 Sf
Photo of Listing #O5899895
Pending

405 Postell Ave

$262,000
Oakland
MLS® # O5899895
3 Beds, 3 Baths, 1,489 Sf
Photo of Listing #O5930614

739 Regina Cir

$217,500
Oakland
MLS® # O5930614
Photo of Listing #G5028807
Reduced 4.8%
Oakland
MLS® # G5028807
Photo of Listing #G5027786
Pending
Oakland
MLS® # G5027786
Photo of Listing #O5921648
Pending
Oakland
MLS® # O5921648
Photo of Listing #O5881101
Oakland
MLS® # O5881101

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 April 16th, 2021 at 9:47am EDT.