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

35 Properties Found. Page 1 of 1.
Photo of Listing #G5000645
Reduced 4.2%
Oakland
MLS® # G5000645
13 Acres
Photo of Listing #O5898034

912 Johns Point Dr

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

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
Reduced 25.7%

N/A

$1,300,000
Oakland
MLS® # O5888880
7 Acres
Photo of Listing #T3269557

101 N Starr St

$1,195,000
Oakland
MLS® # T3269557
3 Beds, 4 Baths, 2,519 Sf
Photo of Listing #O5918332
New
Oakland
MLS® # O5918332
5 Beds, 4 Baths, 3,357 Sf
Photo of Listing #O5890028
Reduced 1.7%

620 N Tubb St

$929,750
Oakland
MLS® # O5890028
6 Beds, 8 Baths, 5,614 Sf
Photo of Listing #O5902064
Reduced 5.4%
Oakland
MLS® # O5902064
4 Beds, 4 Baths, 3,929 Sf
Photo of Listing #O5874578
Oakland
MLS® # O5874578
5 Beds, 5 Baths, 4,009 Sf
Photo of Listing #O5858225
Reduced 14.1%
Oakland
MLS® # O5858225
3,402 Sf
Photo of Listing #O5897287
Pending
Oakland
MLS® # O5897287
5 Beds, 4 Baths, 3,722 Sf
Photo of Listing #O5917541
New

4 S Tubb St

$729,000
Oakland
MLS® # O5917541
2,400 Sf
Photo of Listing #O5903565
Pending
Oakland
MLS® # O5903565
4 Beds, 3 Baths, 2,815 Sf
Photo of Listing #G5025783
Reduced 0.9%
Oakland
MLS® # G5025783
5 Beds, 3 Baths, 2,928 Sf
Photo of Listing #O5889373
Reduced 0.2%

109 W Hull Ave

$599,000
Oakland
MLS® # O5889373
3 Beds, 2 Baths, 3,086 Sf
Photo of Listing #O5911503
Pending
Oakland
MLS® # O5911503
4 Beds, 3 Baths, 2,564 Sf
Photo of Listing #O5910382
Oakland
MLS® # O5910382
4 Beds, 4 Baths, 3,053 Sf
Photo of Listing #G5036483
Oakland
MLS® # G5036483
4 Beds, 3 Baths, 2,386 Sf
Photo of Listing #O5862577
Pending
Oakland
MLS® # O5862577
4 Beds, 3 Baths, 2,626 Sf
Photo of Listing #O5914579
Oakland
MLS® # O5914579
4 Beds, 4 Baths, 3,059 Sf
Photo of Listing #O5914065
Pending

2139 Bay Line Rd

$439,850
Oakland
MLS® # O5914065
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #G5036100
Pending
Oakland
MLS® # G5036100
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O5909409
Pending
Oakland
MLS® # O5909409
4 Beds, 3 Baths, 2,565 Sf
Photo of Listing #G5034424
Pending
Oakland
MLS® # G5034424
3 Beds, 3 Baths, 2,183 Sf
Photo of Listing #O5914320
Pending
Oakland
MLS® # O5914320
3 Beds, 3 Baths, 2,002 Sf
Photo of Listing #O5905591
Pending
Oakland
MLS® # O5905591
3 Beds, 3 Baths, 1,841 Sf
Photo of Listing #V4916695
Reduced 0.6%
Oakland
MLS® # V4916695
4 Beds, 2 Baths, 2,076 Sf
Photo of Listing #O5900039

408 Postell Ave

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

406 Postell Ave

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

524 W Hull Ave

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

405 Postell Ave

$262,000
Oakland
MLS® # O5899895
3 Beds, 3 Baths, 1,489 Sf
Photo of Listing #G5028807
Reduced 4.8%
Oakland
MLS® # G5028807
Photo of Listing #G5027786
Oakland
MLS® # G5027786
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.

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

Listing information last updated on January 25th, 2021 at 2:45pm EST.