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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

36 Properties Found. Page 1 of 1.
Photo of Listing #G5052739
OAKLAND
MLS® # G5052739
4 Acres
Photo of Listing #O6228504

511 Briley Avenue

$1,849,000
OAKLAND
MLS® # O6228504
5 Beds, 5 Baths, 3,665 Sf
Photo of Listing #O6198706
Pending
OAKLAND
MLS® # O6198706
5 Beds, 4 Baths, 5,117 Sf
Photo of Listing #O6195684
Reduced 6.4%
OAKLAND
MLS® # O6195684
5 Beds, 5 Baths, 3,747 Sf
Photo of Listing #O6228993
OAKLAND
MLS® # O6228993
4 Beds, 4 Baths, 3,760 Sf
Photo of Listing #O6218369
Pending

1096 Riverway Drive

$1,475,000
OAKLAND
MLS® # O6218369
4 Beds, 4 Baths, 3,988 Sf
Photo of Listing #O6204736
Pending
OAKLAND
MLS® # O6204736
5 Beds, 5 Baths, 3,460 Sf
Photo of Listing #O6218185
Reduced 0.9%
OAKLAND
MLS® # O6218185
5 Beds, 5 Baths, 3,782 Sf
Photo of Listing #O6214578
Reduced 0.6%
OAKLAND
MLS® # O6214578
3 Beds, 3 Baths, 2,254 Sf
Photo of Listing #O6214378
Reduced 0.8%
OAKLAND
MLS® # O6214378
4 Beds, 3 Baths, 2,240 Sf
Photo of Listing #O6220887
Reduced 5.9%
OAKLAND
MLS® # O6220887
5 Beds, 4 Baths, 3,532 Sf
Photo of Listing #O6222938
Reduced 2.5%

305 Briley Ave

$780,000
OAKLAND
MLS® # O6222938
4 Beds, 3 Baths, 2,282 Sf
Photo of Listing #O6220711
Pending
OAKLAND
MLS® # O6220711
5 Beds, 3 Baths, 3,416 Sf
Photo of Listing #S5109495
OAKLAND
MLS® # S5109495
1 Acres
Photo of Listing #O6225571
OAKLAND
MLS® # O6225571
3 Beds, 3 Baths, 1,995 Sf
Photo of Listing #O6202952
Reduced 3.9%
OAKLAND
MLS® # O6202952
3 Beds, 2 Baths, 2,328 Sf
Photo of Listing #O6185865
Reduced 3%
OAKLAND
MLS® # O6185865
5 Beds, 4 Baths, 3,863 Sf
Photo of Listing #O6229376
OAKLAND
MLS® # O6229376
Photo of Listing #O6229365
Pending
OAKLAND
MLS® # O6229365
4 Beds, 3 Baths, 2,469 Sf
Photo of Listing #O6225251
Pending

20 W Vick Ave

$610,000
OAKLAND
MLS® # O6225251
3 Beds, 2 Baths, 1,320 Sf
Photo of Listing #O6182707
Pending
OAKLAND
MLS® # O6182707
5 Beds, 4 Baths, 3,980 Sf
Photo of Listing #O6212095
Pending
OAKLAND
MLS® # O6212095
3 Beds, 3 Baths, 2,245 Sf
Photo of Listing #O6225887
Reduced 2.8%
OAKLAND
MLS® # O6225887
3 Beds, 2 Baths, 1,842 Sf
Photo of Listing #O6229482
OAKLAND
MLS® # O6229482
Photo of Listing #O6207844
Reduced 3.7%
OAKLAND
MLS® # O6207844
4 Beds, 3 Baths, 1,811 Sf
Photo of Listing #O6205567
Reduced 4.7%
OAKLAND
MLS® # O6205567
3 Beds, 3 Baths, 1,811 Sf
Photo of Listing #O6226398
Pending

633 Strihal Loop

$499,990
OAKLAND
MLS® # O6226398
4 Beds, 2 Baths, 2,478 Sf
Photo of Listing #O6222519
OAKLAND
MLS® # O6222519
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O6200569
Reduced 2.2%
OAKLAND
MLS® # O6200569
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O6151965
OAKLAND
MLS® # O6151965
Photo of Listing #O6152065
OAKLAND
MLS® # O6152065
Photo of Listing #O6229344
OAKLAND
MLS® # O6229344
Photo of Listing #O6209125
Pending
OAKLAND
MLS® # O6209125
2 Beds, 3 Baths, 1,497 Sf
Photo of Listing #O6231707
New
OAKLAND
MLS® # O6231707
3 Beds, 2 Baths, 1,325 Sf
Photo of Listing #O6219699
Pending
OAKLAND
MLS® # O6219699
2 Beds, 3 Baths, 1,472 Sf
Photo of Listing #R4908101
Pending
OAKLAND
MLS® # R4908101
2 Beds, 1 Baths, 1,015 Sf

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 August 14th, 2024 at 5:04am EDT.