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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

28 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 #O6197236
New
OAKLAND
MLS® # O6197236
5 Beds, 6 Baths, 4,813 Sf
Photo of Listing #O6196411
New
OAKLAND
MLS® # O6196411
5 Beds, 7 Baths, 4,584 Sf
Photo of Listing #O6195684
OAKLAND
MLS® # O6195684
5 Beds, 5 Baths, 3,747 Sf
Photo of Listing #O6197807
New
OAKLAND
MLS® # O6197807
5 Beds, 5 Baths, 3,876 Sf
Photo of Listing #O6197343
New

511 Briley Avenue

$1,695,000
OAKLAND
MLS® # O6197343
5 Beds, 5 Baths, 3,665 Sf
Photo of Listing #O6187209
Reduced 1.4%
OAKLAND
MLS® # O6187209
5 Beds, 5 Baths, 4,224 Sf
Photo of Listing #O6154940
Pending

1173 Riverway Drive

$1,190,000
OAKLAND
MLS® # O6154940
4 Beds, 4 Baths, 3,134 Sf
Photo of Listing #O6192156
Pending
OAKLAND
MLS® # O6192156
3 Beds, 3 Baths, 2,164 Sf
Photo of Listing #G5076776
Reduced 0.9%
OAKLAND
MLS® # G5076776
5 Beds, 3 Baths, 3,416 Sf
Photo of Listing #O6191791
Pending
OAKLAND
MLS® # O6191791
4 Beds, 4 Baths, 3,448 Sf
Photo of Listing #O6185010
Pending
OAKLAND
MLS® # O6185010
4 Beds, 2 Baths, 2,438 Sf
Photo of Listing #O6182707
Pending
OAKLAND
MLS® # O6182707
5 Beds, 4 Baths, 4,145 Sf
Photo of Listing #O6195623
Pending
OAKLAND
MLS® # O6195623
4 Beds, 4 Baths, 2,836 Sf
Photo of Listing #O6185865
Reduced 3%
OAKLAND
MLS® # O6185865
5 Beds, 4 Baths, 3,863 Sf
Photo of Listing #O6186159
Pending
OAKLAND
MLS® # O6186159
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O6187083
Pending
OAKLAND
MLS® # O6187083
3 Beds, 3 Baths, 2,028 Sf
Photo of Listing #G5079103
Pending
OAKLAND
MLS® # G5079103
3 Beds, 3 Baths, 2,183 Sf
Photo of Listing #O6193881
OAKLAND
MLS® # O6193881
3 Beds, 3 Baths, 2,069 Sf
Photo of Listing #U8232929
Pending
OAKLAND
MLS® # U8232929
4 Beds, 2 Baths, 2,362 Sf
Photo of Listing #S5102899
OAKLAND
MLS® # S5102899
3 Beds, 2 Baths, 1,956 Sf
Photo of Listing #O6170509
Reduced 1.1%

636 Strihal Loop

$469,900
OAKLAND
MLS® # O6170509
3 Beds, 2 Baths, 2,054 Sf
Photo of Listing #S5102598
OAKLAND
MLS® # S5102598
3 Beds, 3 Baths, 1,744 Sf
Photo of Listing #O6106961
OAKLAND
MLS® # O6106961
3 Beds, 2 Baths, 1,600 Sf
Photo of Listing #O6151965
OAKLAND
MLS® # O6151965
Photo of Listing #O6152065
OAKLAND
MLS® # O6152065
Photo of Listing #S5103184
New
OAKLAND
MLS® # S5103184
3 Beds, 3 Baths, 1,620 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 April 23rd, 2024 at 5:33am EDT.