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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

26 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 #O6133791
Pending
OAKLAND
MLS® # O6133791
4 Beds, 4 Baths, 3,838 Sf
Photo of Listing #R4906404
Reduced 11.3%
OAKLAND
MLS® # R4906404
5 Beds, 4 Baths, 4,475 Sf
Photo of Listing #O6127867
OAKLAND
MLS® # O6127867
5 Beds, 4 Baths, 3,285 Sf
Photo of Listing #W7857561
Reduced 6.6%

50 Demens Street

$649,000
OAKLAND
MLS® # W7857561
4 Beds, 4 Baths, 2,652 Sf
Photo of Listing #O6118911
Reduced 3.9%
OAKLAND
MLS® # O6118911
4 Beds, 4 Baths, 3,008 Sf
Photo of Listing #S5091393
OAKLAND
MLS® # S5091393
4 Beds, 3 Baths, 3,449 Sf
Photo of Listing #O6120576
Reduced 0.8%
OAKLAND
MLS® # O6120576
4 Beds, 3 Baths, 3,049 Sf
Photo of Listing #O6144009
New
OAKLAND
MLS® # O6144009
4 Beds, 3 Baths, 2,638 Sf
Photo of Listing #O6138070
Pending
OAKLAND
MLS® # O6138070
3 Beds, 3 Baths, 2,060 Sf
Photo of Listing #O6127379
Pending
OAKLAND
MLS® # O6127379
3 Beds, 3 Baths, 2,060 Sf
Photo of Listing #O6142090
New
OAKLAND
MLS® # O6142090
4 Beds, 3 Baths, 2,233 Sf
Photo of Listing #O6130146
Pending
OAKLAND
MLS® # O6130146
4 Beds, 3 Baths, 2,239 Sf
Photo of Listing #O6128307
OAKLAND
MLS® # O6128307
4 Beds, 2 Baths, 2,284 Sf
Photo of Listing #O6037342
Reduced 15.8%
OAKLAND
MLS® # O6037342
4 Beds, 2 Baths, 2,495 Sf
Photo of Listing #O6123908
Reduced 2.7%

645 Strihal Loop

$535,000
OAKLAND
MLS® # O6123908
4 Beds, 3 Baths, 2,606 Sf
Photo of Listing #W7855994
Pending
OAKLAND
MLS® # W7855994
3 Beds, 2 Baths, 1,975 Sf
Photo of Listing #O6106984
Pending
OAKLAND
MLS® # O6106984
4 Beds, 3 Baths, 2,213 Sf
Photo of Listing #O6121941
Pending
OAKLAND
MLS® # O6121941
4 Beds, 3 Baths, 2,627 Sf
Photo of Listing #O6132515
Pending
OAKLAND
MLS® # O6132515
3 Beds, 3 Baths, 2,078 Sf
Photo of Listing #O6136019
Pending
OAKLAND
MLS® # O6136019
3 Beds, 3 Baths, 1,744 Sf
Photo of Listing #O6106961
OAKLAND
MLS® # O6106961
3 Beds, 2 Baths, 1,600 Sf
Photo of Listing #O6108540
Reduced 2.8%
OAKLAND
MLS® # O6108540
Photo of Listing #O6134778
Reduced 13.2%
OAKLAND
MLS® # O6134778
Photo of Listing #O6135030
Pending
OAKLAND
MLS® # O6135030
1,970 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 September 25th, 2023 at 2:18am EDT.