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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

27 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 #O6074568
New
OAKLAND
MLS® # O6074568
5 Beds, 5 Baths, 4,277 Sf
Photo of Listing #O6054773

402 E Gulley Avenue

$1,495,000
OAKLAND
MLS® # O6054773
4 Beds, 4 Baths, 3,248 Sf
Photo of Listing #A4510505
Pending
OAKLAND
MLS® # A4510505
5 Acres
Photo of Listing #A4510544
Pending
OAKLAND
MLS® # A4510544
6 Acres
Photo of Listing #T3414179
OAKLAND
MLS® # T3414179
4 Beds, 3 Baths, 2,612 Sf
Photo of Listing #R4906404
Reduced 2.4%
OAKLAND
MLS® # R4906404
5 Beds, 4 Baths, 4,475 Sf
Photo of Listing #O6030431
Pending
OAKLAND
MLS® # O6030431
5 Beds, 4 Baths, 3,562 Sf
Photo of Listing #O6023317
Pending

1364 Foltz Loop

$769,550
OAKLAND
MLS® # O6023317
5 Beds, 4 Baths, 3,562 Sf
Photo of Listing #O6026687
Pending

1328 Foltz Loop

$714,260
OAKLAND
MLS® # O6026687
4 Beds, 3 Baths, 2,281 Sf
Photo of Listing #O6068750
Reduced 4.6%
OAKLAND
MLS® # O6068750
5 Beds, 4 Baths, 3,734 Sf
Photo of Listing #O6030458
Pending
OAKLAND
MLS® # O6030458
4 Beds, 3 Baths, 3,032 Sf
Photo of Listing #O6059632
Pending
OAKLAND
MLS® # O6059632
4 Beds, 3 Baths, 2,136 Sf
Photo of Listing #O6037342
Reduced 15.8%
OAKLAND
MLS® # O6037342
4 Beds, 2 Baths, 2,495 Sf
Photo of Listing #O6075516
New

748 Strihal Loop

$529,900
OAKLAND
MLS® # O6075516
5 Beds, 3 Baths, 2,522 Sf
Photo of Listing #O6070404
Reduced 2.8%
OAKLAND
MLS® # O6070404
3 Beds, 2 Baths, 1,975 Sf
Photo of Listing #O6060579
Reduced 3.8%
OAKLAND
MLS® # O6060579
3 Beds, 3 Baths, 2,020 Sf
Photo of Listing #O6052695
Reduced 3.8%
OAKLAND
MLS® # O6052695
3 Beds, 2 Baths, 2,284 Sf
Photo of Listing #O6035648
Reduced 1%
OAKLAND
MLS® # O6035648
3 Beds, 2 Baths, 1,787 Sf
Photo of Listing #O6042381
Pending
OAKLAND
MLS® # O6042381
3 Beds, 2 Baths, 1,744 Sf
Photo of Listing #S5073318
Reduced 3.2%
OAKLAND
MLS® # S5073318
3 Beds, 3 Baths, 1,759 Sf
Photo of Listing #O6056186
Pending

112 Ryan Court

$442,000
OAKLAND
MLS® # O6056186
3 Beds, 3 Baths, 1,664 Sf
Photo of Listing #O6050921
Reduced 2.9%
OAKLAND
MLS® # O6050921
2 Beds, 2 Baths, 853 Sf
Photo of Listing #G5061730
Reduced 4.8%
OAKLAND
MLS® # G5061730
2 Beds, 2 Baths, 1,046 Sf
Photo of Listing #O6071473
Pending
OAKLAND
MLS® # O6071473
2 Beds, 1 Baths, 615 Sf
Photo of Listing #G5060947
OAKLAND
MLS® # G5060947
3,406 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.

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

Listing information last updated on December 1st, 2022 at 9:34pm EST.