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The Oakland Area of Winter Garden

Known as one of the hidden gems of Florida, Oakland is surrounded by moss-draped oak trees and found on the shores of Lake Apopka. It's a naturally beautiful area of Winter Garden boasting waterfront properties within a serene setting nestled in the Northwestern area of Winter Garden just before Clermont off Hwy 50 in West Orange County.

The Oakland Nature Preserve

One of the best attractions found in Oakland is the Oakland Nature Preserve. Since 1999, this preserve has been providing education to visitors about the native flora and fauna, while providing conservation efforts for the area land. Its open year-round and there's no charge to enjoy the preserve.

Oakland Nature Preserve Trail The Nature Preserve provides plenty of fun with 128 acres of space for environmental education and recreation. It's a popular spot for field trips and summer camps. Many visitors come for the guided tours, hiking trails and special events.

The Boardwalk also attracts many visitors. It's the most popular trail on the preserve and takes you through shaded wetlands to a covered pavilion with views of Lake Apopka. Interpretive signage is found throughout to identify trees and plants. Often, you will spot turtles, alligators and wading birds from the Boardwalk.

Lake Apopka

Another huge part of the culture and recreation of Oakland, Florida is Lake Apopka. It's the second largest lake in the entire state and used to be known as the bass fishing capital of the entire southern United States. The lake is fed by a natural spring and covers about 30,800 acres of surface area.

The Oakland Heritage Festival

Old Mansion in Oakland Florida One of the largest and most popular events held annually in Oakland is the Heritage Festival. This festival provides plenty of fun with more than 2,000 attendees and over 50 vendors every year. It's held at Speer Park in Oakland and helps to support the Oakland Nature Preserve.

Those attending the event get to enjoy hayride tours, a silent auction, boat tours, live music, a number of great speakers, a petting zoo and so much more. There are crafts and activities specifically for children and even some of the more exotic animals on hand. The festival is held in October every year.

Oakland Avenue Charter School

Along with the beautiful nature of the area, Oakland, Florida is home to a 700-student charter elementary school. This school provides a choice for residents with school-aged children outside of the public schools serving the community.

New construction in Oakland Florida

Real Estate in Oakland

A variety of housing options are found in Oakland with homes ranging from about $200K up to more than $1 million. The area does have some undeveloped land for those looking to create a new construction home and there are plenty of waterfront homes and lots available, as well.

Some of the finer waterfront estates provide incredible views of Lake Apopka and may even provide private docks. Oakland attracts a variety of home buyers due to the range of options and prices.

Neighborhoods in the Oakland Area include:

Latest Oakland FL Listings

1016 Catori Road, Oakland $825,000

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the in...

4 Beds
4 Baths
Hull Island/Oakland Ph 2 SubDv.
34787 Zip Code

137 Petris Avenue, Oakland $1,495,000

FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking...

4 Beds
4 Baths
Town/Oakland SubDv.
34760 Zip Code

226 Hammock Preserve Loop, Oakland image

226 Hammock Preserve Loop, Oakland $889,900

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor be...

4 Beds
3 Baths
Oakland Parkb-3 SubDv.
34787 Zip Code

239 Largovista Drive, Oakland $675,900

Welcome to this beautiful and impeccably maintained 4-bedroom, 2.5-bath home in the desirable Johns Landing community of Oakland! This exceptional family home offers spac...

4 Beds
3 Baths
Johns Landing SubDv.
34787 Zip Code

166 Hammock Preserve Loop, Oakland image

166 Hammock Preserve Loop, Oakland $850,000

Under Construction. Rare opportunity to finish a custom AR Homes "Carrabelle" build exactly the way you want it - priced to reflect its current stage. 166 Hammock Preserv...

4 Beds
4 Baths
Oakland Parkb-3 SubDv.
34787 Zip Code

1511 Sweet Apple Street, Oakland — 1511 $364,500

Welcome to 1511 Sweet Apple Street, a well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 20...

3 Beds
3 Baths
Longleaf/Oakland Rep SubDv.
34787 Zip Code

2471 Sky Stone Court, Oakland $559,000

Welcome to 2471 Skystone Ct, located in the desirable Oakland area! This spacious two-story home offers a thoughtfully designed floor plan with 4 bedrooms, 3.5 bathrooms,...

4 Beds
3 Baths
Oakland Trls Ph 1 SubDv.
34787 Zip Code

1112 Hull Island Drive, Oakland $1,400,000

Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and f...

4 Beds
4 Baths
Hull Island At Oakland SubDv.
34787 Zip Code

521 W Herriott Avenue, Oakland $415,000 ▼

PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (larg...

3 Beds
2 Baths
Oakland Town SubDv.
34760 Zip Code

312 Briley Avenue, Oakland $3,295,000

Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thought...

6 Beds
7 Baths
Briley Farm SubDv.
34760 Zip Code

223 Largovista Dr., Oakland $540,000

Virtually Staged. Welcome to this spacious two-story home located in the highly desirable gated community of John's Landing in beautiful Oakland. Offering 4 bedrooms, 2.5...

4 Beds
3 Baths
Johns Landing Ph 2 SubDv.
34787 Zip Code

1603 Johns Cove Ln, Oakland $795,000 ▼

Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and d...

6 Beds
4 Baths
Johns Cove SubDv.
34787 Zip Code

1134 Prado Lane, Oakland $2,545,000 ▼

Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers a...

5 Beds
8 Baths
Grove/Oakland SubDv.
34787 Zip Code

1152 Prado Lane, Oakland $2,615,320

Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the excl...

6 Beds
7 Baths
Grove/Oakland SubDv.
34787 Zip Code

1155 Prado Lane, Oakland $2,575,000

Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charm...

5 Beds
7 Baths
Grove/Oakland SubDv.
34787 Zip Code

2241 White Feather Loop, Oakland $510,000 ▼

Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, a...

3 Beds
3 Baths
Oakland Trls Ph 1 SubDv.
34787 Zip Code

16 Oakland Pointe Circle, Oakland $799,999

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where ch...

5 Beds
3 Baths
Oakland Pointe SubDv.
34760 Zip Code

2017 Boss Hewett Street, Oakland $689,900 ▼

Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps u...

4 Beds
4 Baths
Hull Island/Oakland Ph 2 SubDv.
34787 Zip Code

219 Largovista Drive, Oakland $995,900 ▼

Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home...

5 Beds
4 Baths
Johns Landing SubDv.
34787 Zip Code

250 N Walker Street, Oakland $1,049,000 ▼

Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, ...

4 Beds
3 Baths
Oakland Town SubDv.
34760 Zip Code

38 S Pollard Street, Oakland $619,000 ▼

NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath...

4 Beds
3 Baths
Oakland Town SubDv.
34760 Zip Code

812 Johns Point Drive, Oakland $2,550,000 ▼

Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand...

5 Beds
6 Baths
Johns Cove 43/104 SubDv.
34787 Zip Code

2259 White Feather Loop, Oakland $515,000 ▼

INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq....

4 Beds
3 Baths
Oakland Trls Ph 1 SubDv.
34787 Zip Code

1106 Sarah Mathews Drive, Oakland $1,975,000

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that show...

5 Beds
6 Baths
Grove At The Harvest District SubDv.
34787 Zip Code

1258 Ridge Lake Way, Oakland — Rcb Homes $2,098,000 ▲

Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built tw...