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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

2010 Boss Hewett Street, Oakland $1,450,000

Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concep...

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

20 W Vick Avenue Unit 2, Oakland $1,627,000

Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Off...

4 Beds
4 Baths
Oakland Town SubDv.
34760 Zip Code

20 W Vick Avenue Unit 1, Oakland $1,645,000

Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bed...

4 Beds
4 Baths
Oakland Town SubDv.
34760 Zip Code

726 Regina Circle, Oakland $695,000

Welcome to 726 Regina Circle in Oakland, Florida! This spacious two-story home offers five bedrooms, four bathrooms, and an inviting layout designed to accommodate a vari...

5 Beds
4 Baths
Johns Landing Ph 01 44/47 SubDv.
34787 Zip Code

2199 White Feather Loop, Oakland $489,900

Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direc...

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

2107 Gopher Tortoise Terrace, Oakland image

2107 Gopher Tortoise Terrace, Oakland — 2107 $364,900

Welcome to this beautifully maintained, fully furnished, six-year-old townhome in the charming town of Oakland! Featuring 2 bedrooms, 2.5 baths, and a two-car garage, thi...

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

1213 Foltz Loop, Oakland $849,000 ▼

LOCATION, LOCATION, LOCATION. Come see this BEAUTIFUL, WELL MAINTAINED HOME BUILT IN 2022 WITH A CONSERVATION/PROTECTED PRESERVE VIEW in OAKLAND! This home looks like a M...

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

1316 Southern Sun Drive, Oakland $1,050,000

Discover a private retreat in Hull Island at Oakland, an intimate community of limited residences offering a peaceful, exclusive feel near charming downtown Winter Garden...

5 Beds
4 Baths
Hull Island SubDv.
34787 Zip Code

2561 Sky Stone Court, Oakland $565,000

Virtually Staged. This beautiful 4-bedroom, 2.5-bath home in the charming town of Oakland! Ideally located with no rear neighbors, this home offers comfort, privacy, and ...

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

2224 Gopher Tortoise Terrace, Oakland image

2224 Gopher Tortoise Terrace, Oakland — 2224 $367,500 ▼

Set in Longleaf at Oakland, directly across from Oakland Nature Preserve and the 22-mile West Orange Trail, this END-UNIT TOWNHOME offers a rare combination of natural su...

2 Beds
3 Baths
Longleaf At Oakland SubDv.
34787 Zip Code

100 Mather Smith Drive, Oakland $600,000

A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-...

3 Beds
2 Baths
Oakland Shores SubDv.
34760 Zip Code

2107 Bay Line Road, Oakland $615,000 ▼

Welcome home to Hull Island, where thoughtful upgrades, a private preserve setting, and resort-style amenities come together. Extended driveway upgraded with builder. Thi...

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

2470 Standing Rock Circle, Oakland image

2470 Standing Rock Circle, Oakland $730,000

Virtually Staged. Welcome to 2470 Standing Rock Circle, a beautifully maintained Montclair model by Meritage Homes in the desirable Oakland Trails community. Offering 3,4...

5 Beds
3 Baths
Oakland Trails SubDv.
34787 Zip Code

2273 Standing Rock Circle, Oakland image

2273 Standing Rock Circle, Oakland $479,900

Location, location, location!! Incredible opportunity to own a popular Whitman II model in the desirable Oakland Trails community with direct walkable access to the West ...

3 Beds
3 Baths
Oakland Trls Ph 2 SubDv.
34787 Zip Code

1016 Catori Road, Oakland $800,000 ▼

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 $1,445,000 ▼

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

1511 Sweet Apple Street, Oakland — 1511 $329,950 ▼

Virtually Staged. JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland commu...

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

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 $779,000 ▼

PRICE REDUCED! Make this 6-bedroom, 4-bath home in gated Johns Cove your own in time for the holidays. Set on a private cul-de-sac with no rear neighbors, it offers room ...

6 Beds
4 Baths
Johns Cove SubDv.
34787 Zip Code

1134 Prado Lane, Oakland $2,495,000 ▼

LOCATED IN THE GOLF CART DISTRICT OF DOWNTOWN WINTER GARDEN, PLANT STREET! Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stun...

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

1152 Prado Lane, Oakland $2,665,990 ▲

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...