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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

409 E Gulley Avenue, Oakland $499,999

Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and...

3 Beds
2 Baths
Oakland 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 $850,000

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 $2,595,000

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.
34760 Zip Code

710 Regina Circle, Oakland $659,900 ▼

Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with...

5 Beds
4 Baths
Johns Landing SubDv.
34787 Zip Code

2247 White Feather Loop, Oakland $457,900

Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 s...

3 Beds
3 Baths
Oakland Trails 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

14001 Rugby Street, Oakland $825,000 ▼

One or more photo(s) has been virtually staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park communit...

5 Beds
4 Baths
Verde Park Ph 1 SubDv.
34787 Zip Code

2017 Boss Hewett Street, Oakland $699,900 ▼

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 $1,025,000 ▼

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 $1,125,000 ▼

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms an...

4 Beds
3 Baths
Oakland Town SubDv.
34760 Zip Code

38 S Pollard Street, Oakland $629,999 ▼

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space...

4 Beds
3 Baths
Oakland Town SubDv.
34760 Zip Code

1231 Foltz Loop, Oakland $874,900

Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. ...

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

812 Johns Point Drive, Oakland $2,699,000 ▼

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

2117 Gopher Tortoise Terrace, Oakland image

2117 Gopher Tortoise Terrace, Oakland — 2117 $350,000 ▼

PRICE Improvement and this home can be purchased with NO INCOME VERIFICATION! Be sure to ask about the details! Skip the projects, this 2020 built home is ready for you! ...

2 Beds
3 Baths
Longleaf/Oakland Rep 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.
34760 Zip Code

2065 White Feather Loop, Oakland $539,900 ▼

Welcome to the highly desirable Oakland Trails, where this 2019 Meritage Home combines modern style, energy efficiency, and a thoughtfully designed layout for everyday co...

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

2100 Gopher Tortoise Terrace, Oakland image

2100 Gopher Tortoise Terrace, Oakland $375,000 ▼

Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland commun...

2 Beds
3 Baths
Longleaf/Oakland Rep 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...

4 Beds
4 Baths
Oakland Park SubDv.
34787 Zip Code

620 N Tubb Street, Oakland $1,250,000 ▼

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would al...

6 Beds
8 Baths
Oakland SubDv.
34760 Zip Code

1970 Standing Rock Circle, Oakland image

1970 Standing Rock Circle, Oakland $796,000 ▼

Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails comm...

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

1146 Prado Lane, Oakland $2,130,760

Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a...

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

1173 Prado Lane, Oakland $2,238,120

Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautif...