Oakland Homes for Sale

Located in the sunny, beautiful region of Orange County, Florida lies one of the oldest municipalities in the its county, Oakland. Oakland is known for its extreme diversity and laid-back environment. Oakland is a very close-knit town with a small area of just over 2 square miles. Oakland is scattered with gorgeous oak trees (hence the name Oakland) and has a reputation for its stunning natural beauty. As you may know already, Florida is a state that is mostly comprised of precious wetlands, warm beaches and a sub-tropical climate. The location of Oakland is between Lake Apopka and John’s Lake, making it responsible for overseeing and protecting the 130 acres of wetlands and uplands now known as the Oakland Nature Preserve.

Wondering what types of homes are for sale here in Oakland? Because Florida is such a warm climate, often times homes are built in the same as they can be found in the Mediterranean region, these homes are known as Mediterranean style homes. The mediterranean style consists of red tiled roofs, stucco walls, ornamental doorways and windows and often several floors. Other home styles that can be found in Oakland are Traditional, modern, and condos and townhomes. The prices for most single family homes in Oakland is around $330,000 to over $580,000. Residents of Oakland enjoy the close convenience of beaches, fine dining restaurants, nature trails, boardwalks, shopping venues and so much more. The community sits just west of the city of Orlando which also provides a wide range of amusements like, water parks, shopping malls and gorgeous white sand beaches.

Families moving to the area will be pleased to know that Oakland hosts a number of excellent schools that have been awarded a grade “A” in recent years. The population of Oakland is around 2,500, giving it a small town feel and a very close-knit, friendly place for those looking to relocate. Oakland offers its community so many unique and valuable amenities. If you are interested in purchasing a home here in Oakland, Florida, please don’t hesitate to contact us today so we may be of service to you!

Latest Oakland Homes and Condos for Sale

1511 Sweet Apple Street, Oakland — N/A $399,500

Welcome home to this beautiful 3 bed, 2.5 bath, nearly new, townhome property in sought after Oakland/Winter Garden area, in Longleaf at Oakland community. As you approac...

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

1961 Standing Rock Circle, Oakland image

1961 Standing Rock Circle, Oakland $469,500

PREMIER COMMUNITY! Welcome to Oakland Trails, a community in Oakland, Florida, situated right off of the Florida Turnpike! This 3 bed/2.5 bath home situated on a corner l...

3 Beds
2.5 Baths
Oakland Trails Ph 2 SubDv.
34787 Zip Code

1301 Johns Cove Lane, Oakland $640,000

Large 4 Bedroom 2 Bathroom 3-way split floor plan with an Office and a 2 car Garage. Exclusively located in a gated community with easy access to Florida's Turnpike, 408,...

4 Beds
2 Baths
Johns Cove 43/104 SubDv.
34787 Zip Code

410 E Henschen Avenue, Oakland $700,000

Located in the town of Oakland, which is nestled in between Clermont and Winter Garden, sits this beautiful pool home with a detached guest house with NO HOA and solar pa...

5 Beds
4 Baths
Starr Gardens Oakland SubDv.
34760 Zip Code

1071 Stationside Drive, Oakland $550,000

Totally renovated 3 bedroom, 2 bathroom home located in the heart of Oakland with private sweeping views of the nature preserve! This home has brand new flooring througho...

3 Beds
2 Baths
Trailside Station Rep 44/23 SubDv.
34787 Zip Code

2490 Standing Rock Circle, Oakland image

2490 Standing Rock Circle, Oakland $550,000 ▼

Why wait to build? This home is ready for you now! Located in one of Oakland's premier communites, Oakland Trails is the perfect spot to call home. With 3 bedrooms, 2.5...

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

1316 Southern Sun Drive, Oakland $793,460 ▼

Under Construction. The Newcastle, a beautiful new home for sale in Oakland, is as flexible as it is beautiful featuring a front covered porch and 3-car tandem garage. Wi...

5 Beds
4 Baths
Hull Island SubDv.
34787 Zip Code

210 W Sadler Avenue, Oakland $364,900 ▼

***Price Reduction*** New low price makes this a must see today! Great single-family home with metal roof sits on a large corner lot on a tree lined street in the desirab...

4 Beds
1.5 Baths
Oakland Town SubDv.
34760 Zip Code

1364 Foltz Loop, Oakland $767,550 ▼

Under Construction. The Newcastle offers a welcoming front porch. Once inside you will be welcomed to a high ceiling foyer. This home offers 3562 sf with 5 spacious bedro...

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

1328 Foltz Loop, Oakland $710,260 ▼

Under Construction. This new home in Oakland is a single-story, 3-way-split plan with 4 bedrooms and 3 baths. Find a bedroom with its own full bath right off the foyer at...

4 Beds
3 Baths
Hull Island SubDv.
34787 Zip Code

2724 Bobcat Chase Boulevard, Oakland image

2724 Bobcat Chase Boulevard, Oakland $477,900 ▼

Welcome to this LIKE NEW home located in the desirable town of Oakland. This spacious home offers 3 bedrooms, 2.5 bathrooms, an open floor plan, beautiful kitchen with gr...

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

2208 Gopher Tortoise Terrace, Oakland image

2208 Gopher Tortoise Terrace, Oakland — 2208 $420,000

LOCATED NEAR DOWNTOWN WINTER GARDEN, CLOSE TO THE WINTER GARDEN TRAIL, PLANT STREET, TURNIPIKE AND MUCH MORE. HOUSE OFFERS A 3 BEDROOMS AND 2 AND 1/2 BATH WITH LOTS OF UP...

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

229 Largovista Drive, Oakland $609,990 ▼

Come live in one of Central Florida's most desirable lakefront gated communities, John's Landing. This amazing 5 bedroom, 4 bath home with double car garage, brand new do...

5 Beds
4 Baths
Johns Landing Ph 02 48 138 SubDv.
34787 Zip Code

402 Largovista Drive, Oakland $704,900 ▼

Nestled in one of Central Florida's most desirable lakefront gated communities, John's Landing sits a custom luxury lakeview home measured at 4,470 total square feet. Thi...

3 Beds
2.5 Baths
Johns Landing Ph 01 44/47 SubDv.
34787 Zip Code

16251 W Colonial Drive, Oakland $2,400,000 ▲

PRIME LOCATION HWY 50 FRONTAGE. This C-1 Zoned 3.52 +/- acres is right near the border of booming Winter Garden (population 48,000) and just East of Clermont (population ...

34760 Zip Code

750 Hull Island Drive, Oakland $1,295,000 ▼

These six plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. Th...

34787 Zip Code

800 Hull Island Drive, Oakland $1,495,000 ▼

These five plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. T...