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

1805 Standing Rock Cir, Oakland $399,900

Winter Garden is the #1 selling location in Orlando! 20 mins from downtown Orlando, 20 mins from Walt Disney world, and this property is 10 mins from Downtown Winter Gard...

4 Beds
3 Baths
Oakland Trails SubDv.
34787 Zip Code

1873 White Feather Loop, Oakland $399,999

This beautiful 4 bedroom 3 full bath home could be yours! Near the heart of downtown Winter Garden restaurants, shops and nightlight. This home comes with upgraded modern...

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

1933 White Feather Loop, Oakland $349,900

LOOK NO MORE, THIS BEAUTIFUL 4 BEDROOM 2.5 BATH HOME IN OAKLAND TRAILS COMMUNITY. THIS HOME WAS BUILT ENERGY EFFICIENT BY MERITAGE BUILDER. THIS HOME WILL HELP YOU LIVE A...

4 Beds
2.5 Baths
Oakland Trails SubDv.
34787 Zip Code

322 E Henschen Avenue, Oakland $409,990

Excellent opportunity to own a wonderful Open-Concept, one-story home, with NO HOA! With 4 bedrooms, 2 bathrooms, and an additional room which can be used as an office/gy...

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

620 N Tubb Street, Oakland $945,555

This exquisite gem has endless opportunities. A wellness center, wedding event venue, Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic sta...

6 Beds
7.5 Baths
Oakland SubDv.
34760 Zip Code

109 W Hull Avenue, Oakland $624,900

BRING YOUR BOAT AND YOUR RV!!~NO HOA!~HISTORIC OAKLAND'S FINEST RESIDENCE.~MAJORLY RENOVATED IN PRESERVING THE INTEGRITY & ORIGINAL BEAUTY.~ PINE FLOORS~ TIN ROOF, BRICK ...

3 Beds
2 Baths
Town Of Oakland #6108 SubDv.
34760 Zip Code

2249 Standing Rock Circle, Oakland image

2249 Standing Rock Circle, Oakland $358,920

Brand NEW energy-efficient home ready NOW! Enjoy cooking in this Kipling home's open kitchen with upgraded cabinets and countertops. Upstairs game room is perfect for ent...

3 Beds
2.5 Baths
Oakland Trails SubDv.
34787 Zip Code

Oakland $1,750,000

Rare opportunity for a 11 home development project or an estate home. own 7 (more or less) acres with 251 feet fronting on 2,400 acre Johns Lake. Ideal setting for an est...

34787 Zip Code

410 Largovista Drive, Oakland $1,250,000

First Time Offered and Rare Opportunity! LAKEFRONT and LARGE--this Luxurious one owner custom built home on John's lake is located in the Gated Community of Johns Landin...

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

520 W Sadler Avenue, Oakland $58,900

Beautiful shaded lot in the quickly developing town of Oakland. Build a home or keep this lot for future development. The lot is on the unpaved W Sadler Ave and faces t...

Oakland Town SubDv.
34760 Zip Code

2217 Gopher Tortoise Terrace, Oakland image

2217 Gopher Tortoise Terrace, Oakland — 15 $286,690 ▲

Under Construction. BRAND NEW TOWNHOME - COMPLETE EARLY JANUARY! If you are looking for a low maintenance, peaceful place to call home, look no further. This brand-new to...

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

1152 Hull Island Drive, Oakland $852,835 ▲

Under Construction. With 5 beds, 4 ½ baths, a loft, a sunroom, and a 3-car garage, this plan puts the space where you need it without skimping on the style and design. En...

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

2205 Gopher Tortoise Terrace, Oakland image

2205 Gopher Tortoise Terrace, Oakland — 14 $284,810 ▲

Under Construction. UNDER CONSTRUCTION! If you are looking for a low maintenance, peaceful place to call home, look no further. This town home is located across from Oak...

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

1907 Iron Horse Way, Oakland $455,285 ▲

Under Construction. This 4 bedroom, 3 bath, with loft home offers 2,638 sqft of living space. This home is stately and impressive with a dramatic two-story foyer. Find a ...

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

324 W Oakland Avenue, Oakland $209,900 ▲

THIS LOT IS ZONED COMMERCIAL BUT CAN BE RE ZONED TO RESIDENTIAL. THIS IS 2 LOTS COMBINED THAT CAN ALSO BE SEPARATED. CLOSE TO THE WEST ORANGE TRAIL AND MAJOR HIGHWAYS FO...

Oakland Town SubDv.
34760 Zip Code

301 S Tubb Street Unit D2, Oakland image

301 S Tubb Street Unit D2, Oakland $850,000 ▼

Great unique opportunity to install your own Dental Equipment and have the patients walk into a great investment towards retirement. This space is a 3,402 sq. ft. which ...

Oakland Place Condo SubDv.
34760 Zip Code

623 Largovista Drive, Oakland $199,000 ▲

Rare opportunity! Build your dream home in John Landing Community. This lot has lake views and acess to boat ramp. The community offers tennis courts, park area and fishi...

Johns Landing Ph 01 44/47 SubDv.
34787 Zip Code

739 Regina Circle, Oakland $190,000 ▼

Great Opportunity to build your Dream Home in a Private Established Gated Community on on John's Lake. John's Landing Community is nestled in a serene community in a grea...

Johns Landing Ph 01 44/47 SubDv.
34787 Zip Code

1008 Hull Island Drive, Oakland $699,000 ▼

AMAZING True large 5 bedrooms, 3 full baths split floor plan, w/ large office, formal dining room & vaulted ceilings. open concept kitchen family room with 3 sets of glas...