Homes for Sale in Oakland

Homes in Oakland offer buyers an amazing lifestyle, active trailside and easy access to the shopping and dining of Downtown Winter Garden. The Oakland Realtors of the Erica Diaz Team offer home buyers a quick and easy transaction in most cases closing faster and less money than your average agent. We’ll help you find your next historic Oakland home with shade trees and mature neighborhoods. Take some time to browse the homes below or reach out to the Erica Diaz Team and let us find the dream home for you.

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$500,000

1889 STANDING ROCK CIRCLE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
33Picture(s)
2,041Sqft
Cozy bungalow meets the open aura of contemporary living! Just 5 years old and in mint condition, this 3 bedroom, 2.5 bath is just what you're looking for! The downstairs is all about comfortable living with family and friends. Ceramic flooring works beautifully with the cabinetry, granite and backsplash in this light and bright kitchen. Work from home or play at home in the office.

$250,000

208 OAKLAND AVENUE
SANFORD, Florida

4Bedroom(s)
1Bathroom(s)
13Picture(s)
1,320Sqft
This 3 bedroom 1 bath home will make a great rental to add to your portfolio or great started home. The enclosed back porches could be used as 2 additional bedrooms making it a 5 bedroom. Well maintained shed for storage in the backyard. Come see this home today.

$500,000

633 HULL ISLAND DRIVE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
17Picture(s)
2,200Sqft
Welcome to OAKLAND. NO HOA!!!! This spacious home with an additional detached two car garage is steps away from the West Orange Trail, 2 minutes from the much desired DOWN TOWN WINTER GARDEN shops, restaurants, farmers market, splash pad, and so much more. Located near all the major highways for easy access to where you need to go.

$575,000

229 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
34Picture(s)
3,449Sqft
Back on the market and with a price reduction! 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 double a/c and a screened in pool is the perfect family home.

$470,000

711 STRIHAL LOOP
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
27Picture(s)
2,135Sqft
Welcome Home to Johns Landing! This home is completely renovated inside and out! The split floor plan has 3 generously sized bedrooms and 2 bathrooms.

$369,500

401 HERRIOTT AVENUE
OAKLAND, Florida

2Bedroom(s)
2Bathroom(s)
27Picture(s)
853Sqft
Brand New colonial styled home in the heart of Oakland, Florida. Built entirely in 2022 and completed in August 2022. Spacious kitchen with gorgeous Brazilian granite counter tops and full set of stainless steel appliances that includes upgraded faucet, sink and disposal. Over range microwave and a sit down bar/counter.

$549,900

311 LARGOVISTA DRIVE
OAKLAND, Florida

4Bedroom(s)
2Bathroom(s)
51Picture(s)
3,146Sqft
Price drop for a quick sale! Enter the private gates of the esteemed neighborhood of Johns Landing, a well-maintained community on the shoreline of Johns Lake. Welcome home to your move-in ready gem with an open floor concept and high ceilings that make this home feel grand.

$549,990

2518 STONE CREEK COURT
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
55Picture(s)
1,975Sqft
Virtual Tour https://bit.ly/3C3vfUA Beautiful 3 bed 2 bath home set on end lot in a cul de sac located in the town of Oakland. This is Pulte Arbordale Floor plan with so many upgrades.

$680,000

15348 OAKLAND AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
3Bathroom(s)
42Picture(s)
1,941Sqft
Welcome to this charming historical 3 bed, 3 bath home located a heartbeat from Downtown Winter Garden. Surrounded by hundred-year-old oak trees, you have a unique opportunity to call this once-in-a-lifetime estate dating back to the late 1800s your home. Close to an acre of land for you to enjoy, complete with a historic barn and a chalet.

$699,999

16 OAKLAND POINTE CIRCLE
OAKLAND, Florida

5Bedroom(s)
3Bathroom(s)
38Picture(s)
3,413Sqft
One or more photo(s) has been virtually staged. Come see this one-of-a-kind, beautiful 5-bedroom, 3-bathroom custom built home on a 0.3-acre corner lot in the heart of quaint, historic Oakland.

$475,000

1879 WHITE FEATHER LOOP
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
40Picture(s)
2,029Sqft
Gorgeous Oakland Trails home with ALL of the bells and whistles! Situated on a premium, large lot on the highly-coveted "inner loop," this home boasts head-to-toe stone facade, pavered driveway, and an upgraded tile roof.

$485,000

2027 STANDING ROCK CIRCLE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
19Picture(s)
1,744Sqft
One or more photo(s) has been virtually staged. Fantastic 3 bedroom home in sought after Oakland location. The impeccable kitchen has beautiful quartz counters, stylish tile backsplash, and sleek modern appliances. Lighting, ceiling fans, and fixtures throughout, making this home ready for you to move in right away! The primary bedroom offers a stylish ensuite.

$289,500

406 OAKLAND STREET
LEESBURG, Florida

6Bedroom(s)
2Bathroom(s)
27Picture(s)
1,528Sqft
LOOK.LOOK.................... BETTER RATES THAN THE LENDERS ARE GIVING YOU TODAY !!!!!!!!!!!!!!!!!!!!!!!!GET THIS ASSUMABLE MORTGAGE !!!! ONLY 2.5% INT RATE ......... ................Great income opportunity . Tenants are in place already, Rent is month to month with utilities included. Unless you are looking for a home to live in it yourself.

$605,000

2139 BAY LINE ROAD
OAKLAND, Florida

4Bedroom(s)
3Bathroom(s)
32Picture(s)
2,281Sqft
RARE CONSERVATION VIEWS in Lake front Hull Island community just minutes from picturesque downtown Winter Garden. This 4 bed, 3 bath home is a rare find with incredible views and designer upgrades throughout. Off the foyer, find a bedroom with its own full bath at the front of the home.

$640,000

1301 JOHNS COVE LANE
OAKLAND, Florida

4Bedroom(s)
2Bathroom(s)
21Picture(s)
2,495Sqft
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, Hwy 50 to head in any direction. It is only 20 minutes away from Downtown Orlando and Universal Studios Orlando.

$1,099,999

793 OAKLAND ROAD
ALTAMONTE SPRINGS, Florida

4Bedroom(s)
2Bathroom(s)
63Picture(s)
3,760Sqft
This private luxury Estate nestled in Altamonte Springs is a very rare gem. Enter through private gates to the circular driveway, overlooking a gorgeously landscaped estate, with privacy established by beautiful bougainvillea covered fencing, keeps you tucked away from the neighbors.

$515,000

1071 STATIONSIDE DRIVE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,787Sqft
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 throughout, new appliances, new cabinets, countertops, and lighting, a 3 year old roof, 3 year old AC, 3 year old septic, and so much more.

$714,260

1328 FOLTZ LOOP
OAKLAND, Florida

4Bedroom(s)
3Bathroom(s)
14Picture(s)
2,281Sqft
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 the front of the home. This makes a fantastic guest suite or possible home office, and you can see packages being delivered through the large, front-facing window.

$1,599,000

15198 OAKLAND AVENUE
WINTER GARDEN, Florida

4Bedroom(s)
4Bathroom(s)
11Picture(s)
3,405Sqft
Pre-Construction. To be built. Fall in love with this modern farmhouse masterpiece within Winter Garden’s premier luxury new home community, Oakland Hills! Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.

$815,000

10 W OAKLAND AVE
OCOEE, Florida

4Bedroom(s)
3Bathroom(s)
43Picture(s)
1,720Sqft
Location, Location, Location !!! This will be your only opportunity to purchase this Prime Corner Lot and be part of the Ocoee Master Plan, The City of Ocoee has stated that this could be Rezoned Commercial. This Corner lot is directly across from the New City Hall but will still have a view of Starke Lake. Great opportunity to have it rezoned and be in the middle of Downtown Ocoee Center.
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    Who’s Your Oakland Buyer’s Agent?

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