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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$510,000

1981 WHITE FEATHER LOOP
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
28Picture(s)
2,183Sqft
Wow...location, location, location!! Welcome home to Oakland Trails! This beautiful 3 bedroom/2.5 bath energy efficient Meritage Home has it all. Right away, you will be taken in by the exterior of this home with its large front porch and its views to the "Park"...the park is a community green space that no homes can be built on.

$285,000

3316 OAKLAND ROAD
LAKELAND, Florida

5Bedroom(s)
3Bathroom(s)
51Picture(s)
2,040Sqft
Step into spacious comfort and modern convenience with this expansive home, offering over 2,000 square feet of welcoming living space. Perfect for those craving space to grow, this property presents a rare opportunity to own a slice of tranquility on nearly half an acre of beautifully fenced land.

$702,000

341 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
3Bathroom(s)
34Picture(s)
4,145Sqft
Beautiful, spacious luxury home with serene pond view & located at the highly sought after John's Landing lake-front community on the edge of Oakland & Winter Garden. Over 4,000 sqft. of living space with open layout, formal dining, upstairs loft, laundry room, garden bath, 2 car garage, & so much more! Home backs up to a sizeable pond & has in-ground pool with screened enclosure.

$135,000

618 OAKLAND ROAD
AUBURNDALE, Florida

3Bedroom(s)
2Bathroom(s)
2Picture(s)
1,188Sqft
INVESTORS SPECIAL!! This beauty in the roughs needs some TLC and it can have so much potential! Property is been sold As-Is.

$998,000

32 OAKLAND POINTE CIRCLE
OAKLAND, Florida

4Bedroom(s)
3Bathroom(s)
31Picture(s)
2,277Sqft
One or more photo(s) has been virtually staged. Price improvement just made on this beautiful property! In the heart of historic Oakland, welcome to the ultimate lakefront living experience with an opportunity to own a beautiful, 4 bedroom, 3 full bath home, on .

$675,000

328 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
3Bathroom(s)
78Picture(s)
3,324Sqft
Welcome to this exquisite 5-bedroom, 3.5-bathroom residence boasting 3,234 square feet of luxurious living space. Nestled within a gated community, this modern-designed home offers an elevated standard of living with thoughtful upgrades throughout.

$255,000

411 HULL AVENUE
OAKLAND, Florida

3Bedroom(s)
1Bathroom(s)
4Picture(s)
1,029Sqft
Welcome to a promising canvas awaiting your personal touch! This 3 bedroom, 1.5-bathroom home presents a wonderful opportunity for those with a vision for transforming a space into their dream residence. In need of light rehab, this property allows you to infuse your unique style while creating a comfortable and personalized haven.

$612,000

1191 TRAILSIDE COURT
OAKLAND, Florida

4Bedroom(s)
2Bathroom(s)
39Picture(s)
2,565Sqft
Absolutely stunning 4br/2.5ba home located next to the West Orange Bike Trail in desirable Oakland. The pictures tell the story of this immaculate property that has been completely updated. With roof and AC from 2019, You will love the gourmet kitchen and open floor plan.

$259,000

1948 OAKLAND PARK DRIVE
LAKE WALES, Florida

3Bedroom(s)
2Bathroom(s)
20Picture(s)
1,352Sqft
Sitting at the end of a dead end street, on OVER 1/4 ACRE lot in Lake Wales, this 3 Bedroom, 2 Bath house is a solid starter home or investment opportunity! Inside, you'll find there's plenty of space in the living room for all your entertaining needs that leads out to your very own, fully enclosed Sun Room. Perfect for enjoying the outdoors of Florida year round.

$614,500

320 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
43Picture(s)
3,450Sqft
Spectacular 5 bedroom home is the sought after Gated community of John's Landing. Enter this immaculate home to find a spacious first floor living space consisting of downstairs office/den, Huge living room with built-in shelves, large airy eat in kitchen with sliding glass doors to go outside to a screened covered patio and huge fenced back yard.

$489,900

636 STRIHAL LOOP
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
35Picture(s)
2,054Sqft
Welcome to the epitome of refined living where luxury meets practicality. This immaculate residence, nestled within a gated community, not only boasts a brand-new roof for worry-free living but also showcases exquisite upgrades throughout. Marvel at the sleek granite countertops and stylish backsplash in the chef's kitchen.

$807,000

2340 STANDING ROCK CIRCLE
OAKLAND, Florida

5Bedroom(s)
3Bathroom(s)
45Picture(s)
3,416Sqft
This is it! The Oakland Trails community is where you want to be, a highly sought after and well loved community just minutes from the quaint Winter Garden area. This 5 bedroom 3 bath contemporary home shouts pride of ownership throughout.

$787,595

607 OAKLAND AVENUE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
52Picture(s)
3,406Sqft
This stunning 4-bedroom, 3.5-bath home in Oakland offers luxurious features like custom tile flooring, tray ceilings, and a gourmet kitchen with premium upgrades. The private screened-in pool and wood-burning fireplace in the family room create a perfect retreat. The spacious owner's suite includes a walk-in closet and a glassed-in shower.

$460,000

202 OAKLAND AVENUE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
7Picture(s)
1,600Sqft
Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.
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    Erica Diaz - Winter Garden Realtor

    Who’s Your Oakland Buyer’s Agent?

    Every home buyer should have a buyer’s agent negotiating on their behalf. It’s completely free to the buyer and the Erica Diaz Team can help you close quicker and for less money than the average Oakland realtor. Tell our team of buyers about the perfect Oakland home for you and we’ll find it!