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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$650,000

614 JOHNS LANDING WAY
OAKLAND, Florida

5Bedroom(s)
3Bathroom(s)
45Picture(s)
3,047Sqft
Step into luxury living at Johns Landing, an exclusive gated community. This exquisite home boasts crown molding throughout, a chef's dream kitchen with two built-in ovens, an oversized gas range, and upgraded granite countertops. The walk-in pantry is a gourmet's delight. The family room features a cozy gas fireplace and ample space for relaxation.

$739,000

112 SADLER AVENUE
OAKLAND, Florida

4Bedroom(s)
2Bathroom(s)
53Picture(s)
2,438Sqft
This custom built home is on the market for the first time and is nestled in the heart of Oakland! Sitting on just under a half acre of land, this delightful property offers a perfect blend of comfort, style, and convenience, making it an ideal place to call home.

$1,450,000

1216 HULL ISLAND DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
52Picture(s)
4,224Sqft
Welcome to your unparalleled lakefront sanctuary! This stunning home exudes luxury at every turn, with over $200k in upgrades meticulously added atop the already exquisite builder standards.

$674,900

302 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
86Picture(s)
3,863Sqft
Nestled within the tranquil, gated community at Johns Landing, awaits a captivating opportunity for discerning homeowners seeking to personalize their dream retreat. This 5 Bedrooms 4 bathrooms offer generous space, functionality, and storage.

$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.

$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.

$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.

$479,000

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.

$765,000

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

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    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!