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

1980 STANDING ROCK CIRCLE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
35Picture(s)
2,020Sqft
(Back on the market due to buyer financing issues)***Why wait to build a new home?*** Stunning move in ready Meritage Homes ‘Bailey’ model in the desirable ‘Oakland Trails’ community. Beautiful 3 Bedroom/2 Bathroom home with 2020 sq ft meticulously maintained by the original owner. Very functional floorplan with split bedrooms and centered with luxurious kitchen.

$1,599,900

1216 HULL ISLAND DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
53Picture(s)
4,277Sqft
Your turnkey luxurious lakefront home is here! Move-in ready and we mean ready, as in all the furnishings stay and that is just the beginning of the many amenities that this home offers. This home is set up in such a way that there are no neighbors in the front or the back.

$669,500

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.

$650,000

502 OAKLAND TERRACE
LAKE MARY, Florida

4Bedroom(s)
2Bathroom(s)
39Picture(s)
2,000Sqft
Welcome home to this beautiful and unique 4 bedroom, 2.5 bath South Carolina Plantation house with a separate 1 bedroom carriage house situated on a generous almost half acre lot. The steep A-frame roofline with classic dormer windows and an inviting covered porch create a charming country curb appeal as you approach up the circular driveway.

$952,959

1049 EAGLECREST DRIVE
OAKLAND, Florida

4Bedroom(s)
3Bathroom(s)
14Picture(s)
2,612Sqft
Under Construction. Live your best life in the superb craftsmanship and incredible comfort of The Mabel new home plan. Soaring ceilings and sleek spaces for living and dining make the open floor plan a beautiful place to play host. The streamlined kitchen provides an easy culinary layout for the resident chef while granting a delightful view of the sunny family room and dining area.

$529,900

2518 STONE CREEK COURT
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
68Picture(s)
1,975Sqft
Great Opportunity to own a single-story home in the historic town of Oakland! This home sits on a corner homesite in a Cul de sac that is located directly across the street from the West Orange Trail and the Oakland Nature Preserve. Longleaf At Oakland is just 3 miles from Downtown Winter Garden & The Plant Street Market which makes this home a prime location to live.

$479,999

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.

$319,900

1622 OAKLAND DRIVE
DELTONA, Florida

3Bedroom(s)
2Bathroom(s)
39Picture(s)
1,760Sqft
Check out this well-maintained 3 bedroom 2 bath home in the heart of Deltona Lakes. This spacious home features a split floor plan with the master bedroom on the left side of the home and the other two bedroom and one bathroom are on the right side of the home. There is plenty of living space with a family room, living room and dining room, as well as the screened lanai.

$699,000

832 HULL ISLAND DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
40Picture(s)
3,734Sqft
STUNNER!! Enjoy the serenity of Hull Island in this gorgeous 5 bed 4 bath Newcastle floorplan from M/I Homes. Plenty of natural light greets you as you enter this home. The formal dining connects to the fabulous kitchen adorning quartz countertops, gas cooktop, double ovens, stainless appliances, and a separate area for coffee station. Large island is perfect for gatherings of any size.

$299,900

210 POLLARD STREET
OAKLAND, Florida

2Bedroom(s)
2Bathroom(s)
37Picture(s)
1,046Sqft
PRICE REDUCTION! SPECIAL FINANCING INCENTIVES OFFRED WHEN USING PREFERRED LENDER MAY INCLUDE A $2,000 CREDIT TOWARDS CLOSING COSTS, A FREE APPRAISAL, AND TWO YEARS OF DISCOUNTED PAYMENTS!rnFor that rural feeling and laid-back lifestyle, this charming fully updated cottage, located on an oversized corner lot in Oakland, is just what you’ve been dreaming of! The 2 bedroom, 2 bath home welc

$820,000

341 LARGOVISTA DRIVE
OAKLAND, Florida

5Bedroom(s)
4Bathroom(s)
93Picture(s)
4,475Sqft
OWNER FINANCING or LEASE PURCHASE OPTION AVAILABLE. No qualifying & No credit check! Minimal paperwork & quick closing!rnrnLOCATION, LOCATION, LOCATION...right in the center of Florida, North, South, East, & West, close to everything. It's only 2 minutes to get onto the Florida Turnpike.

$319,900

401 HERRIOTT AVENUE
OAKLAND, Florida

2Bedroom(s)
2Bathroom(s)
25Picture(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.

$1,495,000

402 E GULLEY AVENUE
OAKLAND, Florida

4Bedroom(s)
3Bathroom(s)
8Picture(s)
3,248Sqft
One or more photo(s) has been virtually staged. Pre-Construction. To be built. No HOA! Direct access to the West Orange Trail! Minutes from Downtown Winter Garden’s shops, restaurants and brewery! Oversized lot! New construction! Look no further than this pristine home located in the highly desirable Town of Oakland in Winter Garden.

$449,990

2441 STANDING ROCK CIRCLE
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
31Picture(s)
1,759Sqft
You do not want to miss this outstanding opportunity! Call This phenomenal home is less than five years old and offers tons of upgrades! This property offers nearly 1800 ft.² of beautifully maintained living spaces. The first floor showcases expensive living area with luxury vinyl plank flooring throughout.

$500,000

1150 TRAILSIDE COURT
OAKLAND, Florida

3Bedroom(s)
2Bathroom(s)
48Picture(s)
2,284Sqft
This is a beautiful and spacious home built custom for the current and original owners. In this 3 bedroom 2 bath home you will find a great room, formal living room, formal dining room, and an office/den. Off the open kitchen that over looks the great room, you have a spacious breakfast nook.

$539,000

1301 JOHNS COVE LANE
OAKLAND, Florida

4Bedroom(s)
2Bathroom(s)
15Picture(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.

$1,599,000

15198 OAKLAND AVENUE
WINTER GARDEN, Florida

4Bedroom(s)
4Bathroom(s)
20Picture(s)
3,405Sqft
Under Construction. 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.

$799,900

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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