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.
$398,800
2737 BOBCAT CHASE BOULEVARD
OAKLAND, Florida
4Bedroom(s)
2Bathroom(s)
56Picture(s)
2,473Sqft
check out the video: www.2737bobcatchase.site/mls... Job relocation allows one lucky buyer to skip the building process and move right in for the holidays in this ONE YEAR NEW ...DRIFTWOOD Floor plan in one of the hottest zip codes in America. Set on a quiet cul de sac street and right down street from the community pool, this one checks all your boxes is a very hard price range.
$704,260
1088 HULL ISLAND DRIVE
OAKLAND, Florida
4Bedroom(s)
3Bathroom(s)
2Picture(s)
2,815Sqft
Under Construction. Check out this must-see 1-story 4 bedroom, 3 bath home with large open spaces. Upon entry, a spacious foyer with a tray ceiling leads to the formal dining room, also with a tray ceiling. Two guest rooms, both with walk-in closets, a full guest bathroom with a double sink vanity can be found down the hall.
$75,000
106A OAKLAND DRIVE
EUSTIS, Florida
2Bedroom(s)
2Bathroom(s)
13Picture(s)
1,056Sqft
Nestled on the shores of Trout Lake, Country Club Manor is a 55+ community and offers many amenities. Close to shopping, you can ride your golf cart to the grocery store and its only a few miles to Drs., hospital, restaurants, etc. Upon entering this home, you will feel right at home with the beamed ceiling and warm colors this home offers. The home features newer flooring through out.
$950,000
418 LARGOVISTA DRIVE
OAKLAND, Florida
4Bedroom(s)
4Bathroom(s)
53Picture(s)
3,929Sqft
Beautifully REMODELED MEDITERANEAN LAKE FRONT HOME ON 1/2 ACRE lot on the SKIABLE 2500 ACRE JOHNS LAKE in the awesome town of OAKLAND! Minutes from Downtown Winter Garden Resturants and Shopping, Crooked Can Brewery and the West Orange Trail for your outdoor enjoyment.
$262,000
408 POSTELL AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,489Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Prepare to be wowed by this BRAND NEW Oakland Park home! Unlike anything else in Central Florida designed as a forever-home Another beautiful home brought to you by Signature Custom Homes, a premiere central Florida home builder. Own your slice of the historic city of Oakland. Projected 4 to 6 month build time.
$262,000
406 POSTELL AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,489Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Prepare to be wowed by this BRAND NEW Oakland Park home! Unlike anything else in Central Florida designed as a forever-home Another beautiful home brought to you by Signature Custom Homes, a premiere central Florida home builder. Own your slice of the historic city of Oakland. Projected 4 to 6 month build time.
$262,000
524 HULL AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,489Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Another beautiful home brought to you by Signature Custom Homes, a premiere central Florida home builder. Own your slice of the historic city of Oakland. Unlike anything else in Central Florida designed as a forever-home a projected 4 to 6 month build time.
$262,000
405 POSTELL AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,489Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Prepare to be wowed by this BRAND NEW Oakland Park home! Unlike anything else in Central Florida designed as a forever-home Another beautiful home brought to you by Signature Custom Homes, a premiere central Florida home builder. Own your slice of the historic city of Oakland. Projected 4 to 6 month build time.
$1,120,000
15210 OAKLAND AVENUE
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
9Picture(s)
3,640Sqft
Under Construction. Fall head-over-heels for this modern farmhouse custom masterpiece situated 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.
$1,749,000
912 JOHNS POINT DRIVE
OAKLAND, Florida
5Bedroom(s)
6Bathroom(s)
90Picture(s)
6,065Sqft
This LUXURY LAKEFRONT ESTATE is nestled in the private, gated community of John’s Cove on a large, beautifully landscaped .63 acre homesite. Upon entry into your home, you will be awed by the stunning LAKE VIEWS through magnificent windows and over 30’ ceilings of the grand living area.
$725,000
8161 OAKLAND PLACE
ORLANDO, Florida
5Bedroom(s)
4Bathroom(s)
35Picture(s)
2,935Sqft
Have MULTIPLE CARS, A BOAT, AN RV? Need a place to park them? Want to be in the Windermere/Dr Phillips area but with NO HOA and in an un-incorporated area of Orange County??? LOOK NO FURTHER!!! This acre of land (0.99 acres) and lovely house are waiting for you to call it home.
$775,000
306 TUBB STREET
OAKLAND, Florida
5Bedroom(s)
3Bathroom(s)
35Picture(s)
3,709Sqft
What a rare find! This beautifully remodeled five bedroom, three and a half bathroom Oakland home has historic charm and tons of character. New from top to bottom, the oversized double lot is a stone’s throw away from the west orange trail and boasts a brand new oversized three car garage.
$1,195,000
101 STARR STREET
OAKLAND, Florida
3Bedroom(s)
3Bathroom(s)
18Picture(s)
2,519Sqft
Modern Farmhouse with 4200 sqft under roof. Located in the traditional downtown Oakland area, the home sits among grand oaks reminiscent to old Florida. This home was built in 2020 by custom Home Builder Westmont, using innovative building techniques and environmental standards. Expertly landscaped. This home is a must see.
$364,900
1787 WHITE FEATHER LOOP
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
77Picture(s)
2,183Sqft
It really is all about Location and this Meritage community hit the nail on the head! Tucked away enough to feel private yet convenient enough to the Turnpike, SR50 and adjacent to Killarney Station on the West Orange Trail for your evening walks or bike rides with the family.
$808,665
1232 HULL ISLAND DRIVE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
47Picture(s)
3,722Sqft
Welcome home to this lakefront 5-bed, 4-bath, 3-car garage plan. Upon entry you can’t help but notice the upgraded angled staircase. The formal dining room offers access, past a butler’s pantry alcove and walk-in pantry to the kitchen and open-concept great room. This space is where the lake living begins, with beautiful views of Lake Apopka to soak in.
$385,000
1805 STANDING ROCK CIR
OAKLAND, Florida
4Bedroom(s)
3Bathroom(s)
147Picture(s)
2,418Sqft
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 Garden shopping,dining and nightlife.
$929,750
620 TUBB STREET
OAKLAND, Florida
6Bedroom(s)
7Bathroom(s)
41Picture(s)
5,614Sqft
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 stately residential home. Bring your ideas and take a look. This distinctive 19th Century Oakland Manor House sits on a .8-acre park-like setting in the charming town of Oakland.
$609,000
109 HULL AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
37Picture(s)
3,086Sqft
~VINTAGE ~AMAZING HALF ACRE LOTS IN THE HEART OF HISTORIC OAKLAND~ OVERSIZED 3 AND HALF CAR GARAGE~BRING YOUR BOAT AND YOUR RV!!~NO HOA~ EXTENDED PAVER DRIVEWAY~MAJORLY RENOVATED IN PRESERVING THE INTEGRITY & ORIGINAL BEAUTY.~ PINE FLOORS~ TIN ROOF, BRICK PATIOS,FRONT PORCH, SHADED OLD OAK TREES, HOUSE HAS 2 NEW A/C SYSTEMS, LOT SIZE IS 150x150 .
$856,835
1152 HULL ISLAND DRIVE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
3Picture(s)
4,009Sqft
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. Enjoy beautiful views of Lake Apopka through the plethora of glass on the back of the home. The family room showcases a stunning tray ceiling and beautiful unobstructed views of the lake.
$459,285
1907 IRON HORSE WAY
OAKLAND, Florida
4Bedroom(s)
3Bathroom(s)
4Picture(s)
2,626Sqft
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 bedroom and full bath downstairs, perfect for the guests. The large family room, breakfast nook, and kitchen area all open up to the rear of the home.
$744,000
801 OAKLAND ROAD
ALTAMONTE SPRINGS, Florida
7Bedroom(s)
3Bathroom(s)
57Picture(s)
4,994Sqft
Seller credit to buyer 10k for renovation with accepted offer, come see it today! INVESTOR OPPORTUNITY OR SPRAWLING FAMILY COMPOUND ON 1.56 ACRES...PACKAGE DEAL... LISTING PRICE INCLUDES BOTH (801 Oakland Rd & 797 Oakland Rd). This is an INCREDIBLE OPPORTUNITY with a great location in Altamonte Springs, right on the border of Maitland.
$699,000
1008 HULL ISLAND DRIVE
OAKLAND, Florida
5Bedroom(s)
3Bathroom(s)
61Picture(s)
2,928Sqft
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 glass sliding doors looking out at stunning view of the pool/spa + waterfall, porch (veranda) plus Lake Apopka and Oakland nature preserve. 5" BASEBOARDS throughout, custom trim work around windows and doors.
$286,690
2217 GOPHER TORTOISE TERRACE
OAKLAND, Florida
2Bedroom(s)
2Bathroom(s)
11Picture(s)
1,497Sqft
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 townhome built by Pulte Homes is located across from the Oakland Nature Preserve, where you will find your place to relax and feel undisturbed.
$284,810
2205 GOPHER TORTOISE TERRACE
OAKLAND, Florida
2Bedroom(s)
2Bathroom(s)
8Picture(s)
1,497Sqft
Under Construction. UNDER CONSTRUCTION! If you are looking for a low maintenance, peaceful place to call home, look no further. This town homeis located across from Oakland Nature Preserve, where you will find your place to relax and your own private courtyard.
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!