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Oakland
Homes for sale in Oakland, Florida
Date (newest first)
Price (lowest first)
Price (highest first)
View pictures
16436 Parable Wy, Winter Garden, FL 34787
Almost brand new dream house in the heart of Winter Garden. Conservation on the backyard with privacy! This luxurious...
Houses Oakland
689,990
$
View pictures
14498 Sunbridge Cir, Winter Garden, FL 34787
In the beautiful gated community of Bradford Creek, you are greeted with the neighborhood park as you enter the...
Houses Oakland
845,000
$
View pictures
7931 Winter Wren St, Winter Garden, FL 34787
Welcome to 7931 Winter Wren Street, a stunning 5-bedroom, 2.5-bathroom home nestled in the community of Summerlake in...
Houses Oakland
629,000
$
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12061 Windermere Crossing Cir, Winter Garden, FL 34787
Introducing an exceptional opportunity to reside in Cambridge Crossing, Winter Garden's premier gated community. This...
Houses Oakland
795,000
$
View pictures
16706 Rusty Anchor Rd, Winter Garden, FL 34787
Welcome to your dream home nestled in the exclusive and highly sought-after community, Waterside on John's Lake....
Houses Oakland
949,999
$
View pictures
9250 Cut Shot Dr, Winter Garden, FL 34787
Location, location, location! The luxury, 5 bedroom 3 bath home is located in a solar community of Panther View. The...
Houses Oakland
599,000
$
View pictures
10265 Spring Shores Dr, Winter Garden, FL 34787
Welcome to the Winter Garden community of Waterleigh and this feels like new 4-bedroom, 3-full bath home featuring a...
Houses Oakland
725,000
$
View pictures
1832 Jean Marie Dr, Winter Garden, FL 34787
Nestled in the gated community of Carriage Pointe, this updated single-story home boasts everything inside and out...
Houses Oakland
719,000
$
View pictures
14501 Grove Resort Ave #3526, Winter Garden, FL 34787
Welcome to your dream escape at the Grove Resort! Picture yourself in this 3-bedroom, 2-bathroom Condo Hotel Unit on...
Houses Oakland
574,900
$
View pictures
16331 Honey Harvest St, Winter Garden, FL 34787
Pre-Construction. To be built. MLS # O6188680 REPRESENTATIVE PHOTOS ADDED. Enter the charming oasis that lies within...
Houses Oakland
646,450
$
View pictures
712 Santee Terre Ln, Winter Garden, FL 34787
Expect to be impressed with this beautifully appointed and updated pool home in the desirable Westfield Lakes...
Houses Oakland
750,000
$
View pictures
8222 Topsail Pl, Winter Garden, FL 34787
Welcome home to this like-new luxury home in Lakeshore Preserve, the highly desirable community in Horizon West (West...
Houses Oakland
1,234,000
$
View pictures
5060 Palmetto Park Dr, Winter Garden, FL 34787
Welcome to the pinnacle of luxury living in the beautiful Orchard Hills community, nestled within the charming town...
Houses Oakland
925,000
$
View pictures
1425 Williams Rd, Winter Garden, FL 34787
Welcome to this exquisite home located in the beautifully manicured community of Waterside in Winter Garden. Built...
Houses Oakland
584,900
$
View pictures
16771 Oakboro St, Winter Garden, FL 34787
One or more photo(s) has been virtually staged. DON'T MISS OUT ON THIS BEAUTIFUL CUSTOM Home! UPGRADE GALORE! This...
Houses Oakland
875,000
$
View pictures
15115 Lake Claire Overlook Dr, Winter Garden, FL 34787
Under contract-accepting backup offers. If you are looking for the perfect mix of relaxing sunset LAKEFRONT views...
Houses Oakland
695,000
$
View pictures
3306 Hanging Tide St, Winter Garden, FL 34787
EXTREMELY MOTIVATED SELLER, Discover your ideal retreat nestled in the heart of Winter Garden, Florida, just moments...
Houses Oakland
665,000
$
View pictures
617 S Boyd St, Winter Garden, FL 34787
The property is to be sold AS-IS and requires some renovation. The Seller has never lived in the property and is not...
Houses Oakland
160,000
$
View pictures
2255 Standing Rock Cir, Oakland, FL 34787
Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a...
Houses Oakland
515,000
$
View pictures
216 Jean St, Winter Garden, FL 34787
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Garden, FL! Nestled on over 1/3...
Houses Oakland
399,900
$
View pictures
645 Meadow Glade Dr, Winter Garden, FL 34787
PRIDE OF OWNERSHIP shows throughout this SINGLE-STORY, 3 BEDROOM/2 BATH/2-CAR GARAGE home! As you step inside,...
Houses Oakland
485,000
$
View pictures
14209 Lakeview Park Rd, Winter Garden, FL 34787
MODEL PERFECT & MOVE IN READY HOME in Winter Garden's desirable Lakeview Pointe at Horizon West! This Pulte built...
Houses Oakland
575,000
$
View pictures
16832 Broadwater Ave, Winter Garden, FL 34787
Step into luxury with this stunning 5 bedroom, 4 and a half bath home in one of Winter Garden's Finest Gated...
Houses Oakland
1,325,000
$
View pictures
5180 Citrus Leaf Blvd, Winter Garden, FL 34787
AMAZING OPPORTUNITY! This new construction home will not last long! With an open floorplan and a lot of natural...
Houses Oakland
990,000
$
View pictures
12127 Bracco St, Winter Garden, FL 34787
Amazing! Better than BRAND NEW! This 4-bedroom 2.5 bath with loft beauty is available in the desirable new community...
Houses Oakland
520,000
$
View pictures
9875 Beach Port Dr, Winter Garden, FL 34787
LUXURY LAKEFRONT HOME! Welcome to 9875 Beach Port Dr., This stunning single-family property is situated in the highly...
Houses Oakland
1,350,000
$
View pictures
16306 Honey Harvest St, Winter Garden, FL 34787
Pre-Construction. To be built. MLS # T3512753 REPRESENTATIVE PHOTOS ADDED. Step into the serene sanctuary that...
Houses Oakland
622,440
$
View pictures
927 Copenhagen Way, Winter Garden, FL 34787
Welcome to this sought-after Winter Garden gem! This charming 3-bedroom, 2-bathroom home boasts a spacious layout...
Houses Oakland
400,000
$
View pictures
8905 Sonoma Coast Dr, Winter Garden, FL 34787
Amazing, 5 bedroom, 4 bath, water front home in highly desirable Waterleigh west of Disney. This amazing home has a...
Houses Oakland
820,000
$
View pictures
7536 Tangerine Knoll Loop, Winter Garden, FL 34787
Introducing this meticulously maintained four-bedroom, three-bath home, built in 2018 and boasting a plethora of...
Houses Oakland
739,900
$
View pictures
12260 Bracco St, Winter Garden, FL 34787
Under Construction. Brand new, energy-efficient home available by Apr 2024! Enjoy the functionality of the open...
Houses Oakland
538,685
$
View pictures
1206 Portmoor Way, Winter Garden, FL 34787
Immaculate Golf-Front Oasis in Gated Stoneybrook West, Winter Garden! This Augusta model home offers stunning golf...
Houses Oakland
507,000
$
View pictures
903 Meadow Glade Dr, Winter Garden, FL 34787
Welcome to this enchanting 4-bedroom, 2-bath residence, perfectly placed in the serene Covington Chase community,...
Houses Oakland
510,000
$
View pictures
14501 Grove Resort Ave #2716, Winter Garden, FL 34787
Great commissions and easy to show!! Come One, Come All! This is perfect for a family or anyone looking to use as an...
Houses Oakland
599,000
$
View pictures
16150 Johns Lake Overlook Dr, Winter Garden, FL 34787
SERENITY NOW!!:) ENJOY LAKEFRONT ELEGANCE IN THIS IMMACULATE, LUXURY HOME IN POPULAR GATED COMMUNITY. Imagine...
Houses Oakland
2,375,000
$
View pictures
15726 Shorebird Ln, Winter Garden, FL 34787
This is the LUXURY HOME you have been looking for! Immaculate 4-bedroom, 4-bath on premium corner lot and beautifully...
Houses Oakland
975,000
$
View pictures
3111 Shadow Pond Terrace, Winter Garden, FL 34787
Beautiful Estate Home, Single Family- one Story, more than half Acre Lot in a great Location of Winter Garden, easy...
Houses Oakland
799,000
$
View pictures
14256 Magnolia Ridge Loop, Winter Garden, FL 34787
Welcome to this exquisite two-story residence nestled within the highly sought-after Orchard Hills Community....
Houses Oakland
779,000
$
View pictures
14501 Grove Resort Ave #2436, Winter Garden, FL 34787
Welcome to luxury living at The Grove Resort in Orlando! This stunning condo offers comfort and convenience with its...
Houses Oakland
436,721
$
View pictures
15540 Camp Dubois Crescent, Winter Garden, FL 34787
One or more photo(s) has been virtually staged. **WELCOME HOME** Tucked away in the sought-after Signature...
Houses Oakland
540,000
$
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