Recently Sold Single Family Homes in Oakland, FL

67 homes

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SOLD
FEB 6, 2026
$1,500,000
6 Beds
5 Baths
3,528 sqft
1008 Tilden Oaks Trl,
Winter Garden, FL 34787
CHARLES RUTENBERG REALTY ORLANDO
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SOLD
FEB 6, 2026
$578,000
3 Beds
2 Baths
1,857 sqft
1808 Western Trailway Dr,
Oakland, FL 34760
UNLOCK REALTY GROUP INC
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SOLD
FEB 3, 2026
$592,000
5 Beds
4 Baths
3,903 sqft
219 Largovista Dr,
Oakland, FL 34787
INTERMIX REAL ESTATE INC
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SOLD
JAN 30, 2026
$649,000
5 Beds
4 Baths
4,246 sqft
207 Largovista Dr,
Oakland, FL 34787
COLDWELL BANKER REALTY
SOLD
JAN 29, 2026
$537,000
3 Beds
2.5 Baths
2,010 sqft
2090 Standing Rock Cir,
Oakland, FL 34787
CREEGAN GROUP
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SOLD
JAN 28, 2026
$505,000
4 Beds
2 Baths
2,094 sqft
222 Largovista Dr,
Oakland, FL 34787
ORANGE REALTY PROFESSIONALS LLC
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SOLD
JAN 23, 2026
$450,000
3 Beds
2 Baths
1,554 sqft
2690 Bobcat Chase Blvd,
Oakland, FL 34787
LPT REALTY, LLC
SOLD
JAN 23, 2026
$1,575,000
4 Beds
3.5 Baths
4,171 sqft
1096 Riverway Dr,
Winter Garden, FL 34787
REAL BROKER, LLC
SOLD
JAN 15, 2026
$535,000
4 Beds
2 Baths
2,490 sqft
610 Strihal Loop,
Oakland, FL 34787
WHEATLEY REALTY GROUP
SOLD
JAN 9, 2026
$950,000
5 Beds
3 Baths
3,563 sqft
1304 Foltz Loop,
Oakland, FL 34787
KELLER WILLIAMS WINTER PARK
SOLD
DEC 30, 2025
$737,500
5 Beds
3 Baths
3,493 sqft
1751 Standing Rock Cir,
Oakland, FL 34787
STOCKWORTH REALTY GROUP
SOLD
DEC 23, 2025
$455,000
3 Beds
2.5 Baths
2,089 sqft
2023 White Feather Loop,
Oakland, FL 34787
OPENDOOR BROKERAGE LLC
SOLD
DEC 15, 2025
$4,383,239
5 Beds
6.5 Baths
6,203 sqft
548 Walker St,
Oakland, FL 34760
CORCORAN PREMIER REALTY
SOLD
DEC 8, 2025
$512,500
3 Beds
2.5 Baths
2,152 sqft
1787 White Feather Loop,
Oakland, FL 34787
KELLER WILLIAMS REALTY AT THE PARKS
SOLD
NOV 24, 2025
$2,275,000
5 Beds
4 Baths
4,798 sqft
530 Largovista Dr,
Oakland, FL 34787
PREMIER SOTHEBYS INT'L REALTY
SOLD
NOV 19, 2025
$2,700,000
4 Beds
5 Baths
5,282 sqft
524 N Pollard St,
Oakland, FL 34787
REGENCY REAL ESTATE LLC
SOLD
NOV 13, 2025
$539,000
4 Beds
3 Baths
2,418 sqft
1873 White Feather Loop,
Oakland, FL 34787
FLORIDA CONNEXION PROPERTIES
SOLD
NOV 4, 2025
$710,000
4 Beds
2 Baths
2,495 sqft
1301 Johns Cove Ln,
Oakland, FL 34787
DALTON WADE INC
SOLD
OCT 31, 2025
$580,000
3 Beds
2.5 Baths
1,811 sqft
2642 Bobcat Chase Blvd,
Oakland, FL 34787
SOLD
OCT 30, 2025
$735,000
5 Beds
3 Baths
3,493 sqft
2340 Standing Rock Cir,
Oakland, FL 34787
KELLER WILLIAMS WINTER PARK
SOLD
OCT 29, 2025
$464,000
3 Beds
2.5 Baths
1,744 sqft
2163 White Feather Loop,
Oakland, FL 34787
OPTIMA ONE REALTY, INC.
SOLD
OCT 27, 2025
$367,500
3 Beds
2 Baths
1,336 sqft
500 W Oakland Ave,
Oakland, FL 34760
DALTON WADE INC
SOLD
OCT 24, 2025
$785,000
4 Beds
2 Baths
2,260 sqft
1212 Civitas Way,
Oakland, FL 34787
BHHS FLORIDA REALTY
SOLD
OCT 23, 2025
$1,660,000
6 Beds
5 Baths
3,911 sqft
102 Hammock Preserve Loop,
Oakland, FL 34787
KELLER WILLIAMS ELITE PARTNERS III REALTY
SOLD
OCT 22, 2025
$525,000
4 Beds
2 Baths
2,176 sqft
233 Largovista Dr,
Oakland, FL 34787
EXP REALTY LLC
SOLD
OCT 10, 2025
$1,520,000
5 Beds
6 Baths
4,373 sqft
812 Johns Point Dr,
Oakland, FL 34787
GILKEY REAL ESTATE
SOLD
OCT 9, 2025
$500,000
3 Beds
2.5 Baths
1,811 sqft
1143 Bobcat Chase Blvd,
Oakland, FL 34787
SERHANT

Recently Sold Homes Near Oakland, FL

We found 30 more homes matching your filters just outside Oakland

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SOLD
JUN 30, 2026
$935,000
4 Beds
3.5 Baths
2,667 sqft
744 Lake Brim Dr,
Winter Garden, FL 34787
BHHS FLORIDA REALTY
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SOLD
JUN 30, 2026
$1,295,000
4 Beds
3 Baths
2,834 sqft
912 Landrum Dr,
Winter Garden, FL 34787
DENIZ REALTY PARTNERS LLC
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SOLD
JUN 29, 2026
$3,950,000
5 Beds
5.5 Baths
5,652 sqft
16146 Pendio Dr,
Montverde, FL 34756
BELLA COLLINA REAL ESTATE CO
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SOLD
JUN 25, 2026
$2,353,078
4 Beds
5 Baths
3,902 sqft
1204 Water Maple Dr,
Oakland, FL 34760
REGENCY REAL ESTATE LLC
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SOLD
JUN 24, 2026
$675,000
3 Beds
2.5 Baths
1,772 sqft
936 Kylee Aly,
Winter Garden, FL 34787
REAL BROKER, LLC
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SOLD
JUN 23, 2026
$645,000
4 Beds
3 Baths
2,663 sqft
503 Minnow Creek Ct,
Winter Garden, FL 34787
RE/MAX TITANIUM GROUP
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SOLD
JUN 17, 2026
$740,000
5 Beds
4.5 Baths
3,324 sqft
14416 Travois Way,
Winter Garden, FL 34787
WATSON REALTY CORP
SOLD
JUN 10, 2026
$975,000
4 Beds
2.5 Baths
3,144 sqft
17608 Deer Isle Cir,
Winter Garden, FL 34787
COLDWELL BANKER REALTY
SOLD
MAY 27, 2026
$850,000
4 Beds
3 Baths
2,850 sqft
8 Winters Landing Dr,
Oakland, FL 34787
REGENCY REAL ESTATE LLC
SOLD
MAY 7, 2026
$950,000
5 Beds
4 Baths
3,556 sqft
15226 Sunset Overlook Cir,
Winter Garden, FL 34787
CHARLES RUTENBERG REALTY ORLANDO
SOLD
MAY 6, 2026
$2,045,357
5 Beds
5.5 Baths
3,725 sqft
1225 Water Maple Dr,
Oakland, FL 34760
REGENCY REAL ESTATE LLC
SOLD
APR 30, 2026
$1,075,000
4 Beds
3.5 Baths
2,811 sqft
883 Tilden Oaks Trl,
Winter Garden, FL 34787
COMPASS FLORIDA LLC
SOLD
APR 27, 2026
$2,775,000
5 Beds
4 Baths
4,886 sqft
17737 Deer Isle Cir,
Winter Garden, FL 34787
PREMIER SOTHEBY'S INTL. REALTY
SOLD
APR 27, 2026
$1,790,000
4 Beds
4 Baths
3,616 sqft
15198 E Oakland Ave,
Winter Garden, FL 34787
IAD FLORIDA LLC
SOLD
APR 13, 2026
$509,000
4 Beds
3 Baths
2,736 sqft
17993 Gourd Neck Loop,
Winter Garden, FL 34787
EXIT REALTY TRI-COUNTY
SOLD
APR 6, 2026
$1,525,000
3 Beds
2 Baths
3,340 sqft
15722 E Oakland Ave,
Winter Garden, FL 34787
RE/MAX PRIME PROPERTIES
SOLD
APR 1, 2026
$800,000
3 Beds
2 Baths
1,932 sqft
1087 Huntspoint St,
Winter Garden, FL 34787
OAK AVENUE REAL ESTATE LLC
SOLD
MAR 31, 2026
$225,000
3 Beds
2 Baths
1,134 sqft
13703 Lake Blvd,
Winter Garden, FL 34787
SOLD
MAR 26, 2026
$875,000
4 Beds
2.5 Baths
2,553 sqft
855 Oakland Park Blvd,
Winter Garden, FL 34787
HOMEVEST REALTY
SOLD
MAR 23, 2026
$1,000,000
4 Beds
3.5 Baths
2,837 sqft
1045 Colleton Aly,
Winter Garden, FL 34787
COMPASS FLORIDA LLC
SOLD
MAR 10, 2026
$650,000
4 Beds
4.5 Baths
4,051 sqft
16129 Pendio Dr,
Montverde, FL 34756
SOLD
MAR 10, 2026
$925,700
4 Beds
3.5 Baths
2,461 sqft
1024 Kershaw Dr,
Winter Garden, FL 34787
COLDWELL BANKER REALTY
SOLD
FEB 27, 2026
$1,175,000
4 Beds
3.5 Baths
3,214 sqft
17556 Deer Isle Cir,
Winter Garden, FL 34787
LAKESIDE REALTY WINDERMERE INC
SOLD
FEB 27, 2026
$849,000
3 Beds
2.5 Baths
2,484 sqft
1368 Union Club Dr,
Winter Garden, FL 34787
DENIZ REALTY PARTNERS LLC
SOLD
FEB 27, 2026
$1,320,000
4 Beds
3 Baths
3,056 sqft
1006 Lake Brim Dr,
Winter Garden, FL 34787
OAK AVENUE REAL ESTATE LLC
SOLD
FEB 23, 2026
$2,300,000
4 Beds
5 Baths
3,902 sqft
1118 Sarah Mathews Dr,
Oakland, FL 34760
REGENCY REAL ESTATE LLC
SOLD
FEB 19, 2026
$731,250
3 Beds
2 Baths
1,612 sqft
13206 Shore Dr,
Winter Garden, FL 34787
RE/MAX REALTY UNLIMITED
SOLD
FEB 18, 2026
$845,000
4 Beds
3.5 Baths
2,548 sqft
1428 Union Club Dr,
Winter Garden, FL 34787
COMPASS FLORIDA LLC
SOLD
FEB 13, 2026
$646,000
4 Beds
2.5 Baths
2,882 sqft
111 Lakeview Reserve Blvd,
Winter Garden, FL 34787
RE/MAX PRIME PROPERTIES
SOLD
FEB 13, 2026
$750,000
3 Beds
3 Baths
2,678 sqft
12914 Creekside Ct,
Clermont, FL 34711
SOUTHERN HERITAGE REALTY, INC

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.