Oakland, FL Real Estate Listings

22 real estate listings match this search criteria near Oakland.

Active
49 photos
$890,000
4 bd, 3 ba, 2,246 Sq Ft
150 Hammock Preserve LoopOakland, FL 34787#O6443416
Single Family Residence7 days
Active
30 photos
$600,000
3 bd, 2 ba, 1,571 Sq Ft
100 Mather Smith DriveOakland, FL 34760#O6443938
Single Family Residence7 days
Active
57 photos
$625,000
3 bd, 2 ba, 1,916 Sq Ft
2107 Bay Line RoadOakland, FL 34787#O6443759
Single Family Residence8 days
Active
73 photos
$1,275,000
3 bd, 3 ba, 3,887 Sq Ft
81 Millholland StreetOakland, FL 34760#O6442710
Single Family Residence2 weeks
Active
52 photos
$499,900
3 bd, 2.5 ba, 1,811 Sq Ft
1184 Bobcat Chase BoulevardOakland, FL 34787#O6442799
Single Family Residence8 days
Active
76 photos
$825,000
4 bd, 3.5 ba, 3,085 Sq Ft
1016 Catori RoadOakland, FL 34787#O6440957
Single Family Residence2 weeks
Active
74 photos
$1,495,000
4 bd, 3.5 ba, 3,620 Sq Ft
137 Petris AvenueOakland, FL 34760#O6440357
Single Family Residence2 weeks
Active
58 photos
$515,000
3 bd, 2.5 ba, 1,811 Sq Ft
2696 Bobcat Chase BoulevardOakland, FL 34787#S5158021
Single Family Residence10 days
Active
94 photos
$1,500,000
5 bd, 4 ba, 3,781 Sq Ft
2010 Boss Hewett StreetWinter Garden, FL 34787#O6423216
Single Family Residence12 weeks
Active
67 photos
$2,495,000
5 bd, 6.5 ba, 4,433 Sq Ft
1134 Prado LaneOakland, FL 34787#O6413035
Single Family Residence12 weeks
Active
47 photos
$649,900
4 bd, 4 ba, 2,852 Sq Ft
2017 Boss Hewett StreetOakland, FL 34787#O6402045
Single Family Residence5 months
Active
76 photos
$999,000
4 bd, 2.5 ba, 2,469 Sq Ft
250 N Walker StreetOakland, FL 34760#G5110973
Single Family Residence5 months
Active
13 photos
$2,615,320
6 bd, 6.5 ba, 4,658 Sq Ft
1152 Prado LaneOakland, FL 34787#O6413825
Single Family Residence3 months
Active
10 photos
$2,575,000
5 bd, 6 ba, 4,210 Sq Ft
1155 Prado LaneOakland, FL 34787#O6415007
Single Family Residence3 months
Active
62 photos
$1,644,999
6 bd, 5 ba, 4,104 Sq Ft
1101 Eagles Pass WayWinter Garden, FL 34787#O6408835
Single Family Residence4 months
Active
12 photos
$799,999
5 bd, 3 ba, 3,413 Sq Ft
16 Oakland Pointe CircleOakland, FL 34760#TB8513260
Single Family Residence4 months
Active
4 photos
$1,975,000
5 bd, 5.5 ba, 3,596 Sq Ft
1106 Sarah Mathews DriveOakland, FL 34787#O6375487
Single Family Residence7 months
Active
67 photos
$1,725,000
5 bd, 4 ba, 3,784 Sq Ft
906 Allendale LaneWinter Garden, FL 34787#G5107489
Single Family Residence8 months
Active
70 photos
$1,400,000
4 bd, 3.5 ba, 3,562 Sq Ft
1112 Hull Island DriveOakland, FL 34787#O6434371
Single Family Residence5 weeks
Active
40 photos
$3,295,000
6 bd, 6.5 ba, 5,144 Sq Ft
312 Briley AvenueOakland, FL 34760#O6429415
Single Family Residence9 weeks
Active
47 photos
$199,000
2 bd, 1 ba, 722 Sq Ft
320 W Sadler AvenueOakland, FL 34760#O6436879
Single Family Residence5 weeks
Active
33 photos
$355,000
3 bd, 2.5 ba, 1,620 Sq Ft
1511 Sweet Apple StreetOakland, FL 34787#O6439535
Townhouse3 weeks

Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright ©2026 MLS GRID. All Rights Reserved.

22 real estate listings match this search criteria near Oakland.

Active
49 photos
$890,000
4 bd, 3 ba, 2,246 Sq Ft
150 Hammock Preserve LoopOakland, FL 34787#O6443416
Single Family Residence7 days
Active
30 photos
$600,000
3 bd, 2 ba, 1,571 Sq Ft
100 Mather Smith DriveOakland, FL 34760#O6443938
Single Family Residence7 days
Active
57 photos
$625,000
3 bd, 2 ba, 1,916 Sq Ft
2107 Bay Line RoadOakland, FL 34787#O6443759
Single Family Residence8 days
Active
73 photos
$1,275,000
3 bd, 3 ba, 3,887 Sq Ft
81 Millholland StreetOakland, FL 34760#O6442710
Single Family Residence2 weeks
Active
52 photos
$499,900
3 bd, 2.5 ba, 1,811 Sq Ft
1184 Bobcat Chase BoulevardOakland, FL 34787#O6442799
Single Family Residence8 days
Active
76 photos
$825,000
4 bd, 3.5 ba, 3,085 Sq Ft
1016 Catori RoadOakland, FL 34787#O6440957
Single Family Residence2 weeks
Active
74 photos
$1,495,000
4 bd, 3.5 ba, 3,620 Sq Ft
137 Petris AvenueOakland, FL 34760#O6440357
Single Family Residence2 weeks
Active
58 photos
$515,000
3 bd, 2.5 ba, 1,811 Sq Ft
2696 Bobcat Chase BoulevardOakland, FL 34787#S5158021
Single Family Residence10 days
Active
94 photos
$1,500,000
5 bd, 4 ba, 3,781 Sq Ft
2010 Boss Hewett StreetWinter Garden, FL 34787#O6423216
Single Family Residence12 weeks
Active
67 photos
$2,495,000
5 bd, 6.5 ba, 4,433 Sq Ft
1134 Prado LaneOakland, FL 34787#O6413035
Single Family Residence12 weeks
Active
47 photos
$649,900
4 bd, 4 ba, 2,852 Sq Ft
2017 Boss Hewett StreetOakland, FL 34787#O6402045
Single Family Residence5 months
Active
76 photos
$999,000
4 bd, 2.5 ba, 2,469 Sq Ft
250 N Walker StreetOakland, FL 34760#G5110973
Single Family Residence5 months
Active
13 photos
$2,615,320
6 bd, 6.5 ba, 4,658 Sq Ft
1152 Prado LaneOakland, FL 34787#O6413825
Single Family Residence3 months
Active
10 photos
$2,575,000
5 bd, 6 ba, 4,210 Sq Ft
1155 Prado LaneOakland, FL 34787#O6415007
Single Family Residence3 months
Active
62 photos
$1,644,999
6 bd, 5 ba, 4,104 Sq Ft
1101 Eagles Pass WayWinter Garden, FL 34787#O6408835
Single Family Residence4 months
Active
12 photos
$799,999
5 bd, 3 ba, 3,413 Sq Ft
16 Oakland Pointe CircleOakland, FL 34760#TB8513260
Single Family Residence4 months
Active
4 photos
$1,975,000
5 bd, 5.5 ba, 3,596 Sq Ft
1106 Sarah Mathews DriveOakland, FL 34787#O6375487
Single Family Residence7 months
Active
67 photos
$1,725,000
5 bd, 4 ba, 3,784 Sq Ft
906 Allendale LaneWinter Garden, FL 34787#G5107489
Single Family Residence8 months
Active
70 photos
$1,400,000
4 bd, 3.5 ba, 3,562 Sq Ft
1112 Hull Island DriveOakland, FL 34787#O6434371
Single Family Residence5 weeks
Active
40 photos
$3,295,000
6 bd, 6.5 ba, 5,144 Sq Ft
312 Briley AvenueOakland, FL 34760#O6429415
Single Family Residence9 weeks
Active
47 photos
$199,000
2 bd, 1 ba, 722 Sq Ft
320 W Sadler AvenueOakland, FL 34760#O6436879
Single Family Residence5 weeks
Active
33 photos
$355,000
3 bd, 2.5 ba, 1,620 Sq Ft
1511 Sweet Apple StreetOakland, FL 34787#O6439535
Townhouse3 weeks

Market Overview — Oakland, FL

Showing Oakland, FL

Property type

ResidentialCommercial

Transaction

For SaleFor Lease

Area Average

Median over the active for-sale listings

$424,950
Median Listing Price: 74
Median Days on EXIT Realty: 1,188
Median Sq Ft: $308
Median Price per Sq Ft

Compare

Compare Oakland, FL to another area

Median price, days on market and size comparison by area
Area	Median Listing Price	Median Days on EXIT Realty	Median Sq Ft	Median Price per Sq Ft	Actions
Oakland, FL	$424,950	74	1,188	$308

Market Composition

What's on the market

56%Residential422 active
28%For Lease210 active
6%Commercial Lease45 active
4%Commercial31 active
3%Multi-Family26 active
2%Land14 active
<1%Business3 active

Active listings by price

Under $200K28% · 124
$200K-$400K20% · 90
$400K-$600K21% · 94
$600K-$800K16% · 70
$800K-$1M8% · 35
Over $1M8% · 35

Median Price Trend

Sep 2025: $1,029,766 -52.7%Sep 2026: $486,900

Thinking of selling?

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Nearby Schools

Elementary 10

Oakland Avenue Charter School
Oakland, FL · 0.4 mi away
Tildenville Elementary
Winter Garden, FL · 1.2 mi away
Sunridge Elementary School
Winter Garden, FL · 2.1 mi away
Sunridge Elementary School
Winter Garden, FL · 2.1 mi away
Ucp West Orange Campus
Winter Garden, FL · 2.6 mi away
Ucp West Orange Charter
Winter Garden, FL · 2.7 mi away
Dillard Street Elementary School
Winter Garden, FL · 2.9 mi away
Whispering Oak Elementary School
Winter Garden, FL · 3.1 mi away
William S Maxey Elementary
Winter Garden, FL · 3.2 mi away
Montessori of Winter Garden
Winter Garden, FL · 3.2 mi away

Secondary 3

Lakeview Middle School
Winter Garden, FL · 1.6 mi away
Sunridge Middle School
Winter Garden, FL · 2.0 mi away
Westside Tech
Winter Garden, FL · 3.4 mi away

Other schools 7

Family Christian School
Oakland, FL · 0.6 mi away
Classes4contractors
Winter Garden, FL · 2.5 mi away
Starchild Academy Winter Garden
Winter Garden, FL · 2.6 mi away
Calvary Baptist Church
Winter Garden, FL · 2.7 mi away
Foundation Academy
Winter Garden, FL · 2.7 mi away
Hope Charter School
Winter Garden, FL · 2.8 mi away
Foundation Academy
Winter Garden, FL · 3.6 mi away

Oakland, FL Real Estate Listings

Oakland, FL Real Estate Listings

150 Hammock Preserve LoopOakland, FL 34787#O6443416

100 Mather Smith DriveOakland, FL 34760#O6443938

2107 Bay Line RoadOakland, FL 34787#O6443759

81 Millholland StreetOakland, FL 34760#O6442710

1184 Bobcat Chase BoulevardOakland, FL 34787#O6442799

1016 Catori RoadOakland, FL 34787#O6440957

137 Petris AvenueOakland, FL 34760#O6440357

2696 Bobcat Chase BoulevardOakland, FL 34787#S5158021

2010 Boss Hewett StreetWinter Garden, FL 34787#O6423216

1134 Prado LaneOakland, FL 34787#O6413035

2017 Boss Hewett StreetOakland, FL 34787#O6402045

250 N Walker StreetOakland, FL 34760#G5110973

1152 Prado LaneOakland, FL 34787#O6413825

1155 Prado LaneOakland, FL 34787#O6415007

1101 Eagles Pass WayWinter Garden, FL 34787#O6408835

16 Oakland Pointe CircleOakland, FL 34760#TB8513260

1106 Sarah Mathews DriveOakland, FL 34787#O6375487

906 Allendale LaneWinter Garden, FL 34787#G5107489

1112 Hull Island DriveOakland, FL 34787#O6434371

312 Briley AvenueOakland, FL 34760#O6429415

320 W Sadler AvenueOakland, FL 34760#O6436879

1511 Sweet Apple StreetOakland, FL 34787#O6439535

150 Hammock Preserve LoopOakland, FL 34787#O6443416

100 Mather Smith DriveOakland, FL 34760#O6443938

2107 Bay Line RoadOakland, FL 34787#O6443759

81 Millholland StreetOakland, FL 34760#O6442710

1184 Bobcat Chase BoulevardOakland, FL 34787#O6442799

1016 Catori RoadOakland, FL 34787#O6440957

137 Petris AvenueOakland, FL 34760#O6440357

2696 Bobcat Chase BoulevardOakland, FL 34787#S5158021

2010 Boss Hewett StreetWinter Garden, FL 34787#O6423216

1134 Prado LaneOakland, FL 34787#O6413035

2017 Boss Hewett StreetOakland, FL 34787#O6402045

250 N Walker StreetOakland, FL 34760#G5110973

1152 Prado LaneOakland, FL 34787#O6413825

1155 Prado LaneOakland, FL 34787#O6415007

1101 Eagles Pass WayWinter Garden, FL 34787#O6408835

16 Oakland Pointe CircleOakland, FL 34760#TB8513260

1106 Sarah Mathews DriveOakland, FL 34787#O6375487

906 Allendale LaneWinter Garden, FL 34787#G5107489

1112 Hull Island DriveOakland, FL 34787#O6434371

312 Briley AvenueOakland, FL 34760#O6429415

320 W Sadler AvenueOakland, FL 34760#O6436879

1511 Sweet Apple StreetOakland, FL 34787#O6439535

Market Overview — Oakland, FL

Area Average

Compare

Market Composition

What's on the market

Active listings by price

Median Price Trend

Nearby Schools

Elementary 10

Secondary 3

Other schools 7