Oakland, FL Real Estate & Homes for Sale

100 of 260 results

68 WINDTREE LANE UNIT 201, WINTER GARDEN, FL 34787
Active
$214,000
Condo
2 bd • 2 ba • 918 sq ft
68 WINDTREE LANE UNIT 201, WINTER GARDEN, FL 34787
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
Active
$2,500,000
4 bd • 5 ba • 6,725 sq ft
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
Active
$5,995,000
5 bd • 6 ba • 6,500 sq ft
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
13200 WHISPER BAY DRIVE, CLERMONT, FL 34711
Active
$650,000
3 bd • 3 ba • 2,588 sq ft
13200 WHISPER BAY DRIVE, CLERMONT, FL 34711
2827 SANCTUARY LANE, WINTER GARDEN, FL 34787
Active
$2,750,000
3 bd • 3 ba • 4,096 sq ft
2827 SANCTUARY LANE, WINTER GARDEN, FL 34787
14517 BLACK LAKE PRESERVE STREET, WINTER GARDEN, FL 34787
Active
$660,000
4 bd • 3 ba • 3,169 sq ft
14517 BLACK LAKE PRESERVE STREET, WINTER GARDEN, FL 34787
636 COKE AVENUE, WINTER GARDEN, FL 34787
Active
$342,000
2 bd • 1 ba • 1,050 sq ft
636 COKE AVENUE, WINTER GARDEN, FL 34787
16689 TOCCOA ROW, WINTER GARDEN, FL 34787
Active
$1,290,000
5 bd • 5 ba • 5,560 sq ft
16689 TOCCOA ROW, WINTER GARDEN, FL 34787
1349 CASTLEPORT ROAD, WINTER GARDEN, FL 34787
Active
$720,000
5 bd • 4 ba • 4,382 sq ft
1349 CASTLEPORT ROAD, WINTER GARDEN, FL 34787
16848 VINCI WAY, BELLA COLLINA, FL 34756
Active
$2,950,000
5 bd • 6 ba • 8,327 sq ft
16848 VINCI WAY, BELLA COLLINA, FL 34756
Active
$949,900
6 bd • 4 ba • 4,181 sq ft
14187 JOMATT LOOP, WINTER GARDEN, FL 34787
Active
$1,150,000
5 bd • 4 ba • 5,584 sq ft
14254 SUNRIDGE BOULEVARD, WINTER GARDEN, FL 34787
Active
$874,900
4 bd • 5 ba • 3,908 sq ft
1231 FOLTZ LOOP, OAKLAND, FL 34787
Active
$2,490,000
5 bd • 7 ba • 7,123 sq ft
16902 VINCI WAY, MONTVERDE, FL 34756
Active
$3,292,955
6 bd • 6 ba • 7,681 sq ft
16118 PENDIO DRIVE, MONTVERDE, FL 34756
Active
$935,000
4 bd • 4 ba • 5,541 sq ft
13665 KILLEBREW WAY, WINTER GARDEN, FL 34787
Active
$199,900
Condo
2 bd • 2 ba • 840 sq ft
304 ERON WAY UNIT 2, WINTER GARDEN, FL 34787
Active
$2,098,000
4 bd • 4 ba • 6,280 sq ft
1258 RIDGE LAKE WAY, OAKLAND, FL 34787
Active
$1,399,900
7 bd • 5 ba • 6,196 sq ft
16669 VARONE COVE COURT, WINTER GARDEN, FL 34787
Active
$395,000
3 bd • 3 ba • 2,275 sq ft
2228 GOPHER TORTOISE TERRACE, OAKLAND, FL 34787
Active
$3,997,500
5 bd • 7 ba • 8,417 sq ft
16123 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$1,095,000
4 bd • 4 ba • 2,225 sq ft
64 N PARK AVENUE, WINTER GARDEN, FL 34787
Active
$5,500,000
5 bd • 8 ba • 10,690 sq ft
16834 ARTIMINO LOOP, BELLA COLLINA, FL 34756
Active
$550,000
3 bd • 2 ba • 2,838 sq ft
776 RAINFALL DRIVE, WINTER GARDEN, FL 34787
Active
$375,000
2 bd • 3 ba • 2,275 sq ft
2100 GOPHER TORTOISE TERRACE, OAKLAND, FL 34787
Active
$929,000
4 bd • 5 ba • 4,718 sq ft
1646 HOLCOMB CREEK STREET, WINTER GARDEN, FL 34787
Active
$252,000
3 bd • 2 ba • 2,043 sq ft
651 J W JONES ROAD, WINTER GARDEN, FL 34787
Active
$364,900
2 bd • 3 ba • 2,095 sq ft
2117 GOPHER TORTOISE TERRACE, OAKLAND, FL 34787
Active
$475,000
3 bd • 2 ba • 2,180 sq ft
2281 OAKINGTON STREET, WINTER GARDEN, FL 34787
Active
$745,000
4 bd • 5 ba • 4,166 sq ft
14372 SUNBRIDGE CIRCLE, WINTER GARDEN, FL 34787
Active
$3,150,000
6 bd • 8 ba • 44,534 sq ft
16000 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$205,000
Condo
2 bd • 2 ba • 1,000 sq ft
407 DOUGLAS WAY UNIT 66, WINTER GARDEN, FL 34787
Active
$834,000
3 bd • 4 ba • 2,485 sq ft
131 OAK LAUREL DRIVE, WINTER GARDEN, FL 34787
Active
$4,189,000
5 bd • 6 ba • 7,608 sq ft
15353 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$899,990
5 bd • 4 ba • 4,846 sq ft
14327 WABASSO LOOP, WINTER GARDEN, FL 34787
Active
$279,900
Condo
2 bd • 2 ba • 1,276 sq ft
143 SOUTHERN PECAN CIRCLE UNIT 206, WINTER GARDEN, FL 34787
Active
$659,999
4 bd • 3 ba • 2,469 sq ft
38 S POLLARD STREET, OAKLAND, FL 34760
Active
$796,000
5 bd • 3 ba • 4,682 sq ft
1970 STANDING ROCK CIRCLE, OAKLAND, FL 34787
Active
$2,290,000
4 bd • 5 ba • 4,226 sq ft
16708 BOLSENA DRIVE, BELLA COLLINA, FL 34756
Active
$229,900
2 bd • 2 ba • 1,344 sq ft
1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787
Active
$2,250,000
3 bd • 4 ba • 5,699 sq ft
15220 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$765,000
4 bd • 4 ba • 4,307 sq ft
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
Active
$3,389,000
5 bd • 5 ba • 6,733 sq ft
15393 APENNINE WAY, MONTVERDE, FL 34756
Active
$1,765,000
5 bd • 4 ba • 5,263 sq ft
906 ALLENDALE LANE, WINTER GARDEN, FL 34787
Active
$633,900
5 bd • 4 ba • 4,798 sq ft
13019 SUMMERLAKE WAY, CLERMONT, FL 34711
Active
$700,669
3 bd • 3 ba • 2,857 sq ft
11235 CARDING MILL LANE, WINTER GARDEN, FL 34787
Active
$2,180,000
4 bd • 5 ba • 4,956 sq ft
16809 BOLSENA DRIVE, BELLA COLLINA, FL 34756
Active
$285,000
2 bd • 1 ba • 696 sq ft
634 FOSTER AVENUE, WINTER GARDEN, FL 34787
Active
$288,900
Condo
2 bd • 2 ba • 1,264 sq ft
225 SOUTHERN PECAN CIRCLE UNIT 208, WINTER GARDEN, FL 34787
Active
$865,000
3 bd • 3 ba • 3,193 sq ft
907 EASLEY AVENUE, WINTER GARDEN, FL 34787
Active
$998,000
4 bd • 3 ba • 3,091 sq ft
16827 SANCTUARY DRIVE, WINTER GARDEN, FL 34787
Active
$2,000,000
6 bd • 7 ba • 6,800 sq ft
16077 BARKLY RIDGE COURT, WINTER GARDEN, FL 34787
Active
$235,000
Condo
1 bd • 1 ba • 738 sq ft
131 SOUTHERN PECAN CIRCLE UNIT 201, WINTER GARDEN, FL 34787
Active
$649,000
4 bd • 3 ba • 2,898 sq ft
17186 HICKORY WIND DRIVE, CLERMONT, FL 34711
Active
$1,499,000
6 bd • 8 ba • 6,758 sq ft
620 N TUBB STREET, OAKLAND, FL 34760
Active
$625,000
4 bd • 2 ba • 2,125 sq ft
1075 CHASE DRIVE, WINTER GARDEN, FL 34787
Active
$225,000
Condo
1 bd • 1 ba • 738 sq ft
317 SOUTHERN PECAN CIRCLE UNIT 102, WINTER GARDEN, FL 34787
Active
$360,000
2 bd • 3 ba • 2,095 sq ft
1318 PAINTED BUNTING AVENUE, OAKLAND, FL 34787
Active
$335,000
3 bd • 3 ba • 1,767 sq ft
13527 DANIELS LANDING CIRCLE, WINTER GARDEN, FL 34787
Active
$849,900
5 bd • 3 ba • 5,102 sq ft
13412 FOX GLOVE STREET, WINTER GARDEN, FL 34787
Active
$400,000
3 bd • 2 ba • 1,805 sq ft
632 DHARMA CIRCLE, WINTER GARDEN, FL 34787
Active
$1,975,000
5 bd • 6 ba • 5,911 sq ft
1106 SARAH MATHEWS DRIVE, OAKLAND, FL 34760
Active
$760,000
4 bd • 4 ba • 3,993 sq ft
1692 HIGHBANKS CIRCLE, WINTER GARDEN, FL 34787
Active
$859,000
7 bd • 4 ba • 6,160 sq ft
16004 OLLIVETT STREET, WINTER GARDEN, FL 34787
Active
$556,000
4 bd • 2 ba • 2,958 sq ft
503 FIRST CAPE CORAL DRIVE, WINTER GARDEN, FL 34787
Active
$630,000
4 bd • 3 ba • 3,643 sq ft
17059 HARBOR OAK PARKWAY, WINTER GARDEN, FL 34787
Active
$204,900
2 bd • 2 ba • 918 sq ft
170 WINDTREE LANE, WINTER GARDEN, FL 34787
Active
$195,000
Condo
2 bd • 2 ba • 918 sq ft
11 WINDTREE LANE UNIT B, WINTER GARDEN, FL 34787
Active
$2,495,000
4 bd • 6 ba • 6,808 sq ft
15144 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$915,000
7 bd • 4 ba • 5,284 sq ft
15327 HERON HIDEAWAY CIRCLE, WINTER GARDEN, FL 34787
Active
$375,000
4 bd • 2 ba • 1,842 sq ft
884 KLONDIKE STREET, WINTER GARDEN, FL 34787
Active
$200,000
Condo
2 bd • 2 ba • 918 sq ft
87 WINDTREE LANE UNIT K, WINTER GARDEN, FL 34787
Active
$215,000
3 bd • 2 ba • 1,260 sq ft
17110 LIVE OAK LANE, MONTVERDE, FL 34756
Active
$1,600,000
5 bd • 5 ba • 4,442 sq ft
325 CRYSTAL WOOD DRIVE, WINTER GARDEN, FL 34787
Active
$560,000
4 bd • 4 ba • 2,561 sq ft
2200 ROMANUM DRIVE, WINTER GARDEN, FL 34787
Active
$465,000
3 bd • 3 ba • 2,403 sq ft
900 WALKERS GROVE LANE, WINTER GARDEN, FL 34787
Active
$825,000
5 bd • 4 ba • 4,586 sq ft
13613 LARSEN LANE, WINTER GARDEN, FL 34787
Active
$2,225,000
4 bd • 5 ba • 6,937 sq ft
16733 BOLSENA DRIVE, BELLA COLLINA, FL 34756
Active
$1,399,900
5 bd • 5 ba • 8,402 sq ft
16548 RAVEN ROCK PLACE, WINTER GARDEN, FL 34787
Active
$1,100,000
5 bd • 4 ba • 4,585 sq ft
13536 SUNSET LAKES CIRCLE, WINTER GARDEN, FL 34787
Active
$675,000
4 bd • 3 ba • 3,559 sq ft
402 EGRET PLACE DRIVE, WINTER GARDEN, FL 34787
Active
$1,025,000
5 bd • 3 ba • 3,951 sq ft
1108 RIVERWAY DRIVE, OAKLAND, FL 34787
Active
$3,721,000
6 bd • 6 ba • 7,831 sq ft
17114 MEDICI WAY, BELLA COLLINA, FL 34756
Active
$347,500
3 bd • 3 ba • 1,699 sq ft
15353 OAK APPLE COURT, WINTER GARDEN, FL 34787
Active
$735,000
5 bd • 4 ba • 3,760 sq ft
14345 WABASSO LOOP, WINTER GARDEN, FL 34787
Active
$719,000
3 bd • 3 ba • 3,070 sq ft
1608 HIGHBANKS CIRCLE, WINTER GARDEN, FL 34787
Active
$3,799,000
5 bd • 6 ba • 7,980 sq ft
13542 SUNSET LAKES CIRCLE, WINTER GARDEN, FL 34787
Active
$530,000
4 bd • 2 ba • 3,003 sq ft
2609 SLAGROVE COURT, WINTER GARDEN, FL 34787
Active
$325,000
4 bd • 3 ba • 2,052 sq ft
17436 CHATEAU PINE WAY, CLERMONT, FL 34711
Active
$3,022,550
6 bd • 7 ba • 6,614 sq ft
15381 APENNINE WAY, MONTVERDE, FL 34756
Active
$2,760,840
5 bd • 6 ba • 6,053 sq ft
15414 APENNINE WAY, MONTVERDE, FL 34756
Active
$3,990,000
6 bd • 8 ba • 8,384 sq ft
15544 PENDIO DRIVE, BELLA COLLINA, FL 34756
Active
$1,645,000
4 bd • 4 ba • 4,301 sq ft
261 ZACHARY WADE STREET, WINTER GARDEN, FL 34787
Active
$874,000
5 bd • 3 ba • 3,740 sq ft
276 SUMMER PINE STREET, WINTER GARDEN, FL 34787
Active
$3,490,000
6 bd • 6 ba • 8,970 sq ft
15746 PENDIO DR, MONTVERDE, FL 34756
Active
$799,999
5 bd • 3 ba • 4,190 sq ft
16 OAKLAND POINTE CIRCLE, OAKLAND, FL 34760
Active
$429,900
4 bd • 2 ba • 2,505 sq ft
13256 WHISPER BAY DRIVE, CLERMONT, FL 34711
Active
$659,000
5 bd • 3 ba • 3,656 sq ft
1209 CASTLEPORT ROAD, WINTER GARDEN, FL 34787
Active
$2,800,000
5 bd • 5 ba • 5,721 sq ft
16989 LUCCA LANE, MONTVERDE, FL 34756
Active
$4,200,000
5 bd • 7 ba • 5,855 sq ft
16044 PENDIO DRIVE, BELLA COLLINA, FL 34756
Page 1 of 3 (260 results)
Unlock MLS

Based on information from Unlock MLS (alternatively, from ACTRIS) for the period through 2026-02-11 05:12:32 PST. Neither the Board nor ACTRIS guarantees or is in any way responsible for its accuracy. All data is provided "AS IS" and with all faults. Data maintained by the Board or ACTRIS may not reflect all real estate activity in the market. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some IDX listings have been excluded from this website. Click here for more information

LERA

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.

Houston REALTORS® Information Service

Copyright 2026, Houston REALTORS® Information Service, Inc. The information provided is exclusively for consumers' 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.

Lubbock Association of REALTORS®

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.

Greater El Paso Association of REALTORS®

The data relating to real estate for sale on this web site comes in part from the IDX Program of the Greater El Paso Association of REALTORS®. Real estate listings held by brokerage firms other than Zillow, Inc are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing brokers. Listing data is deemed reliable but not guaranteed. Copyright 2026 the Greater El Paso Association of REALTORS®, MLS Inc. All rights reserved.

Laredo Association of REALTORS®

© 2026 Laredo Multiple Listing Service. Information is deemed to be reliable but not guaranteed. Information is provided exclusively for consumers personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Central Texas MLS

Listing and property data is from an Internet Data Exchange (IDX) provided by the Central Texas MLS. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. 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. Copyright 2026 Central Texas MLS, All Rights Reserved.

Greater Tyler Association of REALTORS®

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

Odessa Board of REALTORS®

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.

Search Homes in Nearby Areas

Nearby Cities

Winter Garden Homes for SaleGotha Homes for SaleOcoee Homes for SaleKillarney Homes for SaleWindermere Homes for SaleClarcona Homes for SaleMontverde Homes for SaleApopka Homes for Sale

Nearby Counties

Orange County Homes for SaleSeminole County Homes for SaleOsceola County Homes for SaleSumter County Homes for Sale

ZIP Codes Near Oakland

3478734778347773476034734347613474034786

Oakland, FL Market Summary

Current MLS market statistics for active listings in this area.

Active listings26
New listings last 30 days2
Median list price$879,950
Median price per sq ft$273
List price range$252,000 - $2,750,000
Median bedrooms4
Median bathrooms3
Median living area2,926 sq ft
Typical HOA fees$105 – $2,077 / month

Medians are based on 26 sampled active listings when available.

Oakland Area Overview

Population3,646
Median Household Income$152,195
Median Age40.5
Land Area2.43 sq mi
Water Area0 sq mi
Population Density1,499.8 / sq mi
Owner-Occupied Housing82.9%

Source: U.S. Census Bureau (ACS 5-year estimates)