YOUR NEXT HOME IS WAITING

Our exceptional agents will help you find it

Oakland

Luxury listings for sale in Oakland

18 of 18 Homes
COMPARE
Contract signed

$3,495,000

402 N POLLARD, Oakland, FL

5 br5 BA, 1 HALF BA5,001 sf
Virtual tour

Listing Courtesy of CORCORAN PREMIER REALTY., CAROLINA DUMIT - 407-325-8963

Contract signed

$3,399,000

515 N NIXON, Oakland, FL

5 br5 BA, 2 HALF BA5,092 sf

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$3,295,000

312 BRILEY Ave, Oakland, FL

6 br6 BA, 1 HALF BA5,144 sf

Listing Courtesy of CORCORAN PREMIER REALTY., CAROLINA DUMIT - 407-325-8963

$3,200,000

15992 W COLONIAL Dr, Oakland, FL

41 br17,021 sf
Virtual tour

Listing Courtesy of REMAX SUNSTATE REALTY., KYLER MORELAND - 407-496-4196

Contract signed

$2,800,000

1128 PRADO Ln, Oakland, FL

6 br6 BA, 1 HALF BA4,658 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$2,615,320

1152 PRADO Ln, Oakland, FL

6 br6 BA, 1 HALF BA4,658 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$2,575,000

1155 PRADO Ln, Oakland, FL

5 br5 BA, 2 HALF BA4,210 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

PRICE REDUCED

$2,550,000

812 JOHNS POINT Dr, Oakland, FL

5 br6 BA4,373 sf
Virtual tour

Listing Courtesy of WRA BUSINESS & REAL ESTATE., ANY ALVES - 407-455-0618

PRICE REDUCED

$2,495,000

1134 PRADO, Oakland, FL

5 br5 BA, 3 HALF BA4,433 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$2,380,160

1173 PRADO Ln, Oakland, FL

5 br5 BA, 1 HALF BA4,204 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$2,310,600

1146 PRADO Ln, Oakland, FL

5 br5 BA, 1 HALF BA3,992 sf

Listing Courtesy of REGENCY REAL ESTATE LLC., HEATHER SPIRAZZA - 407-757-6022

Contract signed

$2,210,000

1164 PRADO Ln, Winter Garden, FL

5 br5 BA, 1 HALF BA4,204 sf
Virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC., ALEXIS ANDERSON - 561-670-5901

$2,098,000

1258 RIDGE LAKE Way, Oakland, FL

4 br4 BA4,557 sf

Listing Courtesy of NEW HOMES REAL ESTATE, INC.., CHRIS HERLIHY - 407-947-2475

$1,975,000

1106 SARAH MATHEWS Dr, Oakland, FL

5 br5 BA, 1 HALF BA3,596 sf

Listing Courtesy of REGENCY REAL ESTATE LLC., HEATHER SPIRAZZA - 407-757-6022

PRICE REDUCED

$1,725,000

906 ALLENDALE, Winter Garden, FL

5 br4 BA3,784 sf

Listing Courtesy of CENTURY 21 CARIOTI., JURGITA BLAKE - 407-402-4308

Contract signed

$1,699,000

1144 HULL ISLAND, Winter Garden, FL

5 br4 BA, 1 HALF BA4,102 sf

Listing Courtesy of ALIGN REAL ESTATE LLC., TIFFANY PANTOZZI - 407-955-9716

PRICE REDUCED

$1,644,999

1101 EAGLES PASS, Winter Garden, FL

6 br5 BA4,104 sf
Virtual tour

Listing Courtesy of LAKESIDE REALTY WINDERMERE INC., KEVIN SULLIVAN - 321-663-3457

$1,500,000

2010 BOSS HEWETT St, Winter Garden, FL

5 br4 BA3,781 sf
Virtual tour

Listing Courtesy of RE/MAX ASSURED., VILMARI CARABALLO - 407-583-9870

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.

LAST UPDATE DATE On SEP 19 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).