Windermere Homes Under $500K for Sale
Every home priced under $500K currently for sale in Windermere — pulled live from the Stellar MLS and updated continuously. Pair this with the free Windermere market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
24+ Homes Under $500K in the Windermere area
$349,900
12417 Cruxbury Dr
Windermere, FL 34786
2 bd · 3 ba · 1,311 sqft
Lakes/Windermere-Lk Reams Twhm
MLS ID #O6439656, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$365,000
8634 Danforth Dr
Windermere, FL 34786
2 bd · 3 ba · 1,380 sqft
Lakes/Windermere-Lk Reams Twnh
MLS ID #O6447780, REAL ESTATE HOUSE FL INC.
Listing provided by Stellar MLS
$430,000
11963 Vermillion Ave
Windermere, FL 34786
3 bd · 3 ba · 1,676 sqft
Windermere Trails
MLS ID #O6447919, METROPOLITAN R.E SOLUTIONS INC.
Listing provided by Stellar MLS
$475,000
11861 Vermillion Ave
Windermere, FL 34786
3 bd · 3 ba · 1,600 sqft
Windermere Trls Prcl 3
MLS ID #O6410430, KARDOSH REALTY.
Listing provided by Stellar MLS
$479,000
10628 Reams Rd
Windermere, FL 34786
4 bd · 3 ba · 1,892 sqft
Windermere Trls Ph 1c
MLS ID #O6455169, FLORIDA REALTY INVESTMENTS.
Listing provided by Stellar MLS
$410,000
11425 Brownstone St
Windermere, FL 34786
3 bd · 3 ba · 1,881 sqft
Lake Burden South Ph 2
MLS ID #O6430411, REDFIN CORPORATION.
Listing provided by Stellar MLS
$364,990
7663 Bramwell St
Windermere, FL 34786
3 bd · 3 ba · 1,398 sqft
Wickham Park 04 05 06 09 10 11 12 01
MLS ID #TB8561943, LOKATION.
Listing provided by Stellar MLS
$400,000
14500 Bridgewater Crossings Blvd
Windermere, FL 34786
4 bd · 3 ba · 1,706 sqft
Tennyson Pk/Summerport
MLS ID #O6449184, NOVA REAL ESTATE SERVICES INC.
Listing provided by Stellar MLS
$405,000
8867 Herencia Aly
Windermere, FL 34786
3 bd · 3 ba · 1,382 sqft
Legado
MLS ID #O6449612, AAA GLOBAL VENTURES PA.
Listing provided by Stellar MLS
$350,000
8214 Serenity Spring Dr #2405
Windermere, FL 34786
3 bd · 3 ba · 1,512 sqft
Oasis Cove 2/Lakeside Village Ph X
MLS ID #O6453473, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$354,000
7430 Bentonshire Ave
Windermere, FL 34786
2 bd · 3 ba · 1,412 sqft
Wickham Park 04 05 06 09 10 11 12 01
MLS ID #O6436022, EXP REALTY LLC.
Listing provided by Stellar MLS
$399,000
8133 Enchantment Dr #1307
Windermere, FL 34786
4 bd · 3 ba · 1,974 sqft
Oasis Cove I/Lakeside Village Ph 01
MLS ID #O6455333, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
$394,900
8218 Mystic View Way #2801
Windermere, FL 34786
3 bd · 3 ba · 1,840 sqft
Oasis Cove Ii/Lakeside Village Ph
MLS ID #O6418357, WEICHERT REALTORS HALLMARK PRO.
Listing provided by Stellar MLS
$319,900
8276 Maritime Flag St #1204
Windermere, FL 34786
3 bd · 2 ba · 1,455 sqft
Lakeside/Lk/Windermere Ph 12
MLS ID #O6449170, HOMEVEST REALTY.
Listing provided by Stellar MLS
$450,000
7129 Thicket Branch Aly
Windermere, FL 34786
3 bd · 3 ba · 1,588 sqft
Ashlin Park Ph 2
MLS ID #O6455110, KAZA REAL ESTATE LLC.
Listing provided by Stellar MLS
$299,500
8180 Boat Hook Loop #109
Windermere, FL 34786
2 bd · 2 ba · 1,161 sqft
Lakeside/Lks
MLS ID #S5150297, ROMAN'S PRO REALTY LLC.
Listing provided by Stellar MLS
$349,000
12930 Vennetta Way
Windermere, FL 34786
3 bd · 3 ba · 1,644 sqft
Lake Sawyer South Ph 3
MLS ID #O6450743, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$320,000
8168 Boat Hook Loop #303
Windermere, FL 34786
3 bd · 2 ba · 1,442 sqft
Lakeside At Lakes Of Windermere
MLS ID #O6435857, SOUTHERN REALTY GROUP LLC.
Listing provided by Stellar MLS
$324,900
14030 Sparkling Cove Ln #603
Windermere, FL 34786
2 bd · 3 ba · 1,232 sqft
Oasis Cove I/Lakeside Village Ph 01
MLS ID #O6424774, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$499,999
11938 Silverlake Park Dr
Windermere, FL 34786
4 bd · 3 ba · 2,074 sqft
Windermere Trls Ph 1c
MLS ID #O6430196, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$350,000
8179 Maritime Flag St #206
Windermere, FL 34786
3 bd · 2 ba · 1,332 sqft
Lakeside/Lks/Windermere
MLS ID #O6447793, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$294,997
8168 Boat Hook Loop #302
Windermere, FL 34786
2 bd · 2 ba · 1,161 sqft
Lakeside/Lks/Windermere
MLS ID #O6445290, BLUE KEY PROPERTY MANAGEMENT.
Listing provided by Stellar MLS
$394,900
12744 Langstaff Dr
Windermere, FL 34786
3 bd · 3 ba · 1,369 sqft
Lakes/Windermere-Lk Reams Twnh
MLS ID #S5154691, MY REALTY GROUP, LLC..
Listing provided by Stellar MLS
$465,000
13731 Calera Aly
Windermere, FL 34786
3 bd · 3 ba · 2,113 sqft
Vineyards/Horizons West Ph 2b
MLS ID #O6452681, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
More Windermere Homes for Sale
All Windermere homes $500K and up, with the live market brief →
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX 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.
Based on information submitted to the MLS GRID as of November 10, 2026 at 9:26 AM ET. 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA