Windermere Homes for Sale with a Pool
Homes with a private pool on the lot, from the MLS private-pool field. Community pools are not counted.
- For sale now
- 112
- Median list price
- $2.92M
- Median $ / sq ft
- $574
- Median days listed
- 101
Newest 24 of 112 pool homes in Windermere
$625,000
5021 Carillon Ln
Windermere, FL 34786
4 bd · 3 ba · 2,427 sqft
Summerport
MLS ID #O6451867, REALTY OF AMERICA.
Listing provided by Stellar MLS
$2,650,000
8205 Stonemason Ct
Windermere, FL 34786
6 bd · 6 ba · 5,706 sqft
Keenes Pointe Unit 3
MLS ID #O6454650, KEENE'S POINTE REALTY.
Listing provided by Stellar MLS
$939,000
9609 Westover Club Cir
Windermere, FL 34786
5 bd · 5 ba · 3,797 sqft
Westover Club Ph 01 44/139
MLS ID #O6434228, ALPHA R.E. OF CENTRAL FL LLC.
Listing provided by Stellar MLS
$2,200,000
2925 Butler Bay Dr N
Windermere, FL 34786
5 bd · 5 ba · 3,839 sqft
Butler Bay
MLS ID #O6454349, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$579,000
9100 Palm Tree Dr
Windermere, FL 34786
3 bd · 2 ba · 1,723 sqft
Silver Woods Ph 01
MLS ID #O6454929, EXP REALTY LLC.
Listing provided by Stellar MLS
$7,450,000
9343 Tibet Pointe Cir
Windermere, FL 34786
7 bd · 10 ba · 8,362 sqft
Keenes Pointe Unit 03 46/104
MLS ID #O6443379, NOVA REAL ESTATE SERVICES INC.
Listing provided by Stellar MLS
$1,450,000
14274 Crest Palm Ave
Windermere, FL 34786
7 bd · 5 ba · 4,443 sqft
Palms/Windermere
MLS ID #TB8537368, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$3,000,000
11539 Lake Butler Blvd
Windermere, FL 34786
5 bd · 5 ba · 5,018 sqft
Lake Butler Estates
MLS ID #O6416913, VINTAGE REALTY GROUP LLC.
Listing provided by Stellar MLS
$4,945,000
5070 Down Point Ln
Windermere, FL 34786
6 bd · 7 ba · 7,349 sqft
Sunset Bay
MLS ID #O6385276, EXP REALTY LLC.
Listing provided by Stellar MLS
$1,895,000
930 East Blvd
Windermere, FL 34786
4 bd · 5 ba · 2,868 sqft
Windermere Town
MLS ID #O6437093, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$3,950,000
11002 Lake Butler Blvd
Windermere, FL 34786
5 bd · 8 ba · 6,248 sqft
Metcalf Park Rep
MLS ID #O6284922, SERENDIPITY REALTY LLC.
Listing provided by Stellar MLS
$584,900
9011 Chapman Oak Ct
Windermere, FL 34786
4 bd · 2 ba · 2,050 sqft
Silver Woods Ph 05
MLS ID #S5148031, TOWNE CENTER REALTY.
Listing provided by Stellar MLS
$2,685,000
8142 Tibet Butler Dr
Windermere, FL 34786
5 bd · 7 ba · 5,747 sqft
Keenes Pointe
MLS ID #O6439814, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$3,995,000
3165 Butler Bay Dr N
Windermere, FL 34786
7 bd · 8 ba · 8,812 sqft
Butler Bay
MLS ID #O6417878, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,775,000
4282 Mckinnon Rd
Windermere, FL 34786
6 bd · 6 ba · 5,869 sqft
Windermere
MLS ID #O6432910, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$1,697,500
2503 Butler Bay Dr N
Windermere, FL 34786
4 bd · 3 ba · 3,297 sqft
Butler Bay
MLS ID #O6413242, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$5,600,000
800 W 2nd Ave
Windermere, FL 34786
5 bd · 5 ba · 5,511 sqft
Aladar On Lake Butler
MLS ID #O6422976, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$6,950,000
6113 Grosvenor Shore Dr
Windermere, FL 34786
7 bd · 8 ba · 8,722 sqft
Keenes Pointe
MLS ID #O6443311, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$2,099,000
6102 S Hampshire Ct
Windermere, FL 34786
4 bd · 6 ba · 4,812 sqft
Keenes Pointe
MLS ID #O6434011, SOUTHERN REALTY GROUP LLC.
Listing provided by Stellar MLS
$3,450,000
703 E 6th Ave
Windermere, FL 34786
4 bd · 5 ba · 5,152 sqft
Windermere
MLS ID #O6453037, PREMIER SOTHEBYS INT'L REALTY.
Listing provided by Stellar MLS
$4,100,000
9144 Isleworth Gardens Dr
Windermere, FL 34786
3 bd · 5 ba · 5,004 sqft
Isleworth
MLS ID #O6397842, MEGAN DOWDY REALTY, LLC.
Listing provided by Stellar MLS
$5,300,000
9615 Windy Ridge Rd
Windermere, FL 34786
6 bd · 8 ba · 9,669 sqft
Windsor Hill
MLS ID #O6449197, KELLER WILLIAMS CLASSIC.
Listing provided by Stellar MLS
$1,100,000
14038 Bluebird Park Rd
Windermere, FL 34786
4 bd · 4 ba · 3,348 sqft
Summerport Ph 02
MLS ID #O6452272, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$1,348,000
7231 Sangalla Dr
Windermere, FL 34786
5 bd · 5 ba · 3,835 sqft
Casa Del Lago-Replat
MLS ID #O6447329, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
Search all Windermere listings on the map →
Windermere pool homes by price
- $500K–$750K5
- $750K–$1M7
- $1M+100
Neighborhoods with the most pool homes for sale
- Isleworth21 listed
- Keenes Pointe15 listed
- Windermere Town4 listed
- Gotha Town4 listed
- Butler Bay3 listed
- Silver Woods3 listed
- Casabella3 listed
- Summerport2 listed
- Lake Butler Estates2 listed
- Windermere2 listed
Windermere pool homes: quick answers
How many pool homes are for sale in Windermere?+
112 pool homes are listed for sale in Windermere, FL right now. Homes with a private pool on the lot, from the MLS private-pool field. Community pools are not counted.
What do pool homes cost in Windermere?+
The median list price is $2.92M (about $574 per square foot), with listings from $579K to $27M.
How long do pool homes in Windermere stay on the market?+
The listings for sale now have been on the market a median of 101 days.
Which Windermere neighborhoods have the most pool homes for sale?+
Isleworth (21), Keenes Pointe (15), Windermere Town (4), Gotha Town (4), Butler Bay (3).
More Windermere homes for sale
Pool Homes in other cities
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 13, 2026 at 12:03 PM 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