Windermere Homes $500K and Up for Sale
Every home priced $500K and up 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.
Live market brief ·
As of November 11, 2026, 183 homes $500K and up are listed for sale in Windermere (ZIP 34786), from $525,000 to $27,000,000, with a median list price of about $1,500,000 (about $426 per square foot). That count includes 181 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,550,000. Listings have been up a median of 96 days; 3 came on the market in the last 7 days; 90 (49%) have cut the asking price, by a median of 6.2%; 40 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 183
- median list price
- $1,500,000
- median price / sq ft
- $426
- median days listed
- 96 days
- new in last 7 days
- 3
- price reductions
- 90 (49%)
- under contract
- 40
Active listings on Stellar MLS via MLS GRID in ZIP 34786, including condos and townhomes, updated automatically. List prices are asking prices, not sale prices.
Newest 24 of 183 Homes $500K and Up in the Windermere area
$862,500
104 E 11th Ave
Windermere, FL 34786
3 bd · 2 ba · 1,834 sqft
Windermere Town
MLS ID #O6455790, ZIRO REALTY.
Listing provided by Stellar MLS
$784,900
14551 Yellow Butterfly Rd
Windermere, FL 34786
5 bd · 4 ba · 3,546 sqft
Stillwater Xings Prcl Sc-13 1
MLS ID #S5160985, HOMESMART.
Listing provided by Stellar MLS
$875,000
8736 Peachtree Park Ct
Windermere, FL 34786
4 bd · 3 ba · 2,773 sqft
Peachtree Park
MLS ID #O6455345, SERHANT.
Listing provided by Stellar MLS
$930,000
6620 Sawyer Shores Ln
Windermere, FL 34786
4 bd · 4 ba · 2,800 sqft
Sawyer Shores Sub
MLS ID #O6452089, COLDWELL BANKER SOLOMON.
Listing provided by Stellar MLS
$3,350,000
5509 Marleon Dr
Windermere, FL 34786
5 bd · 6 ba · 5,483 sqft
Lake Davis Reserve
MLS ID #O6446897, STOCKWORTH REALTY GROUP.
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
$6,750,000
11103 Bridge House Rd
Windermere, FL 34786
5 bd · 8 ba · 9,403 sqft
Reserve At Lake Butler Sound 45/120
MLS ID #O6453159, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$2,700,000
105 Forest St
Windermere, FL 34786
5 bd · 6 ba · 4,430 sqft
Windermere Town
MLS ID #O6450227, ALIGN REAL ESTATE LLC.
Listing provided by Stellar MLS
$2,695,000
11209 Macaw Ct
Windermere, FL 34786
5 bd · 7 ba · 6,105 sqft
Keenes Pointe
MLS ID #O6453916, CORCORAN PREMIER REALTY.
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
$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
$2,200,000
11545 Brickyard Pond Ln
Windermere, FL 34786
8 bd · 9 ba · 4,735 sqft
Lake Burden South Ph I
MLS ID #O6454194, NOVA REAL ESTATE SERVICES INC.
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
$1,100,000
7230 Sangalla Dr
Windermere, FL 34786
4 bd · 4 ba · 2,892 sqft
Casa De Lago Rep
MLS ID #O6453225, RESOURCE ONE REALTY.
Listing provided by Stellar MLS
$580,000
6206 Golden Dewdrop Trl
Windermere, FL 34786
3 bd · 3 ba · 1,984 sqft
Windermere Lndgs Ph 02
MLS ID #O6451210, ATRIUM REALTY, LLC.
Listing provided by Stellar MLS
$1,550,000
5638 Nectarine Dr
Windermere, FL 34786
5 bd · 5 ba · 3,612 sqft
Lake Cawood Cove
MLS ID #O6452714, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$3,600,000
11066 Ullswater Ln
Windermere, FL 34786
5 bd · 7 ba · 7,223 sqft
Reserve At Lake Butler Sound
MLS ID #S5160321, MILA REALTY.
Listing provided by Stellar MLS
$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
$3,250,000
6024 Greatwater Dr
Windermere, FL 34786
5 bd · 6 ba · 6,370 sqft
Keenes Pointe
MLS ID #O6452995, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$559,900
5231 Lemon Twist Ln
Windermere, FL 34786
4 bd · 4 ba · 2,311 sqft
Summerport Ph 03
MLS ID #S5160165, AGENT TRUST REALTY CORPORATION.
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
$630,000
8582 Powder Ridge Trl
Windermere, FL 34786
4 bd · 4 ba · 2,454 sqft
Windermere Trls Ph 3b
MLS ID #S5158690, LPT REALTY, LLC.
Listing provided by Stellar MLS
$799,900
8325 Vivaro Isle Way
Windermere, FL 34786
4 bd · 3 ba · 3,038 sqft
Windermere Isle
MLS ID #O6452086, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$669,000
8631 Greenbank Blvd
Windermere, FL 34786
4 bd · 4 ba · 2,686 sqft
Lakes/Windermere-Peachtree
MLS ID #O6452398, CLASSIC 1 REALTY INC.
Listing provided by Stellar MLS
More Windermere Homes for Sale
Windermere buyer questions
How many homes $500K and up are for sale in Windermere right now?+
As of November 11, 2026, 183 homes $500K and up are listed for sale in Windermere (ZIP 34786), priced from $525,000 to $27,000,000; the middle half are listed between $800,000 and $3,500,000. That count includes 181 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,550,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $500K and up in Windermere?+
The median list price is about $1,500,000, roughly $426 per square foot (active listings in Windermere, November 11, 2026). List price is what sellers are asking, not what homes sell for; Ryan can walk you through what comparable homes have actually closed for in a private consultation.
Are sellers cutting prices on homes $500K and up in Windermere?+
90 (49%) of the active homes $500K and up in Windermere are listed below their original asking price, by a median of 6.2%, as of November 11, 2026. A price cut is a negotiating signal worth asking your agent about, along with how long the home has been listed.
How long have homes $500K and up in Windermere been on the market?+
As of November 11, 2026, the homes $500K and up for sale in Windermere have been listed a median of 96 days, and 3 came on the market in the last 7 days. This measures how long current listings have been up, not how long homes take to sell.
How many homes $500K and up in Windermere are already under contract?+
40 homes $500K and up in Windermere show as pending or under contract as of November 11, 2026, alongside 183 still active. A home can come back on the market if a contract falls through, so it is worth setting an alert.
How do mortgage rates affect what I can afford in Windermere?+
Your monthly payment depends on the price, your down payment, your loan type and your rate, plus Florida taxes, insurance and any HOA dues. See this week's national rate averages and a payment calculator on the mortgage rates page, or ask Ryan, who is a licensed mortgage loan originator (NMLS #1784218, Mortgageinc NMLS #2028516) as well as the broker, for a personal quote. You are never required to use his lending services.
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 11, 2026 at 7:02 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
Buying in Windermere?
Tour with the broker. Ask about financing in the same conversation.
Ryan Solberg is the broker-owner of MaxLife Realty and a licensed mortgage loan originator (NMLS #1784218, Mortgageinc NMLS #2028516), so he can coordinate your home search and your financing. You are never required to use his lending services to work with him as your agent.
Freddie Mac U.S. weekly average, not a quote or an offer to lend.