Windermere Homes Over $2M for Sale
Every home priced over $2M 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 October 2, 2026, 73 homes over $2M are listed for sale in Windermere (ZIP 34786), from $2,099,000 to $27,000,000, with a median list price of about $3,850,000 (about $722 per square foot). Listings have been up a median of 79 days; 6 came on the market in the last 7 days; 30 (41%) have cut the asking price, by a median of 7%; 9 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 73
- median list price
- $3,850,000
- median price / sq ft
- $722
- median days listed
- 79 days
- new in last 7 days
- 6
- price reductions
- 30 (41%)
- under contract
- 9
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.
Highest-priced 24 of 73 Homes Over $2M in Windermere
$27,000,000
5603 Marleon Dr
Windermere, FL 34786
7 bd · 10 ba · 22,108 sqft
Na
MLS ID #O6404938, PREMIER SOTHEBYS INT'L REALTY.
Listing provided by Stellar MLS
$19,500,000
5192 Vardon Dr
Windermere, FL 34786
6 bd · 10 ba · 13,494 sqft
Isleworth Amd 03
MLS ID #O6441344, IRWIN REALTY GROUP LLC.
Listing provided by Stellar MLS
$18,750,000
5036 Latrobe Dr
Windermere, FL 34786
6 bd · 9 ba · 15,337 sqft
Isleworth
MLS ID #O6441249, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$15,900,000
6119 Grosvenor Shore Dr
Windermere, FL 34786
8 bd · 11 ba · 14,068 sqft
Keenes Point
MLS ID #O6421205, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$15,500,000
12488 Park Ave
Windermere, FL 34786
10 bd · 17 ba · 13,425 sqft
Chaine Du Lac
MLS ID #O6395291, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$13,995,000
3057 Porto Lago Ct
Windermere, FL 34786
6 bd · 11 ba · 12,067 sqft
Lake Down Pointe 50 42
MLS ID #O6411245, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$11,900,000
9323 Gladys Garden Ct
Windermere, FL 34786
6 bd · 10 ba · 9,770 sqft
Isleworth
MLS ID #O6381880, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$11,750,000
9832 Laurel Valley Dr
Windermere, FL 34786
6 bd · 10 ba · 11,100 sqft
Isleworth
MLS ID #O6416194, REAL BROKER, LLC.
Listing provided by Stellar MLS
$9,750,000
4226 Downeast Ln
Windermere, FL 34786
5 bd · 3 ba · 5,316 sqft
Na
MLS ID #O6355233, COLDWELL BANKER RESIDENTIAL RE.
Listing provided by Stellar MLS
$8,500,000
5092 Isleworth Country Club Dr
Windermere, FL 34786
4 bd · 5 ba · 7,100 sqft
Isleworth
MLS ID #O6446272, ISLEWORTH 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
$7,250,000
5074 Isleworth Country Club Dr
Windermere, FL 34786
5 bd · 7 ba · 7,099 sqft
Isleworth
MLS ID #O6373191, MEM REALTY GROUP.
Listing provided by Stellar MLS
$7,200,000
5373 Isleworth Country Club Dr
Windermere, FL 34786
5 bd · 6 ba · 5,993 sqft
Isleworth
MLS ID #O6439156, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$6,995,000
9349 Tibet Pointe Cir
Windermere, FL 34786
5 bd · 8 ba · 7,529 sqft
Keenes Pointe
MLS ID #O6404415, CORCORAN PREMIER REALTY.
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
$6,900,000
6055 Louise Cove Dr
Windermere, FL 34786
5 bd · 6 ba · 7,158 sqft
Isleworth West
MLS ID #O6430931, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$6,800,000
9061 Ron Den Ln
Windermere, FL 34786
5 bd · 7 ba · 6,300 sqft
Down Acres Estates
MLS ID #O6417446, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$6,700,000
8342 Boyla Ct
Windermere, FL 34786
8 bd · 10 ba · 8,133 sqft
Keenes Pointe
MLS ID #O6422852, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$6,650,000
9921 Lake Louise Dr
Windermere, FL 34786
5 bd · 7 ba · 6,970 sqft
Isleworth
MLS ID #O6429164, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$6,595,000
6462 Deacon Cir
Windermere, FL 34786
5 bd · 6 ba · 7,178 sqft
Isleworth
MLS ID #O6407107, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$6,500,000
9316 Gladys Garden Ct
Windermere, FL 34786
5 bd · 7 ba · 5,471 sqft
Isleworth
MLS ID #O6420326, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$5,999,000
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
$5,975,000
9725 Chestnut Ridge Dr
Windermere, FL 34786
7 bd · 7 ba · 8,000 sqft
Isleworth
MLS ID #O6370294, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$5,500,000
1330 Lake Olivia
Windermere, FL 34786
6 bd · 8 ba · 6,442 sqft
Lake Olivia Reserve
MLS ID #S5155388, EMPIRE NETWORK REALTY.
Listing provided by Stellar MLS
More Windermere Homes for Sale
All Windermere homes $500K and up, with the live market brief →
Windermere buyer questions
How many homes over $2M are for sale in Windermere right now?+
As of October 2, 2026, 73 homes over $2M are listed for sale in Windermere (ZIP 34786), priced from $2,099,000 to $27,000,000; the middle half are listed between $2,950,000 and $6,650,000. This updates automatically from the Stellar MLS.
What is the median list price for homes over $2M in Windermere?+
The median list price is about $3,850,000, roughly $722 per square foot (active listings in Windermere, October 2, 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 over $2M in Windermere?+
30 (41%) of the active homes over $2M in Windermere are listed below their original asking price, by a median of 7%, as of October 2, 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 over $2M in Windermere been on the market?+
As of October 2, 2026, the homes over $2M for sale in Windermere have been listed a median of 79 days, and 6 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 over $2M in Windermere are already under contract?+
9 homes over $2M in Windermere show as pending or under contract as of October 2, 2026, alongside 73 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 October 2, 2026 at 5:05 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.