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 October 2, 2026, 181 homes $500K and up are listed for sale in Windermere (ZIP 34786), from $500,000 to $27,000,000, with a median list price of about $1,490,000 (about $409 per square foot). That count includes 179 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,490,000. Listings have been up a median of 92 days; 9 came on the market in the last 7 days; 99 (55%) have cut the asking price, by a median of 5.5%; 57 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 181
- median list price
- $1,490,000
- median price / sq ft
- $409
- median days listed
- 92 days
- new in last 7 days
- 9
- price reductions
- 99 (55%)
- under contract
- 57
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 181 Homes $500K and Up in Windermere
$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
$2,400,000
12722 S Lake Sawyer Ln
Windermere, FL 34786
5 bd · 4 ba · 5,139 sqft
Na
MLS ID #O6437802, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$875,000
11727 Delwick Dr
Windermere, FL 34786
4 bd · 3 ba · 2,704 sqft
Reserve/Belmere Ph 04
MLS ID #O6445423, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$3,850,000
4906 Aviva Garden Ct
Windermere, FL 34786
4 bd · 6 ba · 6,605 sqft
Isleworth
MLS ID #O6446042, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$3,999,000
6120 Greatwater Dr
Windermere, FL 34786
5 bd · 6 ba · 5,580 sqft
Keenes Pointe
MLS ID #O6445244, SOUTHERN REALTY GROUP LLC.
Listing provided by Stellar MLS
$3,595,000
9310 Isleworth Gardens Dr
Windermere, FL 34786
3 bd · 5 ba · 4,333 sqft
Isleworth
MLS ID #O6442366, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$565,000
7271 Londale Blvd
Windermere, FL 34786
3 bd · 2 ba · 2,147 sqft
Enclave/Berkshire Park B G H I
MLS ID #O6445539, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$2,350,000
11532 Waterstone Loop Dr
Windermere, FL 34786
4 bd · 6 ba · 4,169 sqft
Waterstone
MLS ID #O6444548, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$1,488,000
12721 Jacob Grace Ct
Windermere, FL 34786
4 bd · 4 ba · 3,763 sqft
Tildens Grove Ph 01 47/65
MLS ID #O6440411, LAKE NONA REALTY LLC.
Listing provided by Stellar MLS
$3,250,000
6126 Payne Stewart Dr
Windermere, FL 34786
3 bd · 4 ba · 2,848 sqft
Isleworth
MLS ID #O6444116, IRWIN REALTY GROUP LLC.
Listing provided by Stellar MLS
$560,000
11543 Charnock Dr
Windermere, FL 34786
4 bd · 3 ba · 2,214 sqft
Westside Village
MLS ID #S5158277, PM ELITE REALTY LLC.
Listing provided by Stellar MLS
$769,000
6727 Merrick Landing Blvd
Windermere, FL 34786
5 bd · 3 ba · 2,773 sqft
Vineyards/Horizons West Ph 18
MLS ID #O6443858, AUTHENTIC REAL ESTATE TEAM.
Listing provided by Stellar MLS
$586,846
13317 Lush Lime Aly
Windermere, FL 34786
3 bd · 3 ba · 1,699 sqft
Lake Cawood Cove
MLS ID #TB8551016, ASHTON WOODS FLORIDA REALTY LLC.
Listing provided by Stellar MLS
$2,995,000
13101 Bellaria Cir
Windermere, FL 34786
6 bd · 9 ba · 7,321 sqft
Bellaria
MLS ID #O6434168, ONE LUXURY INTERNATIONAL LLC.
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
$1,280,000
104 E 1st Ave
Windermere, FL 34786
4 bd · 3 ba · 2,441 sqft
Windermere Town
MLS ID #O6442932, NOVA REAL ESTATE SERVICES INC.
Listing provided by Stellar MLS
$1,100,000
11021 Hawkshead Ct
Windermere, FL 34786
5 bd · 4 ba · 3,557 sqft
Reserve At Lake Butler Sound
MLS ID #O6442835, ACME REAL ESTATE FLORIDA LLC.
Listing provided by Stellar MLS
$950,000
8524 Vivaro Isle Way
Windermere, FL 34786
4 bd · 3 ba · 2,680 sqft
Windermere Isle-Ph 2
MLS ID #G5118124, SERHANT.
Listing provided by Stellar MLS
$945,000
9010 Reflection Pointe Dr
Windermere, FL 34786
4 bd · 4 ba · 3,264 sqft
Windermere Trails
MLS ID #G5117935, PREMIER SOTHEBYS INT'L REALTY.
Listing provided by Stellar MLS
$645,000
7252 Backwoods Trl
Windermere, FL 34786
4 bd · 3 ba · 2,214 sqft
Ashlin Park Ph 2
MLS ID #O6438323, REALSOURCE PROPERTY MANGNT 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
$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
$4,395,000
5186 Vardon Dr
Windermere, FL 34786
6 bd · 6 ba · 4,739 sqft
Isleworth
MLS ID #O6443681, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$649,000
13324 Jervey St
Windermere, FL 34786
4 bd · 4 ba · 2,750 sqft
Lake Sawyer South Ph 01
MLS ID #O6442193, THE SIMON SIMAAN GROUP.
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 October 2, 2026, 181 homes $500K and up are listed for sale in Windermere (ZIP 34786), priced from $500,000 to $27,000,000; the middle half are listed between $800,000 and $3,290,000. That count includes 179 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,490,000. 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 $1,490,000, roughly $409 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 $500K and up in Windermere?+
99 (55%) of the active homes $500K and up in Windermere are listed below their original asking price, by a median of 5.5%, 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 $500K and up in Windermere been on the market?+
As of October 2, 2026, the homes $500K and up for sale in Windermere have been listed a median of 92 days, and 9 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?+
57 homes $500K and up in Windermere show as pending or under contract as of October 2, 2026, alongside 181 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 5:14 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.