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 22, 2026, 183 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 $1,500,000 (about $410 per square foot). That count includes 181 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,570,000. Listings have been up a median of 85 days; 10 came on the market in the last 7 days; 96 (52%) have cut the asking price, by a median of 5.5%; 46 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
- $410
- median days listed
- 85 days
- new in last 7 days
- 10
- price reductions
- 96 (52%)
- under contract
- 46
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
$8,999,999
9621 Windy Ridge Rd
Windermere, FL 34786
9 bd · 16 ba · 20,445 sqft
Windsor Hill
MLS ID #O6451612, CITARELLI REALTY GROUP LLC.
Listing provided by Stellar MLS
$1,475,000
5650 Nectarine Dr
Windermere, FL 34786
5 bd · 5 ba · 3,612 sqft
Lake Cawood Cove
MLS ID #O6451019, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$1,160,000
9601 Ambleside Dr
Windermere, FL 34786
4 bd · 3 ba · 3,018 sqft
Lake Down Shores Rep
MLS ID #O6447280, CENTURY 21 CARIOTI.
Listing provided by Stellar MLS
$3,250,000
12620 S Lake Sawyer Ln
Windermere, FL 34786
4 bd · 6 ba · 4,200 sqft
MLS ID #S5157983, SERHANT.
Listing provided by Stellar MLS
$1,799,000
7413 Lake Albert Dr
Windermere, FL 34786
6 bd · 7 ba · 4,945 sqft
Lake Burden South Ph I
MLS ID #O6451030, GOLFPARK PROPERTIES.
Listing provided by Stellar MLS
$2,899,000
4205 Clarice Ct
Windermere, FL 34786
7 bd · 9 ba · 7,042 sqft
Lake Clarice Plantation
MLS ID #O6450995, LAKESIDE REALTY WINDERMERE INC.
Listing provided by Stellar MLS
$709,000
14038 Eden Isle Blvd
Windermere, FL 34786
4 bd · 3 ba · 2,749 sqft
Bella Notte/Vizcaya Ph 03 A C
MLS ID #O6450925, EXP REALTY LLC.
Listing provided by Stellar MLS
$620,000
13019 Garridan Ave
Windermere, FL 34786
4 bd · 4 ba · 2,461 sqft
Windermere Sound Ph 2
MLS ID #O6451068, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$535,000
4936 Wise Bird Dr
Windermere, FL 34786
4 bd · 3 ba · 2,361 sqft
Summerport Creeks Run
MLS ID #O6450351, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,189,000
17538 Black Rail St
Windermere, FL 34786
5 bd · 5 ba · 4,999 sqft
Enclave
MLS ID #O6449981, KARDOSH REALTY.
Listing provided by Stellar MLS
$2,190,000
6518 Sawyer Shores Ln
Windermere, FL 34786
5 bd · 6 ba · 3,582 sqft
Sawyer Shores Sub
MLS ID #O6449551, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$599,000
13125 Penshurst Ln
Windermere, FL 34786
3 bd · 2 ba · 1,948 sqft
Lakes/Windermere Ph 03 P & Q
MLS ID #O6449706, CASTLE REALTY PROFESSIONAL GROUP LLC.
Listing provided by Stellar MLS
$559,000
4827 Flint Rd
Windermere, FL 34786
3 bd · 2 ba · 2,085 sqft
Summerport Ph 05
MLS ID #O6449449, COMPASS FLORIDA LLC.
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
$2,390,000
6544 Cartmel Ln
Windermere, FL 34786
5 bd · 5 ba · 4,185 sqft
Reserve At Lake Butler Sound Unit 2
MLS ID #O6447314, FLORIDA CONNEXION PROPERTIES.
Listing provided by Stellar MLS
$1,050,000
5944 Caymus Loop
Windermere, FL 34786
4 bd · 3 ba · 2,984 sqft
Keenes Pointe
MLS ID #O6448123, SOUTHERN REALTY GROUP 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
$3,150,000
1815 Windermere Rd
Windermere, FL 34786
4 bd · 5 ba · 4,290 sqft
Not Applicable
MLS ID #O6447555, BALDWIN PARK REALTY LLC.
Listing provided by Stellar MLS
$620,000
8576 Powder Ridge Trl
Windermere, FL 34786
4 bd · 4 ba · 2,661 sqft
Windermere Trails
MLS ID #O6447414, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$595,000
6858 Merrick Landing Blvd
Windermere, FL 34786
3 bd · 2 ba · 2,115 sqft
Vineyards/Horizons West Ph 1a
MLS ID #O6447605, RE/MAX PRIME PROPERTIES.
Listing provided by Stellar MLS
$1,095,000
2009 Westover Reserve Blvd
Windermere, FL 34786
4 bd · 4 ba · 3,607 sqft
Westover Reserve Ph 02
MLS ID #O6447265, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$4,350,000
9602 Maywood Dr
Windermere, FL 34786
5 bd · 5 ba · 5,305 sqft
Lake Down Shores
MLS ID #O6446848, DIAMOND REAL ESTATE GROUP.
Listing provided by Stellar MLS
$1,999,000
8229 Tibet Butler Dr
Windermere, FL 34786
4 bd · 4 ba · 3,912 sqft
Keenes Pointe
MLS ID #O6447628, SOUTHERN REALTY GROUP LLC.
Listing provided by Stellar MLS
$649,000
7030 Mapperton Dr
Windermere, FL 34786
4 bd · 3 ba · 2,455 sqft
Lakes Of Windermere
MLS ID #O6447067, FOLIO REALTY LLC.
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 22, 2026, 183 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 $780,000 and $3,250,000. That count includes 181 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,570,000. 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 $410 per square foot (active listings in Windermere, October 22, 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?+
96 (52%) 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 22, 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 22, 2026, the homes $500K and up for sale in Windermere have been listed a median of 85 days, and 10 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?+
46 homes $500K and up in Windermere show as pending or under contract as of October 22, 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 October 22, 2026 at 3:09 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.