Homes Over $3M in Windermere, FL

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24 of 52 Listings

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24 of 52 Listings

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52 listings

Homes Over $3M in Windermere, FL

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24 of 52 Listings

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Homes Over $3M in Windermere, FL

24 of 52 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

New63

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Active

$8,500,000

4 bd · 5 ba · 7,100 sqft

5092 Isleworth Country Club Dr, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

100Active

$6,950,000

7 bd · 8 ba · 8,722 sqft

6113 Grosvenor Shore Dr, Windermere, FL

Gwen Flynn · COLDWELL BANKER REALTY

100Active

$3,850,000

4 bd · 6 ba · 6,605 sqft

4906 Aviva Garden Ct, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

51Active

$3,595,000

3 bd · 5 ba · 4,333 sqft

9310 Isleworth Gardens Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

74Active

$3,999,000

5 bd · 6 ba · 5,580 sqft

6120 Greatwater Dr, Windermere, FL

Teresa Stewart · SOUTHERN REALTY GROUP LLC

38Active

$3,250,000

3 bd · 4 ba · 2,848 sqft

6126 Payne Stewart Dr, Windermere, FL

Jill Irwin · IRWIN REALTY GROUP LLC

52Active

$4,395,000

6 bd · 6 ba · 4,739 sqft

5186 Vardon Dr, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

60Active

$7,450,000

7 bd · 10 ba · 8,362 sqft

9343 Tibet Pointe Cir, Windermere, FL

Juliana Jardini Da Cunha Igayara De So · NOVA REAL ESTATE SERVICES INC

51Active

$19,500,000

6 bd · 10 ba · 13,494 sqft

5192 Vardon Dr, Windermere, FL

Jill Irwin · IRWIN REALTY GROUP LLC

13Active

$18,750,000

6 bd · 9 ba · 15,337 sqft

5036 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

81Active

$3,290,000

5 bd · 7 ba · 5,502 sqft

4243 Isabella Cir, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

62Active

$7,200,000

5 bd · 6 ba · 5,993 sqft

5373 Isleworth Country Club Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

74Active

$3,300,000

4 bd · 6 ba · 3,966 sqft

515 W 2nd Ave, Windermere, FL

Darrell Nunnelley · VINTAGE REALTY GROUP LLC

23Active

$3,189,000

4 bd · 5 ba · 3,365 sqft

5050 Isleworth Country Club Dr, Windermere, FL

Toni Cafferty · COMPASS FLORIDA LLC

Price Reduced90Active

$3,580,000

5 bd · 7 ba · 5,362 sqft

4302 Isabella Cir, Windermere, FL

Sean Rozanski · JC FLORIDA REALTY LLC

29Active

$3,599,000

5 bd · 7 ba · 5,342 sqft

3986 Isabella Cir, Windermere, FL

Ricardo Konageski da Fonseca · WRA BUSINESS & REAL ESTATE

13Active

$5,500,000

6 bd · 8 ba · 6,442 sqft

1330 Lake Olivia, Windermere, FL

Ana Rubio · EMPIRE NETWORK REALTY

Price Reduced100Active

$3,990,000

6 bd · 7 ba · 6,896 sqft

4201 Isabella Cir, Windermere, FL

Any Alves · WRA BUSINESS & REAL ESTATE

74Active

$3,100,000

4 bd · 5 ba · 4,296 sqft

12102 Montalcino Cir, Windermere, FL

Kristy Cook · EXP REALTY LLC

Price Reduced82Active

$6,900,000

5 bd · 6 ba · 7,158 sqft

6055 Louise Cove Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

100Active

$3,400,000

6 bd · 7 ba · 5,666 sqft

9679 Westover Roberts Rd, Windermere, FL

Tony Davids · TONYDAVIDSHOMES.COM, LLC

81Active

$3,500,000

4 bd · 6 ba · 7,669 sqft

5524 Worsham Ct, Windermere, FL

Ayoub Aitelhaj · ATLIS REALTY GROUP LLC

65Active

$6,650,000

5 bd · 7 ba · 6,970 sqft

9921 Lake Louise Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

41Active

$3,100,000

6 bd · 5 ba · 4,282 sqft

7720 Ficquette Rd, Windermere, FL

Ruthanne Martin · REVEL REALTY LLC

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Windermere housing market

September 2026 · This period is still settling

Selling at 97.2% of asking price

Buyers here are paying below asking. MLS · 42 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $767,500$548,400–$995,000 typical range
Price per sq. ft.: $285
Sales: 30
Paid in cash: 36.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $1,090,000

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 sq. mi.

Source: HJN community data

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 sq. mi.

Source: HJN community data

Windermere housing market

September 2026 · This period is still settling

Selling at 97.2% of asking price

Buyers here are paying below asking. MLS · 42 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $767,500$548,400–$995,000 typical range
Price per sq. ft.: $285
Sales: 30
Paid in cash: 36.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $1,090,000

Homes for sale

248

Median days on market

32 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 2,645 sq. ft.

Registered offenders on the map

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Your Windermere agent

Your Windermere agent

Your Windermere agent

Listing data & MLS disclosures

Windermere housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Windermere, FL community profile

Explore Windermere homes

Your Windermere agent

Listing data & MLS disclosures

Windermere, FL community profile

Windermere housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026