5 Bedroom Homes in Windermere, FL

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3 beds New construction With a pool

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24 of 38 Listings

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5 Bedroom Homes in Windermere, FL

24 of 38 Listings

39Active

38 listings

5 Bedroom Homes in Windermere, FL

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24 of 38 Listings

Map

5 Bedroom Homes in Windermere, FL

24 of 38 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

39Active

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

$1,100,000

5 bd · 4 ba · 3,557 sqft

11021 Hawkshead Ct, Windermere, FL

Heather Unger, PA · ACME REAL ESTATE FLORIDA LLC

63Active

$1,395,000

5 bd · 4 ba · 4,186 sqft

101 Lee St, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

81Active

$3,290,000

5 bd · 7 ba · 5,502 sqft

4243 Isabella Cir, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

79Active

$2,685,000

5 bd · 7 ba · 5,747 sqft

8142 Tibet Butler Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

62Active

$7,200,000

5 bd · 6 ba · 5,993 sqft

5373 Isleworth Country Club Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

61Active

$2,950,000

5 bd · 4 ba · 7,153 sqft

4301 Down Point Ln, Windermere, FL

Yuliya Mariani · MARIANI REALTY GROUP

34Active

$1,500,000

5 bd · 7 ba · 5,312 sqft

13503 Lake Cawood Dr, Windermere, FL

Nick Horton · BANNER INT'L REAL ESTATE

70Active

$1,399,900

5 bd · 3 ba · 3,356 sqft

2540 Hempel Cove Ct, Windermere, FL

Tiffany Pantozzi · ALIGN REAL ESTATE LLC

98Active

$2,500,000

5 bd · 5 ba · 4,661 sqft

5526 Marleon Dr, Windermere, FL

Benjamin Attwood · SERHANT

Price Reduced90Active

$3,580,000

5 bd · 7 ba · 5,362 sqft

4302 Isabella Cir, Windermere, FL

Sean Rozanski · JC FLORIDA REALTY LLC

Price Reduced43Active

$1,755,000

5 bd · 5 ba · 4,219 sqft

1480 Hempel Ave, Windermere, FL

Adriana Sanchez · AROD PARTNERS REALTY

40Active

$969,000

5 bd · 5 ba · 3,797 sqft

9609 Westover Club Cir, Windermere, FL

John Petit · ALPHA R.E. OF CENTRAL FL 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

95Active

$1,500,000

5 bd · 4 ba · 3,656 sqft

17526 Black Rail St, Windermere, FL

Fernando Zucato · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced82Active

$6,900,000

5 bd · 6 ba · 7,158 sqft

6055 Louise Cove Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

Price Reduced69Active

$675,000

5 bd · 5 ba · 2,963 sqft

7236 Penkridge Ln, Windermere, FL

Amine Berrada · ATLAS BLUE REALTY INC

65Active

$6,650,000

5 bd · 7 ba · 6,970 sqft

9921 Lake Louise Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced73Active

$2,250,000

5 bd · 5 ba · 4,504 sqft

9904 Brentford Ct, Windermere, FL

Kevin Sullivan · LAKESIDE REALTY WINDERMERE INC

38Active

$4,495,000

5 bd · 7 ba · 6,159 sqft

6719 Valhalla Way, Windermere, FL

Luis Martins · CELEBRITY GLOBAL REALTY LLC

78Active

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2nd Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

73Active

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced37Active

$1,055,000

5 bd · 5 ba · 4,936 sqft

9117 Outlook Rock Trl, Windermere, FL

Rosanna Rivera · REDFIN CORPORATION

Price Reduced100Active

$6,800,000

5 bd · 7 ba · 6,300 sqft

9061 Ron Den Ln, Windermere, FL

Brynn Allen · CORCORAN PREMIER REALTY

Price Reduced81Active

$3,000,000

5 bd · 5 ba · 5,018 sqft

11539 Lake Butler Blvd, Windermere, FL

Darrell Nunnelley · VINTAGE REALTY GROUP 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

August 2026

Selling at 95.7% of asking price

Buyers here are paying below asking. MLS · 54 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $835,000$498,000–$1,800,000 typical range
Price per sq. ft.: $299
Sales: 57
Paid in cash: 29.8%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 57 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -9.5%

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

Explore Windermere homes

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

August 2026

Selling at 95.7% of asking price

Buyers here are paying below asking. MLS · 54 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $835,000$498,000–$1,800,000 typical range
Price per sq. ft.: $299
Sales: 57
Paid in cash: 29.8%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 57 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -9.5%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your Windermere agent

Your Windermere agent

Your Windermere agent

Listing data & MLS disclosures

Windermere housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 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 Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026