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5 Bedroom Homes in Windermere, FL

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24 of 50 Listings

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24 of 50 Listings

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5 Bedroom Homes in Windermere, FL — Page 2

50 listings

5 Bedroom Homes in Windermere, FL

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24 of 50 Listings

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5 Bedroom Homes in Windermere, FL

24 of 50 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

78Active

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2nd Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced53Active

$798,000

5 bd · 5 ba · 3,373 sqft

4642 River Gem Ave, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

73Active

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced29Active

$745,990

5 bd · 3 ba · 3,285 sqft

7409 Fairgrove Ave, Windermere, FL

Zhe Wang · SUNSTAR REALTY FL INC

Price Reduced59Active

$1,549,000

5 bd · 4 ba · 3,486 sqft

11027 Hawkshead Ct, Windermere, FL

Justyna Tchorni · KENNEDY REALTY GROUP 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

Price Reduced47Active

$1,350,000

5 bd · 4 ba · 3,929 sqft

1700 Lake Roberts Ct, Windermere, FL

David Johnston · CREEGAN GROUP

Price Reduced69Active

$2,474,000

5 bd · 7 ba · 5,366 sqft

6288 Blakeford Dr, Windermere, FL

Keith Renner · NECTAR REAL ESTATE

1Active

$3,750,000

5 bd · 6 ba · 6,182 sqft

9960 6th St, Windermere, FL

Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

Price Reduced48Active

$1,169,900

5 bd · 4 ba · 3,064 sqft

2230 Ridgewind Way, Windermere, FL

Tim Frush · COLDWELL BANKER REALTY

Price Reduced63Active

$879,000

5 bd · 4 ba · 3,182 sqft

11326 Ledgement Ln, Windermere, FL

Jingjing Guan · AAA GLOBAL VENTURES PA

Price Reduced44Active

$1,375,000

5 bd · 6 ba · 5,378 sqft

9527 Queensbury Ct, Windermere, FL

Tamar Hill · THE PROPERTY PROS REAL ESTATE, INC

Price Reduced46Active

$6,595,000

5 bd · 6 ba · 7,178 sqft

6462 Deacon Cir, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced90Active

$6,995,000

5 bd · 8 ba · 7,529 sqft

9349 Tibet Pointe Cir, Windermere, FL

Jay Martin · CORCORAN PREMIER REALTY

Price Reduced66Active

$1,795,000

5 bd · 6 ba · 3,728 sqft

11051 Hawkshead Ct, Windermere, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced64Active

$1,365,000

5 bd · 4 ba · 3,487 sqft

12718 Windermere Isles Pl, Windermere, FL

Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

100Active

$1,490,000

5 bd · 4 ba · 3,492 sqft

11339 Camden Park Dr, Windermere, FL

Martonio Pinto · AMERICAN HORIZONS REALTY

Price Reduced40Active

$930,000

5 bd · 4 ba · 3,820 sqft

6752 Trellis Vine Loop, Windermere, FL

Candice Liceaga · COLDWELL BANKER REALTY

Price Reduced70Active

$7,250,000

5 bd · 7 ba · 7,099 sqft

5074 Isleworth Country Club Dr, Windermere, FL

Armaan Memarpouri · MEM REALTY GROUP

Price Reduced34Active

$639,000

5 bd · 3 ba · 2,511 sqft

13232 Longacre Dr, Windermere, FL

Lucia Kronenberg · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced46Active

$779,900

5 bd · 3 ba · 3,211 sqft

4415 Blue Major Dr, Windermere, FL

Mariana Micheti · M2M REALTY

Price Reduced21Active

$9,750,000

5 bd · 3 ba · 5,316 sqft

4226 Downeast Ln, Windermere, FL

Thad Czapka · COLDWELL BANKER RESIDENTIAL RE

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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

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

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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%