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5 Bedroom Homes in Windermere, FL

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5 Bedroom Homes in Windermere, FL

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24 of 47 Listings

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24 of 47 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

New66Active
$2,390,000
5 bd · 5 ba · 3,975 sqft
6544 Cartmel Ln, Windermere, FL
Debora Segnini · FLORIDA CONNEXION PROPERTIES
93Active
$4,350,000
5 bd · 5 ba · 5,305 sqft
9602 Maywood Dr, Windermere, FL
Tiphany Weeks · DIAMOND REAL ESTATE GROUP
74Active
$3,999,000
5 bd · 6 ba · 5,580 sqft
6120 Greatwater Dr, Windermere, FL
Teresa Stewart · SOUTHERN REALTY GROUP LLC

97Active
$769,000
5 bd · 3 ba · 2,773 sqft
6727 Merrick Landing Blvd, Windermere, FL
Stephanie Demantova Correa · AUTHENTIC REAL ESTATE TEAM
39Active
$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
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
Price Reduced70Active
$1,349,900
5 bd · 3 ba · 3,356 sqft
2540 Hempel Cove Ct, Windermere, FL
Tiffany Pantozzi · ALIGN REAL ESTATE LLC
34Active
$1,500,000
5 bd · 7 ba · 5,312 sqft
13503 Lake Cawood Dr, Windermere, FL
Nick Horton · BANNER INT'L REAL ESTATE
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
$1,695,000
5 bd · 5 ba · 4,219 sqft
1480 Hempel Ave, Windermere, FL
Adriana Sanchez · AROD PARTNERS REALTY
29Active
$3,599,000
5 bd · 7 ba · 5,342 sqft
3986 Isabella Cir, Windermere, FL
Ricardo Konageski da Fonseca · WRA BUSINESS & REAL ESTATE
Price Reduced40Active
$939,000
5 bd · 5 ba · 3,797 sqft
9609 Westover Club Cir, Windermere, FL
John Petit · ALPHA R.E. OF CENTRAL FL LLC
Price Reduced33Active
$2,299,000
5 bd · 6 ba · 4,094 sqft
11113 Lake Butler Blvd, Windermere, FL
Stella Freeman · QUATTRO R E SOLUTIONS LLC
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 ReducedOpen house Sun, Oct 11 · 11:00 AM69Active
$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

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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.

About 5 Bedroom Homes in Windermere, FL

5 Bedroom Homes in Windermere, FL: 47 active listings as of October 11, 2026, 17:53 UTC.

Windermere housing market

September 2026 · This period is still settling

Selling at 97.1% of asking price

Buyers here are paying below asking. MLS · 44 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 29, 2026

Median sale price: $780,000$532,450–$1,219,535 typical range
Price per sq. ft.: $303
Sales: 51
Paid in cash: 47.1%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $1,090,000
Homes for sale: 248
Median days on market: 31 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.

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

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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.

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.

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

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Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

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 97.1% of asking price

Buyers here are paying below asking. MLS · 44 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 29, 2026

Median sale price: $780,000$532,450–$1,219,535 typical range
Price per sq. ft.: $303
Sales: 51
Paid in cash: 47.1%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $1,090,000
Homes for sale: 248
Median days on market: 31 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.