5 Bedroom Homes in Winter Garden, FL

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24 of 34 Listings

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24 of 34 Listings

63Active

34 listings

5 Bedroom Homes in Winter Garden, FL

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24 of 34 Listings

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5 Bedroom Homes in Winter Garden, FL

24 of 34 Listings

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

63Active

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

$749,000

5 bd · 3 ba · 3,766 sqft

2102 Green Ash Ct, Winter Garden, FL

David DeCristo · MARK SPAIN REAL ESTATE

Price Reduced47Active

$925,000

5 bd · 4 ba · 3,104 sqft

5416 Golden Apple Dr, Winter Garden, FL

Wilfred Sierra Sosa, PA · RE/MAX PRIME PROPERTIES

35Active

$1,090,000

5 bd · 5 ba · 3,878 sqft

9845 Emerald Berry Dr, Winter Garden, FL

Eduardo Pavone · ON ME REALTY

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

26Active

$790,000

5 bd · 4 ba · 3,381 sqft

2242 Wintermere Pointe Dr, Winter Garden, FL

Jim Middleton, Jr. · NEXTHOME BEST RESULTS REAL ESTATE

60Active

$2,399,000

5 bd · 5 ba · 4,213 sqft

15675 Panther Lake Dr, Winter Garden, FL

Laura Teixeira, PA · NOBSKA REAL ESTATE LLC

90Active

$1,399,999

5 bd · 5 ba · 4,919 sqft

1720 Lake Roberts Landing Dr, Winter Garden, FL

Daniel Maia Lins de Albuquerque Maia · ACCORD REAL ESTATE SERVICES

88Active

$1,950,000

5 bd · 6 ba · 4,329 sqft

15680 Panther Lake Dr, Winter Garden, FL

Christina Cannon · KELLER WILLIAMS CLASSIC

97Active

$2,250,000

5 bd · 5 ba · 4,132 sqft

16870 Sanctuary Dr, Winter Garden, FL

Jennifer Olmeda · WRA BUSINESS & REAL ESTATE

34Active

$925,000

5 bd · 3 ba · 3,739 sqft

2491 Prairie View Dr, Winter Garden, FL

Ahmad Hassan, PA · COMPASS FLORIDA LLC

47Active

$910,000

5 bd · 4 ba · 3,619 sqft

5620 Mangrove Cove Ave, Winter Garden, FL

Julio Lopez · JCL REALTY INC

61Active

$824,900

5 bd · 4 ba · 3,344 sqft

2202 Redmark Ln, Winter Garden, FL

Amy Chastain · CHASTAIN REAL ESTATE COMPANY LLC

Price Reduced64Active

$2,125,000

5 bd · 6 ba · 4,253 sqft

15475 Shorebird Ln, Winter Garden, FL

Ken Pozek · REAL BROKER, LLC

56Active

$2,050,000

5 bd · 5 ba · 4,832 sqft

9056 Morgana Ct, Winter Garden, FL

Steve Healy · CORCORAN PREMIER REALTY

Price Reduced41Active

$749,995

5 bd · 3 ba · 3,102 sqft

644 Autumn Oaks Loop, Winter Garden, FL

Marc Burke · CONDO METROPOLIS, LLC

Price Reduced67Active

$800,000

5 bd · 3 ba · 3,241 sqft

637 Grassy Stone Dr, Winter Garden, FL

Erica Diaz · HOMEVEST REALTY

44Active

$1,150,000

5 bd · 4 ba · 3,897 sqft

9225 Holliston Creek Pl, Winter Garden, FL

Michael Bouchard · GLOBAL FLORIDA REALTY

Price Reduced100Active

$2,099,000

5 bd · 5 ba · 4,139 sqft

16038 Johns Lake Overlook Dr, Winter Garden, FL

Drew Belani · COMPASS FLORIDA LLC

Price Reduced56Active

$899,000

5 bd · 5 ba · 3,002 sqft

15367 Shonan Gold Dr, Winter Garden, FL

Oscar Rodriguez · B LIVE COMMERCIAL AND RESIDENT

64Active

$759,900

5 bd · 3 ba · 3,249 sqft

13163 Lakeshore Grove Dr, Winter Garden, FL

John Chiumento · LPT REALTY, LLC

94Active

$1,500,000

5 bd · 4 ba · 3,781 sqft

2010 Boss Hewett St, Winter Garden, FL

Vilmari Caraballo · RE/MAX ASSURED

Price Reduced90Active

$1,020,000

5 bd · 4 ba · 3,617 sqft

16044 Citrus Knoll Dr, Winter Garden, FL

Kaitlin Sidders · HOGAN REALTY GROUP INC

Price Reduced51Active

$1,060,000

5 bd · 4 ba · 4,225 sqft

14312 Sunbridge Cir, Winter Garden, FL

Karen Vasquez Rodriguez · REALTY ONE GROUP MAGIC CITY

Price Reduced57Active

$1,080,000

5 bd · 5 ba · 3,624 sqft

15741 Sweet Lemon Way, Winter Garden, FL

Cristiane Carneiro Spindola Rocha Lima · WRA BUSINESS & REAL ESTATE

Open house Sun, Oct 4 · 9:00 AM46Active

$860,000

5 bd · 4 ba · 3,538 sqft

13856 Glynshel Dr, Winter Garden, FL

Mary Dees · CHOICEPOINTE REALTY, INC.

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.

Winter Garden housing market

September 2026 · This period is still settling

Selling at 97.8% of asking price

Buyers here are paying below asking. MLS · 184 sales · as of Sep 29, 2026

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

Median sale price: $750,000$500,400–$1,652,852 typical range
Price per sq. ft.: $262
Sales: 135
Paid in cash: 41.5%

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

Median list price: $565,000

Winter Garden, FL community profile

Population: 50,261
Median income: $102,195
Housing units: 18,962
People per sq. mi.: 562.2
Area: 89.4 sq. mi.

Source: HJN community data

Explore Winter Garden homes

Your Winter Garden 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.

Winter Garden, FL community profile

Population: 50,261
Median income: $102,195
Housing units: 18,962
People per sq. mi.: 562.2
Area: 89.4 sq. mi.

Source: HJN community data

Winter Garden housing market

September 2026 · This period is still settling

Selling at 97.8% of asking price

Buyers here are paying below asking. MLS · 184 sales · as of Sep 29, 2026

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

Median sale price: $750,000$500,400–$1,652,852 typical range
Price per sq. ft.: $262
Sales: 135
Paid in cash: 41.5%

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

Median list price: $565,000

Homes for sale

795

Median days on market

42 days

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

Year-over-year: 27.4%

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

Median home size: 2,211 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your Winter Garden agent

Your Winter Garden agent

Your Winter Garden agent

Listing data & MLS disclosures

Winter Garden 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

Winter Garden, FL community profile

Explore Winter Garden homes

Your Winter Garden agent

Listing data & MLS disclosures

Winter Garden, FL community profile

Winter Garden 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