5 bedroom homes for sale in Winter Garden, FL

19 hours on RocketTour

$6,828 Closing Credit¹

$575,000

5 beds • 3 baths • 2,478 sqft

1637 Mistflower Ln, Winter Garden, FL 34787

#O6317474, Theresa Choo Sau, PA, Listing office: CENTURY 21 CARIOTI

2 days on Rocket

$10,000 Closing Credit¹

$1,390,000

5 beds • 4 baths • 3,850 sqft

15208 Lake Claire Overlook Dr, Winter Garden, FL 34787

#O6310876, Denise Gregorie, Listing office: CLOCK TOWER REALTY

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2 days on Rocket

$10,000 Closing Credit¹

$1,400,000

5 beds • 3.5 baths • 3,910 sqft

9844 Beach Port Dr, Winter Garden, FL 34787

#O6316377, Jay Kendall, Listing office: WATSON REALTY CORP

2 days on Rocket

$10,000 Closing Credit¹

$1,100,000

5 beds • 4 baths • 3,663 sqft

14744 Spotted Sandpiper Blvd, Winter Garden, FL 34787

#O6316157, Maria Ubillus, Listing office: FOLIO REALTY LLC

3 days on RocketTour

$10,000 Closing Credit¹

$850,000

5 beds • 3.5 baths • 4,288 sqft

15318 Sandfield Loop, Winter Garden, FL 34787

#O6315743, Troy Hensley, Listing office: BHHS FLORIDA REALTY

5 days on RocketTour

$10,000 Closing Credit¹

$925,000

5 beds • 4 baths • 3,081 sqft

2258 Rickover Pl, Winter Garden, FL 34787

#O6315149, Aaron Maddox, Listing office: JASON MITCHELL REAL ESTATE FLO

5 days on RocketTour

$10,000 Closing Credit¹

$877,091

5 beds • 4.5 baths • 3,225 sqft

16164 Point Rock Dr, Winter Garden, FL 34787

#O6316002, Paul King, Listing office: DR HORTON REALTY OF CENTRAL FLORIDA LLC

Room to negotiate?

Median Sold Price

$568K

Avg. Sale Time

66 Days

Based on our May 2025 Market Report.

5 days on Rocket

$2,790,000

5 beds • 5 baths • 4,474 sqft

15779 Tangerine Dream Ct, Winter Garden, FL 34787

#2091658, CAROL HOLMES, Listing office: COLDWELL BANKER VANGUARD REALTY

5 days on RocketTour

$10,000 Closing Credit¹

$949,566

5 beds • 4.5 baths • 3,225 sqft

11063 Hollow Bay Dr, Winter Garden, FL 34787

#O6315994, Paul King, Listing office: DR HORTON REALTY OF CENTRAL FLORIDA LLC

6 days on Rocket

$2,790,000

5 beds • 5 baths • 4,474 sqft

15779 Tangerine Dream Ct, Winter Garden, FL 34787

#O6315370, Carol Holmes, LLC, Listing office: COLDWELL BANKER VANGUARD REALTY

6 days on RocketTour

$7,232 Closing Credit¹

$609,000

5 beds • 3 baths • 2,461 sqft

9106 Cut Shot Dr, Winter Garden, FL 34787

#O6315942, Ping Ma, Listing office: KYLIN REALTY LLC

6 days on RocketTour

$10,000 Closing Credit¹

$876,846

5 beds • 4 baths • 2,866 sqft

11027 Hollow Bay Dr, Winter Garden, FL 34787

#O6315826, Paul King, Listing office: DR HORTON REALTY OF CENTRAL FLORIDA LLC

Tour

$10,000 Closing Credit¹

$2,475,000

5 beds • 5 baths • 5,390 sqft

9080 Morgana Ct, Winter Garden, FL 34787

#TB8392583, Stephen Hachey, Listing office: FLAT FEE MLS REALTY

$10,000 Closing Credit¹

$980,000

5 beds • 4 baths • 3,224 sqft

14955 Lebeau Loop, Winter Garden, FL 34787

#O6312041, Merly Esgro, Listing office: IAD FLORIDA LLC

Tour

$10,000 Closing Credit¹

$1,895,000

5 beds • 4.5 baths • 4,508 sqft

960 Civitas Way, Winter Garden, FL 34787

#S5128045, Sue Webb, Listing office: WATSON REALTY CORP.

Tour

$10,000 Closing Credit¹

$2,000,000

5 beds • 4.5 baths • 4,030 sqft

14501 Wabasso Loop, Winter Garden, FL 34787

#G5097763, Breanna Eckerdt, Listing office: COLBERT REALTY GROUP LLC

Tour

$3,798 Closing Credit¹

$319,790

5 beds • 2.5 baths • 2,326 sqft

2227 Chris Dr, Winter Haven, FL 33884

#O6313916, Ben Goldstein, Listing office: LENNAR REALTY

$10,000 Closing Credit¹

$1,999,000

5 beds • 5 baths • 4,474 sqft

16086 Johns Lake Overlook Dr, Winter Garden, FL 34787

#O6312154, Denise Gregorie, Listing office: CLOCK TOWER REALTY

Tour

$9,963 Closing Credit¹

$839,000

5 beds • 4 baths • 2,840 sqft

16124 Azure Key St, Winter Garden, FL 34787

#O6302078, Heather O'Neill, Listing office: FLORIDA HOMES REALTY & MTG

Tour

$2,850,000

5 beds • 6.5 baths • 5,448 sqft

7550 John Hancock Dr, Winter Garden, FL 34787

#O6312554, Marcelo Moura, Listing office: DOUBLE M GROUP COMPANY

Tour

$8,301 Closing Credit¹

$699,000

5 beds • 3.5 baths • 3,074 sqft

1208 Castleport Rd, Winter Garden, FL 34787

#O6312107, Barbara Waltman, Listing office: KELLER WILLIAMS CLASSIC

$9,643 Closing Credit¹

$812,000

5 beds • 4 baths • 2,670 sqft

13075 Sunrise Harvest Dr, Winter Garden, FL 34787

#O6312175, Jasmine Martz, Listing office: OLYMPUS EXECUTIVE REALTY INC

Tour

$8,253 Closing Credit¹

$695,000

5 beds • 3 baths • 2,826 sqft

14936 Masthead Landing Cir, Winter Garden, FL 34787

#O6310420, Beatriz E Dominguez, Listing office: BROKERS REAL ESTATE GROUP INC

Tour

$10,000 Closing Credit¹

$1,690,000

5 beds • 4.5 baths • 4,258 sqft

16768 Sanctuary Dr, Winter Garden, FL 34787

#O6310908, Sidney Galloway, Listing office: GALLOWAY REAL ESTATE

Tour

$10,000 Closing Credit¹

$900,000

5 beds • 4 baths • 3,563 sqft

12649 Dallington Ter, Winter Garden, FL 34787

#S5127375, Andy Neal, Listing office: MAXIM REALTY ORLANDO

Tour

$9,144 Closing Credit¹

$770,000

5 beds • 4 baths • 2,832 sqft

18309 Oliver Twist Way, Winter Garden, FL 34787

#O6310963, Sarah Smith, Listing office: CORCORAN CONNECT LLC

Tour

$10,000 Closing Credit¹

$1,925,000

5 beds • 5.5 baths • 3,513 sqft

16761 Broadwater Ave, Winter Garden, FL 34787

#O6310760, Ben Whidden, Listing office: COMPASS FLORIDA LLC

$10,000 Closing Credit¹

$1,800,000

5 beds • 4.5 baths • 4,176 sqft

557 Lake Cove Pointe Cir, Winter Garden, FL 34787

#O6308183, Erica Diaz, Listing office: HOMEVEST REALTY

$9,797 Closing Credit¹

$825,000

5 beds • 4 baths • 3,429 sqft

13081 Sunrise Harvest Dr, Winter Garden, FL 34787

#O6310740, Abigail Belchick, Listing office: OLYMPUS EXECUTIVE REALTY INC

Tour

$10,000 Closing Credit¹

$959,000

5 beds • 3.5 baths • 4,384 sqft

14572 Black Quill Dr, Winter Garden, FL 34787

#O6310551, Paulo Silva, Listing office: CHARLES RUTENBERG REALTY ORLANDO

Tour

$3,585 Closing Credit¹

$301,890

5 beds • 2.5 baths • 2,112 sqft

2223 Chris Dr, Winter Haven, FL 33884

#TB8386363, Ben Goldstein, Listing office: LENNAR REALTY

Tour

$10,000 Closing Credit¹

$1,250,000

5 beds • 4.5 baths • 3,878 sqft

9845 Emerald Berry Dr, Winter Garden, FL 34787

#O6309186, Gustavo Furtado, Listing office: WRA BUSINESS & REAL ESTATE

Tour

$10,000 Closing Credit¹

$1,100,000

5 beds • 4.5 baths • 3,672 sqft

15378 Gilligan Ct, Winter Garden, FL 34787

#O6308169, Anamaria Marquez, Listing office: REDFIN CORPORATION

$7,778 Closing Credit¹

$655,000

5 beds • 4 baths • 3,096 sqft

646 Marsh Reed Dr, Winter Garden, FL 34787

#O6308142, Denise Gregorie, Listing office: CLOCK TOWER REALTY

$10,000 Closing Credit¹

$1,050,000

5 beds • 4 baths • 3,782 sqft

15420 Southern Martin St, Winter Garden, FL 34787

#O6308403, Maria Maraboto, Listing office: LAKEFIELD REALTY GROUP LLC

$9,956 Closing Credit¹

$838,392

5 beds • 4.5 baths • 3,719 sqft

13187 Telsen St Unit 38, Winter Garden, FL 34787

#O6306148, Gretta Akellino, Listing office: K HOVNANIAN FLORIDA REALTY

Tour

$10,000 Closing Credit¹

$848,838

5 beds • 4.5 baths • 3,719 sqft

13181 Telsen St Unit 39, Winter Garden, FL 34787

#O6306154, Gretta Akellino, Listing office: K HOVNANIAN FLORIDA REALTY

Tour

$10,000 Closing Credit¹

$925,000

5 beds • 4 baths • 3,358 sqft

3430 Turningwind Ln, Winter Garden, FL 34787

#G5093521, Matthew Mobley, Listing office: HANCOCK REALTY GROUP

Tour

$6,882 Closing Credit¹

$579,500

5 beds • 3 baths • 2,212 sqft

913 Bending Oak Trl, Winter Garden, FL 34787

#O6305086, Sonia Dublis, Listing office: COLDWELL BANKER REALTY

$8,728 Closing Credit¹

$735,000

5 beds • 4.5 baths • 3,725 sqft

3294 Hanging Tide St, Winter Garden, FL 34787

#O6305814, Ken Pozek, Listing office: KELLER WILLIAMS ELITE PARTNERS III REALTY

Winter Garden, FL Real Estate Market Overview

There are 118 5-bedroom homes for sale in Winter Garden, FL. The following market insights reflect all property types in the Winter Garden, FL real estate market. The number of homes for sale in Winter Garden, FL increased by 3.5% between April 2025 and May 2025. In May 2025 median list price was $568,001 and the average listing age was 66 days. While more than 23 listings in Winter Garden, FL in May 2025 were sold above asking price, there were more than 38 listings sold at asking price, and more than 111 were sold below.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Winter Garden, FL

Overview

Winter Garden is located in Orange County, Florida. There are roughly 26,418 residents, living in 9,132 households. The average temperature for Winter Garden this time of the year is low of 71F and high of 91F. On average, Winter Garden gets about 7.43 inches of precipitation in June. Most residents are home owners (69%), have a post secondary degree (51%) and are single, no kids (33%).

Data provided by Home Junction

Schools near Winter Garden, FL

Elementary Schools

United Cerebral Palsy West Orange Charter
1297 Winter Garden Vineland Rd Ste 110
Public Charter PK-5
Dillard Street Elementary School
311 N Dillard St
Public District PK-5
Whispering Oak Elementary School
15300 Stoneybrook West Pkwy
Public District PK-5

Middle Schools

Hope Charter
1550 E Crown Point Rd
Public Charter KG-8
Lakeview Middle School
1200 W Bay St
Public Magnet 6-8
Sunridge Middle School
14955 Sunridge Blvd
Public District 6-8

High Schools

Legacy High Charter
1550 E Crown Point Rd
Public Charter 9-12
West Orange High School
1625 Beulah Rd
Public District 9-12

Data provided by Great Schools

5 bedroom homes for sale in Winter Garden, FL

Winter Garden, FL Real Estate Market Overview

What is it like to live in Winter Garden, FL

Overview

Explore popular home types in Winter Garden, FL

Related homes in Winter Garden, FL

Schools near Winter Garden, FL

Housing market reports in Orange County

Homes for sale near Winter Garden, FL

Real estate in Winter Garden neighborhoods

Top real estate cities in Florida