Winter Garden, FL homes for sale & real estate

10 minutes on Rocket

$689,900

4 beds • 3.5 baths • 2,806 sqft

16995 Tradewind Pt, Winter Garden, FL 34787

#O6323444, Andrea Luna, Listing office: AGL BROKERAGE CORP

3 hours on Rocket

$225,000

2 beds • 1.5 baths • 1,188 sqft

341 Ave L NE, Winter Haven, FL 33881

#O6322954, Bo Zhang, Listing office: CENTURY 21 CARIOTI

Room to negotiate?

Median Sold Price

$563.6K

Avg. Sale Time

57 Days

Based on our June 2025 Market Report.

15 hours on RocketTour

$425,000

3 beds • 2.5 baths • 1,717 sqft

15060 Book Club Rd, Winter Garden, FL 34787

#O6307394, Angela Rodriguez, Listing office: DREAM FINDERS REALTY GROUP CORP

16004 Ollivett St, Winter Garden, FL 34787 - view of front facade featuring stucco siding, a front yard, decorative driveway, and a garage

18 hours on Rocket

$945,000

7 beds • 4 baths • 4,704 sqft

16004 Ollivett St, Winter Garden, FL 34787

#S5130060, Paola Almonte, Listing office: REMAX PREMIER PROPERTIES

1 day on RocketTour

$400,000

3 beds • 2.5 baths • 2,194 sqft

1317 Ave A SE, Winter Haven, FL 33880

#P4935343, Don Jerue, Listing office: KELLER WILLIAMS REALTY SMART 1

1 day on Rocket

$759,000

3 beds • 2.5 baths • 2,612 sqft

4251 Willow Bay Dr, Winter Garden, FL 34787

#O6323077, Sandra OConnor, Listing office: EPIC FLORIDA REALTY LLC

1 day on RocketTour

$525,000

5 beds • 2.5 baths • 2,212 sqft

1030 Bending Oak Trl, Winter Garden, FL 34787

#O6322956, Vicky Koehlke, Listing office: CENTURY 21 CARIOTI

1 day on Rocket

$725,000

4 beds • 3 baths • 2,592 sqft

15521 Sandfield Loop, Winter Garden, FL 34787

#O6322818, Erica Diaz, Listing office: HOMEVEST REALTY

1 day on Rocket

$659,995

4 beds • 2.5 baths • 2,128 sqft

16262 Firedragon Dr, Winter Garden, FL 34787

#O6322700, Mackenzie Barton, Listing office: MEMARPOURI REALTY LLC

2 days on RocketTour

$99,000

Land • 0.28 Acres

14855 Astrolyn St, Winter Garden, FL 34787

#O6322162, Lori Love, Listing office: PREMIUM PROPERTIES R.E SERVICE

3 days on RocketTour

$635,000

4 beds • 3.5 baths • 2,600 sqft

15230 Evergreen Oak Loop, Winter Garden, FL 34787

#S5129843, Mariana Haddad, Listing office: LA ROSA REALTY LLC

3 days on RocketTour

$680,000

5 beds • 3 baths • 2,610 sqft

3467 Buoy Cir, Winter Garden, FL 34787

#G5098920, Tina Declercq, Listing office: KELLER WILLIAMS ELITE PARTNERS III REALTY

3 days on RocketTour

$691,485

4 beds • 3 baths • 2,085 sqft

5308 Citrus Leaf Blvd, Winter Garden, FL 34787

#O6312703, Rodrigo Khoury Francisco, Listing office: WRA BUSINESS & REAL ESTATE

4 days on RocketTour

$300,000

3 beds • 1 bath • 1,517 sqft

645 Ave A NE, Winter Haven, FL 33881

#L4954035, Franco Poerio Skubna, Listing office: CENTURY 21 MYERS REALTY

4 days on RocketTour

$599,000

5 beds • 3 baths • 2,461 sqft

9069 Pinch Shot Dr, Winter Garden, FL 34787

#O6322537, Ping Ma, Listing office: KYLIN REALTY LLC

4 days on RocketTour

$719,999

4 beds • 3 baths • 2,072 sqft

15071 Guava Bay Dr, Winter Garden, FL 34787

#O6322519, Alin Zdroba, Listing office: PROPERTIO

4 days on RocketTour

$400,000

3 beds • 2 baths • 1,302 sqft

1531 Tiverton Blvd, Winter Garden, FL 34787

#O6322492, George Rahi, Listing office: COLDWELL BANKER REALTY

4 days on Rocket

$535,000

4 beds • 2.5 baths • 2,521 sqft

621 Lost Grove Cir, Winter Garden, FL 34787

#G5098910, Matthew Wheatley, Listing office: WHEATLEY REALTY GROUP

4 days on RocketTour

$2,164,000

5 beds • 4 baths • 4,328 sqft

10117 Atwater Bay Dr, Winter Garden, FL 34787

#O6322334, Juan Lopez, Listing office: LA ROSA RTY WINTER GARDEN LLC

4 days on RocketTour

$875,000

4 beds • 3 baths • 3,072 sqft

13993 Title Way, Winter Garden, FL 34787

#O6322118, Janaina De Souza, Listing office: GARCIA REALTY GROUP

4 days on RocketTour

$691,945

4 beds • 3.5 baths • 2,489 sqft

11158 Hollow Bay Dr, Winter Garden, FL 34787

#O6322301, Paul King, Listing office: DR HORTON REALTY OF CENTRAL FLORIDA LLC

4 days on Rocket

$745,000

4 beds • 3.5 baths • 3,564 sqft

16564 Silversaw Palm Dr, Winter Garden, FL 34787

#O6321176, Jenny Wemert, Listing office: WEMERT GROUP REALTY LLC

5 days on Rocket

$785,000

5 beds • 4.5 baths • 3,702 sqft

8113 Key W Dove St, Winter Garden, FL 34787

#O6321813, Andrew Martin, Listing office: RE/MAX TOWN CENTRE

5 days on RocketTour

$420,000

3 beds • 2.5 baths • 1,568 sqft

13293 Pontoon Rd, Winter Garden, FL 34787

#O6321868, Mark Raumaker, Listing office: SERHANT

5 days on RocketTour

$569,000

3 beds • 2 baths • 2,089 sqft

8030 John Hancock Dr, Winter Garden, FL 34787

#O6320932, Diana Basch Connery, Listing office: MS LAND & BUILDING LLC

5 days on RocketTour

$850,000

4 beds • 3.5 baths • 3,041 sqft

15343 Lebeau Loop, Winter Garden, FL 34787

#O6321282, Ken Pozek, Listing office: KELLER WILLIAMS ELITE PARTNERS III REALTY

5 days on RocketTour

$1,100,000

5 beds • 4 baths • 3,291 sqft

9207 Busaco Park Way, Winter Garden, FL 34787

#O6317499, Stefany Marcelino, Listing office: REDFIN CORPORATION

5 days on RocketTour

$302,090

4 beds • 2.5 baths • 1,880 sqft

2219 Chris Dr, Winter Haven, FL 33884

#O6322006, Ben Goldstein, Listing office: LENNAR REALTY

5 days on RocketTour

$3,499,999

6 beds • 6.5 baths • 7,428 sqft

10301 Savannah Ridge Ln, Winter Garden, FL 34787

#G5098859, Ranji Seepersaud, PA, Listing office: FORTUNE REALTY OF CLERMONT

5 days on RocketTour

$291,290

4 beds • 2 baths • 1,824 sqft

2138 Chris Dr, Winter Haven, FL 33884

#O6322014, Ben Goldstein, Listing office: LENNAR REALTY

5 days on RocketTour

$330,940

5 beds • 2.5 baths • 2,326 sqft

2163 Chris Dr, Winter Haven, FL 33884

#O6321994, Ben Goldstein, Listing office: LENNAR REALTY

5 days on RocketTour

$629,000

4 beds • 3 baths • 2,365 sqft

7266 Desert Mandarin St, Winter Garden, FL 34787

#S5129564, Pilar Fernandez, Listing office: SIX STAR REALTY GROUP LLC

6 days on Rocket

$560,000

3 beds • 2 baths • 1,954 sqft

7184 Enchanted Lake Dr, Winter Garden, FL 34787

#O6312445, Megan Hedrick, Listing office: MARK SPAIN REAL ESTATE

6 days on Rocket

$997,000

5 beds • 5 baths • 4,272 sqft

3179 Sailing Pier Ave, Winter Garden, FL 34787

#O6321578, Vivian Saavedra, Listing office: LPT REALTY, LLC

6 days on Rocket

$800,000

4 beds • 3.5 baths • 2,219 sqft

1034 Huntspoint St, Winter Garden, FL 34787

#O6321533, Matthew McKee, Listing office: COMPASS FLORIDA LLC

6 days on Rocket

$547,000

4 beds • 2 baths • 2,161 sqft

2315 Black Lake Blvd, Winter Garden, FL 34787

#O6320089, Jeremy Gamble, Listing office: SIMPLESHOWING INC

6 days on RocketTour

$489,900

4 beds • 3.5 baths • 2,303 sqft

9814 Amber Chestnut Way, Winter Garden, FL 34787

#O6321210, Christopher Bessette, Listing office: KELLER WILLIAMS CLASSIC

6 days on Rocket

$215,000

3 beds • 1 bath • 988 sqft

3115 Ave U NW, Winter Haven, FL 33881

#O6321826, Ken Pozek, Listing office: KELLER WILLIAMS ELITE PARTNERS III REALTY

6 days on RocketTour

$649,900

4 beds • 2.5 baths • 2,614 sqft

7816 Winter Wren St, Winter Garden, FL 34787

#O6321729, Matt Tomaszewski, Listing office: CORCORAN PREMIER REALTY

6 days on Rocket

$415,000

3 beds • 2.5 baths • 1,766 sqft

5669 New Independence Pkwy, Winter Garden, FL 34787

#O6320703, Matt Anderson, Listing office: EXP REALTY LLC

Winter Garden, FL Real Estate Market Overview

There are 732 homes for sale in Winter Garden, FL. The following market insights reflect all property types in the Winter Garden, FL real estate market. The inventory of homes for sale in Winter Garden, FL between May 2025 and June 2025 decreased by 1.9%. In June 2025 median list price was $563,670 and the average listing age was 57 days. Over 14 listings were sold over their listed price in June 2025 in Winter Garden, FL. In the same period over 106 listings were sold below the listed price and 24 listings were sold for the listed price.

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 72F and high of 92F. On average, Winter Garden gets about 7.24 inches of precipitation in July. 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