5 bedroom homes for sale in Southwest Orange, FL

1 day on RocketTour

$10,000 Closing Credit¹

$899,999

5 beds • 4.5 baths • 2,844 sqft

11761 Bella Milano Ct, Windermere, FL 34786

#L4953594, Lizzette Bolivar Rubio, Listing office: PMI ORLANDO PARKS

1 day on Rocket

$2,625,000

5 beds • 6 baths • 5,934 sqft

11106 Coniston Way, Windermere, FL 34786

#O6316553, Toni Cafferty, Listing office: COMPASS FLORIDA LLC

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1 day on RocketTour

$10,000 Closing Credit¹

$1,700,000

5 beds • 4.5 baths • 3,868 sqft

11015 Hawkshead Ct, Windermere, FL 34786

#O6316990, Ahmed El Komy, 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

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

$1,299,000

5 beds • 5 baths • 3,874 sqft

8047 Chilton Dr, Orlando, FL 32836

#O6314632, Karen Ferrin Bueno, Listing office: COLDWELL BANKER REALTY

Room to negotiate?

Median Sold Price

$561.6K

Avg. Sale Time

64 Days

Based on our May 2025 Market Report.

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

4 days on Rocket

$5,283 Closing Credit¹

$444,900

5 beds • 2.5 baths • 2,479 sqft

2708 Smithfield Dr, Orlando, FL 32837

#V4943116, Jennifer Clark, Listing office: GLORY INTL. REAL ESTATE CO

4 days on RocketTour

$8,016 Closing Credit¹

$675,000

5 beds • 3.5 baths • 2,543 sqft

14319 Islamorada Dr, Orlando, FL 32837

#O6316278, Camille Kartje Kaiser, PA, Listing office: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

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 Rocket

$10,000 Closing Credit¹

$1,500,000

5 beds • 4 baths • 3,684 sqft

11425 Claymont Cir, Windermere, FL 34786

#O6315915, Ken Pozek, Listing office: KELLER WILLIAMS ELITE PARTNERS III REALTY

5 days on Rocket

$10,000 Closing Credit¹

$875,000

5 beds • 2.5 baths • 2,990 sqft

10241 Pointview Ct, Orlando, FL 32836

#O6314553, Jenny Wemert, Listing office: WEMERT GROUP REALTY LLC

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

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

5 days on RocketTour

$10,000 Closing Credit¹

$1,180,000

5 beds • 5.5 baths • 3,764 sqft

6947 Cucamelon Ct, Windermere, FL 34786

#O6315659, Hamid Dghirni, Listing office: PREMIUM PROPERTIES REAL ESTATE

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

$9,025 Closing Credit¹

$760,000

5 beds • 3 baths • 3,493 sqft

2340 Standing Rock Cir, Oakland, FL 34787

#O6314846, Jennifer Coon, Listing office: KELLER WILLIAMS WINTER PARK

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

6 days on Rocket

$5,494,000

5 beds • 6.5 baths • 4,665 sqft

5199 Latrobe Dr, Windermere, FL 34786

#O6315618, Shane Croft, Listing office: COLDWELL BANKER RESIDENTIAL RE

7 days on RocketTour

$10,000 Closing Credit¹

$1,399,999

5 beds • 3 baths • 2,589 sqft

6665 Lake Cane Dr, Orlando, FL 32819

#G5097899, Jean Tolentino, Listing office: COMPASS FLORIDA LLC

7 days on RocketTour

$7,500,000

5 beds • 6.5 baths • 8,443 sqft

11103 Bridge House Rd, Windermere, FL 34786

#O6315165, Ayoub Aitelhaj, Listing office: THE SIMON SIMAAN GROUP

7 days on RocketTour

$10,000 Closing Credit¹

$940,000

5 beds • 4.5 baths • 3,615 sqft

9257 Outlook Rock Trl, Windermere, FL 34786

#O6315160, Macarena Jimenez, Listing office: ZARIA REALTY GROUP LLC

$4,299,000

5 beds • 6 baths • 6,196 sqft

3428 Chaine Du Lac Blvd, Windermere, FL 34786

#O6314470, Mauro Costa, Listing office: CORCORAN PREMIER REALTY

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

$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

Tour

$10,000 Closing Credit¹

$949,900

5 beds • 4 baths • 3,537 sqft

3372 Bellington Dr, Orlando, FL 32835

#O6313790, Cleve Loveland, Listing office: LOVELAND PROPERTIES

$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

$9,736 Closing Credit¹

$819,900

5 beds • 3.5 baths • 2,880 sqft

390 Anessa Rose Loop, Ocoee, FL 34761

#O6312474, Jenny Dunn, Listing office: STOCKWORTH REALTY GROUP

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

$9,084 Closing Credit¹

$765,000

5 beds • 3.5 baths • 3,430 sqft

13130 Meergate Cir, Orlando, FL 32837

#S5127807, Naf Zaman, Listing office: THE FIRM RE

Tour

$10,000 Closing Credit¹

$1,999,000

5 beds • 5.5 baths • 4,351 sqft

6149 Blakeford Dr, Windermere, FL 34786

#O6312983, Brynn Allen, Listing office: CORCORAN PREMIER REALTY

$10,000 Closing Credit¹

$895,000

5 beds • 4 baths • 3,151 sqft

1638 Whitney Isles Dr, Windermere, FL 34786

#O6310111, Morgan Horsley, Listing office: THE REAL ESTATE COLLECTION LLC

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

$10,000 Closing Credit¹

$1,250,000

5 beds • 3.5 baths • 3,646 sqft

1947 Broadleaf Ct, Windermere, FL 34786

#O6312642, Kevin Sullivan, Listing office: LAKESIDE REALTY WINDERMERE INC

Tour

$9,025 Closing Credit¹

$760,000

5 beds • 3 baths • 2,916 sqft

14131 Islamorada Dr, Orlando, FL 32837

#O6311342, Lauren Endsley, Listing office: PREMIER SOTHEBYS INT'L REALTY

Southwest Orange, FL Real Estate Market Overview

There are 242 5-bedroom homes for sale in Southwest Orange, FL. The following market insights reflect all property types in the Southwest Orange, FL real estate market. The number of homes in Southwest Orange, FL increased by 3.8% between April 2025 and May 2025. The median list price of listings available in May 2025 was $561,639, while the average time on the real estate market was 64 days. In May 2025 more than 36 listings in Southwest Orange, FL were sold above the asking price. During the same period more than 64 listings were sold at asking price, while more than 220 were sold below.

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

What is it like to live in Southwest Orange, FL

Overview

Southwest Orange is located in Orange County, Florida. There are roughly 180,165 residents, living in 62,684 households. The average temperature for Southwest Orange this time of the year is low of 70F and high of 91F. On average, Southwest Orange gets about 7.35 inches of precipitation in June. Most residents are home owners (64%), have a post secondary degree (62%) and are single, no kids (33%).

Data provided by Home Junction

Schools near Southwest Orange, FL

Elementary Schools

Sadler Elementary School
4000 W Oak Ridge Rd
Public District PK-5
Metrowest Elementary School
1801 Lake Vilma Dr
Public District KG-5
Castleview Elementary School
9131 Taborfield Ave
Public District KG-5

Middle Schools

Renaissance Charter School at Hunters Creek
4140 W Town Center Blvd
Public Charter KG-8
OCPS Academic Center for Excellence
701 W Livingston St
Public District PK-8
Chain of Lakes Middle School
8700 Conroy Windermere Rd
Public District 6-8

High Schools

Chancery High Charter
7001 S Orange Blossom Trl
Public Charter 9-12
West Orange High School
1625 Beulah Rd
Public District 9-12
Windermere High School
5523 Winter Garden Vineland Rd
Public District 9-12

Data provided by Great Schools

5 bedroom homes for sale in Southwest Orange, FL

Southwest Orange, FL Real Estate Market Overview

What is it like to live in Southwest Orange, FL

Overview

Explore popular home types in Southwest Orange, FL

Related homes in Southwest Orange, FL

Schools near Southwest Orange, FL

Housing market reports in Orange County

Homes for sale near Southwest Orange, FL

Real estate in Southwest Orange neighborhoods

Top real estate cities in Florida