5 bedroom homes for sale in Windermere, FL

view of front of home with a chimney, a front yard, and a tile roof

view of front of property with a chimney, a front lawn, and a tiled roof

view of front of house featuring a tile roof, a lawn, and a chimney

1 day on RocketVideo tour

$10,000 Closing Credit¹

$1,625,000

5 beds • 4 baths • 4,018 sqft

2931 Sunbittern Ct, Windermere FL 34786

#O6288931, John Cunningham, Listing Office: KELLER WILLIAMS CLASSIC

view of front of house featuring stucco siding, covered porch, and a front yard

view of front of home with stucco siding, a porch, decorative driveway, and a garage

view of exterior entry featuring ceiling fan, covered porch, and stucco siding

1 day on Rocket

$10,000 Closing Credit¹

$879,000

5 beds • 3.5 baths • 3,300 sqft

6244 Little Lake Sawyer Dr, Windermere FL 34786

#O6287439, Michael Spina, Listing Office: INDEPENDENCE REALTY LLC

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

mediterranean / spanish-style home featuring stucco siding, a tiled roof, decorative driveway, and a balcony

mediterranean / spanish-style house featuring stucco siding, decorative driveway, a garage, a balcony, and a tiled roof

1 day on RocketVideo tour

$4,200,000

5 beds • 7.5 baths • 9,909 sqft

3402 Cocard Ct, Windermere FL 34786

#O6289404, Matt Tomaszewski, Listing Office: CORCORAN PREMIER REALTY

bird's eye view featuring a residential view and a water view

view of front of property with stucco siding, a front lawn, a garage, a tiled roof, and decorative driveway

mediterranean / spanish-style house featuring an attached garage, stucco siding, a front lawn, stone siding, and decorative driveway

1 day on Rocket3D tour

$3,000,000

5 beds • 5.5 baths • 5,905 sqft

8336 Boyla Ct, Windermere FL 34786

#O6288146, Simon Simaan, Listing Office: THE SIMON SIMAAN GROUP

view of front of home featuring stone siding, stucco siding, driveway, and a front lawn

view of front of home with decorative driveway, stone siding, an attached garage, and stucco siding

view of front facade with a tile roof, stucco siding, decorative driveway, a garage, and stone siding

1 day on RocketVideo tour

$10,000 Closing Credit¹

$1,299,000

5 beds • 5 baths • 4,041 sqft

1403 Lake Whitney Dr, Windermere FL 34786

#O6289159, Peter Dang, Listing Office: ALLIANCE REAL ESTATE GROUP

view of front of house with a front yard, covered porch, and stucco siding

doorway to property featuring stucco siding

view of patio / terrace with covered porch

2 days on Rocket

$8,016 Closing Credit¹

$675,000

5 beds • 3.5 baths • 3,045 sqft

6613 Duncaster St, Windermere FL 34786

#O6288821, Sarah Carlson, Listing Office: UPSIDE REAL ESTATE INC

mediterranean / spanish house with stucco siding

kitchen with visible vents, ornamental molding, decorative backsplash, a peninsula, and stainless steel appliances

bedroom featuring baseboards, ceiling fan, access to exterior, a raised ceiling, and light colored carpet

3 days on RocketVideo tour

$10,000 Closing Credit¹

$1,295,000

5 beds • 4.5 baths • 3,958 sqft

1613 Glenwick Dr, Windermere FL 34786

#O6285534, Kelly Whitaker, Listing Office: PREMIER SOTHEBYS INT'L REALTY

Room to negotiate?

Median Sold Price

$752K

Avg. Sale Time

64 Days

Based on our February 2025 Market Report.

view of front of property featuring a garage, a shingled roof, board and batten siding, and concrete driveway

kitchen with appliances with stainless steel finishes, washing machine and dryer, a breakfast bar, and white cabinetry

kitchen with a breakfast bar, light countertops, appliances with stainless steel finishes, white cabinetry, and a kitchen island

5 days on RocketVideo tour

$3,942 Closing Credit¹

$331,990

5 beds • 2.5 baths • 2,326 sqft

1807 Teagan Ln, Winter Haven FL 33884

#TB8359417, Ben Goldstein, Listing Office: LENNAR REALTY

mediterranean / spanish-style home with concrete driveway, a front yard, a tiled roof, and stucco siding

birds eye view of property featuring a water view

view of pool featuring a fenced in pool, a fenced backyard, a patio, and an in ground hot tub

6 days on Rocket

$10,000 Closing Credit¹

$1,250,000

5 beds • 4 baths • 4,127 sqft

12820 Butler Bay Ct, Windermere FL 34786

#O6287160, John Muccigrosso, Listing Office: RE/MAX 200 REALTY

mediterranean / spanish house with decorative driveway, an attached garage, a front yard, and stucco siding

hallway with baseboards, wood finished floors, and recessed lighting

6 days on Rocket

$10,000 Closing Credit¹

$899,000

5 beds • 4.5 baths • 3,124 sqft

6926 Trellis Vine Loop, Windermere FL 34786

#O6287872, Deniley Valdes, Listing Office: TALENT REALTY SOLUTIONS

mediterranean / spanish-style house featuring stucco siding, a tiled roof, and a front yard

mediterranean / spanish house with a front yard, a tile roof, and stucco siding

view of exterior entry with a tile roof and stucco siding

6 days on Rocket

$10,000 Closing Credit¹

$2,098,000

5 beds • 4.5 baths • 5,844 sqft

12860 Jacob Grace Ct, Windermere FL 34786

#O6287129, Matt Tomaszewski, Listing Office: CORCORAN PREMIER REALTY

french country home with a shingled roof, metal roof, french doors, and stucco siding

outdoor pool with ceiling fan, french doors, a hot tub, and a patio

7 days on RocketVideo tour

$10,000 Closing Credit¹

$2,298,900

5 beds • 5 baths • 4,197 sqft

1404 Kelso Blvd, Windermere FL 34786

#O6284841, Corinne Defilippis, Listing Office: EXP REALTY LLC

view of front of house featuring decorative driveway

mediterranean / spanish-style home featuring decorative driveway, a tile roof, stucco siding, a balcony, and stone siding

mediterranean / spanish home featuring stone siding, decorative driveway, an attached garage, and a balcony

Video tour

$3,999,999

5 beds • 6 baths • 6,742 sqft

11306 Bridge House Rd, Windermere FL 34786

#O6286072, Andy Williams, Listing Office: LAKESIDE REALTY WINDERMERE INC

view of front facade featuring a front yard, french doors, roof with shingles, and stucco siding

$10,000 Closing Credit¹

$1,195,000

5 beds • 4 baths • 3,419 sqft

2026 Willow Lauren Ln, Windermere FL 34786

#O6282998, Adam Eisen, Listing Office: PLATINUM REALTY GROUP FLORIDA INC

mediterranean / spanish-style house featuring a garage, central AC unit, covered porch, decorative driveway, and stucco siding

view of front of house featuring fence, a front lawn, and stucco siding

view of front facade with a garage, decorative driveway, and stucco siding

$10,000 Closing Credit¹

$875,000

5 beds • 3.5 baths • 3,465 sqft

8330 Vivaro Isle Way, Windermere FL 34786

#O6283971, Alex Vastardis, Listing Office: COLDWELL BANKER REALTY

view of front of property featuring a porch, a front lawn, and stucco siding

view of front facade featuring covered porch, stucco siding, and a front yard

view of front of property featuring a porch, a front yard, fence, and stucco siding

Video tour

$10,000 Closing Credit¹

$1,575,000

5 beds • 4.5 baths • 3,880 sqft

11402 Camden Loop Way, Windermere FL 34786

#O6285044, Brian Hyser, Listing Office: THE AGENCY ORLANDO

mediterranean / spanish-style home featuring stone siding, a front lawn, a tile roof, and stucco siding

view of front facade featuring a tiled roof, decorative driveway, and stucco siding

Video tour

$10,000 Closing Credit¹

$1,475,000

5 beds • 4.5 baths • 3,905 sqft

11234 Willow Gardens Dr, Windermere FL 34786

#O6283926, Stacia Rocheford, Listing Office: ALL REAL ESTATE & INVESTMENTS

mediterranean / spanish-style home featuring decorative driveway, stucco siding, a garage, a tiled roof, and a front lawn

mediterranean / spanish house featuring an attached garage, a tile roof, decorative driveway, stucco siding, and a front yard

mediterranean / spanish-style home with a garage, a tiled roof, decorative driveway, and stucco siding

Video tour

$10,000 Closing Credit¹

$1,850,000

5 beds • 4.5 baths • 3,680 sqft

11856 Vinci Dr, Windermere FL 34786

#S5121318, Oscar Rodriguez, Listing Office: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

view of front of house with covered porch, a front yard, and a garage

view of front of home featuring a garage

Video tour

$8,906 Closing Credit¹

$750,000

5 beds • 3.5 baths • 3,694 sqft

12971 Westside Village Loop, Windermere FL 34786

#S5121081, Eric Jia, Listing Office: NUMBER 1 BROKER, LLC

view of front of house featuring covered porch, a front yard, and a garage

craftsman inspired home with covered porch and a front lawn

view of front facade featuring a garage and a porch

Video tour

$10,000 Closing Credit¹

$900,000

5 beds • 4.5 baths • 3,769 sqft

12791 Westside Village Loop, Windermere FL 34786

#S5121078, Eric Jia, Listing Office: NUMBER 1 BROKER, LLC

view of front facade with a front yard and a garage

Video tour

$8,906 Closing Credit¹

$750,000

5 beds • 4 baths • 3,225 sqft

6974 Trellis Vine Loop, Windermere FL 34786

#S5121073, Eric Jia, Listing Office: NUMBER 1 BROKER, LLC

Video tour

$9,499 Closing Credit¹

$799,900

5 beds • 4.5 baths • 3,769 sqft

12880 Westside Village Loop, Windermere FL 34786

#S5121069, Eric Jia, Listing Office: NUMBER 1 BROKER, LLC

view of front of property featuring a garage

view of front of home with a porch and a garage

foyer with a chandelier, wood-type flooring, and a healthy amount of sunlight

$9,726 Closing Credit¹

$819,000

5 beds • 2.5 baths • 2,772 sqft

8803 Peachtree Park Ct, Windermere FL 34786

#O6281498, Janice Edwards Diaz, PA, Listing Office: PREMIER SOTHEBYS INT'L REALTY

view of front of house with a front lawn and a garage

kitchen with appliances with stainless steel finishes, a kitchen island, washer and dryer, white cabinetry, and a kitchen bar

kitchen featuring a center island, white cabinets, stainless steel appliances, and a breakfast bar area

Video tour

$3,883 Closing Credit¹

$326,990

5 beds • 2.5 baths • 2,326 sqft

1791 Teagan Ln, Winter Haven FL 33884

#TB8351813, Ben Goldstein, Listing Office: LENNAR REALTY

mediterranean / spanish house featuring a balcony and a yard

mediterranean / spanish house featuring a front yard, french doors, and a balcony

drone / aerial view featuring a water view

$7,650,000

5 beds • 6.5 baths • 8,691 sqft

6126 Kirkstone Ln, Windermere FL 34786

#O6278696, Julie Christensen, Listing Office: COMPASS FLORIDA LLC

view of front of home featuring a garage and a front lawn

Video tour

$10,000 Closing Credit¹

$2,495,000

5 beds • 5.5 baths • 5,696 sqft

105 Pine St, Windermere FL 34786

#O6279246, Shelley Heistand, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front of property with a garage and a front lawn

kitchen featuring appliances with stainless steel finishes, white cabinets, a kitchen breakfast bar, a center island, and light tile patterned floors

kitchen with white cabinetry, appliances with stainless steel finishes, and sink

Video tour

$4,037 Closing Credit¹

$339,990

5 beds • 3 baths • 2,451 sqft

1799 Teagan Ln, Winter Haven FL 33884

#TB8348139, Ben Goldstein, Listing Office: LENNAR REALTY

mediterranean / spanish house featuring a balcony and a front yard

view of front of home with a front lawn and a balcony

mediterranean / spanish-style house featuring a garage and a front lawn

$10,000 Closing Credit¹

$1,799,000

5 beds • 4 baths • 3,810 sqft

8424 Lake Burden Cir, Windermere FL 34786

#O6278620, Teresa Stewart, Listing Office: SOUTHERN REALTY GROUP LLC

view of front of home with a garage and a front lawn

view of front of house with a front lawn

Video tour

$10,000 Closing Credit¹

$1,600,000

5 beds • 3 baths • 3,631 sqft

6301 Swanson St, Windermere FL 34786

#V4940762, Maria Galindez, Listing Office: SWANN REAL ESTATE INC

view of mediterranean / spanish-style home

mediterranean / spanish home featuring a garage

$3,499,000

5 beds • 5.5 baths • 6,216 sqft

5067 Latrobe Dr, Windermere FL 34786

#O6278072, Viv Lehman, Listing Office: YOU HAVE REALTY LLC

rear view of house featuring a swimming pool with hot tub, a patio area, and glass enclosure

Video tour

$10,000 Closing Credit¹

$970,000

5 beds • 3.5 baths • 3,720 sqft

8719 Crescendo Ave, Windermere FL 34786

#O6276030, Maria Ubillus, Listing Office: FOLIO REALTY LLC

view of front of property featuring covered porch

view of front of home with a front lawn and covered porch

$10,000 Closing Credit¹

$1,595,000

5 beds • 3.5 baths • 3,840 sqft

11413 Camden Park Dr, Windermere FL 34786

#O6275401, Angela Durruthy, Listing Office: KEENE'S POINTE REALTY

view of front of house featuring a garage and covered porch

view of front of house with a front yard

Video tour

$10,000 Closing Credit¹

$1,699,000

5 beds • 5 baths • 3,520 sqft

6001 Caymus Loop, Windermere FL 34786

#O6276790, Stella Freeman, Listing Office: QUATTRO R E SOLUTIONS LLC

view of front of home featuring a garage and a front yard

living room featuring hardwood / wood-style floors and a high ceiling

$5,300,000

5 beds • 6 baths • 6,188 sqft

11618 Vinci Dr, Windermere FL 34786

#O6271245, Marcio Teixeira, Listing Office: GROUND LEVEL GROUP

mediterranean / spanish-style home featuring a front yard

view of pool with an outdoor fireplace, a patio area, and a gazebo

$10,000 Closing Credit¹

$1,349,000

5 beds • 4 baths • 3,235 sqft

11748 Waterstone Loop Dr, Windermere FL 34786

#O6273185, Immu Korvenmaa, Listing Office: ALIGN REAL ESTATE LLC

neoclassical home featuring a garage, a lawn, and french doors

entrance to property with covered porch and french doors

foyer entrance featuring a wealth of natural light, a chandelier, and crown molding

$10,000 Closing Credit¹

$1,799,000

5 beds • 4.5 baths • 4,347 sqft

6220 Cartmel Ln, Windermere FL 34786

#O6272991, Teresa Stewart, Listing Office: SOUTHERN REALTY GROUP LLC

view of swimming pool with an outdoor fire pit, a patio area, and a lawn

Video tour

$3,200,000

5 beds • 6.5 baths • 5,507 sqft

4326 Isabella Cir, Windermere FL 34786

#O6271069, Robert Arnold, Jr, Listing Office: SAND DOLLAR REALTY GROUP INC

prairie-style house with a garage and a front yard

entrance foyer with light hardwood / wood-style floors and wood walls

Video tour

$10,000 Closing Credit¹

$2,350,000

5 beds • 4.5 baths • 3,685 sqft

6564 Lagoon St, Windermere FL 34786

#O6271044, Fernanda Negromonte, Listing Office: NOVA REAL ESTATE SERVICES INC

mediterranean / spanish-style home with a balcony, a front lawn, and a garage

Video tour

$9,950,000

5 beds • 5.5 baths • 9,403 sqft

11103 Bridge House Rd, Windermere FL 34786

#O6266876, Dianna Desboyaux, Listing Office: SOUTHERN REALTY GROUP LLC

mediterranean / spanish-style house featuring a front lawn

rear view of house featuring a yard and a balcony

view of swimming pool featuring pool water feature and a patio area

Video tour

$4,650,000

5 beds • 6 baths • 7,736 sqft

12540 Park Ave, Windermere FL 34786

#O6265036, Carey Sheffield, Listing Office: ISLEWORTH REALTY LLC

Windermere, FL Real Estate Market Overview

Find your perfect 5 bedroom home in Windermere, FL. Browse 5 in Windermere, FL and connect with a Rocket Homes agent to get your dream home. The number of homes for sale in Windermere, FL increased by 7% between January 2025 and February 2025. The median list price of listings available in February 2025 was $752,068, while the average time on the real estate market was 64 days. In February 2025 more than 6 listings in Windermere, FL were sold above the asking price. During the same period more than 9 listings were sold at asking price, while more than 26 were sold below.

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

5 bedroom homes for sale in Windermere, FL

Windermere, FL Real Estate Market Overview

What is it like to live in Windermere, FL

Overview

Housing types

Advantages

Convenience

Transportation

Explore popular home types in Windermere, FL

Related homes in Windermere, FL

Housing market reports in Orange County

Homes for sale near Windermere, FL

Real estate in Windermere neighborhoods

Top real estate cities in Florida