Windermere

Windermere Real Estate Listings
9508 Windy Ridge Rd, Windermere
  • Residential
  • 7 Beds
  • 14.00 Baths
  • 51,000 sq ft

9508 Windy Ridge Rd, Windermere

$28,500,000
9912 Lake Louise Dr, Windermere
  • Residential
  • 11 Beds
  • 14.00 Baths
  • 25,466 sq ft

9912 Lake Louise Dr, Windermere

$23,000,000
5115 Fairway Oaks Dr, Windermere
  • Residential
  • 7 Beds
  • 11.00 Baths
  • 15,063 sq ft

5115 Fairway Oaks Dr, Windermere

$10,999,000 ↓ $2,501,000
5372 Isleworth Country Club Dr, Windermere
  • Residential
  • 8 Beds
  • 9.00 Baths
  • 13,230 sq ft

5372 Isleworth Country Club Dr, Windermere

$8,600,000 ↓ $650,000
5318 Isleworth Country Club Dr, Windermere
  • Residential
  • 6 Beds
  • 10.00 Baths
  • 12,128 sq ft

5318 Isleworth Country Club Dr, Windermere

$7,200,000
11055 Bridge House Rd, Windermere
  • Residential
  • 6 Beds
  • 9.00 Baths
  • 10,452 sq ft

11055 Bridge House Rd, Windermere

$6,750,000
5506 Isleworth Country Club Dr, Windermere
  • Residential
  • 6 Beds
  • 9.00 Baths
  • 8,049 sq ft

5506 Isleworth Country Club Dr, Windermere

$6,650,000
5354 Isleworth Country Club Dr, Windermere
  • Residential
  • 5 Beds
  • 6.00 Baths
  • 9,811 sq ft

5354 Isleworth Country Club Dr, Windermere

$6,300,000
5020 Down Point Ln, Windermere
  • Residential
  • 5 Beds
  • 8.00 Baths
  • 9,621 sq ft

5020 Down Point Ln, Windermere

$5,949,000
5501 Isleworth Country Club Dr, Windermere
  • Residential
  • 5 Beds
  • 8.00 Baths
  • 6,956 sq ft

5501 Isleworth Country Club Dr, Windermere

$5,295,000
6342 Deacon Cir, Windermere
  • Residential
  • 5 Beds
  • 6.00 Baths
  • 7,008 sq ft

6342 Deacon Cir, Windermere

$4,900,000
11103 Bridge House Rd, Windermere
  • Residential
  • 5 Beds
  • 7.00 Baths
  • 9,403 sq ft

11103 Bridge House Rd, Windermere

$4,850,000

Real Estate Statistics
Property Types (active listings)
Average Price: $1,305,322
Total Listings: 443
Avg. Days On Market: 207
Avg. Price/SQFT: $259
Highest Price: $28,500,000
Lowest Price: $177,900
Avg. Property Age: 14 YEARS
Basic Statistics (active listings)

Browse Windermere Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
Photo of Listing #O5746245
  • Residential
  • 7 Beds
  • 14.00 Baths
  • 51,000 SqFt

9508 Windy Ridge Rd

$28,500,000
Photo of Listing #O5714911
  • Residential
  • 11 Beds
  • 14.00 Baths
  • 25,466 SqFt

9912 Lake Louise Dr

$23,000,000
Photo of Listing #O5433535
  • Residential
  • 7 Beds
  • 11.00 Baths
  • 15,063 SqFt

5115 Fairway Oaks Dr

$10,999,000
Photo of Listing #O5700351
  • Residential
  • 8 Beds
  • 9.00 Baths
  • 13,230 SqFt

5372 Isleworth Country Club Dr

$8,600,000
Photo of Listing #O5713515
  • Residential
  • 6 Beds
  • 10.00 Baths
  • 12,128 SqFt

5318 Isleworth Country Club Dr

$7,200,000
Photo of Listing #O5711522
  • Residential
  • 6 Beds
  • 9.00 Baths
  • 10,452 SqFt

11055 Bridge House Rd

$6,750,000
Photo of Listing #O5573526
  • Residential
  • 6 Beds
  • 9.00 Baths
  • 8,049 SqFt

5506 Isleworth Country Club Dr

$6,650,000
Photo of Listing #O5713089
  • Residential
  • 5 Beds
  • 6.00 Baths
  • 9,811 SqFt

5354 Isleworth Country Club Dr

$6,300,000
Photo of Listing #O5701437
  • Residential
  • 5 Beds
  • 8.00 Baths
  • 9,621 SqFt

5020 Down Point Ln

$5,949,000
Photo of Listing #O5740376
  • Residential
  • 5 Beds
  • 8.00 Baths
  • 6,956 SqFt

5501 Isleworth Country Club Dr

$5,295,000
Photo of Listing #O5735188
  • Residential
  • 5 Beds
  • 6.00 Baths
  • 7,008 SqFt

6342 Deacon Cir

$4,900,000
Photo of Listing #O5745102
  • Residential
  • 5 Beds
  • 7.00 Baths
  • 9,403 SqFt

11103 Bridge House Rd

$4,850,000
Photo of Listing #O5571293
  • Residential
  • 5 Beds
  • 6.00 Baths
  • 8,400 SqFt

9711 Deacon Ct

$4,774,000
Photo of Listing #O5746188
  • Residential
  • 8 Beds
  • 10.00 Baths
  • 8,781 SqFt

8304 Lake Burden Cir

$4,295,000
Photo of Listing #A4408859
  • Residential
  • 6 Beds
  • 9.00 Baths
  • 8,393 SqFt

9313 Tibet Pointe Cir

$4,250,000
Photo of Listing #O5707203
  • Residential
  • 4 Beds
  • 7.00 Baths
  • 9,034 SqFt

6121 Greatwater Dr

$4,200,000
Photo of Listing #O5710520
  • Residential
  • 5 Beds
  • 7.00 Baths
  • 7,388 SqFt

9934 Lake Louise Dr

$4,000,000
Photo of Listing #O5556718
  • Land
  • 0 Beds
  • 0.00 Baths
  • 0 SqFt

10988 Down Yonder Ln

$3,999,999

Want to learn more about Maitland homes for sale? Orlando Hub Real Estate is your Maitland real estate specialists - we have the market insights and are here to to answer any questions you might have! Contact us so we can help you find the perfect Maitland home for you!

Are you interested in finding a home in Windermere? At Orlando Hub Real Estate, we're here to help, we have the market insights and years of experience in this area. Contact us  so we can help you find the perfect Windermere home for you. 

Learning More About Windermere 

Windermere started off a long time ago as a quant town for fishing. The lakes that surround Windermere form the Butler Chain of Lakes. As far back as the 1800's, little fishing houses could be seen along the waterways around the Windermere chain of lakes. As more and more discovered the beauty of Windermere, it expanded beyond the fishing village that it once was and started turning into a proper town. 

One of the beauties of Windermere is that the roads within the town limits have always been dirt roads and will remain dirt roads. This helps to keep the lakes pristine and without run-off from regularly paved roads. 

Why Windermere Is Known

Years ago Windermere became recognized as a wonderful place for golfers. From Arnold Palmer really getting the trend going, to this day it is known worldwide as having some of the golf courses in the world. 

The choices range from the all famous Bay Hill to Keene's Point and of course Isle Worth's golf course. You never really know who you might see out of the golf course, maybe a famous golfer or actor - there are a lot of them within the city limits. 

Luxury Waterfront Homes In Windermere

Windermere is known for their gorgeous waterways and their famous bird island. Surrounding the water are beautiful homes all with wonderful views of the lakes. A really good thing is that there is still places where new construction can happen. 

Location Of Windermere

Windermere is close enough to the Disney attractions to be able to hear the fireworks each and every night. It's also very close to restaurant row located on Sand Lake Road. Lastly you're minutes from being on the turnpike which can take you south all of the way to Miami and north to Gainesville and I-75. 

The Schools Of Windermere

All schools in Windermere are located within the Orange County Public School District, Windermere has some really good educational opportunities at each level from elementary to high school. 

Elementary schools include Windermere, Keenes Crossing and Sunset Park. All three of the schools are rated at least an 8/10, with Windermere Elementary coming in at a 9/10. All 3 of the schools have programs for students to participate in the arts and music. They even have their own Orchestra at Windermere Elementary. 

Middle schools include Bridgewater, Chain of Lakes and Gotha Middle. All schools cover AVID, Band, Chorus and a number of other activities for the students to get involved with.

High schools include West Orange, Olympia and the all new Windermere high school. All of these schools have wonderful activities for kids to be involved with. Olympia recently won awards for being one of the best high schools to prepare students for college. All of the schools also top rated for their STEM classes that prepare students for the future of tomorrow. 

If you're considering Windermere as a place you'd like to call home, Contact Orlando Hub Real Estate to find out what properties are available today. 

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on December 12th, 2018 at 3:31pm CST.

What's Your Home Worth? Find out now, for Free.

Let's Go