Windermere Florida Windermere Florida Lake Downtown Windermere Florida Windermere Florida Town Hall

Windermere real estate is surrounded by the picturesque Butler Chain of Lakes, providing the perfect setting for one of Central Florida's most elegant and unique communities. Beautiful waters, gorgeous landscapes, and lavish golf courses come together to create some of the finest and most scenic luxury real estate known to the region. Populated by breathtaking lakefront properties, Windermere, FL attracts those with a strong appreciation for the finer things in life.

Windermere, FL Homes for Sale

255 Properties Found. Page 1 of 6.
Photo of Listing #O5890318

9508 Windy Ridge Rd

$30,000,000
Windermere
MLS® # O5890318
6 Beds, 14 Baths, 51,000 Sf
Photo of Listing #O5714911
Enhanced

9912 Lake Louise Dr

$23,000,000
Windermere
MLS® # O5714911
11 Beds, 14 Baths, 25,466 Sf
Photo of Listing #O5883078
Reduced 15.4%

9927 Giffin Ct

$16,500,000
Windermere
MLS® # O5883078
12 Beds, 15 Baths, 31,000 Sf
Photo of Listing #O5895605
Windermere
MLS® # O5895605
5 Beds, 8 Baths, 12,778 Sf
Photo of Listing #O5834063
Windermere
MLS® # O5834063
8 Beds, 9 Baths, 13,230 Sf
Photo of Listing #S5038054

6010 Cartmel Ln

$7,000,000
Windermere
MLS® # S5038054
6 Beds, 9 Baths, 14,150 Sf
Photo of Listing #O5872952
Reduced 2.2%
Windermere
MLS® # O5872952
6 Beds, 10 Baths, 12,298 Sf
Photo of Listing #O5903029
Windermere
MLS® # O5903029
6 Beds, 9 Baths, 10,452 Sf
Photo of Listing #S5036746

5507 Worsham Ct

$5,959,000
Windermere
MLS® # S5036746
5 Beds, 9 Baths, 10,200 Sf
Photo of Listing #O5701437
Reduced 16.8%

5020 Down Point Ln

$4,949,000
Windermere
MLS® # O5701437
8 Beds, 8 Baths, 9,621 Sf
Photo of Listing #O5868103
Reduced 2.1%

12624 Park Ave

$4,623,000
Windermere
MLS® # O5868103
6 Beds, 7 Baths, 6,996 Sf
Photo of Listing #O5877250

6025 Greatwater Dr

$3,899,000
Windermere
MLS® # O5877250
7 Beds, 8 Baths, 7,812 Sf
Photo of Listing #O5866407
Enhanced
Windermere
MLS® # O5866407
5 Beds, 7 Baths, 7,463 Sf
Photo of Listing #O5878174
Reduced 1.5%
Windermere
MLS® # O5878174
5 Beds, 7 Baths, 7,426 Sf
Photo of Listing #O5907662
New
Windermere
MLS® # O5907662
8 Beds, 10 Baths, 8,808 Sf
Photo of Listing #O5855410
Windermere
MLS® # O5855410
5 Beds, 7 Baths, 7,070 Sf
Photo of Listing #O5906379
Windermere
MLS® # O5906379
4 Beds, 6 Baths, 5,518 Sf
Photo of Listing #O5896580
Windermere
MLS® # O5896580
7 Beds, 10 Baths, 9,594 Sf
Photo of Listing #O5898616
Windermere
MLS® # O5898616
6 Beds, 9 Baths, 8,393 Sf
Photo of Listing #O5890500
Windermere
MLS® # O5890500
5 Beds, 7 Baths, 6,360 Sf
Photo of Listing #O5882687

6233 Greatwater Dr

$3,495,000
Windermere
MLS® # O5882687
6 Beds, 8 Baths, 7,757 Sf
Photo of Listing #O5879567
Windermere
MLS® # O5879567
3 Beds, 6 Baths, 6,598 Sf
Photo of Listing #O5895339

4233 Down Point Ln

$3,199,958
Windermere
MLS® # O5895339
6 Beds, 7 Baths, 6,478 Sf
Photo of Listing #O5893267

12516 Park Ave

$3,150,000
Windermere
MLS® # O5893267
6 Beds, 8 Baths, 8,172 Sf
Photo of Listing #O5828068
Reduced 3.1%

12616 Park Ave

$3,099,000
Windermere
MLS® # O5828068
5 Beds, 7 Baths, 7,620 Sf
Photo of Listing #O5832554

11056 Bayshore Dr

$2,995,000
Windermere
MLS® # O5832554
5 Beds, 8 Baths, 4,626 Sf
Photo of Listing #S5040014
Windermere
MLS® # S5040014
5 Beds, 5 Baths, 4,458 Sf
Photo of Listing #O5859910
Windermere
MLS® # O5859910
6 Beds, 8 Baths, 8,078 Sf
Photo of Listing #O5870571

914 W 2nd Avenue

$2,899,000
Windermere
MLS® # O5870571
5 Beds, 6 Baths, 7,222 Sf
Photo of Listing #O5873782

9702 Wild Oak Dr

$2,799,900
Windermere
MLS® # O5873782
6 Beds, 10 Baths, 8,307 Sf
Photo of Listing #O5898398
Windermere
MLS® # O5898398
3 Beds, 4 Baths, 4,225 Sf
Photo of Listing #O5892462
Windermere
MLS® # O5892462
4 Beds, 7 Baths, 6,189 Sf
Photo of Listing #O5899098

4260 Isabella Cir

$2,677,000
Windermere
MLS® # O5899098
4 Beds, 6 Baths, 7,971 Sf
Photo of Listing #O5888997
Reduced 0.6%

4077 Isabella Cir

$2,675,000
Windermere
MLS® # O5888997
6 Beds, 8 Baths, 7,544 Sf
Photo of Listing #O5880944

13119 Casabella Dr

$2,655,000
Windermere
MLS® # O5880944
5 Beds, 7 Baths, 6,855 Sf
Photo of Listing #O5863151
Windermere
MLS® # O5863151
5 Beds, 7 Baths, 6,531 Sf
Photo of Listing #O5775680
Reduced 5.2%
Windermere
MLS® # O5775680
4 Beds, 6 Baths, 4,505 Sf
Photo of Listing #O5888371
Windermere
MLS® # O5888371
5 Beds, 6 Baths, 6,745 Sf
Photo of Listing #O5825450
Reduced 4.9%
Windermere
MLS® # O5825450
5 Beds, 7 Baths, 7,263 Sf
Photo of Listing #O5898442

2608 Midsummer Dr

$2,350,000
Windermere
MLS® # O5898442
5 Beds, 5 Baths, 5,536 Sf
Photo of Listing #O5895831
Windermere
MLS® # O5895831
4 Beds, 4 Baths, 3,957 Sf
Photo of Listing #O5883033

4285 Isabella Cir

$2,350,000
Windermere
MLS® # O5883033
6 Beds, 8 Baths, 7,430 Sf
Photo of Listing #O5899362

4333 Isabella Cir

$2,193,000
Windermere
MLS® # O5899362
6 Beds, 7 Baths, 6,857 Sf
Photo of Listing #O5902025

11209 Macaw Ct

$2,100,000
Windermere
MLS® # O5902025
6 Beds, 7 Baths, 5,609 Sf
Photo of Listing #O5888968
Windermere
MLS® # O5888968
5 Beds, 9 Baths, 7,031 Sf
Photo of Listing #O5888668

2730 Midsummer Dr

$2,100,000
Windermere
MLS® # O5888668
4 Beds, 4 Baths, 3,452 Sf
Photo of Listing #O5871364
Reduced 4.8%

522 W 2nd Ave

$2,000,000
Windermere
MLS® # O5871364
6 Beds, 6 Baths, 5,399 Sf
Photo of Listing #O5850349
Reduced 4.8%

6115 S Hampshire Ct

$1,999,000
Windermere
MLS® # O5850349
5 Beds, 6 Baths, 6,231 Sf

Windermere, FL Real Estate

Located 14 miles southwest of Downtown Orlando, residents of Windermere can enjoy the excitement of world famous attractions and big city life, while returning home to the gorgeous guard gated communities that provide family and estate homes the serenity and shelter of quiet small town living. To preserve the small town feel, town officials have gone to great lengths to divert city traffic and overdevelopment, making the Town of Windermere, FL one of the most exclusive and sought after communities in all Orlando Real Estate.

Immaculate estates and luxury homes characterize Windermere real estate, and are available in a wide range of architecture styles guaranteed to please those with the most particular tastes. These beautiful Windermere homes are located on finely manicured stretches of land, complete with stunning lakefront views of Central Florida's magnificent sunsets.

Great schools, incredible recreational opportunities, beautiful terrain, and convenient proximity to Downtown Orlando and its many attractions have earned Windermere the prestigious title of Florida's number one neighborhood to live for family and children. Offering something special for everyone, Windermere is one of the Sunshine State's soundest real estate investments.

Windermere Florida Downtown

Aside from the luxury homes in Windermere, the area is also pampered by a wealth recreation. A vast system of inland lakes and canals come together to make up the Butler Chain of Lakes. The Butler Chain of Lakes provides an enormous variety in water based activities for all Windermere residents. Days of boating, swimming, water skiing, and fishing are within reach all year round. The exclusive Country Club's and famed Golf Courses at Windermere Club, Keene's Pointe, and Isleworth allow golfers to experience world class golf outings just minutes from home.

Additional Windermere Real Estate Information:

The History of Windermere  |  Town of Windermere Town Logo  |  Windermere Parks & Recreation

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 DBA Stellar MLS.

Listing information last updated on November 29th, 2020 at 3:15pm EST.