Windermere may be one of the most unique towns in the Orlando Metropolitan area. Named for the largest lake in England, Windermere is a small town of 2,040, but it is also one of the wealthiest locations in the entire Orlando Metro area. Real estate-wise, Windermere is surrounded by upscale gated communities, many of which are home to professional and superstar athletes such as Tiger Woods. Many local residents live in or visit Windermere because they crave the privacy it can offer and enjoy all the comforts of upscale, small town living. Windermere is the ultimate in exclusivity and works hard to oblige its residents and visitors by limiting heavy vehicles from entering to preserve its roads and limiting traffic in many areas to locals only.

Real Estate Statistics

Average Price $2.7M
Lowest Price $315K
Highest Price $25M
Total Listings 116
Avg. Days On Market 103
Avg. Price/SQFT $446

Property Types (active listings)


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5507 Worsham Ct, WINDERMERE


5507 Worsham Ct ISLEWORTH, WINDERMERE FL 34786

5 Beds 7 Baths 10,200 SqFt Residential MLS® # O6098484
13750 Ancilla Boulevard, WINDERMERE


13750 Ancilla Boulevard SUMMERPORT PH 03, WINDERMERE FL 34786

2 Beds 2 Baths 1,155 SqFt Residential MLS® # O6098432
9247 Legado Drive, WINDERMERE


9247 Legado Drive LEGADO, WINDERMERE FL 34786

4 Beds 3 Baths 2,779 SqFt Residential MLS® # O6099255
6241 Blakeford Drive, WINDERMERE


6241 Blakeford Drive KEENES POINTE, WINDERMERE FL 34786

5 Beds 4 Baths 3,556 SqFt Residential MLS® # O6098198
1810 Westover Reserve Boulevard, WINDERMERE


1810 Westover Reserve Boulevard WESTOVER RESERVE PH 01, WINDERMERE FL 34786

4 Beds 5 Baths 3,764 SqFt Residential MLS® # O6098382
2661 Stanton Hall Court, WINDERMERE


2661 Stanton Hall Court MANORS AT BUTLER BAY PH 01, WINDERMERE FL 34786

4 Beds 2 Baths 2,200 SqFt Residential MLS® # O6099066
12525 Montalcino Circle, WINDERMERE


12525 Montalcino Circle CASA DEL LAGO REP, WINDERMERE FL 34786

4 Beds 4 Baths 3,117 SqFt Residential MLS® # O6098658
11545 Brickyard Pond Lane, WINDERMERE


11545 Brickyard Pond Lane LAKE BURDEN SOUTH PH I, WINDERMERE FL 34786

6 Beds 7 Baths 5,159 SqFt Residential MLS® # O6099125
8057 Tibet Butler Drive, WINDERMERE


8057 Tibet Butler Drive KEENES POINTE UNIT 2, WINDERMERE FL 34786

4 Beds 4 Baths 4,062 SqFt Residential MLS® # O6097457
11444 Misty Oak Alley, WINDERMERE


11444 Misty Oak Alley ASHLIN PARK PH 1, WINDERMERE FL 34786

4 Beds 3 Baths 2,361 SqFt Residential MLS® # S5081995
11952 Camden Park Drive, WINDERMERE


11952 Camden Park Drive KEENES POINTE, WINDERMERE FL 34786

5 Beds 4 Baths 3,337 SqFt Residential MLS® # O6098551
11431 Buckley Wood Lane, WINDERMERE


11431 Buckley Wood Lane KEENES POINTE, WINDERMERE FL 34786

4 Beds 5 Baths 3,715 SqFt Residential MLS® # O6098017
8531 Eagles Loop Circle, WINDERMERE


8531 Eagles Loop Circle KEENES POINTE UT 06 50 95, WINDERMERE FL 34786

4 Beds 4 Baths 3,169 SqFt Residential MLS® # O6097855
5717 Oxford Moor Boulevard, WINDERMERE


5717 Oxford Moor Boulevard OXFORD MOOR 47/30, WINDERMERE FL 34786

4 Beds 4 Baths 5,508 SqFt Residential MLS® # O6095769
12816 Water Point Boulevard, WINDERMERE


12816 Water Point Boulevard WATERFORD POINTE, WINDERMERE FL 34786

5 Beds 4 Baths 4,433 SqFt Residential MLS® # O6095587
11129 Lake Butler Boulevard, WINDERMERE


11129 Lake Butler Boulevard WAUSEON RIDGE, WINDERMERE FL 34786

3 Beds 2 Baths 2,098 SqFt Residential MLS® # O6098234
6005 Down Point Lane, WINDERMERE


6005 Down Point Lane SUNSET BAY, WINDERMERE FL 34786

5 Beds 9 Baths 6,481 SqFt Residential MLS® # O6097911
9306 Blanche Cove Drive, WINDERMERE


9306 Blanche Cove Drive ISLEWORTH, WINDERMERE FL 34786

5 Beds 8 Baths 14,856 SqFt Residential MLS® # O6097686
11237 Camden Park Drive, WINDERMERE


11237 Camden Park Drive KEENES POINTE UNIT 7, WINDERMERE FL 34786

4 Beds 4 Baths 3,492 SqFt Residential MLS® # S5082268
5139 Isleworth Country Club Dr, WINDERMERE


5139 Isleworth Country Club Dr ISLEWORTH, WINDERMERE FL 34786

7 Beds 8 Baths 13,973 SqFt Residential MLS® # O6097345
10430 Birch Tree Lane, WINDERMERE


10430 Birch Tree Lane WINDERMERE DOWNS PH 03, WINDERMERE FL 34786

6 Beds 5 Baths 3,579 SqFt Residential MLS® # O6095442
1439 Whitney Isles Drive, WINDERMERE


1439 Whitney Isles Drive WHITNEY ISLES/BELMERE PH 02, WINDERMERE FL 34786

5 Beds 4 Baths 3,230 SqFt Residential MLS® # O6094608
9718 Green Island Cove, WINDERMERE


9718 Green Island Cove ISLEWORTH, WINDERMERE FL 34786

4 Beds 6 Baths 4,724 SqFt Residential MLS® # O6095851
7467 Lake Albert Drive, WINDERMERE


7467 Lake Albert Drive LAKE BURDEN SOUTH PH 2, WINDERMERE FL 34786

6 Beds 7 Baths 5,140 SqFt Residential MLS® # O6097180


Living or vacationing in Windermere provides you access to a variety of leisurely activities. The town’s location allows for quick and easy trips to all the theme parks, shopping malls, world-class restaurants, and concert venues that Orlando has to offer; not to mention all the area’s first-rate golf courses and outdoor recreational amenities that all of Florida is known for. On the side of small town appeal, Windermere is surrounded by gorgeous sand bottom lakes that are ideal for swimming, fishing, and boating, and the town’s quaint Main Street is home to some lovely shopping boutiques, cafés, and local establishments that are unique to only this part of Florida. For the avid golfer, Windermere, as mentioned, is home to several immaculate country clubs, which includes the Golden Bear Club at Keene’s Pointe. For those unfamiliar with the Golden Bear Club, this Jack Nicklaus Signature golf course has breathtaking vistas and challenging holes that every golfer would enjoy and appreciate. Development-wise, Windermere is always looking to grow and become an even better community for its luxury-seeking residents. Looking to increase self-sufficiency for the locals of Windermere, investors are currently planning to expand and create downtown shopping complexes that are in step with the small hometown feel that the town and its residents are trying to maintain.


Overall, the population of Windermere is quite affluent. With a median income of $94,556, the town is among the top 15% wealthiest communities in America. Windermere is also a very family oriented town with an average family size of 3.05 and 70.3% of homes being married couples living together. The town also offers several quality public and private schools for families to choose from. NeighborhoodScout, a search engine for homebuyers, recently issued a special report indentifying Windermere as the best town for families and children in Florida. They drew this conclusion by analyzing data from the National Center for Education Statistics, the US Bureau of Census, the US Justice Department, the FBI, and the Office of Federal Housing Enterprise Oversight.



Windermere is the ideal location for someone who wants to live or vacation in a small town with charm and privacy, but who also wants to enjoy the finer things at the same time. The homes here are smart economic investments, as they have maintained strong values even through the recent economic downturn. The development going on in an effort to expand the shopping, dining, and amenities offered in town will only increase home values, as Windermere becomes an even stronger self-sufficient microcosm. If you’re interested in the luxury real estate for sale situated within the Windermere, FL community, contact us today to learn more or to setup a private showing of some of the most exclusive Windermere properties currently on the market.

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