Windermere

IS WINDERMERE THE PLACE FOR YOU?


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 $2.2M
Lowest Price $295K
Highest Price $27M
Total Listings 227
Avg. Days On Market 109
Avg. Price/SQFT $449

Property Types (active listings)

Windermere

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New
5373 Isleworth Country Club Drive, WINDERMERE

$7,200,000

5373 Isleworth Country Club Drive ISLEWORTH, WINDERMERE FL 34786-8929

5 Beds 6 Baths 5,993 SqFt Residential MLS® # O6439156 Disney: 8.19 miles
New
4301 Down Point Lane, WINDERMERE

$2,950,000

4301 Down Point Lane DOWN POINT SUB, WINDERMERE FL 34786-8412

5 Beds 4 Baths 7,153 SqFt Residential MLS® # O6439832 Disney: 9.67 miles
New
6243 Andreozzi Lane, WINDERMERE

$720,000

6243 Andreozzi Lane PROVIDENCE PH 01 50 03, WINDERMERE FL 34786-7314

4 Beds 2 Baths 2,516 SqFt Residential MLS® # O6439730 Disney: 7.78 miles
New
12417 Cruxbury Drive, WINDERMERE

$360,000

12417 Cruxbury Drive LAKES/WINDERMERE-LK REAMS TWHM, WINDERMERE FL 34786-9460

2 Beds 3 Baths 1,311 SqFt Residential MLS® # O6439656 Disney: 4.59 miles
New
515 W 2nd Avenue, WINDERMERE

$3,300,000

515 W 2nd Avenue WINDERMERE TOWN, WINDERMERE FL 34786-8514

4 Beds 6 Baths 3,966 SqFt Residential MLS® # O6439554 Disney: 9.29 miles
New
9764 Gotha Road, WINDERMERE

$450,000

9764 Gotha Road GOTHA TOWN, WINDERMERE FL 34786-8104

2 Beds 1 Bath 1,216 SqFt Residential MLS® # O6439109 Disney: 11.47 miles
New Open House
13730 Lensdale Lane, WINDERMERE

$375,000

13730 Lensdale Lane SOUTHBRIDGE VILLAGE, WINDERMERE FL 34786-7369

4 Beds 3 Baths 1,640 SqFt Residential
Sun, Sep 13th, 2026 @ 12pm - 2pm
MLS® # O6439354
Disney: 7.80 miles
New
5050 Isleworth Country Club Drive, WINDERMERE

$3,189,000

5050 Isleworth Country Club Drive ISLEWORTH, WINDERMERE FL 34786

4 Beds 5 Baths 3,365 SqFt Residential MLS® # O6438618 Disney: 9.05 miles
New
7033 Bramlea Lane, WINDERMERE

$647,000

↑ $17,000

7033 Bramlea Lane LAKES WINDERMERE PH 01 49 108, WINDERMERE FL 34786-6624

3 Beds 3 Baths 2,229 SqFt Residential MLS® # O6438579 Disney: 6.71 miles
4415 Blue Major Drive, WINDERMERE

$779,900

↓ $25,100

4415 Blue Major Drive SUMMERPORT PH 05, WINDERMERE FL 34786-3192

5 Beds 3 Baths 3,211 SqFt Residential MLS® # O6359496 Disney: 9.29 miles
New
5379 Isleworth Country Club Drive, WINDERMERE

$3,400,000

5379 Isleworth Country Club Drive ISLEWORTH, WINDERMERE FL 34786-8929

4 Beds 4 Baths 3,872 SqFt Residential MLS® # O6438449 Disney: 8.19 miles
New
8104 Jailene Drive, WINDERMERE

$759,000

8104 Jailene Drive LAKE SAWYER SOUTH PH 05, WINDERMERE FL 34786-6747

4 Beds 4 Baths 2,886 SqFt Residential MLS® # O6437963 Disney: 5.87 miles
New
14077 Ancilla Boulevard, WINDERMERE

$399,000

14077 Ancilla Boulevard SUMMERPORT EDENS HAMMOCK, WINDERMERE FL 34786-3217

3 Beds 3 Baths 1,651 SqFt Residential MLS® # O6437694 Disney: 8.53 miles
12264 Montalcino Circle, WINDERMERE

$5,390,000

12264 Montalcino Circle CASA DEL LAGO REP, WINDERMERE FL 34786-5672

4 Beds 7 Baths 7,872 SqFt Residential MLS® # O6404587 Disney: 6.29 miles
2540 Hempel Cove Ct, WINDERMERE

$1,399,900

2540 Hempel Cove Ct LAKE DOWN COVE, WINDERMERE FL 34786-8214

5 Beds 3 Baths 3,356 SqFt Residential MLS® # O6436594 Disney: 10.56 miles
13048 Garridan Avenue, WINDERMERE

$445,000

13048 Garridan Avenue WINDERMERE SOUND PH 2, WINDERMERE FL 34786-6433

3 Beds 3 Baths 1,748 SqFt Residential MLS® # O6437967 Disney: 6.36 miles
13503 Lake Cawood Drive, WINDERMERE

$1,500,000

13503 Lake Cawood Drive LAKE CAWOOD ESTS REP, WINDERMERE FL 34786-7000

5 Beds 7 Baths 5,312 SqFt Residential MLS® # TB8542427 Disney: 8.21 miles
13239 Jervey Street, WINDERMERE

$710,999

13239 Jervey Street LAKE SAWYER SOUTH PH 01, WINDERMERE FL 34786-6367

4 Beds 4 Baths 2,745 SqFt Residential MLS® # O6436893 Disney: 6.63 miles
13844 Amelia Pond Drive, WINDERMERE

$600,000

13844 Amelia Pond Drive SUMMERPORT PHASE 1, WINDERMERE FL 34786-3114

4 Beds 3 Baths 2,670 SqFt Residential MLS® # O6401590 Disney: 9.08 miles
13325 Lush Lime Alley, WINDERMERE

$641,681

13325 Lush Lime Alley LAKE CAWOOD COVE, WINDERMERE FL 34786

3 Beds 3 Baths 1,714 SqFt Residential MLS® # TB8544045 Disney: 8.52 miles
5526 Marleon Drive, WINDERMERE

$2,500,000

5526 Marleon Drive LAKE DAVIS RESERVE A & B, WINDERMERE FL 34786-7019

5 Beds 5 Baths 4,661 SqFt Residential MLS® # S5156252 Disney: 8.24 miles
9021 Via Di Canti, WINDERMERE

$550,000

9021 Via Di Canti ROYAL ESTATES, WINDERMERE FL 34786

5 Beds 4 Baths 2,268 SqFt Residential MLS® # O6437659 Disney: 4.79 miles
12989 Westside Village Loop, WINDERMERE

$1,187,000

12989 Westside Village Loop WESTSIDE VILLAGE, WINDERMERE FL 34786-6779

4 Beds 4 Baths 2,665 SqFt Residential MLS® # O6437718 Disney: 6.10 miles
4844 Flint Road, WINDERMERE

$529,000

4844 Flint Road SUMMERPORT PH 05, WINDERMERE FL 34786-3179

3 Beds 2 Baths 2,085 SqFt Residential MLS® # O6436938 Disney: 9.24 miles

SURROUNDED BY GORGEOUS SAND BOTTOM LAKES

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.

AMONG AMERICA'S TOP 15% WEALTHIEST COMMUNITIES

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.

ADDITIONAL WINDERMERE REAL ESTATE RESOURCES


HOMES MAINTAIN STRONG VALUE THROUGH TOUGH TIMES

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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