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 $2.4M
Lowest Price $295K
Highest Price $30M
Total Listings 233
Avg. Days On Market 98
Avg. Price/SQFT $458

Property Types (active listings)

Windermere

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New
5579 Somersby Road, WINDERMERE

$395,000

5579 Somersby Road TENNYSON PK/SUMMERPORT, WINDERMERE FL 34786-3207

3 Beds 3 Baths 1,579 SqFt Residential MLS® # TB8517100 Disney: 8.72 miles
New
6533 Cartmel Ln, WINDERMERE

$1,595,000

6533 Cartmel Ln RESERVE AT LAKE BUTLER SOUND, WINDERMERE FL 34786-5423

5 Beds 4 Baths 3,751 SqFt Residential MLS® # O6425396 Disney: 7.00 miles
New
6119 Grosvenor Shore Drive, WINDERMERE

$15,900,000

6119 Grosvenor Shore Drive KEENE'S POINT, WINDERMERE FL 34786-5660

7 Beds 9 Baths 14,068 SqFt Residential MLS® # O6421205 Disney: 6.24 miles
New
11429 Brownstone Street, WINDERMERE

$460,000

11429 Brownstone Street LAKE BURDEN SOUTH PH 2, WINDERMERE FL 34786-5716

4 Beds 3 Baths 1,910 SqFt Residential MLS® # O6421245 Disney: 5.85 miles
New
14030 Sparkling Cove Lane 603, WINDERMERE

$330,000

14030 Sparkling Cove Lane 603 OASIS COVE I/LAKESIDE VILLAGE PH 01, WINDERMERE FL 34786-6808

2 Beds 3 Baths 1,232 SqFt Residential MLS® # O6424774 Disney: 5.74 miles
New
13303 Penshurst Lane, WINDERMERE

$669,900

13303 Penshurst Lane WINDERMERE SOUND, WINDERMERE FL 34786-6694

5 Beds 5 Baths 2,959 SqFt Residential MLS® # O6423867 Disney: 6.60 miles
New Open House
9225 Mcdavid Court, WINDERMERE

$799,999

9225 Mcdavid Court ROBERTS LANDING, WINDERMERE FL 34786-8121

4 Beds 2 Baths 2,713 SqFt Residential
Sat, Jul 18th, 2026 @ 11am - 1pm
MLS® # O6424617
Disney: 11.20 miles
New
13419 Lemon Orchard Bend, WINDERMERE

$599,990

↓ $6,277

13419 Lemon Orchard Bend LAKE CAWOOD COVE, WINDERMERE FL 34786

3 Beds 3 Baths 1,699 SqFt Residential MLS® # TB8528688 Disney: 8.45 miles
New
1629 Hempel Avenue, WINDERMERE

$2,500,000

1629 Hempel Avenue GOTHA TOWN, WINDERMERE FL 34786-8117

6 Beds 4 Baths 4,858 SqFt Residential MLS® # O6418226 Disney: 11.08 miles
New
13328 Overstreet Road, WINDERMERE

$639,900

13328 Overstreet Road LAKE SAWYER SOUTH, WINDERMERE FL 34786-6684

4 Beds 3 Baths 2,648 SqFt Residential MLS® # O6423949 Disney: 6.73 miles
New
9433 Palm Tree Drive, WINDERMERE

$560,000

9433 Palm Tree Drive SILVER WOODS PH 03, WINDERMERE FL 34786-8813

3 Beds 2 Baths 1,819 SqFt Residential MLS® # O6423262 Disney: 8.86 miles
New
4642 River Gem Avenue, WINDERMERE

$825,000

4642 River Gem Avenue SUMMERPORT PH 05, WINDERMERE FL 34786-3180

5 Beds 5 Baths 3,373 SqFt Residential MLS® # O6422241 Disney: 9.29 miles
New
13431 Bellaria Circle, WINDERMERE

$3,250,000

13431 Bellaria Circle BELLARIA, WINDERMERE FL 34786-7403

4 Beds 5 Baths 5,616 SqFt Residential MLS® # P4939244 Disney: 9.03 miles
New
8342 Boyla Court, WINDERMERE

$6,700,000

8342 Boyla Court KEENES POINTE, WINDERMERE FL 34786-5320

8 Beds 10 Baths 8,133 SqFt Residential MLS® # O6422852 Disney: 5.91 miles
New
11564 Mizzon Drive 102, WINDERMERE

$295,000

11564 Mizzon Drive 102 LAKESIDE/LKS/WINDERMERE, WINDERMERE FL 34786

2 Beds 2 Baths 1,161 SqFt Residential MLS® # O6423023 Disney: 5.71 miles
New
7231 Sangalla Drive, WINDERMERE

$1,300,000

7231 Sangalla Drive CASA DEL LAGO-REPLAT, WINDERMERE FL 34786-5679

5 Beds 5 Baths 3,835 SqFt Residential MLS® # O6422598 Disney: 6.40 miles
6241 Blakeford Drive, WINDERMERE

$1,795,000

6241 Blakeford Drive KEENE'S POINTE, WINDERMERE FL 34786-5606

4 Beds 4 Baths 3,556 SqFt Residential MLS® # O6417788 Disney: 6.79 miles
2009 Woody Drive, WINDERMERE

$1,200,000

2009 Woody Drive WINDERMERE DOWNS, WINDERMERE FL 34786-8016

4 Beds 3 Baths 3,540 SqFt Residential MLS® # O6422132 Disney: 10.80 miles
7060 Ventnor Drive, WINDERMERE

$444,900

7060 Ventnor Drive PRESTON SQUARE, WINDERMERE FL 34786-5913

3 Beds 3 Baths 1,642 SqFt Residential MLS® # S5153025 Disney: 6.48 miles
13845 Bridgewater Crossings Blvd, WINDERMERE

$474,900

↓ $14,100

13845 Bridgewater Crossings Blvd SUMMERPORT TRAIL PH 2, WINDERMERE FL 34786

3 Beds 3 Baths 1,636 SqFt Residential MLS® # O6421552 Disney: 8.24 miles
2053 Woody Drive, WINDERMERE

$679,000

2053 Woody Drive WINDERMERE DOWNS, WINDERMERE FL 34786-8016

3 Beds 3 Baths 2,177 SqFt Residential MLS® # O6421738 Disney: 10.72 miles
2512 Tryon Place, WINDERMERE

$1,190,000

↓ $40,000

2512 Tryon Place MANORS AT BUTLER BAY PH 02, WINDERMERE FL 34786-3412

4 Beds 3 Baths 3,478 SqFt Residential MLS® # O6422154 Disney: 10.10 miles
11446 Jasper Kay Terrace 103, WINDERMERE

$330,000

11446 Jasper Kay Terrace 103 LAKESIDE AT LAKES OF WINDERMERE, WINDERMERE FL 34786

3 Beds 2 Baths 1,442 SqFt Residential MLS® # O6420653 Disney: 5.79 miles
13219 Charfield Street, WINDERMERE

$565,000

13219 Charfield Street LAKE SAWYER SOUTH PH 2, WINDERMERE FL 34786

3 Beds 2 Baths 1,706 SqFt Residential MLS® # O6420991 Disney: 6.31 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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