Windermere

Community Info

  • Price Range:
    $489,900-$20,000,000

About Windermere

Why Live in Windermere Florida

The Town of Windermere is one of the nicest small towns in Florida. It is located on the secondary roads about 15 miles west-southwest of downtown Orlando on the Butler Chain of Lakes.

These lakes are popular places for waters skiing, boating and fishing. Windermere is a residential community with a population in 2022 of less than 4,000.

Windermere, Florida is a small, vibrant city in Orange County, Florida. It’s one of the best and popular suburbs of Orlando, especially for wealthy people.

Windermere is known for its luxurious lakefront homes, famous residents and a quiet, charming atmosphere.

Windermere is in Orange County and is one of the best places to live in Florida. Living in Windermere offers residents a sparse suburban feel and most residents own their homes. Residents of Windermere tend to lean conservative. The public schools in Windermere are highly rated.

  1. Windermere is one of the most affluent cities in Florida. It enjoys a low crime rate and an above average income.
  2. Isleworth is the most prestigious gated community in Orlando, FL's most prestigious neighborhood – Windermere. If you're looking for the best of the best gated community homes for sale in Windermere, FL, look no further than Isleworth.
  3. In 2021, the median household income of Windermere households was $131,392. Windermere households made slightly more than Tierra Verde households ($130,938) and Chaires households ($130,208) . However, 3.6% of Windermere families live in poverty.
  4. The unemployment rate in Windermere is 5.5% (U.S. avg. is 6.0%). Recent job growth is Positive. Windermere jobs have increased by 3.9%.
  5. Compared to the rest of the country, Windermere's cost of living is 28.3% higher than the U.S. average
  6. November, April and March are the most pleasant months in Windermere, while August and July are the least comfortable months.
  7. The median home cost in Windermere is Real Estate: $689,100. Home appreciation the last 10 years has been 24.2%.
  8. Windermere public schools spend $9,506 per student. The average school expenditure in the U.S. is $12,383. There are about 15.9 students per teacher in Windermere

Even though it is a very small town, the greater Windermere area has been steadily growing. Real estate prices are much higher here than most other sections of Orange County

The quiet neighborhoods of Windermere are located on an isthmus between Lake Down and Lake Butler. The downtown area has a small-town feel.

In more recent years, plush golf course developments like Isleworth, home of Tiger Woods, Shaquille O'Neal and other celebrities, have popped up on the edges of Windermere.

Some of these luxury homes are on one of the many golf courses, and others are on Lake Butler and Lake Down.

Windermere’s location is one of the best parts of the city. It offers a lovely blend; big-city excitement, but with small-town quality of life.

Depending on traffic, Walt Disney World is approximately 20 minutes away from the City of Windermere. Downtown Orlando is about 12 miles away.

Windermere Luxury Homes for Sale by Orlando Best Real Estate

Call Orlando Best Real Estate @ 407.961.8412 for Windermere Luxury Homes for Sale. We Have all the MLS Listings for Windermere Luxury Homes & the entire Orlando Area.

Orlando Luxury Homes and Communities

7 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
11900 LAKE BUTLER BOULEVARD
 $20,000,000 7 / 8
 10,649sf Y / Y
5271 ISLEWORTH COUNTRY CLUB DR
 $8,775,000 7 / 1
 11,403sf N / Y
225 MAGNOLIA STREET
 $4,899,000 7 / 1
 5,935sf Y / Y

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
9832 LAUREL VALLEY DRIVE
 $9,490,000 6 / 7
 11,100sf Y / Y
5157 LATROBE DRIVE
 $4,777,000 6 / 8
 5,721sf N / Y
4065 ISABELLA CIRCLE
 $3,699,000 6 / 7
 8,064sf N / Y
4029 ISABELLA CIRCLE
 $3,549,000 6 / 6
 7,217sf N / Y
1003 OAKDALE STREET
 $2,650,000 6 / 5
 4,599sf Y / Y
13596 GORGONA ISLE DRIVE
 $1,490,000 6 / 4
 3,794sf N / Y
8352 LOOKOUT POINTE DRIVE
 $1,050,000 6 / 4
 5,098sf N / N
8298 LOOKOUT POINTE DRIVE
 $974,000 6 / 4
 4,319sf N / N
7180 BEEK STREET
 $820,000 6 / 4
 3,648sf N / N
11410 RAPALLO LANE
 $769,000 6 / 5
 3,336sf N / N

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
5525 ISLEWORTH COUNTRY CLUB DR
 $14,250,000 5 / 5
 9,511sf N / Y
5074 ISLEWORTH COUNTRY CLUB DR
 $8,325,000 5 / 6
 6,937sf N / Y
11103 BRIDGE HOUSE ROAD
 $7,500,000 5 / 5
 8,443sf Y / Y
5507 WORSHAM COURT
 $7,500,000 5 / 7
 10,200sf N / Y
6126 KIRKSTONE LANE
 $7,150,000 5 / 6
 8,691sf N / Y
5199 LATROBE DRIVE
 $5,494,000 5 / 6
 4,665sf N / Y
6109 ORTA COURT
 $4,600,000 5 / 5
 5,895sf Y / Y
805 W 2ND AVENUE
 $4,398,000 5 / 4
 4,783sf Y / Y
801 W 2ND AVENUE
 $4,395,000 5 / 6
 5,639sf Y / Y
3428 CHAINE DU LAC BOULEVARD
 $4,299,000 5 / 5
 6,196sf N / Y
13125 CASABELLA DRIVE
 $4,200,000 5 / 5
 7,561sf Y / Y
11013 ULLSWATER LANE
 $3,290,000 5 / 4
 6,705sf N / Y
800 W 2ND AVENUE
 $2,900,000 5 / 4
 5,111sf Y / Y
5067 LATROBE DRIVE
 $2,850,000 5 / 6
 6,219sf N / Y
409 W 2ND AVENUE
 $2,499,000 5 / 4
 4,688sf N / Y
11113 LAKE BUTLER BOULEVARD
 $2,499,000 5 / 5
 4,094sf N / N
4279 ISABELLA CIRCLE
 $2,299,000 5 / 4
 4,345sf N / Y
729 MAIN STREET
 $2,100,000 5 / 4
 3,950sf N / Y
11056 CLIPPER COURT
 $1,850,000 5 / 6
 6,375sf N / Y
11015 HAWKSHEAD COURT
 $1,700,000 5 / 4
 3,868sf N / Y
6220 CARTMEL LN
 $1,699,000 5 / 4
 4,347sf N / Y
17551 BLACK RAIL STREET
 $1,550,000 5 / 4
 3,972sf N / Y
3443 WILD MYRTLE COURT
 $1,200,000 5 / 3
 2,918sf N / Y
2602 TRYON PLACE
 $955,900 5 / 3
 2,564sf N / Y
11761 BELLA MILANO COURT
 $899,999 5 / 4
 2,844sf N / N
8713 IRON MOUNTAIN TRAIL
 $899,000 5 / 3
 3,718sf N / N
2128 LAKE CRESCENT COURT
 $856,000 5 / 2
 2,987sf N / Y
11774 VIA LUCERNA CIRCLE
 $850,000 5 / 4
 2,871sf N / N
7409 FAIRGROVE AVENUE
 $800,000 5 / 3
 3,357sf N / N
11514 VIA LUCERNA CIRCLE
 $749,990 5 / 4
 2,871sf N / N
11578 ASHLIN PARK BOULEVARD
 $648,800 5 / 3
 2,396sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
11018 LAKE BUTLER BOULEVARD
 $3,500,000 4 / 3
 3,923sf Y / Y
11617 WATERSTONE LOOP DRIVE
 $2,950,000 4 / 4
 4,957sf Y / Y
6120 PAYNE STEWART DR
 $2,799,000 4 / 4
 3,636sf N / N
3413 LILAS COURT
 $2,300,000 4 / 4
 5,084sf N / Y
4108 DOWNEAST LANE
 $2,295,000 4 / 3
 3,150sf Y / N
6143 CARTMEL LANE
 $2,250,000 4 / 5
 4,582sf N / Y
6550 CARTMEL LANE
 $2,199,000 4 / 4
 4,257sf N / Y
5025 DOWN POINT LANE
 $2,175,000 4 / 4
 5,071sf N / Y
3130 BUTLER BAY DRIVE N
 $1,899,950 4 / 4
 4,490sf N / Y
830 OAKDALE STREET
 $1,875,000 4 / 4
 3,670sf N / Y
11019 KENTMERE COURT
 $1,799,000 4 / 4
 3,813sf N / Y
3417 BAY MEADOW COURT
 $1,600,000 4 / 4
 2,681sf N / Y
6533 CARTMEL LANE
 $1,548,000 4 / 3
 3,751sf N / Y
11706 WATERSTONE LOOP DRIVE
 $1,459,900 4 / 3
 3,586sf N / Y
2931 SUNBITTERN COURT
 $1,425,000 4 / 3
 4,018sf N / Y
11754 WATERSTONE LOOP DRIVE
 $1,400,000 4 / 3
 3,049sf N / Y
11707 HAMPSTEAD STREET
 $1,225,000 4 / 3
 3,419sf Y / Y
11507 CENTER LAKE DRIVE
 $1,099,000 4 / 3
 3,766sf N / N
6426 MONTCLAIR BLUFF LANE
 $995,000 4 / 3
 3,080sf N / Y
11314 LEDGEMENT LANE
 $989,000 4 / 3
 3,080sf N / Y
13413 HOPKINTON COURT
 $949,000 4 / 3
 2,642sf N / N
7508 LAKE ALBERT DRIVE
 $945,000 4 / 3
 3,059sf N / Y
13838 BLUEBIRD PARK ROAD
 $935,000 4 / 3
 2,897sf Y / Y
11130 PARK AVENUE
 $895,000 4 / 2
 1,925sf N / N
9538 LAVILL COURT
 $829,000 4 / 3
 2,748sf N / Y
12755 WESTSIDE VILLAGE LOOP
 $815,000 4 / 3
 3,064sf N / N
9601 AMBLESIDE DRIVE
 $800,000 4 / 2
 3,018sf N / N
9676 WILD OAK DRIVE
 $799,000 4 / 2
 2,856sf N / Y
11837 CAVE RUN AVENUE
 $789,900 4 / 3
 3,407sf N / N
7971 BROFIELD AVE
 $749,900 4 / 3
 2,805sf N / N
6799 HELMSLEY CIRCLE
 $748,000 4 / 3
 2,876sf N / N
13519 BICTON LANE
 $745,000 4 / 3
 2,745sf N / N
9025 HORIZON POINTE TRAIL
 $739,000 4 / 3
 3,264sf N / N
7214 TATTANT BOULEVARD
 $685,000 4 / 2
 2,211sf N / Y
6957 NORTHWICH DRIVE
 $660,000 4 / 3
 2,667sf N / N
11313 VIA ANDIAMO
 $650,000 4 / 3
 2,727sf N / N
4833 PALM TREE COURT
 $649,900 4 / 2
 2,020sf N / Y
6971 TETTENHALL LANE
 $649,000 4 / 3
 2,920sf N / N
12724 BIDEFORD AVENUE
 $630,000 4 / 3
 3,072sf N / N
9319 WOODBREEZE BOULEVARD
 $609,500 4 / 2
 1,798sf N / N
5231 LEMON TWIST LANE
 $600,000 4 / 2
 2,136sf N / N
5032 BEACH RIVER ROAD
 $599,000 4 / 2
 2,306sf N / N
5263 BEACH RIVER ROAD
 $595,000 4 / 3
 2,432sf N / N
8359 LOOKOUT POINTE DRIVE
 $589,000 4 / 4
 2,604sf N / N
12868 HOLDENBURY LANE
 $580,000 4 / 2
 2,460sf N / N
13252 VENNETTA WAY
 $579,000 4 / 3
 2,413sf N / N
7349 ELLA LANE
 $574,900 4 / 3
 2,461sf N / N
11091 BAGLEY ALY
 $544,900 4 / 2
 2,222sf Y / N
12109 SILVERLAKE PARK DRIVE
 $489,900 4 / 2
 2,063sf N / N

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
11923 LAKE BUTLER BOULEVARD
 $1,630,000 3 / 2
 2,238sf N / N
111 MAIN STREET
 $999,000 3 / 2
 2,272sf N / N
235 OAKDALE STREET
 $950,000 3 / 2
 2,562sf N / Y
AVENUE
 $699,000 3 / 2
 1,864sf N / N
11316 RAPALLO LANE
 $599,000 3 / 2
 1,925sf N / N
12679 CALDERDALE AVENUE
 $579,900 3 / 2
 1,681sf N / N
8160 IRON MOUNTAIN TRAIL
 $565,000 3 / 2
 2,009sf N / N
12255 JOSHUA TREE TRAIL
 $549,900 3 / 2
 2,149sf N / N
8839 ABBOTSBURY DRIVE
 $549,500 3 / 2
 1,875sf N / N
6728 DUNCASTER STREET
 $539,000 3 / 2
 2,088sf N / N
4813 RIVER GEM AVENUE
 $529,999 3 / 2
 2,085sf Y / N
12795 BOSWORTH AVENUE
 $529,999 3 / 2
 1,696sf N / N
13324 LONGACRE DRIVE
 $510,000 3 / 2
 2,058sf N / N
12751 CALDERDALE AVENUE
 $509,998 3 / 2
 1,696sf N / N
11037 BAGLEY ALLEY
 $499,999 3 / 2
 1,904sf N / N

Property Location

Community Info

  • Windermere
  • Price Range:
    $489,900-$20,000,000

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