Windermere, FL Real Estate & Homes for Sale

100 of 351 results

13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
Active
$2,500,000
4 bd • 5 ba • 6,725 sq ft
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
Active
$5,995,000
5 bd • 6 ba • 6,500 sq ft
13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
3103 SEIGNEURY DRIVE, WINDERMERE, FL 34786
Active
$2,700,000
8 bd • 6 ba • 6,900 sq ft
3103 SEIGNEURY DRIVE, WINDERMERE, FL 34786
8704 CRESTGATE CIRCLE, ORLANDO, FL 32819
Active
$1,890,000
5 bd • 6 ba • 14,607 sq ft
8704 CRESTGATE CIRCLE, ORLANDO, FL 32819
8225 BRYCE CANYON AVENUE, WINDERMERE, FL 34786
Active
$560,000
4 bd • 3 ba • 2,554 sq ft
8225 BRYCE CANYON AVENUE, WINDERMERE, FL 34786
12001 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786
Active
$1,775,000
3 bd • 3 ba • 5,205 sq ft
12001 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786
8767 IRON MOUNTAIN TRAIL, WINDERMERE, FL 34786
Active
$870,000
5 bd • 4 ba • 4,450 sq ft
8767 IRON MOUNTAIN TRAIL, WINDERMERE, FL 34786
8822 WINTER GARDEN VINELAND ROAD, ORLANDO, FL 32836
Active
$15,000,000
3 bd • 3 ba • 4,758 sq ft
8822 WINTER GARDEN VINELAND ROAD, ORLANDO, FL 32836
11545 BRICKYARD POND LANE, WINDERMERE, FL 34786
Active
$2,200,000
8 bd • 9 ba • 6,447 sq ft
11545 BRICKYARD POND LANE, WINDERMERE, FL 34786
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
Active
$3,390,000
4 bd • 5 ba • 4,843 sq ft
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
Active
$979,000
5 bd • 4 ba • 4,812 sq ft
7904 WESTMINSTER ABBEY BOULEVARD, ORLANDO, FL 32835
Active
$300,000
Condo
2 bd • 2 ba • 1,300 sq ft
7679 SUGAR BEND DRIVE UNIT 7784, ORLANDO, FL 32819
Active
$3,000,000
5 bd • 5 ba • 4,160 sq ft
19 MAIN STREET, WINDERMERE, FL 34786
Active
$3,500,000
4 bd • 4 ba • 4,280 sq ft
43 MAIN STREET, WINDERMERE, FL 34786
Active
$1,396,000
6 bd • 5 ba • 4,058 sq ft
13596 GORGONA ISLE DRIVE, WINDERMERE, FL 34786
Active
$5,100,000
4 bd • 6 ba • 7,246 sq ft
5243 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
Active
$689,000
5 bd • 3 ba • 3,429 sq ft
13232 LONGACRE DRIVE, WINDERMERE, FL 34786
Active
$3,999,999
5 bd • 8 ba • 9,127 sq ft
11002 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786
Active
$1,490,000
5 bd • 4 ba • 4,621 sq ft
11339 CAMDEN PARK DRIVE, WINDERMERE, FL 34786
Active
$670,000
4 bd • 4 ba • 2,297 sq ft
8582 POWDER RIDGE TRAIL, WINDERMERE, FL 34786
Active
$750,000
4 bd • 4 ba • 4,365 sq ft
11903 CAVE RUN AVENUE, WINDERMERE, FL 34786
Active
$430,000
3 bd • 3 ba • 2,272 sq ft
13366 ABUELA ALLEY, WINDERMERE, FL 34786
Active
$1,400,000
5 bd • 4 ba • 3,976 sq ft
11537 CLAYMONT CIR, WINDERMERE, FL 34786
Active
$685,000
3 bd • 3 ba • 3,599 sq ft
8445 SHADY GLEN DRIVE, ORLANDO, FL 32819
Active
$680,000
5 bd • 4 ba • 3,721 sq ft
6712 THORNHILL CIRCLE, WINDERMERE, FL 34786
Active
$900,000
4 bd • 5 ba • 4,412 sq ft
11835 GOLD CREEK TRAIL, WINDERMERE, FL 34786
Active
$3,900,000
5 bd • 6 ba • 8,062 sq ft
6049 LADY BET DRIVE, ORLANDO, FL 32819
Active
$3,725,000
5 bd • 4 ba • 6,355 sq ft
58 MAIN STREET, WINDERMERE, FL 34786
Active
$3,200,000
4 bd • 5 ba • 6,461 sq ft
4819 ALEXANDRA GARDEN COURT, WINDERMERE, FL 34786
Active
$3,400,000
4 bd • 4 ba • 6,151 sq ft
9731 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
Active
$834,000
4 bd • 4 ba • 3,708 sq ft
6631 CRESTMONT GLEN LANE, WINDERMERE, FL 34786
Active
$999,500
4 bd • 3 ba • 3,871 sq ft
8920 VIA BELLA NOTTE, ORLANDO, FL 32836
Active
$1,130,000
8 bd • 5 ba • 5,475 sq ft
6152 GOLDEN DEWDROP TRAIL, WINDERMERE, FL 34786
Active
$2,899,000
5 bd • 4 ba • 4,642 sq ft
10203 TROUT ROAD, ORLANDO, FL 32836
Active
$1,520,000
4 bd • 5 ba • 3,962 sq ft
1703 ROBERTS LANDING ROAD, WINDERMERE, FL 34786
Active
$1,825,000
4 bd • 5 ba • 6,860 sq ft
11226 MACAW COURT, WINDERMERE, FL 34786
Active
$3,700,000
5 bd • 7 ba • 1,007 sq ft
6857 VALHALLA WAY, WINDERMERE, FL 34786
Active
$995,000
4 bd • 4 ba • 4,258 sq ft
11162 LEDGEMENT LANE, WINDERMERE, FL 34786
Active
$17,250,000
7 bd • 9 ba • 22,728 sq ft
11900 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786
Active
$749,000
3 bd • 2 ba • 2,868 sq ft
14050 FAIRWAY WILLOW LANE, WINTER GARDEN, FL 34787
Active
$15,500,000
10 bd • 17 ba • 17,652 sq ft
12488 PARK AVENUE, WINDERMERE, FL 34786
Active
$3,699,000
3 bd • 5 ba • 7,467 sq ft
4812 ALEXANDRA GARDEN COURT, WINDERMERE, FL 34786
Active
$789,900
4 bd • 4 ba • 4,955 sq ft
475 DOUGLAS EDWARD DRIVE, OCOEE, FL 34761
Active
$395,000
4 bd • 3 ba • 2,107 sq ft
8484 LEELAND ARCHER BOULEVARD, ORLANDO, FL 32836
Active
$949,999
4 bd • 4 ba • 4,675 sq ft
2237 BAESEL VIEW DRIVE, ORLANDO, FL 32835
Active
$929,000
6 bd • 4 ba • 4,385 sq ft
8854 OAK LANDINGS COURT, ORLANDO, FL 32836
Active
$13,500,000
5 bd • 10 ba • 12,788 sq ft
7011 VIA CARMEL WAY, ORLANDO, FL 32819
Active
$629,900
3 bd • 2 ba • 2,942 sq ft
13622 DARCHANCE ROAD, WINDERMERE, FL 34786
Active
$719,900
4 bd • 3 ba • 2,598 sq ft
7665 MOUNT CARMEL DRIVE, ORLANDO, FL 32835
Active
$985,000
4 bd • 4 ba • 3,765 sq ft
8800 OAK LANDINGS COURT, ORLANDO, FL 32836
Active
$1,100,000
4 bd • 5 ba • 4,841 sq ft
2313 ROAT DRIVE, ORLANDO, FL 32835
Active
$385,000
3 bd • 3 ba • 2,399 sq ft
12210 LANGSTAFF DRIVE, WINDERMERE, FL 34786
Active
$7,495,000
6 bd • 9 ba • 10,798 sq ft
9108 SHEEN SOUND STREET, ORLANDO, FL 32836
Active
$10,900,000
6 bd • 8 ba • 9,122 sq ft
6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786
Active
$895,000
4 bd • 3 ba • 2,901 sq ft
13542 GORGONA ISLE DRIVE, WINDERMERE, FL 34786
Active
$1,398,900
5 bd • 4 ba • 3,288 sq ft
5701 TARAWOOD DRIVE, ORLANDO, FL 32819
Active
$1,390,000
6 bd • 5 ba • 6,553 sq ft
17538 BLACK RAIL STREET, WINDERMERE, FL 34786
Active
$760,000
6 bd • 6 ba • 4,058 sq ft
11410 RAPALLO LANE, WINDERMERE, FL 34786
Active
$5,900,000
5 bd • 9 ba • 19,706 sq ft
9639 WESTOVER ROBERTS ROAD, WINDERMERE, FL 34786
Active
$465,000
3 bd • 3 ba • 1,974 sq ft
12353 VIA DERNA PLACE, WINDERMERE, FL 34786
Active
$839,999
Condo
3 bd • 3 ba • 6,875 sq ft
5941 CHESAPEAKE PARK UNIT GE, ORLANDO, FL 32819
Active
$1,499,000
6 bd • 6 ba • 6,000 sq ft
8273 WILSON TERRACE, ORLANDO, FL 32819
Active
$554,555
4 bd • 2 ba • 2,178 sq ft
9319 WOODBREEZE BOULEVARD, WINDERMERE, FL 34786
Active
$510,547
3 bd • 3 ba • 2,818 sq ft
8214 AMBROSE COVE WAY, ORLANDO, FL 32819
Active
$300,000
Condo
2 bd • 2 ba • 1,300 sq ft
7784 SUGAR BEND DRIVE UNIT 7784, ORLANDO, FL 32819
Active
$6,000,000
7 bd • 7 ba • 11,952 sq ft
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
Active
$1,175,000
5 bd • 4 ba • 4,235 sq ft
715 MAGNOLIA STREET, WINDERMERE, FL 34786
Active
$825,000
4 bd • 3 ba • 4,094 sq ft
9018 VIA BELLA NOTTE, ORLANDO, FL 32836
Active
$2,950,000
5 bd • 4 ba • 10,041 sq ft
4301 DOWN POINT LANE, WINDERMERE, FL 34786
Active
$5,000,000
6 bd • 9 ba • 12,557 sq ft
9721 CARILLON PARK DRIVE, WINDERMERE, FL 34786
Active
$3,200,000
4 bd • 5 ba • 3,889 sq ft
2 CHASE ROAD, WINDERMERE, FL 34786
Active
$3,900,000
4 bd • 5 ba • 7,172 sq ft
5151 LATROBE DR, WINDERMERE, FL 34786
Active
$5,500,000
4 bd • 5 ba • 5,911 sq ft
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
Active
$2,175,000
4 bd • 5 ba • 5,088 sq ft
436 E 7TH AVENUE, WINDERMERE, FL 34786
Active
$1,495,000
4 bd • 4 ba • 5,046 sq ft
8734 CRESTGATE CIRCLE, ORLANDO, FL 32819
Active
$4,995,000
6 bd • 7 ba • 10,799 sq ft
5070 DOWN POINT LANE, WINDERMERE, FL 34786
Active
$1,875,000
5 bd • 4 ba • 6,019 sq ft
13420 BONICA WAY, WINDERMERE, FL 34786
Active
$999,000
4 bd • 3 ba • 3,239 sq ft
8525 BOWDEN WAY, WINDERMERE, FL 34786
Active
$4,590,000
7 bd • 8 ba • 11,491 sq ft
5745 EMERINGTON CRESCENT, ORLANDO, FL 32819
Active
$769,995
3 bd • 2 ba • 2,978 sq ft
9237 SABAL PALM CIRCLE, WINDERMERE, FL 34786
Active
$2,500,000
5 bd • 4 ba • 8,316 sq ft
6606 SAWYER SHORES LANE, WINDERMERE, FL 34786
Active
$1,890,000
4 bd • 4 ba • 4,863 sq ft
6560 LAKE BURDEN VIEW DRIVE, WINDERMERE, FL 34786
Active
$1,997,000
6 bd • 5 ba • 6,914 sq ft
8830 GREY HAWK POINT, ORLANDO, FL 32836
Active
$756,000
Condo
3 bd • 3 ba • 3,033 sq ft
5925 CHESAPEAKE PARK UNIT 54, ORLANDO, FL 32819
Active
$539,000
3 bd • 2 ba • 2,324 sq ft
8629 GRANADA BOULEVARD, ORLANDO, FL 32836
Active
$959,000
4 bd • 3 ba • 3,395 sq ft
9144 GALLEON COURT, ORLANDO, FL 32819
Active
$1,460,000
4 bd • 4 ba • 5,422 sq ft
2509 RIDGEWIND WAY, WINDERMERE, FL 34786
Active
$680,000
5 bd • 4 ba • 4,290 sq ft
8552 POWDER RIDGE TRAIL, WINDERMERE, FL 34786
Active
$625,000
4 bd • 4 ba • 3,660 sq ft
8632 ABBOTSBURY DRIVE, WINDERMERE, FL 34786
Active
$1,399,000
3 bd • 4 ba • 4,277 sq ft
8358 VIA VITTORIA WAY, ORLANDO, FL 32819
Active
$4,850,000
7 bd • 8 ba • 13,977 sq ft
9575 WESTOVER ROBERTS ROAD, WINDERMERE, FL 34786
Active
$409,900
3 bd • 3 ba • 2,116 sq ft
11686 WATER RUN ALY, WINDERMERE, FL 34786
Active
$2,175,000
6 bd • 6 ba • 6,780 sq ft
713 MAIN STREET, WINDERMERE, FL 34786
Active
$458,000
3 bd • 3 ba • 2,640 sq ft
12333 VIA DERNA PLACE, WINDERMERE, FL 34786
Active
$750,000
5 bd • 3 ba • 4,785 sq ft
2205 WINTERMERE POINTE DRIVE, WINTER GARDEN, FL 34787
Active
$1,999,900
5 bd • 5 ba • 7,592 sq ft
5421 TILDENS GROVE BOULEVARD, WINDERMERE, FL 34786
Active
$27,000,000
7 bd • 10 ba • 34,320 sq ft
5603 MARLEON DRIVE, WINDERMERE, FL 34786
Active
$1,245,000
4 bd • 3 ba • 4,500 sq ft
9211 HIDDEN BAY LANE, ORLANDO, FL 32819
Active
$516,000
3 bd • 2 ba • 2,210 sq ft
8509 SANDBERRY BOULEVARD, ORLANDO, FL 32819
Active
$464,000
4 bd • 2 ba • 2,488 sq ft
469 MICKLETON LOOP, OCOEE, FL 34761
Page 1 of 4 (351 results)
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Central Texas MLS

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Windermere, FL Market Summary

Current MLS market statistics for active listings in this area.

Active listings212
New listings last 30 days56
Median list price$1,299,450
Median price per sq ft$375
List price range$299,500 - $30,000,000
Median bedrooms4
Median bathrooms4
Median living area3,490 sq ft
Typical HOA fees$1 – $4,800 / month

Medians are based on 212 sampled active listings when available.

Windermere Area Overview

Population3,086
Median Household Income$177,778
Median Age50.3
Land Area1.91 sq mi
Water Area0.75 sq mi
Population Density1,619.9 / sq mi
Owner-Occupied Housing95.6%

Source: U.S. Census Bureau (ACS 5-year estimates)