Winter Garden, FL - Most Valuable Residential Properties in 2025
Updated on November 19, 2025.
According to data from official Florida government agencies, among residential properties in Winter Garden, FL, the following were the most valuable residential properties by Just Value in 2025. The most valuable residential property was 14629 ISLEVIEW DR ($4.48M), followed by 14401 ISLEVIEW DR ($4.29M), 17819 WESTBAY CT ($4.06M), and 17619 DEER ISLE CIR ($3.42M).
The chart below shows the top 10 valuable residential properties, and the table below shows the top 200.
You can see similar information for other Florida cities.
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Data Source: Official Government Sites.
Winter Garden, FL - Most Valuable Residential Properties in 2025
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| Address | Just Value ($) |
|---|---|
| 14629 ISLEVIEW DR, Winter Garden, FL 34787 | 4476760 |
| 14401 ISLEVIEW DR, Winter Garden, FL 34787 | 4286670 |
| 17819 WESTBAY CT, Winter Garden, FL 34787 | 4059890 |
| 17619 DEER ISLE CIR, Winter Garden, FL 34787 | 3421030 |
| 10450 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 3356996 |
| 12408 WALKER POND RD, Winter Garden, FL 34787 | 3171900 |
| 6507 POINT HANCOCK DR, Winter Garden, FL 34787 | 3155690 |
| 14527 PORTER RD, Winter Garden, FL 34787 | 3151950 |
| 5600 AVALON RD, Winter Garden, FL 34787 | 3032580 |
| 17545 DEER ISLE CIR, Winter Garden, FL 34787 | 3006430 |
| 10022 FOX MEADOW TRL, Winter Garden, FL 34787 | 2966513 |
| 7307 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 2963500 |
| 14645 ISLEVIEW DR, Winter Garden, FL 34787 | 2919070 |
| 7827 SKIING WAY, Winter Garden, FL 34787 | 2902680 |
| 6627 POINT HANCOCK DR, Winter Garden, FL 34787 | 2781700 |
| 14613 ISLEVIEW DR, Winter Garden, FL 34787 | 2766320 |
| 14409 ISLEVIEW DR, Winter Garden, FL 34787 | 2752830 |
| 6621 POINT HANCOCK DR, Winter Garden, FL 34787 | 2741060 |
| 7803 SKIING WAY, Winter Garden, FL 34787 | 2728670 |
| 6519 POINT HANCOCK DR, Winter Garden, FL 34787 | 2726600 |
| 15568 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2726360 |
| 15614 ESPALIER WAY, Winter Garden, FL 34787 | 2713970 |
| 14527 ISLEVIEW DR, Winter Garden, FL 34787 | 2681680 |
| 15586 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2653080 |
| 7851 SKIING WAY, Winter Garden, FL 34787 | 2625470 |
| 10651 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 2616139 |
| 7843 SKIING WAY, Winter Garden, FL 34787 | 2590670 |
| 7819 SKIING WAY, Winter Garden, FL 34787 | 2569610 |
| 6711 POINT HANCOCK DR, Winter Garden, FL 34787 | 2542940 |
| 10616 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 2536179 |
| 6615 POINT HANCOCK DR, Winter Garden, FL 34787 | 2529320 |
| 7811 SKIING WAY, Winter Garden, FL 34787 | 2521100 |
| 4230 REX DR, Winter Garden, FL 34787 | 2519860 |
| 17683 DEER ISLE CIR, Winter Garden, FL 34787 | 2480710 |
| 10601 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 2464457 |
| 14314 UNITED COLONIES DR, Winter Garden, FL 34787 | 2458210 |
| 6543 POINT HANCOCK DR, Winter Garden, FL 34787 | 2455100 |
| 15544 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2453050 |
| 10031 COLT LN, Winter Garden, FL 34787 | 2448046 |
| 6603 POINT HANCOCK DR, Winter Garden, FL 34787 | 2444200 |
| 15592 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2434020 |
| 17074 ALPS ST, Winter Garden, FL 34787 | 2425325 |
| 14700 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2424550 |
| 17000 SANDHILL RD, Winter Garden, FL 34787 | 2412460 |
| 6531 POINT HANCOCK DR, Winter Garden, FL 34787 | 2412250 |
| 6717 POINT HANCOCK DR, Winter Garden, FL 34787 | 2411780 |
| 4302 REX DR, Winter Garden, FL 34787 | 2406946 |
| 15538 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2406180 |
| 15556 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2400620 |
| 14605 ISLEVIEW DR, Winter Garden, FL 34787 | 2391220 |
| 17704 CHAMPAGNE DR, Winter Garden, FL 34787 | 2375401 |
| 17733 DEER ISLE CIR, Winter Garden, FL 34787 | 2373170 |
| 6513 POINT HANCOCK DR, Winter Garden, FL 34787 | 2365090 |
| 6525 POINT HANCOCK DR, Winter Garden, FL 34787 | 2337420 |
| 17017 MARSH RD, Winter Garden, FL 34787 | 2335853 |
| 14628 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2309090 |
| 17650 DANGLER RD, Winter Garden, FL 34787 | 2304320 |
| 7859 SKIING WAY, Winter Garden, FL 34787 | 2302670 |
| 7257 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 2273280 |
| 16881 BROADWATER AVE, Winter Garden, FL 34787 | 2259050 |
| 15610 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2255460 |
| 14637 ISLEVIEW DR, Winter Garden, FL 34787 | 2255420 |
| 14503 ISLEVIEW DR, Winter Garden, FL 34787 | 2232720 |
| 14544 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2229800 |
| 14634 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2226850 |
| 15138 SHONAN GOLD DR, Winter Garden, FL 34787 | 2219540 |
| 14417 ISLEVIEW DR, Winter Garden, FL 34787 | 2216000 |
| 6645 POINT HANCOCK DR, Winter Garden, FL 34787 | 2205330 |
| 14514 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2198420 |
| 900 W PLANT ST, Winter Garden, FL 34787 | 2192545 |
| 16887 BROADWATER AVE, Winter Garden, FL 34787 | 2189540 |
| 7579 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 2184770 |
| 7177 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 2184740 |
| 15204 SHONAN GOLD DR, Winter Garden, FL 34787 | 2183670 |
| 14730 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2181900 |
| 14290 UNITED COLONIES DR, Winter Garden, FL 34787 | 2173290 |
| 14532 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2169980 |
| 15626 ESPALIER WAY, Winter Garden, FL 34787 | 2165850 |
| 12151 WALKER POND RD, Winter Garden, FL 34787 | 2164965 |
| 14520 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2155030 |
| 7754 MINUTEMEN LOOP, Winter Garden, FL 34787 | 2147820 |
| 10118 COLT LN, Winter Garden, FL 34787 | 2144386 |
| 10010 COLT LN, Winter Garden, FL 34787 | 2142238 |
| 14718 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2141000 |
| 14356 UNITED COLONIES DR, Winter Garden, FL 34787 | 2128080 |
| 7724 MINUTEMEN LOOP, Winter Garden, FL 34787 | 2123870 |
| 14543 ISLEVIEW DR, Winter Garden, FL 34787 | 2123070 |
| 14621 ISLEVIEW DR, Winter Garden, FL 34787 | 2114230 |
| 14308 UNITED COLONIES DR, Winter Garden, FL 34787 | 2106750 |
| 14502 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2101280 |
| 7301 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 2100020 |
| 15580 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2097970 |
| 14706 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2096450 |
| 15522 SHOREBIRD LN, Winter Garden, FL 34787 | 2095310 |
| 7835 SKIING WAY, Winter Garden, FL 34787 | 2092740 |
| 14622 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2088670 |
| 15526 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 2085210 |
| 17817 DANGLER RD, Winter Garden, FL 34787 | 2082980 |
| 14610 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2080840 |
| 14344 UNITED COLONIES DR, Winter Garden, FL 34787 | 2064240 |
| 7221 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 2061110 |
| 15186 SHONAN GOLD DR, Winter Garden, FL 34787 | 2060580 |
| 7574 JOHN HANCOCK DR, Winter Garden, FL 34787 | 2057200 |
| 14712 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2054990 |
| 15851 TURKEY ISLAND CIR, Winter Garden, FL 34787 | 2054890 |
| 10021 COLT LN, Winter Garden, FL 34787 | 2050629 |
| 16094 JOHNS LAKE OVERLOOK DR, Winter Garden, FL 34787 | 2048930 |
| 14556 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2041880 |
| 7786 MINUTEMEN LOOP, Winter Garden, FL 34787 | 2037550 |
| 9201 TOWER PINE DR, Winter Garden, FL 34787 | 2036815 |
| 15711 PANTHER LAKE DR, Winter Garden, FL 34787 | 2033410 |
| 7748 MINUTEMEN LOOP, Winter Garden, FL 34787 | 2029300 |
| 15795 TURKEY ISLAND CIR, Winter Garden, FL 34787 | 2028970 |
| 14200 LARKSPUR LAKE DR, Winter Garden, FL 34787 | 2028100 |
| 10699 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 2027439 |
| 14604 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2026020 |
| 15843 TURKEY ISLAND CIR, Winter Garden, FL 34787 | 2024930 |
| 17549 DEER ISLE CIR, Winter Garden, FL 34787 | 2021825 |
| 7430 JOHN HANCOCK DR, Winter Garden, FL 34787 | 2019250 |
| 15608 ESPALIER WAY, Winter Garden, FL 34787 | 2017730 |
| 10301 SAVANNAH RIDGE LN, Winter Garden, FL 34787 | 2016097 |
| 14724 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 2015140 |
| 7012 BILLIE CT, Winter Garden, FL 34787 | 2012910 |
| 7526 JOHN HANCOCK DR, Winter Garden, FL 34787 | 2011370 |
| 5370 BOWMAN DR, Winter Garden, FL 34787 | 2008960 |
| 15096 SHONAN GOLD DR, Winter Garden, FL 34787 | 2008790 |
| 15114 SHONAN GOLD DR, Winter Garden, FL 34787 | 2004600 |
| 5340 BOWMAN DR, Winter Garden, FL 34787 | 2003000 |
| 15211 FARM STAND CT, Winter Garden, FL 34787 | 2002800 |
| 7580 JOHN HANCOCK DR, Winter Garden, FL 34787 | 2001700 |
| 15084 SHONAN GOLD DR, Winter Garden, FL 34787 | 1995050 |
| 7657 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 1993940 |
| 14511 ISLEVIEW DR, Winter Garden, FL 34787 | 1993650 |
| 7549 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 1993460 |
| 7627 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 1991840 |
| 5364 BOWMAN DR, Winter Garden, FL 34787 | 1987790 |
| 7496 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1987680 |
| 7472 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1985120 |
| 14433 ISLEVIEW DR, Winter Garden, FL 34787 | 1982210 |
| 7592 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1979790 |
| 7502 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1977630 |
| 7567 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 1975980 |
| 15663 PANTHER LAKE DR, Winter Garden, FL 34787 | 1975560 |
| 15819 EMERALD POINTE DR, Winter Garden, FL 34787 | 1971500 |
| 7780 MINUTEMEN LOOP, Winter Garden, FL 34787 | 1968800 |
| 15612 GIANT FOXTAIL CT, Winter Garden, FL 34787 | 1968230 |
| 15108 SHONAN GOLD DR, Winter Garden, FL 34787 | 1966250 |
| 7550 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1964400 |
| 15550 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 1963970 |
| 7233 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 1963700 |
| 7024 BILLIE CT, Winter Garden, FL 34787 | 1962160 |
| 15613 GIANT FOXTAIL CT, Winter Garden, FL 34787 | 1961400 |
| 7165 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 1957080 |
| 14284 UNITED COLONIES DR, Winter Garden, FL 34787 | 1955690 |
| 14441 ISLEVIEW DR, Winter Garden, FL 34787 | 1952740 |
| 15603 PANTHER LAKE DR, Winter Garden, FL 34787 | 1949700 |
| 3376 AVALON RD, Winter Garden, FL 34787 | 1947979 |
| 14664 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 1947850 |
| 15204 E OAKLAND AVE, Winter Garden, FL 34787 | 1947100 |
| 15150 SHONAN GOLD DR, Winter Garden, FL 34787 | 1945720 |
| 15787 TANGERINE DREAM CT, Winter Garden, FL 34787 | 1944850 |
| 15598 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 1944650 |
| 15606 GIANT FOXTAIL CT, Winter Garden, FL 34787 | 1942450 |
| 7769 SUMMERLAKE POINTE BLVD, Winter Garden, FL 34787 | 1941260 |
| 16815 BROADWATER AVE, Winter Garden, FL 34787 | 1940200 |
| 7171 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 1939910 |
| 14508 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 1936790 |
| 16797 BROADWATER AVE, Winter Garden, FL 34787 | 1936450 |
| 7531 GREEN MOUNTAIN WAY, Winter Garden, FL 34787 | 1935830 |
| 17726 DANGLER RD, Winter Garden, FL 34787 | 1935820 |
| 14646 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 1934980 |
| 6639 POINT HANCOCK DR, Winter Garden, FL 34787 | 1934790 |
| 15717 PANTHER LAKE DR, Winter Garden, FL 34787 | 1934770 |
| 15863 BURCH ISLAND CT, Winter Garden, FL 34787 | 1932930 |
| 17635 DEER ISLE CIR, Winter Garden, FL 34787 | 1931720 |
| 16779 BROADWATER AVE, Winter Garden, FL 34787 | 1931700 |
| 7442 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1930850 |
| 7239 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 1930810 |
| 15216 E OAKLAND AVE, Winter Garden, FL 34787 | 1930700 |
| 7760 MINUTEMEN LOOP, Winter Garden, FL 34787 | 1930600 |
| 7334 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1926340 |
| 7556 JOHN HANCOCK DR, Winter Garden, FL 34787 | 1924510 |
| 15827 TURKEY ISLAND CIR, Winter Garden, FL 34787 | 1923190 |
| 16839 BROADWATER AVE, Winter Garden, FL 34787 | 1921260 |
| 16126 JOHNS LAKE OVERLOOK DR, Winter Garden, FL 34787 | 1919110 |
| 7203 WILD BLACKBERRY TRL, Winter Garden, FL 34787 | 1916820 |
| 15669 PANTHER LAKE DR, Winter Garden, FL 34787 | 1916530 |
| 16803 BROADWATER AVE, Winter Garden, FL 34787 | 1913910 |
| 16821 BROADWATER AVE, Winter Garden, FL 34787 | 1913840 |
| 7706 MINUTEMEN LOOP, Winter Garden, FL 34787 | 1912830 |
| 6651 POINT HANCOCK DR, Winter Garden, FL 34787 | 1911910 |
| 16833 BROADWATER AVE, Winter Garden, FL 34787 | 1910360 |
| 16767 BROADWATER AVE, Winter Garden, FL 34787 | 1906770 |
| 14519 ISLEVIEW DR, Winter Garden, FL 34787 | 1906040 |
| 14535 ISLEVIEW DR, Winter Garden, FL 34787 | 1905330 |
| 684 LARGE OAK LN, Winter Garden, FL 34787 | 1905100 |
| 12702 STONEYBROOK WEST PKWY, Winter Garden, FL 34787 | 1901749 |
| 15532 AVENUE OF THE ARBORS, Winter Garden, FL 34787 | 1901470 |
| 16809 BROADWATER AVE, Winter Garden, FL 34787 | 1901390 |
| 14640 AVENUE OF THE RUSHES, Winter Garden, FL 34787 | 1900940 |
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