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- $ 100,000
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- $ 200,000
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332 Properties Available In Windermere
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![7642 FAIRGROVE AVE, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6229308/d49eb196/1736214659/w600_original_BMBRDsIwCADQE7UIbcb0AP754w2g1DojbpElJp5-77nvW1wAomRx-a8f-UVuq4O_Y3wXg8Vl9IDb9c6lENFcEFC0TVgt2Vw5VTxpOmunJMTMMj0amubX1scRAAD__w-jpg.webp)
$ 430,000
7642 FAIRGROVE AVE, Windermere, FL 34786
Townhouse
Listed by PREMIER SOTHEBYS INT'L REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6364 LAKE SMITH CIR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6223235/f774e957/1729638969/w600_original_BMBRDoIwDADQE20tjK2bB_DPH29QaZkYK8SSmHh63vM4dr8AeIps_N8-_PM4bwb29v5dBVbjrg63653SkAkbNagoiMvCIRXlMGWsoY6lhVkfpUw05kEkvnbtZwAAAP__-jpg.webp)
$ 445,000
6364 LAKE SMITH CIR, Windermere, FL 34786
Townhouse
Listed by VESTI LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4 CHASE RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6227521/3553fb95/1731798069/w600_original_BMBRDoIwDADQE23FVWzrAfzzxxuU0U2MFWJJTDw977nvW1wBArO6_teP_iLX1cHf0b_LDItrt4D77UFYCGXgC3CpSNPMiYxrOg9mSVobUxkLy9TkhIb5tVk_AgAA__8-jpg.webp)
$ 935,000
4 CHASE RD, Windermere, FL 34786
Single Family Home
Listed by THE REAL ESTATE COLLECTION LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5518 WORSHAM CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6227090/e807e396/1735917373/w600_original_BMBRDsIgDADQE0EDdIx6AP_88QZNV3DGusWSmHh632PO0y8AXiIb_443fz3KYWAvH599g914qMPtel9LrilnWqAKrwk3DbVRD9jTElojCYgNS8-qlCQ-Tx3_AAAA__8-jpg.webp)
$ 6,650,000
5518 WORSHAM CT, Windermere, FL 34786
Single Family Home
Listed by ISLEWORTH REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12848 JACOB GRACE CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6224633/8f8d79fd/1737274569/w600_original_BMBdDsIwCADgE7XQHwU8gG--eAPSrXVG3CJNTDy932POwy8AXqKa_va3fj223cBePj7bApvpWB1u1zuVJIkIGST1c5HMAbn0UE_UgiypBskNKbNU7Bifxzr-AQAA__8-jpg.webp)
$ 1,590,000
12848 JACOB GRACE CT, Windermere, FL 34786
Single Family Home
Listed by BHHS FLORIDA REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12025 LAKE BUTLER BLVD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6226132/dca0c3a7/1730506573/w600_original_BMBRDsIgDADQE0GBFkk9gH_-eIOOLjhj3WJJTDz93nPOw68AjlFM_vtHfh77bmBvH99NYTMZq8P99mhYsKQLVkidlXKioGnhQLlyYK4ltKzaMzWmhePrWMcZAAD__w-jpg.webp)
$ 1,299,990
12025 LAKE BUTLER BLVD, Windermere, FL 34786
Single Family Home
Listed by ADAIR REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![13643 LAKE CAWOOD DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6223787/fb23698d/1722517270/w600_original_BMBRDoIwDAbgE221Un6YB_DNF29QoJsYK8SSmHh6v8dx7HEhii6r62976zfyvDn5K9pnXWh1bRZ0u96HjlHQg8kqxoUrp2nGKQkLUhnPlgTCGCbpi9X83K39AwAA__8-jpg.webp)
$ 3,590,000
13643 LAKE CAWOOD DR, Windermere, FL 34786
Single Family Home
Listed by JWJ REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8631 VIA TRIESTE DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6224053/0f802a61/1721160973/w600_original_BMBRDsIwCADQE7XYQcfwAP754w0oNnVG3CJLTDy973Ece5wBArO6_ra3fiPb5uCvGJ_1Dqvr6AHXy42x8DzJcoLJZDYhTlyKJhJqSbhhWko1RWpda83PvY9_AAAA__8-jpg.webp)
$ 2,500
8631 VIA TRIESTE DR, Windermere, FL 34786
Townhouse
Listed by REALSOURCE PROPERTY MANGNT LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![11025 LEDGEMENT LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRT3541400/82a83d6c/1721156482/w600_original_BMDRDcJACADQie64ihRxAP_8cQNQetaIbaSJidP3PbdtzTNAYtXQ__LRX9b7EhDv7N_5AXNo94Tr5cY4EDXmEZoa8skPZXLkcmwqxYSoDKOgTo2FzOpr9b4HAAD__w-jpg.webp)
$ 1,065,000
11025 LEDGEMENT LN, Windermere, FL 34786
Single Family Home
Listed by LPT REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9905 LANAI VIEW CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6221639/1e2bf909/1738873877/w600_original_BMBRDoIwDADQE3UdXdmoB_DPH29QKk6MFWJJTDy973Ece5wQoyR1_W1v_UayzdFf0T_rDVfXvgReztdWhiET8YgkUxbOCsp3AyaeQa02qEImbR5tKjU996X_AwAA__8-jpg.webp)
$ 2,999,000
9905 LANAI VIEW CT, Windermere, FL 34786
Single Family Home
Listed by CHARLES RUTENBERG REALTY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12245 PARK AVE, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRFC302108/36ff3263/1730304084/w600_original_BMBRDoIwDADQE21lFBj1AP754w1K20yMFWKXmHh636P3My4AgZmdf8ebv5HlcPBXtM-usDs3C7hd7xUHWonKADpqXVAkGUlJ0zbNiUqlhGSyzOumMpb8PK39AwAA__8-jpg.webp)
$ 3,390,000
12245 PARK AVE, Windermere, FL 34786
Single Family Home
Listed by THE SELBY GROUP, INC.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5138 FAIRWAY OAKS DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6214823/8b8b0a20/1732305691/w600_original_BMBRDsIgDADQE0EHDko9gH_-eIO2TpyxbrEkJp5-7znG7mcAP0U2_m8f_nnUzcDe3r_rHVbjvjhcLzfMlLBOeQKhIrVgDZKLhJl4DvSoGFJrqkVTI8rxtS_9CAAA__8-jpg.webp)
$ 3,250,000
5138 FAIRWAY OAKS DR, Windermere, FL 34786
Single Family Home
Listed by RE/MAX PROPERTIES SW
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![13885 BLUEBIRD POND RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6220855/a2169ec9/1724552169/w600_original_BMBRDsIgDADQE0HpBnZ6AP_88QZlLThj3WJJTDy97zHG4RcAnyMb__Y3fz2uu4G9vH82gc24q8Pteqc5LbSUlEGUWkPCUOvKIeNUQj3nHCQ1ORWdsCjG56H9HwAA__8-jpg.webp)
$ 3,150
13885 BLUEBIRD POND RD, Windermere, FL 34786
Single Family Home
Listed by AAA GLOBAL VENTURES PA
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8156 BOAT HOOK LOOP #305, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6220652/09132121/1738287973/w600_original_BMBRDsIgDADQE0FLYaF6AP_88QYVOpyxbrEkJp7e95jz8DOA5ygmv_0tX49tN7CXj8_WYTMZ6nC93GpGJsIlA6bai6YWhDiFokRB-N7DKlzSemp1QYzPQ8c_AAD__w-jpg.webp)
$ 315,000
8156 BOAT HOOK LOOP #305, Windermere, FL 34786
Condo
Listed by URBAN-O REAL ESTATE SOLUTION
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5000 DOWN POINT LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6220332/bb3140fb/1736213454/w600_original_BMBRDsIgDAbgE0GZgAUP4Jsv3uB3Kzhj3WJJTDz9vucYu12ILHoo_tsHP_PzpqRv6991oVXRxeh2vXMMnEIuE3Fr4CUHx3OqLhU0h3oSV-oZsTxyjTL51y79CAAA__8-jpg.webp)
$ 4,495,000
5000 DOWN POINT LN, Windermere, FL 34786
Single Family Home
Listed by SOUTHERN REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9679 WESTOVER ROBERTS RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6216452/8b65e352/1729886680/w600_original_BMBdDsIwCADgE7WkPzLxAL754g2go3VG3CJNTDy932POwy8AXiIb__Y3fz223cBePj7bCpvxUIfb9b5kwkT1lCCvmkruEoQKhopnDdxaDZxFOvFSsGt8Hjr-AQAA__8-jpg.webp)
$ 3,250,000
9679 WESTOVER ROBERTS RD, Windermere, FL 34786
Single Family Home
Listed by STOCKWORTH REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![11154 PARK AVE, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6210864/fc2bae95/1736214486/w600_original_BMBRDsIgDADQE0EB25V6AP_88QbdmDhj3WJJTDy97zHG4WcAP0U1_e1v_XpcdgN7ef9sDTbTvjpcLzcuNbGIZECtUqbEgRpSwJo4zIIaMpVMbbpzmZf4PNb-DwAA__8-jpg.webp)
$ 899,000
11154 PARK AVE, Windermere, FL 34786
Single Family Home
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![11954 PROVINCIAL WAY, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6214196/b2975b78/1734283870/w600_original_BMBRDsIwCADQE1GMsAkewD9_vAEts86IW6SJiaf3PcbY84yYVCzst73tm6VtgfHK_lkd17C-JF4vt9NRVIVV0K1ORJVBZG7AVAWUvcFhUmVXkrvP5bkv_R8AAP__-jpg.webp)
$ 2,299,000
11954 PROVINCIAL WAY, Windermere, FL 34786
Single Family Home
Listed by CLOCK TOWER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9313 Tibet Pointe CIR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/43/RX-10997166/f81b4a56/1725086011/w600_original_JMBhDoUgCADgEz1QfDHtNs5mrjSYcv_1o6-Z6Y5Yjge0icmCpXne2rNVmQOKDKwdydHfsY8--UiBeQvJfX4Cl55vAAAA__8-jpg.webp)
$ 7,999,000
9313 Tibet Pointe CIR, Windermere, FL 34786
Single Family Home
Listed by Metropolitan R.E Solutions Inc
![2119 WILLOW BRICK RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6214365/d88253aa/1738441878/w600_original_BMBdDoIwDADgE3XtVmbBA_jmizfofjIxVoglMfH0fM_j2P2K6BzU9L999Oehbob29vFdG66mozvebw9JC2WKC-NMSajKBWLXApMoQ8nCMDWJc8slVabw2vs4AwAA__8-jpg.webp)
$ 899,000
2119 WILLOW BRICK RD, Windermere, FL 34786
Single Family Home
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6226 CARTMEL LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6211378/6b42cd9a/1736213998/w600_original_BMBRDsIwCADQE7VA6ZjxAP754w1Yi3VG3CJLTDy973Ece5wBgrO6_ra3fiO3zcFfMT5rh9V1WMD1cpvLqWBBEmCziVCW1KwuqXLHpDRzol4nFGlF6J6fu41_AAAA__8-jpg.webp)
$ 1,899,999
6226 CARTMEL LN, Windermere, FL 34786
Single Family Home
Listed by CHARLES RUTENBERG REALTY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1125 LASCALA DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6211004/6e25544a/1723484285/w600_original_BMBRDoIwDADQE21lZZbVA_jnjzcotU6MFWJJTDw977nvW5wBYszi8l8_8ousq4O_o3-XOywu3QKul9uErRTEgYDLrCNZS3xiSpVEEtOsaagP1CYVrUz5tVk_AgAA__8-jpg.webp)
$ 3,450
1125 LASCALA DR, Windermere, FL 34786
Single Family Home
Listed by BHHS FLORIDA REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8738 IRON MOUNTAIN TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5106197/fc6892e7/1736214444/w600_original_BMBRDsIgDADQE0E7Cin1AP754w2KEJyxbrFLTDz93vM4dr8AOEU1_W8f_Xl8bAb29vldO6ymczjcrndOlRAXzlBFFs6iQXttIXNLQUQolDJ6Q6VUUOJrH_MMAAD__w-jpg.webp)
$ 899,000
8738 IRON MOUNTAIN TRL, Windermere, FL 34786
Single Family Home
Listed by CENTURY 21 BE3
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9832 LAUREL VALLEY DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6211352/41a1e1e5/1734629474/w600_original_BMDLDcIwDAbgiRKTPqjNANy4sMEf7IYiTCtcCYnp-z33fYsLUfQZjv_6wS_yY3Xyd7TvorQ4mgXdrvep4yJSppHKibsBOidGlTRUcBIzTWbjXEXRw875tVk7AgAA__8-jpg.webp)
$ 10,475,000
9832 LAUREL VALLEY DR, Windermere, FL 34786
Single Family Home
Listed by ISLEWORTH REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)