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- $ 100,000
- $ 150,000
- $ 200,000
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- $ 800,000
- Any
- $ 200,000
- $ 300,000
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- $ 1,000,000
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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)
![7282 BACKWOODS TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6260409/d9f84184/1733955372/w600_original_BMBRDsIwCADQE7VsHU2ZB_DPH2-AAnVG3CJNTDy97zHGESeAWDI7__Y3fyPfdwd_Rf9sAptz14DL-dpwpnmthCA8obKVtFqxhFQlUcWWbqhLMeE2lZqfh_Z_AAAA__8-jpg.webp)
$ 729,000
7282 BACKWOODS TRL, Windermere, FL 34786
Single Family Home
Listed by FOLIO REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12285 JOSHUA TREE TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6263857/fc6c6c99/1734636679/w600_original_BMBRDsIwCADQE7VIWVLiAfzzxxuAQp0Rt0gTE0-_95xzzzNAUpWQ__aRX9b7FhDvHN_1AWvIsITr5daXxg25EVB3opP30t2wLM29iBoXUlFENhXH-tptHAEAAP__-jpg.webp)
$ 567,000
12285 JOSHUA TREE TRL, 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)
![12755 WESTSIDE VILLAGE LOOP, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6264079/322afdda/1733958970/w600_original_BMDdDcJACADgie64H2KpA_jmixsg0LNGbCNNTJze73Ece5wBomd2_m1v_kaWzcFfMT6rwuo8LOB6uU3YiErFBq3eT4vSnES6JZxsSURSUq-ovRRWnlt-7jb-AQAA__8-jpg.webp)
$ 4,350
12755 WESTSIDE VILLAGE LOOP, Windermere, FL 34786
Single Family Home
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)
![9664 WEATHERSTONE CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6263072/05652ff9/1738512068/w600_original_BMBRDoIwDADQE20FKSv1AP754w26rpkYK8SSmHh63vM49rgCxJTF5b995BdZNwd_R_-uDVaXbgH324PwUoZ54QJDUWZES9zIEqphqkRTUq5VlnFspnN-7dbPAAAA__8-jpg.webp)
$ 2,899,999
9664 WEATHERSTONE CT, Windermere, FL 34786
Single Family Home
Listed by PREMIER SOTHEBY'S INTL. REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1140 KELSO BLVD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6263154/0c944662/1733690769/w600_original_BMDRDcJACADQiTgoJdI6gH_-uAF3xbNGbCNNTJze9ziOPc-IORYL-21v-2ZpW2C8sn_WBdew7onXy02FTzzLIDjrfbSlKbjSAMLEYJM7eBOqPBlVr-W5e_8HAAD__w-jpg.webp)
$ 2,650,000
1140 KELSO BLVD, 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)
![7313 PENKRIDGE LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6263212/b1ce046d/1733715069/w600_original_BMBRDoIwDAbgE211_yplHsA3X7xBkTExVohdYuLp-Z69734h8hzV9L999OfxsRnZ29t3nWk1bdXpdr0LY-AMCGWBCOocprGcApdlCNMoCJlxXkoqnJDia6_tCAAA__8-jpg.webp)
$ 2,800
7313 PENKRIDGE LN, Windermere, FL 34786
Townhouse
Listed by THOMAS LYNNE REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2812 MARQUESAS CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6262787/cd7e81fe/1737406872/w600_original_BMBRDsIgDADQE0HpoKx6AP_88QaVdThj3WJJTDy97zHG4WcAz1FMfvtbvh7bbmAv759tgc2kq8P1cpvLRKkiMTBjKylpwIw1lBnXwO1EYVqpLFlV6j3H56H9HwAA__8-jpg.webp)
$ 3,150,000
2812 MARQUESAS CT, 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)
![7645 FORDSON LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6263071/6d4b78a3/1733607072/w600_original_BMBdDoIwDADgE22F_bXxAL754g1qVybGCrEkJp6e73kcu18APEc2_m8f_nmUzcDePr5rh9V4qMPteseS2lQxV2ipTtTkEZC6hIJLDSyYg5Y592XWpETxtes4AwAA__8-jpg.webp)
$ 465,000
7645 FORDSON LN, Windermere, FL 34786
Townhouse
Listed by COLDWELL BANKER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6818 TRELLIS VINE LOOP, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5116794/f9533b82/1733533271/w600_original_BMBRDsIgDADQE0GlFMY8gH_-eIOm63DGusWSmHj6vecYh18BPEc2_u8f_nmU3cDe3r_bAptxV4f77TERljrjnAFZGiaSgPnSAq1pCpxbDUUW1MqUVi3xdWg_AwAA__8-jpg.webp)
$ 649,000
6818 TRELLIS VINE LOOP, Windermere, FL 34786
Single Family Home
Listed by NUMBER 1 BROKER, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![7024 MAPPERTON DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6262542/c6faa2cb/1733417171/w600_original_BMBBDsIgEAXQE8GkMCD1AO7ceINv_WCN2MYhMfH0fc8xdjuLWPTo-G8f_MwvW5f-tvZdH7J2NJpcL7eTBp1K1ChKpvukdERdnJYSHJiymwNSrqicc_Kvne0IAAD__w-jpg.webp)
$ 3,000
7024 MAPPERTON DR, Windermere, FL 34786
Single Family Home
Listed by GOLDEN PACIFIC REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![11446 JASPER KAY TER #306-1026, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6262334/f7b8d328/1733433372/w600_original_BMBRDsIgDADQE0FBxpp4AP_88QYttDhj3WJJTDz93nPOw68AXiIZ_fcP_Ty23cDePr5bh81oiMP99sDlUiqWmgGVuHCVkCVxWDRrYOwa0tq4I66pN4yvQ8YZAAD__w-jpg.webp)
$ 2,250
11446 JASPER KAY TER #306-1026, Windermere, FL 34786
Condo
Listed by AMERICAN ELITE GLOBAL LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12023 GOLD CREEK TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6261968/ee067dc4/1733343380/w600_original_BMBRDsIwCADQE7VMpB3zAP754w2QYp0Rt0gTE0_ve4yxxwkgjllcfttbvpF1c_BX9M_aYHXpFnA5X2dCJC68QCtLwYk1EdZbIm2WxA5TqoWZUOt8t5qfu_V_AAAA__8-jpg.webp)
$ 1,500,000
12023 GOLD CREEK TRL, Windermere, FL 34786
Single Family Home
Listed by BUILD 2 RENT DIRECT, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![7321 BRIGHTLAND ST, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6262112/72918d69/1733319074/w600_original_BMBRDsIgDADQE0FZraV4AP_88QZlEJyxbrEkJp7e95jz8AuAn6Ka_va3fj2uu4G9fHy2Bpvp6A636z0TovBCDK2esebCgduaApVFgmLnkLJQ0qLCqcbn0cc_AAD__w-jpg.webp)
$ 440,000
7321 BRIGHTLAND ST, Windermere, FL 34786
Townhouse
Listed by CENTURY 21 CARIOTI
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8526 GREENBANK BLVD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5116507/570e2387/1733346975/w600_original_BMBRDsIgDADQE5VSQMo8gH_-eINWGc5Yt9glJp5-77nvm58RPQcx-a8f-Xm4r4b29vFdHriYjO54vdy4JDpNnAhn4RhJBZgKQ0m5QWtzhSkrV-1VKWp4bX0cAQAA__8-jpg.webp)
$ 2,675
8526 GREENBANK BLVD, Windermere, FL 34786
Single Family Home
Listed by AVID REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1003 OAKDALE ST, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6261656/75ad4e83/1737833472/w600_original_BMBRDoIwDADQE22FUVrmAfzzxxt0s0yMFWKXmHh63rP3wy8APkUx-e8f-Xmsu4G9vX23B2wmTR1u1ztjGhdM4wxKvNZCGgiHEnCZOUiehlASZcmyKmONr0PbGQAA__8-jpg.webp)
$ 2,950,000
1003 OAKDALE ST, Windermere, FL 34786
Single Family Home
Listed by VINTAGE REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5516 REMSEN CAY LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6261911/28576dd3/1733270471/w600_original_BMBRDsIgDADQE5WmhYzhAfzzxxsUKDhj3WKXmHh63-M8D78gegxi8tvf8vXQdkN7-fxsHTeTqY636z0n5pgXYhzKbc0LARMTpF4VJI4CNQ3ppbaitIbnofMfAAD__w-jpg.webp)
$ 949,000
5516 REMSEN CAY LN, Windermere, FL 34786
Single Family Home
Listed by THE PROPERTY STOP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![729 MAIN STREET, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5116063/17d2c607/1733184972/w600_original_BMBRDsIgDAbgE0FhwCoewDdfvMGfCjhj3WJJTDy932POw85EljwUv_2Nr3nZlfRl47PdaVOMZnS93DjHEgqvhXpYkmTAccziMhBdrafkAselC0ptffXPo41_AAAA__8-jpg.webp)
$ 2,295,000
729 MAIN STREET, Windermere, FL 34786
Single Family Home
Listed by COLDWELL BANKER RESIDENTIAL RE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12015 OTTERBROOKE TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6261208/2bfd1fb7/1733018473/w600_original_BMBBDoIwEAXQE7Vj668DHsCdG2_wW6FiHCEOiYmn9z32ffOziB8jjb_1za_HtprYy_tnucti7JPL9XJT5MMJOY2iGJK2iqCFKaDMCFQOoc4JBSOYW43Pber_AAAA__8-jpg.webp)
$ 3,290
12015 OTTERBROOKE TRL, Windermere, FL 34786
Single Family Home
Listed by SHINING OAK REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6245 LITTLE LAKE SAWYER DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6260736/9cbb225f/1736214574/w600_original_BMBRDoIwDADQE3UtFe3qAfzzxxuUbUyMFWJJTDw977nvW1wR45TM7b9-7BeprI7-jv5dKi5uvQXebw8ZB6WswkgXOmsVBTYWGHMdQIsozDLNjaZMhS29ttaPAAAA__8-jpg.webp)
$ 2,497,000
6245 LITTLE LAKE SAWYER DR, Windermere, FL 34786
Single Family Home
Listed by LAKEFIELD REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![7608 BILLINGHAM ST, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6260031/fd2815e8/1736214553/w600_original_BMDRDQIhDADQiaDIAbUO4J8_blBLxTPWu1gSE6f3Pebc_QTgS2Tj3_bmr0fZDOzl47N2WI2HOlzOVywHTDm3Bnpr9ypaQl4ShdIFA3fJgfBIqRasSDU-dx3_AAAA__8-jpg.webp)
$ 409,000
7608 BILLINGHAM ST, Windermere, FL 34786
Townhouse
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)
![10726 REAMS RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6260638/c3451a2f/1738692184/w600_original_BMBRDsIgDAbgE0FBkA0P4Jsv3uCndjhj3WJJTDz9vucYu12ILHko_tsHP_O8Kenb-nd90KroYnS73qcc5zmEKVBuS-N4ro4LkssQuMqLOC6nFFqNEa341y79CAAA__8-jpg.webp)
$ 549,000
10726 REAMS RD, Windermere, FL 34786
Single Family Home
Listed by EPIC REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5892 SOTER LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6259990/bae65f89/1735277471/w600_original_BMBRDsIgDADQE0HB4goewD9_vEFZO5yxbrFLTDy973Ecu18AHCMb_7Y3fz3Om4G9fHxWgdV4qMPteqeSp4q5EqjW3Bst4bTMJRRqPbQpcRBMks7YhTnH567jHwAA__8-jpg.webp)
$ 478,900
5892 SOTER LN, Windermere, FL 34786
Townhouse
Listed by KELLER WILLIAMS CLASSIC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12983 WESTSIDE VILLAGE LOOP, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6259749/4821c93b/1738297871/w600_original_BMBRDsIgDADQE0FbxK54AP_88QYdQ5yxbrEkJp5-7znG7hcAP0U1_W8f_Xmsm4G9vX_XBVbT3hxu1_uUiZGIE0iTM0qdA1NNIZfHEkqe5iCUCrEgK1J87a0fAQAA__8-jpg.webp)
$ 997,000
12983 WESTSIDE VILLAGE LOOP, Windermere, FL 34786
Single Family Home
Listed by WRA BUSINESS & REAL ESTATE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![14042 SPARKLING COVE LN #606, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5116116/54ae8721/1736525772/w600_original_BMBRDoIwDAbgE21lrmOZB_DNF29QKP_EWCGWxMTT8z2PY_crkecoJv_tIz-P82Zkb-_fVWk16YvT_faonMZUWhuolqoT0hyQBIEVOUzjZQjgDAYrWinxtS_9DAAA__8-jpg.webp)
$ 399,990
14042 SPARKLING COVE LN #606, Windermere, FL 34786
Townhouse
Listed by REALTY HUB
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)