- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
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332 Properties Available In 34786
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![13272 ROXBORO RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6241032/9e5e1ccd/1728667872/w600_original_BMBRDsIgDADQE0HBIgwP4J8_3qC2Hc5Yt9glJp5-77nvm18AHCMZ_dcP_TzyamBvH99FYDEa6nC73hvWgnnCBL3nOlE9h8wthfJQCoQqIck8n5Q7Syvxtek4AgAA__8-jpg.webp)
$699,000
13272 ROXBORO RD, Windermere, FL 34786
Listed by FLORIDA CONNEXION PROPERTIES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![904 MAIN ST, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6241373/b2eda163/1733415372/w600_original_BMBdDoIwDADgE3UF-jPiAXzzxRsUNibGCrFLTDy936P3My6IQcncfsfbvpHWw9Ff0T57wd2t1cDb9Z5JhWTKIxKvG-smMC9SgFUFlqEwsNI4cM0z6ZSeZ23_AAAA__8-jpg.webp)
$4,299,000
904 MAIN ST, Windermere, FL 34786
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)
![8476 IRON MOUNTAIN TRAIL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6241484/d5a582e3/1736214682/w600_original_BMBRDsIgDAbgE0EZZY55AN988QZ_gOKMdYslMfH0-55jHHYlMvZQ_PcPfubLrqRv69-t0qbozeh-eyx8mZe8ZqYiZcKam0sik0tI7IAaHBgSYo1hjuJfR-tnAAAA__8-jpg.webp)
$450,000
8476 IRON MOUNTAIN TRAIL, Windermere, FL 34786
Listed by HR 19 REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![13285 GORGONA ISLE DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRS5112050/0ce7f855/1726263073/w600_original_BMDLDcIwDAbgiRKL386jDMCNCxsYU0IRphWuhMT0fI993-JIFJzV9be-9RvZVid_xfgsN1pcxxx0Pl0aV8gELtSLCJpcU8EdSQ6M1LXWJCowg9rUen5u8_gHAAD__w-jpg.webp)
$418,000
13285 GORGONA ISLE DR, Windermere, FL 34786
Listed by LA ROSA REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6719 VALHALLA WAY, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6240640/9951a12f/1736214594/w600_original_BMBdDsIgDAfwE0GBf10zD-CbL96gfIgz4hZLYuLp_T3mPOxMZPA69Le_9Wu-7IPGy_pnq7QN7c3oerkJFmCVEGg5Yc2S2DVJcIyqLsciLlaOnDjcUbJ_Hq3_AwAA__8-jpg.webp)
$4,899,000
6719 VALHALLA WAY, Windermere, FL 34786
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)
![5056 ISLEWORTH COUNTRY CLUB DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6239895/bbc13d0e/1726083087/w600_original_BMBRDsIwCADQE1FYYFA9gH_-eAPSLnVG3CJLTDz93vM49rwiJhcP_28f_2VpW2C8c3zXjmv4WBLvt4exTqZMit2ttosSTEoCYtagdlYQdp5nqS5M5bUv4wwAAP__-jpg.webp)
$3,799,999
5056 ISLEWORTH COUNTRY CLUB DR, Windermere, FL 34786
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)
![11668 BLACK RAIL ST, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6239914/bddcf2fb/1725911173/w600_original_BMBRDsIgDAbgE0E3wP7iAXzzxRsUizhj3WKXmHh6v8e-b34i8hzF5Le-5evxthrZy8dnUVpMRne6nK_IPKMCTPfUVTlzOE6phIKWQ5vbIQCoqWiVSVN8bn38AwAA__8-jpg.webp)
$510,000
11668 BLACK RAIL ST, Windermere, FL 34786
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)
![7231 RAMBLING WATER WAY, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6239588/781fc381/1736881273/w600_original_BMBRDsIwCADQE7WsgB31AP754w2I1DojbpElJp5-77nvW5wBgrK6_teP_iLfVwd_x_guBovr6AHXy22mOjVkFpgJq-BDEpdWEptgEjJKdEIx69Wm0vJr6-MIAAD__w-jpg.webp)
$3,150
7231 RAMBLING WATER WAY, Windermere, FL 34786
Listed by REAL ESTATE FIRM OF ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6223 ROSEATE SPOONBILL DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6237075/b3cad7c5/1724962581/w600_original_BMBRDoIwDADQE211tivVA_jnjzcog06MFWJJTDw977nvW1wBArO6_teP_iK31cHf0b_LBItrnwPut8eAFenEpUJjNGPENApJoqGVpHYuCS9kUx3ZRCW_trkfAQAA__8-jpg.webp)
$5,495
6223 ROSEATE SPOONBILL DR, Windermere, FL 34786
Listed by GATE PROPERTIES & MANAGEMENT INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12428 SUMMERPORT LN, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6236319/e7371ac0/1737220574/w600_original_BMBdDsIwCADgE7X0B4Z4AN988QbY1TojbpElJp5-33PfNz8DeI1q-l8_-vPYVgN7-_guMyymoztcLzeulCsVFqApTYV6CoXbKaBKDlrvHB6oqeGcBYvE19bHEQAA__8-jpg.webp)
$2,995,000
12428 SUMMERPORT LN, Windermere, FL 34786
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)
![9648 MCCORMICK PL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6234876/9fde531a/1724381169/w600_original_BMBRDsIgDADQE0ERCnUewD9_vAEtiDPWLZbExNPvPefc7QJgyVet_-1Tf-ZlU9C3je_aYNU6usHteqeEdMolIEjEUnJMrlMkhw8pjkNeXGOSJSCfuZF_7X0cAQAA__8-jpg.webp)
$4,000,000
9648 MCCORMICK PL, Windermere, FL 34786
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)
![6149 GROSVENOR SHORE DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6233554/d7f2c884/1724183176/w600_original_BMBRDoIwDAbgE20dWwnDA_jmizf4Kd3EWCGWxMTT-z3O8_ALkZcIw29_4-tRdiN7ef9sK22Grk63630qzImnMVNqbZEBOTSkMfC6DKHyXIPUghk5q4jG56H9HwAA__8-jpg.webp)
$11,999,999
6149 GROSVENOR SHORE DR, Windermere, FL 34786
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)
![8130 TIBET BUTLER DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6233779/1262e9e4/1738290672/w600_original_BMBdEgExDAfwE7XRLykH8ObFDf5Iao3YHemMGaf3e8y5-ZHIS4Tht77x9Xhbjezl47PcaTEMcTqfLlxq5cQ1kQBN9VCCtp2Eykjh2jPCviTuObeuQHxuMv4BAAD__w-jpg.webp)
$1,900,000
8130 TIBET BUTLER DR, Windermere, FL 34786
Listed by ONE STOP SERVICE REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12002 MCKINNON RD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6232517/505e6975/1736213916/w600_original_BMBRDoIwDADQE20t0G7FA_jnjzeoUifGCrFLTDw979n7HieAmLK6_reP_iLfNwd_R_uuC6yuzQIu52udCOdCZYAiS2WmMSmOlMhQktjA6VFvZRasKMz5tVs7AgAA__8-jpg.webp)
$1,650,000
12002 MCKINNON RD, Windermere, FL 34786
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)
![9143 WOODBREEZE BLVD, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRR4908213/411276d9/1736214678/w600_original_BMBRDoIwDAbgE3V1XUmHB_DNF2_wT3BirBBLYuLp-Z77vsWZOUqC479-8It0X539Hf27TLw4-hx8vdysqIwyiLAOVerJlEZtRpph1KYmVE3xKMjQjPTa5n4EAAD__w-jpg.webp)
$576,999
9143 WOODBREEZE BLVD, Windermere, FL 34786
Listed by SUN ATLANTIC GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![11823 OTTERBROOKE TRL, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6233467/6ead7200/1736213956/w600_original_BMBRCsIwDAbgE7XB_o1dPIBvvniDbAt1YtwwBcHT-z3GOOJCFMjq-tvf-o287E7-iv7ZVtpcuwXdrveGitYKhGAArEmqtnCqhU9J5umcuAoby1RknfPzsP4PAAD__w-jpg.webp)
$1,015,000
11823 OTTERBROOKE TRL, Windermere, FL 34786
Listed by FLORIDA REALTY RESULTS LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![14450 DESERT HAVEN ST #GE, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6233504/4d6a5006/1729104382/w600_original_BMBRDoIwDAbgE20tW0fBA_jmizf4ZXNirBBLYuLp_R7HsfuJyHOE4be98fW4bEb28v5ZK62G3pwu56tmydM8aaaxjEmrtgDIEqSkIUA4BebEBfU-3HiOz731fwAAAP__-jpg.webp)
$409,000
14450 DESERT HAVEN ST #GE, Windermere, FL 34786
Listed by OPENDOOR BROKERAGE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8745 VIA TAVOLERIA WAY, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6232942/7b06ee78/1723751395/w600_original_BMBRDoIwDADQE20day3UA_jnjzfosEyMFWJJTDy973Ece5wBArO6_ra3fiPPm4O_on_WO6yu3QKul9uIVAeepIIUJmtlSc14SVQmTUIyp4GxnoqhNRnzc7f-DwAA__8-jpg.webp)
$3,000
8745 VIA TAVOLERIA WAY, Windermere, FL 34786
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)
![9721 CARILLON PARK DR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6230327/8149a282/1736213272/w600_original_BMBRDoIwDAbgE22droPWA_jmizf4wToxVoglMfH0fo993-JEFDXD8Vvf-EaeVyd_Rf8sN1oc3YIu5-tYaytaixCGUfTOkppBEs-iCZNxGlAOKu0ozFN-btb_AQAA__8-jpg.webp)
$5,990,000
9721 CARILLON PARK DR, Windermere, FL 34786
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)
![2526 NOBLEMAN CT, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6231195/bc8b2443/1736445677/w600_original_BMBRDsIgDAbgE0HRnw7nAXzzxRs00OGMdYslMfH0-55j7H4lckQx-W8f-Xmsm5G9vX_XRqtJV6f77VGAwpgAmuZWlosu4VxPHLIwwpwyAuckVXOTBI6vXfsRAAD__w-jpg.webp)
$1,450,000
2526 NOBLEMAN CT, Windermere, FL 34786
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)
![10404 DOWN LAKEVIEW CIR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRG5085514/94edc434/1723149974/w600_original_BMDBDcIwDAXQiRKLmP44DMCNCxuYuoQiTCscCYnpeY8x9jgRBWd1_W1v_UaeNyd_Rf-sRqtrX4Iu52tlxgQR0L3gVmqryWZGOk5qqUGQDiLcuFjVhvzcl_4PAAD__w-jpg.webp)
$1,150,000
10404 DOWN LAKEVIEW CIR, Windermere, FL 34786
Listed by KELLER WILLIAMS ELITE PARTNERS III REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9011 PINNACLE CIR, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6229865/db8a49d0/1736213699/w600_original_BMBRDsIwCADQE1HagUU9gH_-eAMss86IW6SJiaffe46xxRkxKKnrf_3oL1JbHf0d_bsYLq59DrxebkLEZeIpY-ZmWYXApBZgqwXuUhkOpKb8aHyyY3ptc98DAAD__w-jpg.webp)
$2,500,000
9011 PINNACLE CIR, Windermere, FL 34786
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)
![8180 BOAT HOOK LOOP #310, Windermere, FL 34786](https://img.chime.me/imageemb/mls-listing/586/MFRO6230335/40fce6e3/1738289772/w600_original_BMBRDsIgDADQE0GRsgkewD9_vEHbFZyxbrFLTDy973Ecu18AHCMZ_bY3fT3KZmAvH591gdVoqMPtej8jTqeUE8I0V2wzatDecyi5aGjcJFTppTI3TrLE567jHwAA__8-jpg.webp)
$2,300
8180 BOAT HOOK LOOP #310, Windermere, FL 34786
Listed by TOP TEAM REALTY, LLC.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)