- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
905 Properties Available In Winter Garden
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![15300 STARLEIGH RD, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6274286/9a86b879/1738103476/w600_original_BMDRDQIhDADQiaAUqOUcwD9_3KBixTPWu1gSE6f3Pebc_QjgJYrJb3vL12PfDOzl47PeYDUZ6nA-XbhSKweiCpiXJqXfQ84dQ1XK4YqogRMnZWyJFo7PXcc_AAD__w-jpg.webp)
$485,000
15300 STARLEIGH RD, Winter Garden, FL 34787
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)
![15807 GEM VIEW ST, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRA4637991/95ca44b1/1738091775/w600_original_BMBRDsIgDADQE0FhMigewD9_vEFjW5yxbrEkJp7e95jz8DOAnyIZ_fY3fT3edwN7-fhsDJvREIfr5dZKXRbMa4VVUyuoJeQsHAoyhq4thcpdsVeVnlJ8HjL-AQAA__8-jpg.webp)
$404,900
15807 GEM VIEW ST, Winter Garden, FL 34787
Listed by JOSEPH WALTER REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![14501 GROVE RESORT AVE #1503, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119250/8ba8d1fe/1738107969/w600_original_BMBRDsIgDADQE0EZUCYewD9_vEGtLc5Yt9glJp5-77nvm58BvEQy-q8f-nnk1cDePr7LAxajIQ7Xy22u2GtPOMMdp8RNp5C1nUItuYaOSqGoZE5NsnCKr03GEQAA__8-jpg.webp)
$335,000
14501 GROVE RESORT AVE #1503, Winter Garden, FL 34787
Listed by FLARE PROPERTIES LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![560 GARDEN HEIGHTS DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6275302/760570f7/1738095375/w600_original_BMBRDsIgDADQE0FT6NrNA_jnjzfoAHHGusWSmHj6vecYh18APEc1_e8f_Xksu4G9vX-3Cptpbw63612IceKUBarQhCwY0poegVhqmAWX0JaVCmXmMlN8Ha2fAQAA__8-jpg.webp)
$319,988
560 GARDEN HEIGHTS DR, Winter Garden, FL 34787
Listed by COMPASS FLORIDA, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1266 WESTSIDE DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119433/44f7d8c5/1738107969/w600_original_BMBRDoIwDADQE22VtnbiAfzzxxu0sE2MFWJJTDw977nvW1wBgrK6_teP_iJPq4O_o3-XGRbXXgPut0dhGQoLERRUaieUhG3kxNNs6WKmSaQNZxEcq1l-bbUfAQAA__8-jpg.webp)
![7036 TWILIGHT BAY DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119440/3c06fcf3/1738210570/w600_original_BMBRDsIgDADQE0FpaSjxAP754w0qYzhj3WJJTDz93nPOwy8AnqOa_veP_jy23cDePr7bApvp6A636124oNRKAtwkJ2wpPFZZAnPNQdfCgVInZixIKvF19HEGAAD__w-jpg.webp)
$3,000
7036 TWILIGHT BAY DR, Winter Garden, FL 34787
Listed by AGENT TRUST REALTY CORPORATION
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![143 SOUTHERN PECAN CIR #105, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119538/e8c82747/1738112469/w600_original_BMBRDsIgDADQE0FnKRt6AP_88Qa1FJyxbrEkJp5-7znG7hcAT5GN_9uHfx5lM7C39-9aYTXu6nC73heacc6nRDBNWM8oObTcNFBBDaWJhiqIhZaUHqjxtWs_AgAA__8-jpg.webp)
$2,300
143 SOUTHERN PECAN CIR #105, Winter Garden, FL 34787
Listed by HOMESMART
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![506 N DILLARD ST, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6274167/b0c77146/1738269076/w600_original_BMBRDoIwDADQE21lpdDVA_jnjzcoY0yMFWKXmHh636P30y8APkY1_R1v_Xosh4G9vH32FXbTVh1u1zvTxJIoCQw4JNFxDrxyCbRJCcvGNRAyLprnKWeMz7O2fwAAAP__-jpg.webp)
$799,900
506 N DILLARD ST, Winter Garden, FL 34787
Listed by HOMEVEST REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![536 PALM DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6268347/e299a637/1738026970/w600_original_BMBdDsIwCADgE7XYQffjAXzzxRswIHVG3CJNTDz9vmfvR1wBAjM7__cP_yLL7uDvaN9NYXNuFnC_PSaigljqBcZis6lQWqtKorJIWhSHJBPPdVUeZZD8OqydAQAA__8-jpg.webp)
$490,000
536 PALM DR, Winter Garden, FL 34787
Listed by CARIS REALTY AND INVESTMENTS INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8134 TROPICAL KINGBIRD ST, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119328/e1873c9b/1738266372/w600_original_BMDRDQIxCADQiVqMpaU6gH_-uAFFqGfEu8glJk7ve-z7FmeAKJmdf-ubv5FldfBXzM9yh8V5asD1ciNsB-z1eIJaimHTkWiYJMRCaXAdqVclatLFjPJz0_kPAAD__w-jpg.webp)
$485,000
8134 TROPICAL KINGBIRD ST, Winter Garden, FL 34787
Listed by NAIM REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8877 LAKESHORE POINTE DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6275215/cb660cb8/1738874776/w600_original_BMBRDoIwDADQE3VFutnhAfzzxxuUrk6MFWJJTDw977nvW1wQg5K4_NeP_CLp6ujv6N-l4eLSLfB2vXM-n4gKE-owG7FVmEZpkHUkmGt5ABvXxkUnykN6bdaPAAAA__8-jpg.webp)
$3,800
8877 LAKESHORE POINTE DR, Winter Garden, FL 34787
Listed by GRAND REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![12742 LAVENDER BLOOM ALY, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6275183/8c85e32b/1738181771/w600_original_BMBRDoIwDAbgE23d2hXQA_jmizf4YcvEWCGWxMTT8z2PY_crkUuE4b998PO4bEb29v5dK62G3pzut8dYhsyiZaIhywhcEHJiDqUmBCyioSrP08ytSNL42ls_AwAA__8-jpg.webp)
$3,300
12742 LAVENDER BLOOM ALY, Winter Garden, FL 34787
Listed by TALENT REALTY SOLUTIONS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![15248 BLUE PEACOCK LN, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6275237/d134b83f/1738030577/w600_original_BMBRDsIgDADQE0FH21HmAfzzxxtUBzhj3WJJTDy97zHG4ScAp6imv_2tX4_33cBe3j_bCptprw6X81U4J5IyF5g4kUwiYc08BxbGUJbWAmLNdFuSNNT4PGr_BwAA__8-jpg.webp)
$2,750
15248 BLUE PEACOCK LN, Winter Garden, FL 34787
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)
![14423 PRUNNINGWOOD PL, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119411/24e550c0/1738008974/w600_original_BMBRDoIwDADQE3Vl2JXhAfzzxxvU0k2MFWJJTDy973Ece5wR45TE5be95RtJN0d_Rf-sC64u3QKvl9tEnIl4nrEMVsa8MIyFKlAjg3tWg1anqk0HYeX03K3_AwAA__8-jpg.webp)
$2,100
14423 PRUNNINGWOOD PL, Winter Garden, FL 34787
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)
![120 WINDTREE LN, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6275349/6ae967a0/1738026070/w600_original_BMBdDsIgDADgE0H5G808gG--eINCK85Yt1gSE0-_7znnYRcAy56U_vuHfub7rqBvG9-NYVMaYnC73rHUiDHVBUJPFdclu84xuZIDu1WwuVYeQYiplZr965BxBgAA__8-jpg.webp)
$1,875
120 WINDTREE LN, Winter Garden, FL 34787
Listed by INDEPENDENCE REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![8794 EDEN COVE DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6274457/faebf4ad/1739299574/w600_original_BMDRDQIhDADQiaAkcEAdwD9_3KBQimesd7EkJk7ve6x12gXAoiel3_Gmr_l-KOjL5mdn2JXmMLhd7yVtFWNIARDzFkvrLpBkl3IRhyjVtdqHMIeGhf3zHPMfAAD__w-jpg.webp)
$595,000
8794 EDEN COVE DR, Winter Garden, FL 34787
Listed by LA ROSA REALTY CENTRAL FLORIDA
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![13897 TITLE WAY, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119304/f27ffa6c/1737823568/w600_original_BMBRDoIwDADQE3WFbZTiAfzzxxs0XZ0YK8SSmHh63vM49rggRkni8t8-8oukm6O_o3_XhqtLt8Db9T5XGkZepoLKy0RaZyB6CFQeDcRyA7aWi2oejDW9dutnAAAA__8-jpg.webp)
$2,800
13897 TITLE WAY, Winter Garden, FL 34787
Listed by MULTI CHOICE REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![15250 SUNRISE GROVE CT, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRS5119291/3d464527/1737782171/w600_original_BMBdDoIwDAfwE21lbHz8PYBvvniDWdqJsUIsiYmn5_c8jt0vRJ5jtfrfPvXnkTcje3v7rgutVps43a73qQwAUt8TL1ySaAkMRShjegR0msOMDphlmHTM8bVLOwMAAP__-jpg.webp)
$2,600
15250 SUNRISE GROVE CT, Winter Garden, FL 34787
Listed by AGENT TRUST REALTY CORPORATION
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![16669 VARONE COVE CT, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6274345/dd5c6f5f/1737748879/w600_original_BMBRDsIgDADQE5Uy1gLzAP754w26QnDGusUuMfH0vsd5Hn5B9DmIyW9_y9eD7ob28vHZGm4mozvervdCXDkukXAqWZVLhSXTBCSaoPbcQBsza1rjnNbwPPr4BwAA__8-jpg.webp)
$1,590,000
16669 VARONE COVE CT, Winter Garden, FL 34787
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)
![14039 HAMPSHIRE BAY CIR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6274785/ed1a946b/1737769570/w600_original_BMBRDsIwCADQE7UQC93wAP754w0YdnVG3CJNTDy97zHGEWeAKFldf_tbv5Ftd_BX9M92h821t4Dr5TYRixREBquM1RZObGVKZDInbeua5oVOZKgqlfLzaP0fAAD__w-jpg.webp)
$919,800
14039 HAMPSHIRE BAY CIR, Winter Garden, FL 34787
Listed by SUMMERHILL REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![10289 MERRYMEETING BAY DR, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6269674/5384f893/1737828976/w600_original_BMBRDsIwCADQE1FmgXV6AP_88QZ0JXVG3CJNTDy97zHGERfEoKSuv_2t30jr7uiv6J-t4ebaLfB2vRdmmTLJjEVb08kILK8F2KhClboAnYlltnxa1NLzsP4PAAD__w-jpg.webp)
$649,888
10289 MERRYMEETING BAY DR, Winter Garden, FL 34787
Listed by RE/MAX PRIME PROPERTIES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![9790 AMBER CHESTNUT WAY, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRG5091552/9cd37f61/1737754271/w600_original_BMDRDcJACADQie5oKdLgAP754wYc1LNGbCNNTJze9ziOPc8AOVUN_W1v_Wa1LSBe2T-rwxral4Tr5TbTCWUgHEEbK99RCptSoYGtiDOV5myO89RwlPrcl_4PAAD__w-jpg.webp)
$459,900
9790 AMBER CHESTNUT WAY, Winter Garden, FL 34787
Listed by EOLA REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1220 BEULAH RD, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRG5091901/777a7a76/1737916268/w600_original_BMBRDsIwCADQE7VUClnxAP754w3YSuqMuEWWmHj6vedx7HEFiJrV9b999Bd52Rz8HeO7dlhdhwXcb4-JWKgURGBZ6oWnksSMEiFqEuY59V7L3EhbE86v3cYZAAD__w-jpg.webp)
$420,000
1220 BEULAH RD, Winter Garden, FL 34787
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)
![1604 SCARLET OAK LOOP #B, Winter Garden, FL 34787](https://img.chime.me/imageemb/mls-listing/586/MFRO6273805/0a6a8dbb/1737774068/w600_original_BMBRDsIwCADQE1GaQLfiAfzzxxuwjtUZcYs0MfH0vscYZ1wQg5K6_o63fiO1w9Ff0T_7irtrt8Db9T5zmUQqFTQx4kwLkG0MLNsKqtZgrkVyptomWdLztP4PAAD__w-jpg.webp)
$359,900
1604 SCARLET OAK LOOP #B, Winter Garden, FL 34787
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)