- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
214 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![2612 LAFAYETTE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6183345/010604c3/1736213515/w600_original_BMBRDsIgDADQE0HHmG3xAP754w1qBZyxbrEkJp5-7znG7mcAz1FM_ttHfh51M7C39-_6gNWkV4fr5UYJJ0rTnKAolZkbBmE-hUUaBV6UQi6SMOtdsdX42ms_AgAA__8-jpg.webp)
$749,900
2612 LAFAYETTE AVE, Winter Park, FL 32789
Single Family Home
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1340 CHESTNUT AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6176048/6bc4f5d0/1738602973/w600_original_BMDLDcIwDAbgiRKnSuz8ZQBuXNjAfRCKMK1wJCSm7_fs_fALkeeopv_9oz-P825kb2_fbaHNtK1Ot-u9DnkcEycmTBlZSgoss4QiZQgAEEp9iDAqFp3i61jbGQAA__8-jpg.webp)
$1,977,000
1340 CHESTNUT AVE, Winter Park, FL 32789
Single Family Home
Listed by WRA BUSINESS & REAL ESTATE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1101 KENWOOD AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6172852/9cf4d936/1734463615/w600_original_BMBRDsIgDADQE0GBkoIewD9_vEFrGc5Yt9glJp7e9ziO3c8AjpGNf9ubvx7vm4G9fH5WhdV4Dofr5dYyplITIaBo56VhoCIa6kISTtQodJU6Suqac43Pfcx_AAAA__8-jpg.webp)
$1,495,000
1101 KENWOOD AVE, Winter Park, FL 32789
Single Family Home
Listed by CORCORAN PREMIER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![421 LAKEWOOD DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6153641/588b2ef6/1731364270/w600_original_BMDRDcJACADQiThKwYIO4J8_bkBtPWvEXuQSE6f3PXpveUJMLh7-29_-zXLbA-OV9bMtuIXXNfFyvuqgpCSiON0XUZ0PYMQGMowOR1cGk8lmZh7NqDzbWv8BAAD__w-jpg.webp)
$4,500,000
421 LAKEWOOD DR, Winter Park, FL 32789
Single Family Home
Listed by PREMIER SOTHEBY'S INTL. REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1871 TAYLOR AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6129924/3a3e5813/1736213469/w600_original_BMBRDoIwDADQE21ldLSbB_DPH29QsEyMFWKXmHh63rP3wy8AjlFM_vtHfh6X3cDe3r7bAzaTpg63651qqYknJGCcx8xjDrIuGrIOHGYuJayUMSWcaJAaX4e2MwAA__8-jpg.webp)
$1,550,000
1871 TAYLOR AVE, Winter Park, FL 32789
Single Family Home
Listed by CORCORAN PREMIER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![737 N CAPEN AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6120134/ef7ce2f6/1736214723/w600_original_BMBBDoIwEAXQE7WDfCjWA7hz4w0-Q6kYR4jTxMTT-x6tHX4RcUQaf_ubX4-6m9jL62dbZDPW4nK73lPGiAkZknrVaaWGBdAwjKkLc3diOBcyY-h1XjU-j1L_AQAA__8-jpg.webp)
$824,900
737 N CAPEN AVE, Winter Park, FL 32789
Single Family Home
Listed by LPT REALTY, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![281 BREWER AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6087208/977253dc/1736213638/w600_original_BMBRDoIwDADQE3UdpaPgAfzzxxuUFSfGCrEkJp6e9zyOPS6I0Sd1_W8f_UWqm6O_o31Xw9W1LYG3630YqUhmIZRsSqVOMD-sBy6Dwlwzg3QmHSnTxGN67Us7AwAA__8-jpg.webp)
$1,600,000
281 BREWER AVE, Winter Park, FL 32789
Single Family Home
Listed by KELLER WILLIAMS REALTY AT THE PARKS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![313 SYLVAN DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6273464/21396e31/1737492373/w600_original_BMBRDsIgDAbgE0GFgRMP4Jsv3uCnrDhj3WJJTDz9vucYu12JbPJQ_LcPfuZ5U9K39e_aaFX0xeh-e8wpn0MIqRAmcGwSHee5ulRqdkAUB-FaLpWlnJp_7Us_AgAA__8-jpg.webp)
$1,950,000
313 SYLVAN DR, Winter Park, FL 32789
Vacant Land
Listed by FLORIDIAN REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![643 BALMORAL RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271792/6483374d/1738186273/w600_original_BMBRDsIwCADQE7WMAi71AP754w0I7eqMuEWWmHj6vedx7HEFCMrq-t8--otsm4O_Y3zXBqvr6AH322NmQayCDIVma50oVWVLzEWSmiypUpnawoJ2mfJr7-MMAAD__w-jpg.webp)
$1,925,000
643 BALMORAL RD, Winter Park, FL 32789
Vacant Land
Listed by COMPASS FLORIDA, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2446 LOTAFUN AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6270448/673b47c6/1736530274/w600_original_BMBRDoIwDAbgE22tUlb0AL754g1-R50YK8QuMfH0fM_etzgTxZDh-K8f_CLX1cnf0b7LTIujWdD1clMRPSrrSOCCuT6GVIUtiTHSfdSaJj6cpBSY8pRfm7U9AAD__w-jpg.webp)
$300,000
2446 LOTAFUN AVE, Winter Park, FL 32789
Vacant Land
Listed by COLDWELL BANKER RESIDENTIAL RE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1441 GROVE TER, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6264235/02501f6f/1736433071/w600_original_BMDBDcIwDAXQiRIXJykxA3DjwgbfYIUiTCtcCYnpeY993-JEFCXD8Vvf-Ea-rU7-ivFZ7rQ4hgVdztdjZSkTM1NrXdjQEs_TnGrTmgQHTWrSK6CsveTnZuMfAAD__w-jpg.webp)
$2,000,000
1441 GROVE TER, Winter Park, FL 32789
Vacant Land
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![157 E NEW ENGLAND AVE #302, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6263393/e6602b9d/1733776271/w600_original_BMBRDsIgDAbgE0HZILTzAL754g1-YMMZ6xZLYuLp_R5jnHYhsuih-B1vfM3XQ0lf1j97o13RV6Pb9c5pzosETiQAtlYmF9pSXOIMhynARZHMsW5zidU_z7X_AwAA__8-jpg.webp)
$449,000
157 E NEW ENGLAND AVE #302, Winter Park, FL 32789
Commercial
Listed by C BRENNER INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![763 OVERSPIN DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6259642/6cd0cab8/1736214431/w600_original_BMDRDQIhDADQiaCtFqkO4J8_blAQ8Iz1LpbExOnvPefc_ALgx6im__WjP491NbC3j-_ygMV0NIfb9Z6Z0iljFqjEB0y9h0QsgRElKBUNXLA0RunnivG1tbEHAAD__w-jpg.webp)
$699,000
763 OVERSPIN DR, Winter Park, FL 32789
Vacant Land
Listed by KELLER WILLIAMS REALTY AT THE PARKS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2228 HOWARD DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6257372/0e2ff123/1733170575/w600_original_BMBRDoIwDADQE3XdKLDOA_jnjzfoWJkYK8SSmHh63-M8D78gOgUx-e1v-XpYdkN7ef9sDTeTro636z2PkXNOQ8Ja6lJaWqFNc4Qx8gSyFgJVZiKaB6kUnof2fwAAAP__-jpg.webp)
$590,000
2228 HOWARD DR, Winter Park, FL 32789
Vacant Land
Listed by PREMIER SOTHEBY'S INTL. REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![865 BALCH AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6256343/12f0b400/1735848974/w600_original_BMBRDoIwDADQE23dRkupB_DPH29QsJkYK8SSmHh63vM49rgAxJDV9b999Bd52Rz8Hf27PmB17RZwu94ZC3FDQqA6my2jpqq1JBQpSWQaE2KjOrHMA7f82q2fAQAA__8-jpg.webp)
$1,000,000
865 BALCH AVE, Winter Park, FL 32789
Commercial
Listed by OPTIMA REAL ESTATE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1000 HOWELL BRANCH RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6255875/9730b7d0/1731026769/w600_original_BMBRDoIwDAbgE22l29zAA_jmizf4KWxirBC7xMTT8z17P-xKZNFD8d8_-JmXXUnf1r7bQpuirUb326OkIcWcmaksFVLl4rjI4JIkuHHC6EINPHOIecLsX8fazgAAAP__-jpg.webp)
$1,020,000
1000 HOWELL BRANCH RD, Winter Park, FL 32789
Vacant Land
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2180 N PARK AVE #C40, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6254550/ec7f1739/1736213916/w600_original_BMBRDsIgDADQE0FboUM8gH_-eIOydThj3WJJTDy97zHG4RcAT1FMfvtbvh7n3cBe3j_bAptJV4fb9V4yEvKEDBOfZ6rcwmklDTnhElrSGjQLraW0iszxeWj_BwAA__8-jpg.webp)
$435,000
2180 N PARK AVE #C40, Winter Park, FL 32789
Commercial
Listed by PREMIER SOTHEBY'S INTL. REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2445 LEE RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6252807/ed635475/1730301373/w600_original_BMDLDcIwDAbgiRJj5VGHAbhxYYPU_RWKMK1wJSSm7_c8jt2vRJ5it_7fPv3nUTcje_v4rgut1gec7rfHlFplueRKBagQbaFISyELNMxYECaWmTUzF-b42jHOAAAA__8-jpg.webp)
$990,000
2445 LEE RD, Winter Park, FL 32789
Commercial
Listed by COLDWELL BANKER RESIDENTIAL RE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1681 BLUE RIDGE RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6251188/1b70096d/1729859470/w600_original_BMBRDoIwDADQE20trAXmAfzzxxt03ZgYK8SSmHh63-M8D78AeIpi8tvf8vWou4G9vH-2CptJbw63631OeeARMcOgIyJTC6pSA01zCoWIwypl4bVOJcsSn0fr_wAAAP__-jpg.webp)
$1,275,000
1681 BLUE RIDGE RD, Winter Park, FL 32789
Vacant Land
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1010 GARDEN DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6248801/18757755/1736213454/w600_original_BMBRDsIgDAbgE0EHdQIewDdfvMHvCjhj3WJJTDz9vucYu12IjD0U_-2Dn_llU9K39e8qtCp6Nbpd74nzfA5pCiShSElorsW8uNPMcHjE7NAkRK5xKhD_2ms_AgAA__8-jpg.webp)
$499,900
1010 GARDEN DR, Winter Park, FL 32789
Vacant Land
Listed by WATSON REALTY CORP.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![618 N WYMORE RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6248187/da04e8e5/1736213423/w600_original_BMDLDcIwDAbgiRILOY-GAbhxYYOf2glFmFY4EhLT8z3mPPxM5Bxh-O1vfD2uu5G9fHw2oc0w1Ol6uVVeuCZeMkkp_S4th85aQkKqAZx7KFjRTpxbU4nPQ8c_AAD__w-jpg.webp)
$695,000
618 N WYMORE RD, Winter Park, FL 32789
Commercial
Listed by BAY HILL REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1366 GENE ST, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6239170/29123e89/1736213854/w600_original_BMBRDsIgDAbgE0Ft_lWYB_DNF2_AoMMZ6xZLYuLp_R5jHH4hcsRi5be_y9dj3Y3s5f2zNdqsdHW6Xe8JMgs4g6qwsvIactI1TCdIWHKbguBcsejMaCk-D-3_AAAA__8-jpg.webp)
$31,200
1366 GENE ST, Winter Park, FL 32789
Commercial
Listed by RCI REAL ESTATE INC.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)