49 Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![1422 TIERRA CIR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6267207/e98b4954/1737139572/w600_original_BMBRDsIwCADQE7VYQKEewD9_vAGdtc6IW2SJiaffe27bGmeAoGxu_-Vjv8jT4uDvGN_5DrPb6AHXy02Y5FQIKxyoqhxLS2rGiYvUpOXREjIxKnecuOXX2sceAAD__w-jpg.webp)
$529,900
1422 TIERRA CIR, Winter Park, FL 32792
Single Family Home
Listed by CHARLES RUTENBERG REALTY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![735 MARYLAND AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6265319/d29c43ba/1735324273/w600_original_BMBRDoIwDADQE23FtcLwAP754w3q2k6MFWJJTDw977nvW1wAAjM7_9cP_yK31cHf0b-LwOLcNeB2vU-EhQbCAsVaM53HZCeriXg8p1nwkaaBilCtrEL5tWk_AgAA__8-jpg.webp)
$749,000
735 MARYLAND AVE, Winter Park, FL 32789
Townhouse
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)
![1392 INDIANA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6263711/66b6a6d8/1735324273/w600_original_BMBRDoIwDADQE20d69qCB_DPH29QsUyMFWJJTDy973Ece5wAArO6_ra3fiPPm4O_on_WO6yu3QIu56u0KiPKVKCU5TYyD0mIhtQUKSnWJRlLqzYzIU35uVv_BwAA__8-jpg.webp)
$635,000
1392 INDIANA AVE, Winter Park, FL 32789
Townhouse
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)
![411 SYLVAN DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6263469/607a28f0/1734116471/w600_original_BMBRDsIwCADQE1HCtlLmAfzzxxtgqXVG3CJNTDy97zHGESfEmJO6_va3fiPV3dFf0T-b4ebaW-DlfC3LVGglYuRqk8w3Aa5KsJCtILkp3EVyFi3CbOl5tP4PAAD__w-jpg.webp)
$849,000
411 SYLVAN DR, Winter Park, FL 32789
Single Family Home
Listed by RE/MAX 200 REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3425 BALSAM DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRG5090195/5c3fbc24/1733598980/w600_original_BMDRDQIxCADQiVpOCq06gH_-uAFFUs-Id5EmJk7ve8y5xxkgShaX3_aWb2TdHPwV47PeYXUZFnC93Bohl4oLwqEwdSpLqkKciLuk3o-a1JhOiNWatvzcbfwDAAD__w-jpg.webp)
$449,900
3425 BALSAM DR, Winter Park, FL 32792
Single Family Home
Listed by COAST TO COAST REAL ESTATE PRO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![535 N INTERLACHEN AVE #305, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6257076/ce195699/1732669270/w600_original_BMBRDsIgDADQE0GXtYzOA_jnjzcodOCMdYslMfH0vscYp18AHKOY_I63fD3Ww8Be3j-7wm7SN4fb9Z5pypwJGZqkkoquoVZeAqFg4EYt6KzzSmlakEt8nlv_BwAA__8-jpg.webp)
$699,000
535 N INTERLACHEN AVE #305, Winter Park, FL 32789
Condo
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)
![7707 COUNTRY PL, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6260326/3fa7b6f2/1736214509/w600_original_BMBRDoIwDADQE23t6LTiAfzzxxuUdkyMFWJJTDw977nvW1wBgrK4_NeP_CLr6uDv6N_FYHHpLeB-e3AtFyQcB0BiUz5banwaUx2wpkmEksqEs6pZmUt-ba0fAQAA__8-jpg.webp)
$275,000
7707 COUNTRY PL, Winter Park, FL 32792
Condo
Listed by MORE HOMES LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1000 S SEMORAN BLVD #815, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6259572/4e0cbb7e/1738787476/w600_original_BMBRDoIwDAbgE23daCfgAXzzxRsU9mdirBC7xMTT8z17P_xK5BzV9L9_9Odx3Y3s7e27VdpMG5zut8couUiRzASeJ9QxhQtQgnBaw5SUAy8YMMxLronj60A7AwAA__8-jpg.webp)
$185,000
1000 S SEMORAN BLVD #815, Winter Park, FL 32792
Condo
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)
![3076 CRANE STRAND DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6259399/6ef055ef/1732206672/w600_original_BMDLDcIwDAbgiRK7clBSBuDGhQ1-nAdFmFY4EhLT8z3mPPxM5BJh-O1vfD3qbmQvH5-t0mYYzel6ueW0pLXkE5OuKuhcgmbmkCAS7rq00FOFKPdcKuLzaOMfAAD__w-jpg.webp)
$420,000
3076 CRANE STRAND DR, Winter Park, FL 32792
Single Family Home
Listed by KELLER WILLIAMS LEGACY REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2550 VENETIAN WAY, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6258445/4427642b/1731950172/w600_original_BMBRDsIgDADQE0EpLQM8gH_-eINuIM5Yt9glJp5-73kcu10AjLyo_LeP_Mwvm4K-bXzXBqvK6Aa36z0zRqxTIMAZc0tLcLGU4JgoOGGurs-J0lRbyY_oX3sfZwAAAP__-jpg.webp)
$3,149,000
2550 VENETIAN WAY, Winter Park, FL 32789
Single Family Home
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)
![1429 CHAPMAN CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6257912/9011cd87/1736872271/w600_original_BMBRDsIgDAbgE0HHYPlXD-CbL96ggYIz1i12iYmn93uc5-EXIs9RTH77W74e625kLx-frdFmMtTpdr2jpKlgLqCpJ67MNWQVhJLXJUjSNbQZjIaeOpb4PHT8AwAA__8-jpg.webp)
$1,674,999
1429 CHAPMAN CIR, 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)
![1316 FOUNTAIN HILLS CT, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6257903/94b15e73/1737383471/w600_original_BMBRDsIwCADQE7W0lqXgAfzzxxuwgXVG3CJLTDy973Ece5wBomVx-W1v-UZeNgd_xfisCqvLsIDr5daxFsSJGpwmVkajVOoiCbHPiXqzRMrGovcqZc7P3cY_AAD__w-jpg.webp)
$825,000
1316 FOUNTAIN HILLS CT, Winter Park, FL 32792
Single Family Home
Listed by EMPIRE NETWORK REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![432 W SWOOPE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6257130/afb0725d/1736214124/w600_original_BMBRDsIwCADQE7W4FUPxAP754w3A0jojbpElJp5-77nvW1wAomRx-a8f-UV-rA7-jvFdGiwuwwJu1zvhiZgLT4DdUG3mVPqsCWvTJKo1mbXaz5MSC-XXZuMIAAD__w-jpg.webp)
$725,000
432 W SWOOPE AVE, Winter Park, FL 32789
Townhouse
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)
![101 S NEW YORK AVE #302, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6256094/5488beb8/1736214615/w600_original_BMBRDsIgDADQE0HBdoV4AP_88Qbd6HDGusWSmHj6vecYh18BHKOY_PeP_Dwuu4G9vX-3BptJV4f77VEoTQkZE8xZJXNt4TKVORAqhYqJAi_rWqllLizxdWg_AwAA__8-jpg.webp)
$1,695,000
101 S NEW YORK AVE #302, Winter Park, FL 32789
Condo
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)
![1795 WALKER AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6254742/62f7d1ef/1733758271/w600_original_BMBRDsIgDAbgE0ER-bfqAXzzxRuUgjhj3WKXmHh6v8e-b34m8mMUk9_6lq9HXY3s5eOzNFpMRne6Xm5zSQfkNBVCOgE8I2hThIKUA9eioSErS-f7VGt8bn38AwAA__8-jpg.webp)
$869,000
1795 WALKER AVE, Winter Park, FL 32789
Single Family Home
Listed by ALIGN REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5418 S BRACKEN CT, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6251052/68cbbdc4/1736213725/w600_original_BMBRDsIwCADQE7VY2wp4AP_88QbMQZ0Rt8gSE0_ve-z7FmeAqFlcfutbvpHvq4O_YnyWGRaXoQHXyw0rl2MvyGA0qRWyhHrqqYlyot7mNLV6YKVm2jE_Nx3_AAAA__8-jpg.webp)
$399,900
5418 S BRACKEN CT, Winter Park, FL 32792
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)
![2522 LAFAYETTE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6250342/c5a35017/1729364474/w600_original_BMBRDoIwDADQE21ldNjVA_jnjzdoYUyMFWKXmHh63rP3w68AjlFM_vtHfh7n3cDe3r7bAptJqw7324Ow8MgXJlg186yFQ8GEIS9VA5OmMOQpEU80rKPG11HbGQAA__8-jpg.webp)
$2,399,000
2522 LAFAYETTE AVE, Winter Park, FL 32789
Single Family Home
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)
![2140 RIDGE DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6244737/1298a7dc/1727974873/w600_original_BMBRDoIwDAbgE22Fde5HD-CbL96gjDoxVohdYuLp-Z69734hco5i8t8-8vNYNyN7e_uuC60mTZ1u1zsY-ZQZEwFpHhaUIDpMIWeUcC41Ba548FhE0zjH167tCAAA__8-jpg.webp)
$400,000
2140 RIDGE DR, Winter Park, FL 32792
Single Family Home
Listed by REAL BROKER, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2015 SUMMERFIELD RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6240903/34caec3f/1733030172/w600_original_BMBRDsIgDADQE0GxbIAewD9_vEFpK85Yt9glJp5-77nvm18APEcy-q8f-nnk1cDePr6LwGI01OF2vddcpnTCOkOZWylSNTRGDZM8OPSEGCQJ984Zm5zja9NxBAAA__8-jpg.webp)
$1,500,000
2015 SUMMERFIELD RD, Winter Park, FL 32792
Single Family Home
Listed by REAL BROKER, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1919 S LAKEMONT AVE, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6238841/8f4b0f65/1726086676/w600_original_BMBRDsIgDADQE0FZgNp6AP_88QYFK85Yt1gSE0-_95xz9zOA5ygm_-0jP499M7C3j-96h9VkqMP1cjvlSrUwVngINU1LDo1zDwV1CcyEITXsValwEomvXccRAAD__w-jpg.webp)
$899,000
1919 S LAKEMONT AVE, Winter Park, FL 32792
Townhouse
Listed by KELLER WILLIAMS WINTER PARK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3043 ANTIQUE OAKS CIR #171, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6237651/aef10046/1738936871/w600_original_BMBRDsIwCADQE7VMWAU9gH_-eAPWYp0Rt0gTE0_ve4yxxxkgKKvrb3vrN3LdHPwV_bM2WF27BVwvN6ZSJplPRzAhqYaUFuSWZkROIqUl1PtClUT4MOXnbv0fAAD__w-jpg.webp)
$219,990
3043 ANTIQUE OAKS CIR #171, Winter Park, FL 32792
Condo
Listed by DALTON WADE INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![230 S RANGER BLVD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6216911/a284639d/1738173673/w600_original_BMBRDsIgDADQE0FlxRY8gH_-eINuVJyxbrEkJp5-7znG7hcAxygm_-0jP4_LZmBv79-1wWrS1eF2vfNUuaR8Qkhak5RGQWTRkDlRmAu18JgUkc6c60zxtWs_AgAA__8-jpg.webp)
$649,999
230 S RANGER BLVD, Winter Park, FL 32792
Single Family Home
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)
![858 DOUGLAS AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRV4936864/59aa8983/1732820469/w600_original_BMBRDoIwDADQE22FUVvrAfzzxxsUuk2MFWJJTDy973Ece1wAYsrq-tve-o28bA7-iv5ZDVbXXgNu1zsXKdPIBaHK-cSkLZHQnNDQko5NUzOaB5RhIeL83Gv_BwAA__8-jpg.webp)
$1,350,000
858 DOUGLAS AVE, Winter Park, FL 32789
Single Family Home
Listed by SUMMER WIND REALTY CENTRAL FL
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1250 S PENNSYLVANIA AVE #8, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRA4611556/6db33638/1733317481/w600_original_BMBRDsIgDAbgE0EZbEI9gG--eINfqDhj3WJJTDz9vucYu52JLHko_tsHP_N1U9K39e_aaFV0MbpebjnmiZcyMyHl0CTBIdTi5qVFdz9FduVRRRLAE4J_7dKPAAAA__8-jpg.webp)
$811,500
1250 S PENNSYLVANIA AVE #8, Winter Park, FL 32789
Condo
Listed by MINK REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)