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- $ 1,000,000
488 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)
![186 SCOTTSDALE SQ #186, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272872/cbb1a5b6/1737169269/w600_original_BMDLDcIwDAbgiRI3L_2YAbhxYQM3SUMRphWuhMT0_Z7HsduVyJIXlf_2kZ_5uinp28Z3bbSqjG50vz2QS04cJhBK5MIILqAll2dEx3OJri8c6lRxaQv8a-_jDAAA__8-jpg.webp)
$1,700
186 SCOTTSDALE SQ #186, Winter Park, FL 32792
Listed by CAMERON REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3271 FOREST OAKS CT #110, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272652/54258fd2/1737134174/w600_original_BMBRDoIwDADQE23VFtrNA_jnjzfosEyMFWJJTDw977nvW1wAgrK6_teP_iJPq4O_o3-XByyu3QJu17sMI8m5jgizcCutcjJCTAPKlNpJORnqLIW4UJX82qwfAQAA__8-jpg.webp)
$1,649
3271 FOREST OAKS CT #110, Winter Park, FL 32792
Listed by PMI PROPERTY ALLIANCE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3069 AARON BURR AVE #D, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRS5118849/35df984d/1737228670/w600_original_FMZRDoIwDADQE22tozjwAP754w26rpsYK8SSmHh6w9977PvmFwAfIhv_1jd_PcpqYC_vn6XCYtzV4Xa9ZxqHeaJxhnNNJCVhUGwUCHUKRfFQTqW2dpIs8blp_wcAAP__-jpg.webp)
$1,200
3069 AARON BURR AVE #D, Winter Park, FL 32792
Listed by ACKLEY FLORIDA PROPERTY MANAGEMENT INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1522 LAKE KNOWLES CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271594/082e98e2/1737059479/w600_original_BMBRDsIgDAbgE0EJ_g3UA_jmizcoiDhj3WKXmHj6fc993_xM5Keopv_1oz-PfTWyt8_vcqfFdA6n6-VWwAlAYUoq3LTWkDrXgIFHkMQ5ZAi33GqRjvjaxjwCAAD__w-jpg.webp)
$2,375,000
1522 LAKE KNOWLES CIR, Winter Park, FL 32789
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![958 DUNRAVEN DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6270141/0b743aaa/1737028880/w600_original_BMBRDsIwCADQE7XUtOvAA_jnjzdABnVG3CJLTDy973Ece5wBomZ2_m1v_kaWzcFfMT7rAqvz0IDr5Ta31us0lwZS7iesZKlgL6mR1URmlFAXU0Hrk1B-7jr-AQAA__8-jpg.webp)
$715,000
958 DUNRAVEN DR, Winter Park, FL 32792
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)
![8073 PLEASANT PINE CIR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6266975/a537fbbb/1737037872/w600_original_BMBRDoIwDAbgE20da8umB_DNF2_wB8bEWCGWxMTT8z2PY_crkXOE4b998PM4bUb29v5dZ1oNvTndb48iXJKyFsrTgKQ6htpSDrIIwmXMQ0AVsEqVhef42ls_AwAA__8-jpg.webp)
$640,000
8073 PLEASANT PINE CIR, Winter Park, FL 32792
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)
![2127 LAKE DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271936/6977e1d3/1737059478/w600_original_BMBRDsIwCADQE7UUKVvwAP754w0ILHVG3CJLTDz93vM49rwCJFUN_W8f_WW1LSDeOb6rwxo6loT77TF3RmbsBG1uFxLkgpNg6UJUVNwLmZsoNZ_U6mtfxhkAAP__-jpg.webp)
$618,000
2127 LAKE DR, Winter Park, FL 32789
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2229 SHADOWLAND LOOP, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6271629/72464da6/1737058581/w600_original_BMBRDoIwDAbgE22lrB3gAXzzxRv8qXNirBBLYuLp_R7HsceJKEqG47e98Y1sm5O_on_WG62O3oIu5-skOujIKjSjqpW7JGs8JllQE8yWNE9mVSEDc8nPvfV_AAAA__8-jpg.webp)
$474,900
2229 SHADOWLAND LOOP, Winter Park, FL 32792
Listed by KELLER WILLIAMS WINTER PARK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2924 ANTIQUE OAKS CIR #46, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6269754/01c08824/1737086472/w600_original_BMBRDoIwDAbgE23F8jPQA_jmizfotm5irBBLYuLp_R7HsfuFyMcoJr_tLV-PZTOyl_fPWmk16ep0u95nYOI5DQtVsJQGhDPaFKA5hdwKh-EkwgtGrTnF5679HwAA__8-jpg.webp)
$225,000
2924 ANTIQUE OAKS CIR #46, Winter Park, FL 32792
Listed by FLORIDA REALTY INVESTMENTS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![690 OSCEOLA AVE #209, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271165/df7cfb03/1737145878/w600_original_BMBRDoIwDADQE3XdaEHwAP754w26MibGymKXmHh63rP35ldEpyAm_-MjPw96GNrb63dfcTepxfF-e1yYFyKeCUUn3VIeQXNMwMoF8jBGmOYoyyppo0HDq5V6BgAA__8-jpg.webp)
$399,999
690 OSCEOLA AVE #209, Winter Park, FL 32789
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)
![334 SCOTTSDALE SQ #334, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRV4940331/fc4c290d/1736955074/w600_original_BMBRDsIgDADQE0GLLdR5AP_88QZFCM5Yt1gSE0-_95xz9wuAU1TT__bRn8fHZmBvH9-1wWo6usPtehfOCZkyA56WkhK3QLJIYCYJmmsNdMZWupBWLPG193EEAAD__w-jpg.webp)
$140,000
334 SCOTTSDALE SQ #334, Winter Park, FL 32792
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)
![1871 LINDEN RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6271036/229c1af7/1736866872/w600_original_BMBRDoIwDAbgE3Ud3T8ZHsA3X7xBQZgYK4tdYuLp_R69Nz8zewpq-jve-vWwHMb28vrZ77yb1tX5ermNwBSBdOIomDEPGyWRjQAMVCZZKCJLGZGhuYRnW-s_AAD__w-jpg.webp)
$500,000
1871 LINDEN RD, Winter Park, FL 32792
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1055 S KENTUCKY AVE #3, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRR4908718/5aa217fd/1737658875/w600_original_BMBRDoIwDAbgE20d2KU_HsA3X7xBQ8fEWCGWxMTT8z2PY48rUVyyuv63j_4iz5uTv6N_V6PVtbeg--0hzBMYZSCxotMoNTEEiRezhDogYYYp1zaiLPm1t34GAAD__w-jpg.webp)
$2,600
1055 S KENTUCKY AVE #3, Winter Park, FL 32789
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1055 S KENTUCKY AVE #4, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRR4908720/043ece51/1737648975/w600_original_BMDLDcIwDADQiRI3JV8G4MaFDYzthCJMKxwJiel5jzkPOwPYyaPib3_j1zztCvqy8dkYNsUhBtfLrcTYWs1rhdBlpSzBycLJxV7Z3RsFxzmFnkqkpZB_HjL-AQAA__8-jpg.webp)
$2,400
1055 S KENTUCKY AVE #4, Winter Park, FL 32789
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1116 FAIRWAY DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6265989/a56601d3/1737662480/w600_original_BMBRDsIwCADQE7VkQqXzAP754w2AtXVG3CJLTDy973Ece1wAArO4_La3fCPb5uCvGJ91gdVltIDb9c6ENOHMDKUv51J6TY3EElXUJMSYVNRoqnqau-Xn3sY_AAD__w-jpg.webp)
$599,900
1116 FAIRWAY DR, Winter Park, FL 32792
Listed by INNOVATIVE REALTY, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1354 TIERRA CIR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6271121/a4e6294c/1736795773/w600_original_BMBRDsIgDADQE0GFtZR6AP_88QadYzhj3WJJTDy97zHG4WcAn6Ka_va3fj3edwN7ef9sC2ymvTlcLzdGlDzlVADTWitTC1h4DpjkFIR0DstaubBkEqT4PFr_BwAA__8-jpg.webp)
$475,000
1354 TIERRA CIR, Winter Park, FL 32792
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)
![2667 FITZHUGH RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6270871/6626b96d/1736834477/w600_original_BMBRDsIgDADQE0Hb2Q7mAfzzxxsUBJyxbrFLTDy973Ecu58B_BTV9Le99euxbgb28vFZ77CajuZwvdwSc56JUGDpXapkDjItJfDUKCgShoLcc0pc6izxubfxDwAA__8-jpg.webp)
$100,000
2667 FITZHUGH RD, Winter Park, FL 32792
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)
![273 SCOTTSDALE SQ #273, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6269958/f75d9dc5/1736810169/w600_original_BMBRDsIgDADQE0EZLdvwAP754w2aduCMdYslMfH0vscYp18AHCMb_443fz3KYWAv759dYTfum8Ptel-ISp1KzqCprVW1hJRlDrSgBp4RQ20NJ6GU1izxeW79HwAA__8-jpg.webp)
$94,900
273 SCOTTSDALE SQ #273, Winter Park, FL 32792
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)
![2504 TUSCALOOSA TRL, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271070/006309dd/1736789475/w600_original_BMBRDoIwDADQE21doabgAfzzxxt0o50YK8SSmHh63vM49rgCxJjF5b995Be5bQ7-jv5dF1hdugbcbw8mmhELT2CMUmwY04SDJmKpSbhYatSWOle7KFl-7drPAAAA__8-jpg.webp)
$4,530
2504 TUSCALOOSA TRL, Winter Park, FL 32789
Listed by LIPPI REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1055 S KENTUCKY AVE #1, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRR4908696/112a8ac6/1736806572/w600_original_BMDLDcIwDAbgiRILOeTBANy4sMEfOw1FmFa4EhLT8z2OY_cLkXOE4be98fUom5G9fH5WpdUwh9Ptei8plVT4XElLl4zGoS1DQ8paQ1vQQkfPEKnMpxqf-5j_AAAA__8-jpg.webp)
$2,600
1055 S KENTUCKY AVE #1, Winter Park, FL 32789
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1055 S KENTUCKY AVE #2, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRR4908714/559b6c69/1736835374/w600_original_BMBRDsIgDADQE0GZ0JZ5AP_88QYdRZyxbrFLTDy973Ecu58BPEcx-W1v-Xpsm4G9fHxWhdVkdIfr5calzIjTzECUU-p3CnVpGkqSJVRUCtoyniozTpjic-_jHwAA__8-jpg.webp)
$2,400
1055 S KENTUCKY AVE #2, Winter Park, FL 32789
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)