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- $ 100,000
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- Any
- $ 200,000
- $ 300,000
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485 Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Year Built (Newest)
- Square Feet (Biggest)
![3901 WOODGLADE CV, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRG5092637/52b37161/1738961177/w600_original_BMBdDsIwCADgE1GE1VI9gG--eAP6szojbpElJp5-33PfN78i-hTU9L9-9Oehrob29vFdGi6mozvebw-JwkkuxEh8zlwlw5Q0QixMkLkkIDnNpTZu1Ofw2vo4AgAA__8-jpg.webp)
$569,500
3901 WOODGLADE CV, Winter Park, FL 32792
Listed by OLYMPUS EXECUTIVE REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![311 SANDLEWOOD TRL #4, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6278389/c6ae451d/1738877472/w600_original_BMBRDsIgDAbgE0FTBsN4AN988QblX4cz1i2WxMTT73uOcfiVyKcoJv_9Iz-P2I3s7f27LbSZdHW63x41V86cUiKsSBdwCSujhFzmGlqb5qCQxlgkiyK-Du1nAAAA__8-jpg.webp)
$315,000
311 SANDLEWOOD TRL #4, Winter Park, FL 32789
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)
![7104 WRENWOOD WAY, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6277459/aa364b86/1738757769/w600_original_BMBRDoIwDADQE22VUrfiAfzzxxu0ZU6MFWJJTDw977nvW1wAYszi8l8_8otsq4O_o3-XGRaX3gJu13ulwoWnOsBZrSIKp0FpToRsiaeCCXXURnIik0d-ba0fAQAA__8-jpg.webp)
$485,000
7104 WRENWOOD WAY, Winter Park, FL 32792
Listed by KELLER WILLIAMS ADVANTAGE REAL
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![210 E LAKE SUE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6272327/56f951ca/1738596777/w600_original_BMBRDsIgDADQE0HnKLZ4AP_88QZ1FJyxbrEkJp5-7znG7hcAT1FM_ttHfh6XzcDe3r9rhdWkq8PteifMMyFmgqJyTm3isHCVgJSnUHJr4YQPLnUmVk7xtWs_AgAA__8-jpg.webp)
$3,130,000
210 E LAKE SUE AVE, Winter Park, FL 32789
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)
![817 ANTONETTE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6276468/58ff0698/1738589471/w600_original_BMBdDoIwDADgE23dT6HUA_jmizcoK06MFWJJTDw93_M4dr8AeI1i8t8-8vPYNgN7e_-uCqtJXxxu1zvhONTKhUGmxLkMKVBTDEgzBc44h5oUuYyaH1OLr33pZwAAAP__-jpg.webp)
$1,995,000
817 ANTONETTE AVE, 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)
![535 N INTERLACHEN AVE #203, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6276980/99259fec/1738631769/w600_original_BMBdDsIwCADgE7X0Zwp4AN988QZItzojbpEmJp5-33OM3S8AXqOY_LeP_DzqZmBv79-1wWrSZ4fb9Y7TGSulgpC4ZlLJoZFKmNJJAy_EobSFcyoPRsnxtc_9CAAA__8-jpg.webp)
$550,000
535 N INTERLACHEN AVE #203, Winter Park, FL 32789
Listed by PARK VIEW REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1470 PLACE PICARDY, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6275888/706d6693/1738376175/w600_original_BMBRDsIwCADQE7Wwwkr1AP754w2QNXVG3CJLTDy973Ece5wBgrK6_ra3fiPb5uCvGJ91gdV19IDr5SZcibAUAWKdCSdMUmdOTN1SM2kJT8tdayG0qeXn3sc_AAD__w-jpg.webp)
$1,950,000
1470 PLACE PICARDY, 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)
![2779 PRINCE JOHN RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6275001/a6bca10d/1738271778/w600_original_BMDBDcIwDAXQiRIHYmyVAbhxYYPfxoQiTCscCYnpeY8x9jgTRc1w_LY3vpGXzclf0T9ro9XRLeh6uSlLERUuhHvD0XBIqEUT6zynSVRSW6Z6UmNTID936_8AAAD__w-jpg.webp)
$575,000
2779 PRINCE JOHN RD, 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)
![2823 CADY WAY, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6274967/da5a0ae5/1738248372/w600_original_BMBRDsIwCADQE7VgKZv1AP754w1IwTojbpElJp5-77nvW1wAgrK4_NeP_CL31cHfMb6LwuIyLOB2vc91Qp4LVkAqJ1bWxBOWVLtQah1bUnsY6Zm4iebXZuMIAAD__w-jpg.webp)
$550,000
2823 CADY WAY, 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)
![3377 HAMLET LOOP, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6267093/ccd53e8a/1738957394/w600_original_BMBRDoIwDADQE21FulrwAP754w3q2k2MFWJJTDw977nvW1wAArO4_NeP_CLX1cHf0b-LwuLSLeB2vXNBxvFME-ikVawMaRibpdIekmaSknBu9cSEyqT5tVk_AgAA__8-jpg.webp)
$399,000
3377 HAMLET 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)
![2207 WINTER WOODS BLVD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6274389/22fce211/1738955775/w600_original_BMBdDsIgDADgE0FT_gYewDdfvEGlFGesW-wSE0-_73kcu10ALHpS-m8f-pnvm4K-bX5XhlVpDoPb9b6kXEuOIUBeujwYh2PE6pKU7ho2cSQJgzCVFqt_7WOeAQAA__8-jpg.webp)
$479,000
2207 WINTER WOODS BLVD, Winter Park, FL 32792
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)
![1937 ELAND AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6273477/161a7f6c/1738096273/w600_original_BMBRDsIwCADQE7WIoxQ8gH_-eAPmap0Rt0gTE0_ve4yxxwkgpmxuv-1t38i3zcFf0T_rAqtbbwGX87VSYSxyEKjCZoglmZAkYtGkOrekiMux0n3SmfNzb_0fAAD__w-jpg.webp)
$475,000
1937 ELAND AVE, Winter Park, FL 32789
Listed by MILLER GRANT AND COMPANY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![607 DUNBLANE DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6273641/042d4ee9/1738021569/w600_original_BMBRDsIgDADQE0Gz0bLhAfzzxxuUteCMdYslMfH0vscYp18APEU2_h1v_nrcDgN7ef_sArtxV4fb9b4gZUoTIug2i2RuodRKASdtoaSZg5a2SM3rypTi89T-DwAA__8-jpg.webp)
$795,000
607 DUNBLANE DR, Winter Park, FL 32792
Listed by NETWORTH REALTY OF ORLANDO, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![631 CALLAHAN ST, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6274344/b6fd2834/1737734472/w600_original_BMBRDsIgDADQE0EZrLZ6AP_88QYdFJyxbrFLTDy973Ecu18AvEQx-W1v-Xqsm4G9fHzWBqvJUIfb9U4zMqaSMnQlXVLq4US1hZm5hHPLGJi1Yyae6rTE567jHwAA__8-jpg.webp)
$630,000
631 CALLAHAN ST, Winter Park, FL 32789
Listed by CORCORAN PREMIER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1375 SUFFOLK RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6273083/8fb85934/1737471671/w600_original_BMBRDsIwCADQE7UotEg9gH_-eANmsc6IW2SJiaffe27bGmeAoKyu_-Wjv8j3xcHfMb5zh9l1WMD1cjuVWpERGQ5dem36SEeqmEqzKQmbJJpIqDTkIphfq409AAD__w-jpg.webp)
$799,000
1375 SUFFOLK RD, Winter Park, FL 32789
Listed by MAINFRAME REAL ESTATE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2855 CADY WAY, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272945/acb41876/1737757871/w600_original_BMBRDoIwDADQE3VtR1nBA_jnjzeoG06MFWJJTDy973Ece5wQY0jm9tve9o1UN0d_Rf-sDVe3vgRezleVUVTmiZAnm-9EA2gtCiKU4VaYoeWmlSlroTE996X_AwAA__8-jpg.webp)
$568,000
2855 CADY WAY, Winter Park, FL 32792
Listed by GLOBAL PROPERTIES SALES & MGMT
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![567 OSCEOLA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6270491/d745931a/1737744371/w600_original_BMBRDsIwCADQE7VMWlf0AP754w0YQp0Rt0gTE0_ve4yxxxkgSmbn3_bmb2TZHPwV_bPeYXXuGnC93FqtrdBUCAQn02ORVJmWVBFbWpQPaTYyMTvpjJifu_Z_AAAA__8-jpg.webp)
$1,250,000
567 OSCEOLA AVE, Winter Park, FL 32789
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)
![1611 WALNUT AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6270191/a7d1a46b/1738255572/w600_original_BMBRDoIwDADQE3Udo6zDA_jnjzcorEyMFWKXmHh636P30y-IPgYx-R1v-XpYD0N7efvsFXeTpo63652JMuWJI-aFZtnSAKlOCrQVgmUVglJ5jInjrEMJz1PbPwAA__8-jpg.webp)
$1,295,000
1611 WALNUT AVE, Winter Park, FL 32789
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)
![1433 INDIANA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6265592/872ae360/1736434873/w600_original_BMBRDoIwDAbgE2017fwBD-CbL97gz4YTY4VYEhNPz_fc9y0uImGZzv_64S9yXV38Hf27NFmcfQ65Xe9DMTspFNKaTXUckQZqS8WMaaKe04NWYEBVIL-2uR8BAAD__w-jpg.webp)
$2,000
1433 INDIANA AVE, Winter Park, FL 32789
Listed by SAND DOLLAR REALTY GROUP INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![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
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)
![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
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)