- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
213 Properties Available In 32789
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![740 #3 KILLARNEY BAY CT #7-3, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6249823/4c8b4a31/1736214121/w600_original_BMBRDsIwCADQE1Eaawb1AP754w2AkjojbpElJp7e9ziOPS-I2YqE_La3fLPYFhivnJ914BoyPfF2vVNj4kqVkEzFWRlOunQ4C1fobAsMVe7WhqtRee4-_wEAAP__-jpg.webp)
$384,400
740 #3 KILLARNEY BAY CT #7-3, Winter Park, FL 32789
Condo
Listed by MICHAEL O'SHAUGHNESSY, INC.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![648 CALLAHAN ST, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6250649/2aad10e3/1736214212/w600_original_BMBRDoIwDADQE3Vl4ErnAfzzxxsUaCfGCrEkJp6e9zyOPa6IMSRx-W8f-UWaN0d_R_uuC64uTQPvt8c41K7PPTHqMlWtnYGJMVwoE0yjGWTmUpS4KM3ptWs7AwAA__8-jpg.webp)
$899,000
648 CALLAHAN ST, Winter Park, FL 32789
Single Family Home
Listed by MILLENIUM REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2821 CHANTILLY AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6249965/079ea77e/1736019972/w600_original_BMBRDsIgDADQE0E3ugD1AP754w3aynDGusWSmHj6vecYh18AHCMb__cP_zzqbmBv79_tAZtxbw63671grXPCZQJV1lxKDrklCssqHIhIwlqTsEyzoFJ8Ha2fAQAA__8-jpg.webp)
$525,000
2821 CHANTILLY AVE, Winter Park, FL 32789
Single Family Home
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)
![2228 AZALEA PL, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6250411/ac2cd0a0/1736213993/w600_original_BMBRDsIgDADQE0FtChM8gH_-eINCK85Yt1gSE0-_95xz9wuAU2Tj__bhn8e-Gdjbx3cVWI2HOtyu9zOVmkrNBI-lC1I7BeXeQ8oooZUFQ8ZGpMhSk8bXruMIAAD__w-jpg.webp)
$5,400,000
2228 AZALEA PL, 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)
![1818 MONDRIAN CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6248828/7059ea2c/1728907269/w600_original_BMBRDoIwDADQE22lUkbnAfzzxxu0rkyMFWJJTDy973Ece5wBYszi8tve8o183xz8Ff2zNlhdugVcL7d55KlUJAKdaTA0S9wKJ9JlSFVPSxIsaqwTVmv5uVv_BwAA__8-jpg.webp)
$775,000
1818 MONDRIAN CIR, 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)
![920 GLORIOSA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRG5088048/0e9629e2/1736213561/w600_original_BMBRDsIgDADQE0HNgEI9gH_-eINSC85Yt9glJp7e9ziO3c8AniIb_7Y3fz3KZmAvn5_1DqvxVIfr5VZTy3lBWgCFdAj2IBUl5KQ9tEEltIFUqWtJ5RSfu85_AAAA__8-jpg.webp)
$435,000
920 GLORIOSA AVE, Winter Park, FL 32789
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)
![1391 RICHMOND RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6246352/339d1f79/1728328594/w600_original_BMDRDYJADAbgiXpVii1xAN98cYMfrp4YK8ReYuL0fo_e9zwzpxQEftsb3yzLFhyvbJ-18hponny93ExsUh0Oxj7D1Qw0Y5xoVAdBIFRd79WH5agnKc_d2z8AAP__-jpg.webp)
$3,892,000
1391 RICHMOND RD, Winter Park, FL 32789
Single Family Home
Listed by STOCKWORTH REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![210 CHELTON CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6239351/62a3dcf1/1737136875/w600_original_BMBRDoIwDADQE20trJThAfzzxxt0sE6MFWKXmHh636P30y8AnqKY_I63fD2uh4G9vH32DXaTVh1u1_ucGEdMywQknHMmCsiDBlprCcuEEmYdlDcthXSMz7O2fwAAAP__-jpg.webp)
$5,695,000
210 CHELTON 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)
![1001 TUSCANY PL, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6245474/88324c50/1727904686/w600_original_BMBdDoIwDADgE2212U87D-CbL96gMDoxVoglMfH0fM_j2P0K4CmKyX_7yM_jvBnY28d37bCajMXhfntQoporlQtow4aa5pAK9ZAn5cCIJUyYWZlrkdbja1_GGQAA__8-jpg.webp)
$1,069,000
1001 TUSCANY PL, Winter Park, FL 32789
Single Family Home
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)
![140 E MORSE BLVD #J, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6245393/9952fd9c/1727455572/w600_original_FMTBDUIhDADQiaCGNlQcwJsXN2g-_YixQiyJidObf3mPtaZfAByjmPzGW74et2FgL2-fXqGbNHW4Xe-MnBOVwnBOVU-MGIiUDvZQdqGApCI50VYxx-fU9g8AAP__-jpg.webp)
$2,890,000
140 E MORSE BLVD #J, Winter Park, FL 32789
Condo
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)
![1371 LYNDALE BLVD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6245047/2b765891/1736213400/w600_original_BMBRDsIwCADQE7XooNR6AP_88QYotM6IW2SJiaffe27bGmeAwCwu_-Ujv8iPxcHfMb6zwuwyLOB6uVWsBfkwMfTK5a5HTYYnSaSlp0atJcIJGTsZk-bXamMPAAD__w-jpg.webp)
$1,495,000
1371 LYNDALE BLVD, 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)
![654 W MORSE BLVD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6240628/ca1315e9/1736214083/w600_original_BMBRDsIwCADQE7VEWAvzAP754w0IsjojbpElJp7e9ziOPc8ASVVDf9tbv1ltC4hXjs96hzV0eML1cmPqRI0mhJlP1nDBwm5Sptm1iDUuXbqxC6otUp-7j38AAAD__w-jpg.webp)
$6,975,000
654 W MORSE BLVD, Winter Park, FL 32789
Single Family Home
Listed by KELLY PRICE & COMPANY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1008 DUPONT AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6241497/209bdb23/1726260423/w600_original_BMBRDsIgDADQE0Gz0gH1AP754w26FXHGusWSmHj6vecYh18APEUx-e8f-XlcdwN7e_9uCptJbw63672kPFfMSKCpkD4YA_G8BGLEsBSuIU9CjVedqJb4Olo_AwAA__8-jpg.webp)
$499,000
1008 DUPONT AVE, Winter Park, FL 32789
Single Family Home
Listed by ANDREWS REAL ESTATE & INVESTMENT SERVICES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![660 ARJAY WAY, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6237059/a8a87220/1734473771/w600_original_BMBRDsIgDADQE0Fh7WrnAfzzxxsUBzhj3WJJTDy97zHG4WcAx6imv_2tX4_33cBe3j_bCptprw7Xy-2EM6LwwpBz4ZQmCrrMLRBlCkJJwiS5CVcpa2nxedT-DwAA__8-jpg.webp)
$1,549,000
660 ARJAY WAY, Winter Park, FL 32789
Single Family Home
Listed by STOCKWORTH REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![840 W COMSTOCK AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6238899/eeda7419/1725656478/w600_original_BMBRDsIwCADQE7V0sg7iAfzzxxtQhnVG3CJNTDy97zHGEWeAwCwuv_0t38i6O_gr-mdbYXPpFnC93Agr02kuBNzuOq04JcFiaa5KqYnVZIs2US2FecnPw_o_AAD__w-jpg.webp)
$1,470,000
840 W COMSTOCK 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)
![700 MELROSE AVE J 1 AVE #J1, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6238852/9123a3c3/1736185572/w600_original_BMBRDoIwDAbgE22djHbDA_jmizf4sWNirBBLYuLp_R7HsfuZyHOE4be98fV434zs5f2zKq2G3pyul1vJXLkmnkjkNGlWBIWUMErigGWZQy1cxiENgrnF5976PwAA__8-jpg.webp)
$390,000
700 MELROSE AVE J 1 AVE #J1, 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)
![1451 LYNDALE BLVD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6237975/7e43fdae/1736214378/w600_original_BMBRDoIwDADQE21ljLWrB_DPH2_QYZkYK8SSmHh63vM4dr8AeI5i8t8-8vM4bwb29v5dH7CadHW4Xe-UC44jTQWS5qqYMVQmCdNCHNoyYGht5lSVhsIpvnbtZwAAAP__-jpg.webp)
$1,999,993
1451 LYNDALE BLVD, Winter Park, FL 32789
Single Family Home
Listed by REALTY ONE GROUP MVP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![850 GEORGIA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6236795/aa422cc9/1731175271/w600_original_BMBRDoIwDADQE221awfMA_jnjzeoLUyMFWJJTDy973Ece5wBgrK4_La3fCPr5uCv6J_VYHXpc8D1chuplkptqkDMiGZDQlwkMVNL90U5lXaaTEl0GEt-7nP_BwAA__8-jpg.webp)
$3,950,000
850 GEORGIA AVE, 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)
![1730 WINCHESTER DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6235073/dd9e2e5a/1724454070/w600_original_BMBRDsIgDADQE0EhHWvnAfzzxxt0UHDGusUuMfH0vsd5Hn4BcIxi8tvf8vVYdwN7-fhsDTaToQ63651wIs6UEKourc8lhTX3FibiElhLD7Ssc5aaiDHH56HjHwAA__8-jpg.webp)
$3,295,000
1730 WINCHESTER DR, Winter Park, FL 32789
Single Family Home
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)
![1764 ELIZABETHS WALK, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6234031/2e0e93bd/1724799769/w600_original_BMDLDcIwDAbgiRJDkzQxA3DjwgY_zoMiTCtcCYnp-z33fbMLkQUPxX_94GdeViV92_gulRbFaEa36z2HmKaSTmeSwvJAK66jJxdzjo5zFYeJYwoz-lzZv7Y2jgAAAP__-jpg.webp)
$1,899,900
1764 ELIZABETHS WALK, 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)
![1640 ORANGE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6233881/699782ca/1725734774/w600_original_BMBdDsIwCADgE7WElv7MA_jmizcAi3VG3CJLTDy93-M4dj8BeI5s_Nve_PV42wzs5fOzDliNpzpczteWiZZW6wJYEiLSPXSUHqiJhs5JQtaqQ1jSKCU-d53_AAAA__8-jpg.webp)
$2,100
1640 ORANGE AVE, Winter Park, FL 32789
Single Family Home
Listed by INT'L PROFESSIONAL REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![731 MIDGET DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6232383/18054062/1736213336/w600_original_BMBRDsIwCADQE7XQlELqAfzzxxsg1jojbpElJp5-77nvW5wAomZ1_a8f_UW21cHfMb_LHRbXOQIu56tUQmZqBbpVlEeXxFwskTRLXRolxNuwhmSlcH5tYx4BAAD__w-jpg.webp)
$850,000
731 MIDGET DR, 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)
![279 RIPPLING LN, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6230955/c00625c4/1734457571/w600_original_BMBRDoIwDADQE20tFtfNA_jnjzcotE6MFWJJTDw977nvW1wAgrK4_NeP_CLPq4O_o38XhcWlW8DtemeiwoVOCKaVWEdNszRK49QeqSKWxITWhkkHq-f82qwfAQAA__8-jpg.webp)
$1,795,000
279 RIPPLING LN, Winter Park, FL 32789
Single Family Home
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)
![821 CARVER ST, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6230165/9eed3d1e/1736214725/w600_original_BMBRDsIgDADQE0HHwHZ4AP_88Qaldjhj3WJJTDy97zHG4WcAz5GNf_ubvx5lN7CX9892h824q8P1cqOcC2GaJkBctJZVwmnNJRRsS2hMHOa5pqaVSJLE56H9HwAA__8-jpg.webp)
$340,000
821 CARVER ST, Winter Park, FL 32789
Single Family Home
Listed by INNOVATIVE REALTY, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)