- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
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217 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![100 S INTERLACHEN AVE #111, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6279777/0835beff/1739463374/w600_original_BMBRDsIwCADQE7UUAdk8gH_-eANsmzojbpElJp5-77nvW1wAgrK5_deP_SLX1cHfMb5Lg8Vt9IDb9a6sIieUAqiEJBOl6cw18WOuyVhK0oaNrXOZC-XX1scRAAD__w-jpg.webp)
$725,000
100 S INTERLACHEN AVE #111, 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)
![2258 E HOWARD DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRS5118820/7dabeaba/1738179975/w600_original_BMBRDsIgDADQE0HRwqAewD9_vAG2Dc5Yt1gSE0-_95xz9wuAY-zW_9un_zzyZmBvH99VYLU-1OF2vddccClUEbidW8qNQhbikJNIeFRMASkx0akV1SW-dh1HAAAA__8-jpg.webp)
$1,299,990
2258 E HOWARD DR, Winter Park, FL 32789
Listed by NAIM REAL ESTATE LLC
![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)
![1690 ONECO AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6279805/62c74a7e/1739550672/w600_original_BMBRDsIgDAbgE0FVWigewDdfvMHvQJyxbrFLTDz9vue2rX4m8hRh-C8f_DxOi5G9fXznRrNhdKfr5Va4iFTWRA06VdZ7yCdOgfsxB-AhASU3UZZDRYmvtY89AAD__w-jpg.webp)
$1,195,000
1690 ONECO AVE, 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)
![328 LAKE FAIR LN, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6279048/c3377e4f/1739548880/w600_original_BMBRDsIgDADQE5U66Qb1AP754w3KVnDGOmJJTDy97zFG9wuixyAmv-MtXw_rYWgvb599w92kqePtek-U4syUJ6y5yFx4gXPVDERRgdeisFUmWTSRnKbw7Nr-AQAA__8-jpg.webp)
$425,000
328 LAKE FAIR LN, Winter Park, FL 32789
Listed by RE/MAX 200 REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1585 CHESTNUT AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6280166/2f209f0e/1739465177/w600_original_BMBRDsIwCADQE7VoyqB4AP_88QbIsM6IW2SJiaf3PfZ9yxNAtqqhv_Wt36y2BsQrx2eZYQkdnnA5XxmZkEgOQD5bJ9TSpU0FG_ZyU7bCal1IJvbjvT43H_8AAAD__w-jpg.webp)
$1,250,000
1585 CHESTNUT AVE, Winter Park, FL 32789
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)
![533 BALMORAL RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6280397/7ce3c242/1739477779/w600_original_BMBRDsIwCADQE7XQCNZ5AP_88QZ0sDojbpEmJp5-7znGHleAOGVx-W8f-UWeNwd_R_-uCqtLt4D77VGpVkTGM1ysIbaypImUE7VFk6DURHMhYy6TMuXXbv0IAAD__w-jpg.webp)
$949,900
533 BALMORAL RD, Winter Park, FL 32789
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)
![350 KILLARNEY BAY CT #5, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6279997/1d343941/1739485871/w600_original_BMBRDsIwCADQE7U021rAA_jnjzcgo9QZcYssMfH0vsd5HnEBiDmLy29_yzfyujv4K8ZnU9hcRg-4Xe-4YGXmRsBKJKQ1tTJpWriXRIZTsrbWIrOxKebn0cc_AAD__w-jpg.webp)
$399,900
350 KILLARNEY BAY CT #5, Winter Park, FL 32789
Listed by FOLIO REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2412 CHANTILLY AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6278049/7931437f/1739393179/w600_original_BMBdDoIwDADgE21dabMfD-CbL96gjDoxVoglMfH0fM_j2P0C4BTF5L995Oexbwb29vFdF1hNhjrcrvfCJRFmrpAbUU9tCjhXCVxbCtKFwlJwUn1k4hnja9dxBgAA__8-jpg.webp)
$2,395,000
2412 CHANTILLY 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)
![1777 INDIANA AVE #B, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6279381/5deba3ac/1739216771/w600_original_BMBRDsIgDADQE0EpMpp6AP_88QbNoDhj3WJJTDz93nPOw68Afoli8t8_8vO47gb29vHdGmwmozvcbw8qVJaMWCFVakSqQatiKIgl8LJqSJlZkLH1lOPr6OMMAAD__w-jpg.webp)
$2,650
1777 INDIANA AVE #B, Winter Park, FL 32789
Listed by THE REALTY MEDICS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1932 TEMPLE DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6278588/a086c9e1/1738938671/w600_original_BMBRDsIwCADQE7WUriviAfzzxxsQWOqMuEWWmHj6vedx7HEFiCmLy3_7yC-ybg7-jvFdDVaXsQTcbw9qhHwpFWGqczdVSt36nBqZJCaWxFwKt1qQFPNrX8YZAAD__w-jpg.webp)
$1,295,000
1932 TEMPLE DR, 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)
![1806 MONDRIAN CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6277810/36845c9b/1738845070/w600_original_BMBRDsIwCADQE7VQoWV6AP_88QbUkTojbpElJp5-77nvW1wAgrK6_teP_iI_Vgd_x_guMyyuwwJu17twO0tBqVC4GVfqqZ_mntgQkzLWhNREpkLGk-bXZuMIAAD__w-jpg.webp)
$699,900
1806 MONDRIAN CIR, 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)
![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)
![2500 LEE RD #202, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6277579/c99a57a4/1738956673/w600_original_BMDRDQIhDADQiaB4lFIcwD9_3KBixTPWu1gSE6f3Pebc_QjgOYrJb3vL12PfDOzl47PeYDUZ6nA-XSpSS8uBEpTMTaqWwKQ1IGIP115S4Ds11LJQyhyfu45_AAAA__8-jpg.webp)
$260,000
2500 LEE RD #202, Winter Park, FL 32789
Listed by THE ANDERSON GROUP & CO PL
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1500 GAY RD #10C, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6278065/8d5f5f50/1738801870/w600_original_BMDBDcIwDAXQiRLTxCbAANy4sMFvbIUiTCtcCYnpeY993-JCFDXD8Vvf-Ebuq5O_YnwWpcUxLOh2vTduh8p8FKooXdSQiigSnydLmFHSrFMv3OykYvm52fgHAAD__w-jpg.webp)
$247,500
1500 GAY RD #10C, Winter Park, FL 32789
Listed by REALCOM REAL ESTATE SERVICES INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1850 WHITEHALL DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6277639/7eb9d616/1738786579/w600_original_BMBdDsIgDADgE0HZ-Cl4AN988QaVNjhj3WJJTDz9vuech10ALHpS-u8f-pnvu4K-bXw3hk1piMHtesdU2oI5J6ihrpIxuYChuxRicbX15rhEoYKPlRf2r0PGGQAA__8-jpg.webp)
$3,400
1850 WHITEHALL 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)
![100 E ROCKWOOD WAY, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6276192/0be3a1ca/1738701082/w600_original_BMBRDsIgDAbgE0FFyCoewDdfvMFP6XDGusUuMfH0-577vvmVyHOE4b9-8PMoq5G9fXyXTothqNP99uAylVynxDRr1VTnFiQjh8KVA5pK4J4gOF_aqSO-Nh1HAAAA__8-jpg.webp)
$3,295,000
100 E ROCKWOOD WAY, 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)
![622 PENN PL, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRTB8346569/f77f86c8/1738701977/w600_original_BMBRDsIgDAbgE5UybZl4AN988Qb_kOGMdcSSmHh6v8cY3c_Mfgww_PY3vh7Kbmwvb5_tzpuhVefr5TZLyjHlNPE0L2vRqHSAgkQ1UhYFLSeUKrICivDstf0DAAD__w-jpg.webp)
$1,950,000
622 PENN PL, Winter Park, FL 32789
Listed by COMMUNITY REALTY ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1762 MONDRIAN CIR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6276921/38071fd1/1738670485/w600_original_BMBRDsIwCADQE7VUOql4AP_88QbAap0Rt8gSE0_ve-z7FmeAqFlcfutbvpFtdfBXjM8yw-IyesD1cmsTNcRyqFAF7-WoPZ2YOU2KLSkjJTJSYjOdC-Xn1sc_AAD__w-jpg.webp)
$925,000
1762 MONDRIAN CIR, 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)