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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)
![3084 HEARTLEAF PL, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRNS1083572/133fd6a4/1737150370/w600_original_BMDdDQIxCADgiVq0f4AD-OaLG2A56xnxLtLExOn9HnPufgLwHMXkt73l67FvBvby8VkVVpOxOFzOVyw1t9aIoSbsSAcNysceCt053ArnkBQVk0hVofjcl_EPAAD__w-jpg.webp)
$559,900
Single Family Home
3084 HEARTLEAF PL, Winter Park, FL 32792
Under contract-accepting backup offers. This Winter Park, Tuskawilla area residence is located in the highly desirable "...
Listed by RE/MAX SIGNATURE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5134 LAKE HOWELL RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6266476/f17097f0/1737132372/w600_original_BMBRCsIwDAbgE7WRpUmoB_DNF2_wr4Y6sW6YguDp_R5zHnEmCs4Y-O1vfCO3fdB4Rf9sd9oGugddLzcrLMblpCTCBi-auC0tFVhNa0VNpoKVVRZXz8_D-z8AAP__-jpg.webp)
$340,000
Single Family Home
5134 LAKE HOWELL RD, Winter Park, FL 32792
Welcome to this lovingly maintained, one-owner home in the heart of Winter Park! This 3-bedroom, 2-bathroom gem offers a...
Listed by KELLER WILLIAMS WINTER PARK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2498 TIMBERLINE DR #2498, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272342/7851988c/1737227780/w600_original_BMBRDsIgDADQE0FpLRY8gH_-eIMGGM5Yt9glJp7e9ziO3S8Afopq-tve-vXYNgN7-fysHVbTORxu17twJqmIDJ3Tcl5QQhamwJRq0FJywIKVpFEfLcXnPuY_AAD__w-jpg.webp)
$239,900
Condo
2498 TIMBERLINE DR #2498, Winter Park, FL 32792
Cedarwood Village-Affordable living in a great location in Winter Park. This 2 bedroom, 2 bath, 1295 SF condominium offe...
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4944 TANGERINE AVE #4944, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6271089/ed826d01/1737124272/w600_original_BMBRDoIwDAbgE23t5J86D-CbL96g1DIxVoglMfH0fM9tW-NCFEMWl__ykV9kXZz8Hf07P2h26RZ0u95PQCtoqGQ8yFjVknI7J0zFkuCAVI4TowqPrJpfq_U9AAD__w-jpg.webp)
$225,000
Condo
4944 TANGERINE AVE #4944, Winter Park, FL 32792
Welcome to this delightful 2-bedroom, 2-bath end-unit condominium, offering the perfect blend of comfort and style! As y...
Listed by WATSON REALTY CORP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![257 SCOTTSDALE SQ #257, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272625/811dd2ae/1737144978/w600_original_BMBdDoIwDADgE20N3U-HB_DNF2_QsjoxVoglMfH0fM_j2P0C4Cmy8X_78M_jshnY28d37bAaD3W4Xe-US6oTUgMpjNrzI2CbMeTaKchcakiVeEJRWVqKr13HGQAA__8-jpg.webp)
$124,500
Condo
257 SCOTTSDALE SQ #257, Winter Park, FL 32792
Great Winter Park location SINGLE UNIT, 1st floor, 2 bedroom, 2 bath well mantain condo with tile flooring. Close to Ful...
Listed by RC REALTY GROUP INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![344 STARLING RD, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6272852/a3bb3776/1737162071/w600_original_BMDLDcIwDADQiRLnSygDcOPCBo6xQxGmFY6ExPR9zzl3uwBY9qj43z74M0-bgr5tfNcHrIqDDW7Xeyu15NxKhBOxSI3JCVVypcnizj2hi51D6CEtHJp_7TyOAAAA__8-jpg.webp)
$4,500
Single Family Home
344 STARLING RD, Winter Park, FL 32789
Welcome your new Home in the heart of beautiful Winter Park, Florida! This move-in ready, modern residence boasts three ...
Listed by HANCOCK REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1864 MAYWOOD RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272735/99d5856e/1737145878/w600_original_BMBRDsIgDADQE0FxFEs9gH_-eIOOTpyxbrEkJp5-7znG7hcAz1FM_ttHfh7bZmBv799VYTXpi8PteicsmakwgvI0aUkcKCUN-KAcqp4xaJtPc63SJFN87Us_AgAA__8-jpg.webp)
$2,345
Single Family Home
1864 MAYWOOD RD, Winter Park, FL 32792
This 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, Par...
Listed by REAL PROPERTY MANAGEMENT AND REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![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
Condo
186 SCOTTSDALE SQ #186, Winter Park, FL 32792
This updated 2/2 condo is move-in ready. Enjoy stainless appliances, luxury vinyl flooring, spacious kitchen, living are...
Listed by CAMERON REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Townhouse
3271 FOREST OAKS CT #110, Winter Park, FL 32792
Welcome to this beautifully updated townhouse, ideally located in the sought-after Winter Park community. Featuring 2 sp...
Listed by PMI PROPERTY ALLIANCE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Condo
3069 AARON BURR AVE #D, Winter Park, FL 32792
Enjoy this 1 bedroom 1 bathroom condo located at The Colonies in Winter Park. Close to UCF, Full Sail University and cen...
Listed by ACKLEY FLORIDA PROPERTY MANAGEMENT INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Single Family Home
1522 LAKE KNOWLES CIR, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to this charming one owner home nestled on the shores of Lake Knowles in...
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![370 E LAKE SUE AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271717/de223780/1737043272/w600_original_BMBRDsIgDADQE0HBMgoewD9_vEFdK85Yt9glJp5-77nvm58BHCMb_9cP_zzOq4G9fXwXgcV4qMP1cqMypV4rJhBCzhkfIVWRUJByaK2cQqIp99b1rnONr03HEQAA__8-jpg.webp)
$1,239,900
Single Family Home
370 E LAKE SUE AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to 370 E. Lake Sue Avenue, a beautifully renovated 3-bedroom, 3 full bat...
Listed by REALTY HUB
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Single Family Home
958 DUNRAVEN DR, Winter Park, FL 32792
*** WONDERFUL WINTER PARK ***LOCATION, LOCATION, LOCATION!!! This Fantastic 4 Bedroom 3 Bath Home is Welcoming for Every...
Listed by COLDWELL BANKER RESIDENTIAL RE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Single Family Home
8073 PLEASANT PINE CIR, Winter Park, FL 32792
Under contract-accepting backup offers. Discover your dream home at **8073 Pleasant Pine Cir, Winter Park, FL 32792**. T...
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Single Family Home
2127 LAKE DR, Winter Park, FL 32789
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled in a peaceful, lakefront...
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Townhouse
2229 SHADOWLAND LOOP, Winter Park, FL 32792
Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood! This spacious 3 bedroom, 2.5 bath...
Listed by KELLER WILLIAMS WINTER PARK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2007 NATALEN RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6269037/00903d08/1737027069/w600_original_BMBRDsIgDADQE0HL6ErwAP754w06LDhj3WKXmHj6vedx7H4B8BzF5L995OexbQb29vFdH7CaDHW4Xe-FKFPhGYGRMpc0B-0LB6pTC7WhhI6ohEtKU-3xtes4AwAA__8-jpg.webp)
$449,000
Single Family Home
2007 NATALEN RD, Winter Park, FL 32792
Under contract-accepting backup offers. Discover the perfect opportunity to live in the heart of Winter Park, Florida! T...
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2259 MINNESOTA AVE, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRTB8339609/e369feeb/1737074770/w600_original_BMBRDsIgDAbgE0EzGMI8gG--eIN_bcUZ6xZLYuLp_R5jHH4m8hxh-O1vfD3ybmQv759NaDN0dbpebnUuKbVTWUhQ86SKgCxLmO9rCZgaB1Xh2iqvmhCfh_Z_AAAA__8-jpg.webp)
$310,000
Single Family Home
2259 MINNESOTA AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Charming 3-Bedroom Home in the Heart of Winter Park! Welcome to 2259 Minnesota A...
Listed by LPT REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Condo
2924 ANTIQUE OAKS CIR #46, Winter Park, FL 32792
Welcome to Winter Park Living! This spacious 2nd-floor, 2-bedroom condo features soaring high ceilings, fresh paint, and...
Listed by FLORIDA REALTY INVESTMENTS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Condo
690 OSCEOLA AVE #209, Winter Park, FL 32789
Welcome to 690 Osceola Avenue, a lakefront complex in the heart of Winter Park. This sleek, modern residence offers the ...
Listed by PREMIER SOTHEBY'S INTL. REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Condo
334 SCOTTSDALE SQ #334, Winter Park, FL 32792
CASH ONLY. Desirable Winter Park Location with highly rated schools! Down the street Full Sail University, close to famo...
Listed by CHARLES RUTENBERG REALTY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1695 LEE RD #A208, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6270687/168d28d0/1736947871/w600_original_BMBRDsIwCADQE1HayqB6AP_88QZMS50Rt8gSE0_ve-z7FifEOCR1_a1v_Ua6rY7-ivFZ7ri4jh54OV-FSI7cSsUqTF3UYCqzAGViUJ4K8Gw1m3FujdJz6-MfAAD__w-jpg.webp)
$1,350
Condo
1695 LEE RD #A208, Winter Park, FL 32789
Charming 1-bedroom, 1-bathroom condo with an in-unit washer & dryer in the desirable Waterfall Cove community of Winter ...
Listed by MTRE GROUPE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Single Family Home
1871 LINDEN RD, Winter Park, FL 32792
Under contract-accepting backup offers. Experience the Charm of Brittany in Winter Park <br> <br>Welcome to this enchant...
Listed by FANNIE HILLMAN & ASSOCIATES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_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
Condo
1055 S KENTUCKY AVE #3, Winter Park, FL 32789
Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dini...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)