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![1518 PINEWOOD DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271617/6627d214/1737495073/w600_original_BMBRDsIwCADQE7Vg17XBA_jnjzeAQeqMuEWWmHj6vedx7HEFiCmz83_78C_ysjn4O8Z3VVidhwXcb49eZ5yx9QJUtXS5UJLCS6piJQnJlFgJCVtTNMmv3cYZAAD__w-jpg.webp)
$1,750
1518 PINEWOOD DR, Winter Park, FL 32789
Single Family Home
Listed by SPECIALIZED PROPERTY MANAGEMENT
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
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)
![5405 JUSTINE WAY, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6273248/5a303c9e/1737398771/w600_original_BMBdDoIwDADgE20NrD_OA_jmizdoyjYxVoglMfH0fM_j2OMKECWr63_76C-ybQ7-jvFdF1hdRwu43x6CRDxPTKCsKoWmdGHDhL1KqjhTEisLGrbesebX3sYZAAD__w-jpg.webp)
$429,900
5405 JUSTINE WAY, Winter Park, FL 32792
Single Family Home
Listed by TBRO REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5102 LAKE HOWELL RD, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272918/0e17dc4c/1737572479/w600_original_BMBRDsIwCADQE7WMFnH1AP754w2IsDojbpEmJp5-7znGHheAqFlc_ttHfpEfm4O_o39XhdWlW8Dtej_TiRhbKcAqczPDRAtaIiyaROuUKhsurUw6M-fXbv0IAAD__w-jpg.webp)
$400,000
5102 LAKE HOWELL RD, Winter Park, FL 32792
Single Family Home
Listed by COLDWELL BANKER REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1695 LEE RD #A209, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6271289/03ea9fa3/1737382571/w600_original_BMBRDoIwDADQE22FrXTTA_jnjzcotEyMFWKXmHh63rP3w68AniMb__cP_zwuu4G9vX03gc24qcP99iiIF6JpJKgJxwFlCVolB2QuYV5lCFLTnGlaNXGJr0PbGQAA__8-jpg.webp)
$144,900
1695 LEE RD #A209, Winter Park, FL 32789
Condo
Listed by FUSILIER REALTY GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1975 BISCAYNE DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6273072/17d1dee3/1737338469/w600_original_BMDLDcIwDADQiRKT-pPCANy4sIExVijCtMKVkJie99j3LU8AiVVDf-tbv1ltDYhXjs9yhyV0eMLlfO3EPOHUCHoTNz5KOZh7oS5cZsVWxFypkQne5vrcfPwDAAD__w-jpg.webp)
$1,125,000
1975 BISCAYNE DR, Winter Park, FL 32789
Single Family Home
Listed by SOGO REAL ESTATE SERVICES LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1792 KILLARNEY DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6273004/c0055985/1737284468/w600_original_BMBRDsIwCADQE7WEwgLzAP754w1obeqMuEWamHj6veecR1wAgrK5_feP_SK33cHfMb7bAza30QNu17vwwuuyKoFhVeJWkyjWxKKajJhS4SKdpRkWzK-jjzMAAP__-jpg.webp)
$699,000
1792 KILLARNEY DR, Winter Park, FL 32789
Single Family Home
Listed by THE AGENCY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1904 HOUNDSLAKE DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6272912/8f9370aa/1737235873/w600_original_BMDRDQIhDADQiaAVClQH8M8fN6jYwzPWu1gSE6f3Pebc_QTgOYrJb3vL12PfDOzl47PeYTUZ6nA5XxsVqogtgRwxC1cOpS8tUE4aGAuHTFgxddXbYYnPXcc_AAD__w-jpg.webp)
$499,900
1904 HOUNDSLAKE DR, Winter Park, FL 32792
Single Family Home
Listed by URBANISTA BROKERS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1506 CHESTNUT AVE., Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6272231/1a8435fd/1737132373/w600_original_BMBRDsIgDADQE0FJW1b0AP754w06GDhj3WKXmHj6vedx7H4FcIpq-t8--vNYNwN7-_iuDVbTsTjcbw_hjFxIMmTUOaV0CSqEgStzmAtjoKl36bW0plN87cs4AwAA__8-jpg.webp)
$2,495,000
1506 CHESTNUT 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)
![1484 VIA SANGRO PL, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6268124/0312a544/1737129673/w600_original_BMBBDsIgEAXQE8GQdLB8D-DOjTf4MgRrxDYOiYmn9z3mPPws4kvk4G9_8-ux7kPGy_tnM9kGe3O5Xm6rasprKlnAZBm0oHY_BS2tBlCXABRQUa0B8Xm0_g8AAP__-jpg.webp)
$990,000
1484 VIA SANGRO PL, Winter Park, FL 32792
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)
![675 OVERSPIN DR, Winter Park, FL 32789](https://img.chime.me/imageemb/mls-listing/586/MFRO6272606/a8fcae9a/1737135075/w600_original_BMBRDoIwDAbgE22lLQX1AL754g1-BkyMFWKXmHh6v0drR1yIQjMcv_2Nb-SyO_kr6mebaXPUJeh2vY-9qQ3GAwFFyzoiTTwj9Wyazug0ma6TiAp3J8nPY6n_AAAA__8-jpg.webp)
$930,000
675 OVERSPIN 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)
![1037 FAIRWAY DR, Winter Park, FL 32792](https://img.chime.me/imageemb/mls-listing/586/MFRO6271235/2569c708/1737144977/w600_original_BMBRDoIwDAbgE22ldGDwAL754g3-uP0TY4VYEhNP7_c4jj3OImEZjt_2xjfyfXPxV_TPWmV19BZyvdxOpSzTqDoIyQlL0cRKS4VqCXPTZPNAVjSzEfm5t_4PAAD__w-jpg.webp)
$675,000
1037 FAIRWAY DR, Winter Park, FL 32792
Single Family Home
Listed by LEGACY REALTY & BROKERS LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![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
3084 HEARTLEAF PL, Winter Park, FL 32792
Single Family Home
Listed by RE/MAX SIGNATURE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
2498 TIMBERLINE DR #2498, Winter Park, FL 32792
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)
![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
4944 TANGERINE AVE #4944, Winter Park, FL 32792
Condo
Listed by WATSON REALTY CORP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
257 SCOTTSDALE SQ #257, Winter Park, FL 32792
Condo
Listed by RC REALTY GROUP INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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/1738954887/w600_original_BMBRDsIgDADQE0FxFEs9gH_-eIOOTpyxbrEkJp5-7znG7hcAz1FM_ttHfh7bZmBv799VYTXpi8PteicsmakwgvI0aUkcKCUN-KAcqp4xaJtPc63SJFN87Us_AgAA__8-jpg.webp)
$2,295
1864 MAYWOOD RD, Winter Park, FL 32792
Single Family Home
Listed by REAL PROPERTY MANAGEMENT AND REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
186 SCOTTSDALE SQ #186, Winter Park, FL 32792
Condo
Listed by CAMERON REALTY GROUP LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
Townhouse
Listed by PMI PROPERTY ALLIANCE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
Condo
Listed by ACKLEY FLORIDA PROPERTY MANAGEMENT INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
Single Family Home
Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
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)
![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
Single Family Home
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h40_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
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)