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- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
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1,156 Properties Available In Winter Haven
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![1576 LEAMINGTON LN, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRL4948740/660fb09a/1731186071/w600_original_BMDLDcIwDADQiRLnY5qYAbhxYQPn01CEaYUjITF933POQ68AGi0L__cP_9TWXUDeOr5bg014dIX77ZHQLR4v3kFpIRVMqwl-IYOxVEO1B4MtEuc1O8JsX0cfZwAAAP__-jpg.webp)
$331,955
1576 LEAMINGTON LN, Winter Haven, FL 33884
Listed by ADAMS HOMES REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1584 LEAMINGTON LN, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRL4948733/93816081/1731183385/w600_original_BMBRDsIwCADQE7W0g1rjAfzzxxswwDojbpElJp5-77nvW1wAAjM7_9cP_yLL6uDvGN9FYXEeFnC73juVU63UCsyGba6FkxbpiQQ1cTtbIuxTe5CiTZJfm40jAAD__w-jpg.webp)
$321,660
1584 LEAMINGTON LN, Winter Haven, FL 33884
Listed by ADAMS HOMES REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![708 REFLECTIONS DR, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6256448/5c2d98d0/1731197770/w600_original_BMBRDsIwCADQE7V0bQPWA_jnjzcgAnVG3CJLTDy973Ece5wBomV2_m1v_ka-bw7-ivlZBVbnqQHXy416wbosDQFllEGkifuJUhfqaVRpSashoplJ0fzcdf4DAAD__w-jpg.webp)
$254,900
708 REFLECTIONS DR, Winter Haven, FL 33884
Listed by OAK AVENUE REAL ESTATE LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![6762 BRENTWOOD DR NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4932683/c8107ede/1731180672/w600_original_BMDRDcJACADQiTiwRy04gH_-uAFX8awR20gTE6f3PfZ9yxNi1mJhv_Vt3yzzGhiv7J_lhktY98TL-ToxjYeBhVBaVT3ODET3AZhcQUwUqmvjRuI8jeW5ef8HAAD__w-jpg.webp)
$160,000
6762 BRENTWOOD DR NE, Winter Haven, FL 33881
Listed by RE/MAX HERITAGE PROFESSIONALS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1935 AUSTIN TER, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRL4948611/14825e61/1731123975/w600_original_BMDBDcIwDAXQiRIT5ytOGYAbFzYw1IQiTCtcCYnpeY993-JIFDWr62996zfybXXyV4zPMtPiOizofLoIDly4yEQ8AXZHTeitJZTe0rUyEs9aYF2sVcnPzcY_AAD__w-jpg.webp)
$650,000
1935 AUSTIN TER, Winter Haven, FL 33884
Listed by LA ROSA REALTY PRESTIGE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2827 SUNSET DR NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFROM686822/a47226a7/1731102372/w600_original_BMBRDsIwCADQE1Go0OI8gH_-eAOykTojbpElJp7e9ziOPS-IycXCftvbvlnmLTBeOT7rgmvY8MTb9a6sKswi6NZFtTcg7wxCk8P5ZBNobUurRpVmKs_dxz8AAP__-jpg.webp)
$649,900
2827 SUNSET DR NW, Winter Haven, FL 33881
Listed by RE/MAX PREMIER REALTY LADY LK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1865 WOODPOINTE DR, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRP4932664/15a3fb5f/1731099675/w600_original_BMBRDsIgDADQE0HLQBo8gH_-eIOGFpyxbrFLTDz93vM4dr8CeI5s_N8-_PPYNwN7-_yuAqvxVIf77UEFc0bMC1AdpdWyBOHRQxGpofWkAYUS6cBElxZfu84zAAD__w-jpg.webp)
$499,900
1865 WOODPOINTE DR, Winter Haven, FL 33884
Listed by RE/MAX HERITAGE PROFESSIONALS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![108 LAKE REGION BLVD N, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4948706/0622532e/1731179779/w600_original_BMBRDsIgDADQE0ERJi0ewD9_vEHXTpyxbrEkJp5-7znG7hcAL5GN_9uHfx5lM7C39--qsBr3xeF2veOUzoVSJUgzZqp5DkhVwyRSQmtYAueHNhLWU5X42pd-BAAA__8-jpg.webp)
$469,900
108 LAKE REGION BLVD N, Winter Haven, FL 33881
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1800 4TH ST NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4932685/ce03b196/1731113169/w600_original_BMBRDsIgDAbgE0HBIV08gG--eIN_XcEZ6xZLYuLp_R5jHH4h8inC8Nvf-HqU3che3j_bSpuhq9PteueSzqeZU6amlSFZQ6myhoIFYVZGaDLlpebGSCk-D-3_AAAA__8-jpg.webp)
$299,999
1800 4TH ST NW, Winter Haven, FL 33881
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1446 DOUGLAS CT, Winter Haven, FL 33880](https://img.chime.me/imageemb/mls-listing/586/MFRP4932677/caaeea23/1731084374/w600_original_BMBRDoIwDAbgE22drqPgAXzzxRu08GdirBBLYuLp_R7HsceFKGpW19_21m_keXPyV_TPutDq2hF0u96FC7dxLExVMEkrLU2ClvgsNRnD0jzgZIDpIEt-7uj_AAAA__8-jpg.webp)
$1,900
1446 DOUGLAS CT, Winter Haven, FL 33880
Listed by PROPERTY MANAGEMENT OF POLK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3003 BRENTON MANOR LOOP, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6256239/23de44e6/1733239871/w600_original_BMBRDsIgDADQE0FLVmjwAP754w3qoDhj3WJJTDz93nPOwy8AvkQx-e8f-XlcdwN7-_huDTaT0R1u1zsTZipUK3TWwrmlgPxogSphqEtOgRsmxVW0iMbX0ccZAAD__w-jpg.webp)
$1,900
3003 BRENTON MANOR LOOP, Winter Haven, FL 33881
Listed by FOURSQUARE REAL ESTATE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3002 PLANTATION RD, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRP4932668/926bea7e/1730957469/w600_original_BMBRDsIwCADQE1FGQAkewD9_vAG2XZ0Rt8gSE0-_99z3LS-IycXD_-vHf1nqGhjvHN-l4RI-euLteleZWIyM0ZqouD1AaTYQUwVTImjTuWvl2f1Uy2vr4wgAAP__-jpg.webp)
$479,900
3002 PLANTATION RD, Winter Haven, FL 33884
Listed by JOHN WOOD REALTY, INC.
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3659 PLYMOUTH DR, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRP4932623/3379e255/1730997072/w600_original_BMBRDsIwCADQE7XQja3WA_jnjzcAJHVG3CJNTDy97zHGEWeAmDM7__Y3fyPr7uCv6J_tDptzt4Dr5VYJy9IKImBbTpXrmsxQE7VJkohakkmpNJKZeM3Pw_o_AAD__w-jpg.webp)
$399,900
3659 PLYMOUTH DR, Winter Haven, FL 33884
Listed by CENTURY 21 AT YOUR SERVICE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3180 LAKE DR NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4932656/309c3adf/1730992575/w600_original_BMBRDsIwCADQE7XUQuzwAP754w1wgzojbpEmJp5-7znGHheAwCwu_-0jv8jz5uDv6N91gdWla8Dtem9U6sQ4ITApNqycVFtNVEpNfDZLRm0pJ6X5QZZfu_YjAAD__w-jpg.webp)
$399,000
3180 LAKE DR NW, Winter Haven, FL 33881
Listed by KELLER WILLIAMS SUBURBAN TAMPA
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3027 BUCKEYE POINTE DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5114569/645f3b1d/1732213878/w600_original_BMBRDsIwCADQE7XQtah4AP_88QaskDojbpElJp5-77nvW1wBomZx-a8f-UXuq4O_Y3wXhcVlWMD99jhXJqqFL0Da56IFE83MqZ2UkrBRMsWpN5uwoebXZuMIAAD__w-jpg.webp)
$368,000
3027 BUCKEYE POINTE DR, Winter Haven, FL 33881
Listed by G FIRST REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3537 RALEIGH DR, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255179/322f4183/1731177971/w600_original_BMDLDcIwDADQiRLnY5fPANy4sIFrJ6EI0wpXQmL6vue-b34F8BrZ-L9--OdRVgN7-_guCovxaA732-OEqeBEpUCvF1LJEnpWDchCYa55CiXhuUurpGmOr62NIwAA__8-jpg.webp)
$350,000
3537 RALEIGH DR, Winter Haven, FL 33884
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)
![4668 OSTERO ST, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255887/78bf6cf3/1731008774/w600_original_BMBRCsIwDAbgE7VZbEaZB_DNF2_wJ3Z1YtwwBcHT-z3GOOJMFCXD8dvf-Ea23clf0T_bnTZHb0HXy63KJMInWaiYsmq1NNtUkghrAlckLLC1zkXWxvl5tP4PAAD__w-jpg.webp)
$332,990
4668 OSTERO ST, Winter Haven, FL 33884
Listed by DR HORTON REALTY OF CENTRAL FLORIDA LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4672 OSTERO ST, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255949/3d0c7ca4/1731015072/w600_original_BMBRDsIgDADQE0GBIV09gH_-eIPaFZyxbrFLTDy973Ecu58BfIps_Nve_PUom4G9fHzWBVbjoQ7Xyw1rqqeW8gT3uRAtmEPX1kOlMgcqlIJizygiCVuLz13HPwAA__8-jpg.webp)
$330,990
4672 OSTERO ST, Winter Haven, FL 33884
Listed by DR HORTON REALTY OF CENTRAL FLORIDA LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4664 OSTERO ST, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255832/adf0f5c5/1731003373/w600_original_BMBRDsIwCADQE7XUltDhAfzzxxuAsjojbpElJp5-77nvW5wBomVx-a8f-UW-rw7-jvFdHrC4DAu4Xm4dC1YimoCUW9eCqZ5MEqppYprnJE07K09NS82vzcYRAAD__w-jpg.webp)
$294,990
4664 OSTERO ST, Winter Haven, FL 33884
Listed by DR HORTON REALTY OF CENTRAL FLORIDA LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4660 OSTERO ST, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255759/9b510c6d/1730996172/w600_original_BMBRDsIgDADQE0EJZWvxAP754w3KqDhj3WKXmHj6vedx7H4BcIxi8t8-8vO4bAb29vFdO6wmQx1u1zuVVBJlnmDqLS8kc2ASDEVqDlWxhT6j1saY-FHia9dxBgAA__8-jpg.webp)
$292,990
4660 OSTERO ST, Winter Haven, FL 33884
Listed by DR HORTON REALTY OF CENTRAL FLORIDA LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![316 MONTEGO CT SE, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRP4932678/e48e1d7b/1731037569/w600_original_BMBRDsIgDADQE0FBKhQP4J8_3qBbO5yxbrFLTDy973Ecu18AvEQ2_m1v_nqcNwN7-fisAqvxUIfb9d4wIeVzaUBLLW3WU0i5SsCFOHSZOPQsqSPqRLXF567jHwAA__8-jpg.webp)
$249,900
316 MONTEGO CT SE, Winter Haven, FL 33884
Listed by ALLSTATE REALTY SERVICES
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![384 WINTER RIDGE BLVD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4948694/c5921e1f/1731031269/w600_original_BMBRDoIwDAbgE23F9WcDD-CbL96gwzIxVohdYuLp_R69H34mco5i8tvf8vW47Eb28vbZ7rSZNHW6Xm4FA0piZMoZqw56CpApBZSZw8RYA3isdUx1mbXG56HtHwAA__8-jpg.webp)
$169,000
384 WINTER RIDGE BLVD, Winter Haven, FL 33881
Listed by XCELLENCE REALTY, INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![7094 FAIRVIEW VILLAGE CIR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4948675/9cf1d178/1731011472/w600_original_BMBRDsIgDADQE0GLZR3zAP754w1qBZyxbrEkJp5-7znG7mcApygm_-0jP4-6Gdjb-3d9wGrSq8P1cpsz5nQiROAZFZE48KQUMlMJd60lpKWkTFNbWmrxtdd-BAAA__8-jpg.webp)
$119,900
7094 FAIRVIEW VILLAGE CIR, Winter Haven, FL 33881
Listed by KELLER WILLIAMS REALTY SMART
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![312 KAYDEN CV, Winter Haven, FL 33884](https://img.chime.me/imageemb/mls-listing/586/MFRO6255669/59691054/1731019572/w600_original_BMBRDsIgDAbgE0FZIWx4AN988QZ_2okz1i2WxMTT73uOcfiFyHOE4b9_8PMou5G9vX83pc3QV6fb9T6XlGduS6EqFS0xB5WHhiLLFJCqBm5ZG5TBOsXXsfYzAAD__w-jpg.webp)
$2,150
312 KAYDEN CV, Winter Haven, FL 33884
Listed by AUTHENTIC REAL ESTATE TEAM
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)