- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
352 Properties Available
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![256 LAKE SMART CIR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4946974/d5b3476b/1736778671/w600_original_BMBRDsIwCADQE7UwAUk9gH_-eANWsc6IW2SJiaf3PfZ9yxNAUrWw3_q2b9a-BsQrx2e5wRI2POFyvioxq6IQiOsBacIi1HphYSztPk-lIzUnnfkoXp-bj38AAAD__w-jpg.webp)
$367,000
Single Family Home
256 LAKE SMART CIR, Winter Haven, FL 33881
You will NOT find a better home on the market than this one for the price!! Welcome to 256 Lake Smart Cir, where you'll ...
Listed by THE MARKET REALTY COMPANY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![828 27TH ST NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6235962/890f9f85/1736214232/w600_original_BMBRDsIwCADQE7VMW9bgAfzzxxsAHXVG3CJLTDy973Ece1wAomR2_m1v_kbWzcFfMT5rh9V5LAG3670VnBBbRTDDNmvFNLWTpKpnSiKVklkXKmpCc8_PfRn_AAAA__8-jpg.webp)
$245,900
Single Family Home
828 27TH ST NW, Winter Haven, FL 33881
Come see it this beautiful, remodeled home, including new roof, new ac, new windows and much more/// Really nice backyar...
Listed by SOLARE REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5716 LAKESIDE LANDINGS BLVD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6235730/46fa3b4d/1736214505/w600_original_BMBRDsIwCADQE7W0oaTgAfzzxxuQjtUZcYssMfH0vsd5HnEBCMzq-tvf-o08dgd_xfxsC2yu0wJu13vHJp2wM-Cota6dExnX1FYqSZqVJDSQGrKURfPzsPkPAAD__w-jpg.webp)
$299,000
Single Family Home
5716 LAKESIDE LANDINGS BLVD, Winter Haven, FL 33881
Under contract-accepting backup offers. Discover the charm of this well-maintained home at 5716 Lakeside Landings Blvd, ...
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)
![605 SARNER PASS WAY, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931754/0787b775/1736445677/w600_original_BMBRDsIwCADQE7VEYUA9gH_-eAM22zojbpEmJp5-7znGHheAwGxu_-1jv8jL5uDv6N_1AatbrwG3612QVAvJBHIuiu3ESUlKoiqcDI0Tt8WmRqo8z_m1134EAAD__w-jpg.webp)
$419,500
Single Family Home
605 SARNER PASS WAY, Winter Haven, FL 33881
What a beauty inside and out. This spacious home offers plenty of room. This two story home will not disappoint and the ...
Listed by FLORIDA HOMES REALTY & MORTGAGE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![5069 BRENTON MANOR AVE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4946979/2a738106/1727202670/w600_original_BMBRDoIwDADQE21FVljxAP754w1KWyfGCrFLTDy979H7EWeAKJmdf_ubv5Fld_BXtM-msDk3C7hebrUgLjicEEZG4tnGNEuhhPVOaRWhZJNinQZaddH8PKz9AwAA__8-jpg.webp)
$250,000
Single Family Home
5069 BRENTON MANOR AVE, Winter Haven, FL 33881
Under contract-accepting backup offers. **MULTIPLE OFFERS RECEIVED. SELLERS ARE ASKING FOR HIGHEST AND BEST BY TUESDAY, ...
Listed by BHHS FLORIDA PROPERTIES GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3555 HARBOR CIR NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931713/0f25e594/1724452270/w600_original_BMDRDcJACADQiThswePqAP754waUkrNGbCNNTJze9ziOPS-ISUVDf9tbv1lsC4xX9s-64BraPfF2vQtxpXGaBEfh-cyDglQy4FYZ2mAGsjC7eyOZT-W5e_8HAAD__w-jpg.webp)
$239,900
Single Family Home
3555 HARBOR CIR NW, Winter Haven, FL 33881
LAKEFRONT COMMUNITY--HARTRIDGE HARBOR IS WINTER HAVEN'S BEST-KEPT SECRET. The development is NOT age restricted. This 2...
Listed by QUINN & COMPANY REALTORS, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1502 NE BUCKEYE RD NE #2, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRA4620747/f66b9a99/1736213974/w600_original_BMBRDoIwDADQE211bkXwAP754w3a0k6MFWJJTDw977nvW1wBomZy-q8f-kWW1cHf0b_LDItT14D77XGpDds41QaFBE82W2IsktowaeKxWhItcqaBTRjza9N-BAAA__8-jpg.webp)
$229,900
Townhouse
1502 NE BUCKEYE RD NE #2, Winter Haven, FL 33881
Experience lakefront living at its best in this 2-story townhouse with 3 bedroom 3 bath on Lake Buckeye, located just m...
Listed by KURUVILA REALTY ASSOCIATES LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![202 AVENUE P NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6234336/b964c570/1733279470/w600_original_BMBRDsIgDAbgE0EZ4EAP4Jsv3uBfV3DGusWSmHh6v8cYh12ILHkofvsbX_O8K-nL-mdbaVN0Mbpd7yXlUz3nUGjiKi02dinK5DJSdcu8wi2hIESU3Gb2z0P6PwAA__8-jpg.webp)
$185,000
Single Family Home
202 AVENUE P NE, Winter Haven, FL 33881
Under contract-accepting backup offers. Priced below appraised value!!! This property presents an incredible investment ...
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)
![1025 W W LAKE HAMILTON DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5110693/cb71d95b/1736213360/w600_original_BMBRDsIgDAbgE0Fn_iLDA_jmizeAteCMdYtdYuLp_R7HsfuFyBGr1d_2rl-Py2ZkLx-fVWi1OtTpdr1nMKeCKZHMk6bWe5g15cAdEhpQguQT2nIGc5H43HX8AwAA__8-jpg.webp)
$379,900
Single Family Home
1025 W W LAKE HAMILTON DR, Winter Haven, FL 33881
MUST SEE!! Come and see this GORGEOUS HOME located less than 10 minutes from Sample Park and The Country Club of Winter ...
Listed by VITAL REALTY GROUP INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![205 AVENUE U NW, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931646/ea35651a/1724094074/w600_original_BMBRDsIgDAbgE0FH6AZ4AN988QbNX8QZ6xa7xMTT73sex-4XIs9RTP7bR34esRnZ28d3VVpNRne6Xe8lcyrLMk2Eqmj6qAGaOHBDDq0WDlJnngGk0jm-9j7OAAAA__8-jpg.webp)
$280,000
Single Family Home
205 AVENUE U NW, Winter Haven, FL 33881
PRICE REDUCTION!! Discover your private oasis in this spacious 4-bedroom, 3-bathroom single-family home. Nestled on a qu...
Listed by LA ROSA REALTY PRESTIGE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![547 HIGHFIN DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5110172/b2b9bb4f/1723720593/w600_original_BMBRDoIwDADQE3VFiu3wAP754w0KHRNjZbFLTDy979F7iwtiUFLX3_HWb6T1cPRX1M9uuLvWEni73oVIJs75jJlXtpMOILIZTAMTLDQrlFlHI5aNlzE9W6n_AAAA__8-jpg.webp)
$350,000
Single Family Home
547 HIGHFIN DR, Winter Haven, FL 33881
PRICE IMPROVEMENT. This immaculate home, built in 2021, embodies modern elegance with carefully chosen upgrades and fini...
Listed by CORCORAN CONNECT LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2 CASARENA CT, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4946621/9511c67a/1723393870/w600_original_BMBRDsIgDAbgE0FZyvIPD-CbL96gdIgz1i2WxMTT73uOcfiFyDmKyX__yM-j7kb29v7dVtpMenO6Xe9g5rSgFEKrRVERNE8IORUOdVoQHuBc57Rqkjm-jtbPAAAA__8-jpg.webp)
$354,500
Single Family Home
2 CASARENA CT, Winter Haven, FL 33881
One or more photo(s) has been virtually staged. PRICE REDUCED!!! Come and see this Amazing Contemporary CHAIN OF LAKES H...
Listed by ELEVATE REAL ESTATE BROKERS
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![341 HAMILTON SHORES DR. NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4946733/9045c489/1736212946/w600_original_BMBRDsIgDADQE0EpZbJ6AP_88QYVKc5Yt9glJp5-77nvm58BnKKY_NeP_Dy21cDePr7LAxaT0R2ul1slmk6MSMBzLglTDkqooWDlMGelwNpravdUp9Lia-vjCAAA__8-jpg.webp)
$999,999
Single Family Home
341 HAMILTON SHORES DR. NE, Winter Haven, FL 33881
Experience the epitome of luxury living in this custom Mediterranean-style Arther Rutenberg home, completed in 2015, loc...
Listed by HARPER READ REALTY GROUP INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4850 ST JAMES CT, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931386/8d2005a5/1731806169/w600_original_BMBRDoIwDADQE3WlW8nQA_jnjzcopZsYK8SSmHh63vM49rgiRkni8t8-8oukm6O_o3_XBVeXboH326OWzNNQR8JpUFK-KHArC_BIBjPVDC3PTE2NVSi9dutnAAAA__8-jpg.webp)
$275,000
Single Family Home
4850 ST JAMES CT, Winter Haven, FL 33881
Priced to Sell at $275,000! Motivated sellers have priced this home to sell quickly, and they are reviewing all offers....
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![592 LAKE SMART BLVD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5109431/2fb6a328/1737465370/w600_original_BMDRDcJACADQiTjkoIdxAP_8cQNa2rNGbCNNTJze9ziOPS-IycXCftvbvlmmLTBe2T-r4xrW58Tb9a5cVZtww5FdnBaF8zQqSGUDq9rgROyD2DIQeXnuc_8HAAD__w-jpg.webp)
$485,990
Single Family Home
592 LAKE SMART BLVD, Winter Haven, FL 33881
Step into timeless elegance with this beautifully updated 5-bedroom, 3-bath home in the heart of Winter Haven. Situated ...
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)
![4127 ISLAND LAKES DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931524/dda37759/1736213898/w600_original_BMBRDoIwDAbgE21F2sn0AL754g3-lHVirBBLYuLp-Z77vsWVKDjD8V8_-EXW1cnf0b_LTIujt6D77TExS5EyFOKLAtw0FUNNYvWc6mm0JG3SQU2AecyvrfUjAAD__w-jpg.webp)
$2,700
Single Family Home
4127 ISLAND LAKES DR, Winter Haven, FL 33881
One or more photo(s) has been virtually staged. Welcome to this exquisite 3-bedroom, 2-bathroom chain of lakes home with...
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![3112 WOODHILL RD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6230294/51d1e7fc/1722978974/w600_original_BMBdDsIwCADgE7V0LUj1AL754g0I_XFG3CJLTDy93-M4dr8AeIli8tve8vWom4G9fH7WBqvJ7A63651LoZQZE7STlMR5hFx7C3hGDJWUgtIyVJfEVEd87n3-AwAA__8-jpg.webp)
$1,450
Single Family Home
3112 WOODHILL RD, Winter Haven, FL 33881
Completely Renovated 2 bedroom 1 bath, new stainless-steel appliances, washer and dryer inside units, vinyl wood like fl...
Listed by BRICKSTONE REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![141 ANDREAS ST, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5109821/89b75557/1724879774/w600_original_BMBRDoIwDADQE3UF2lnnAfzzxxt0FCbGCrFLTDy979H7ERfEoKSuv_2t30jz7uivaJ_NcHNtS-DtehciGqeBBMlysTIq1CwGLFOFc50ZTiyrrjYwlZyex9L-AQAA__8-jpg.webp)
$358,000
Single Family Home
141 ANDREAS ST, Winter Haven, FL 33881
Welcome to this Immaculate 4-bedrooms 2.1-bath, It could be your perfect family home or investment property. As you ente...
Listed by LA ROSA REALTY KISSIMMEE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1712 LIME DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6227523/2c22c42b/1736214149/w600_original_FMjRDcJACADQiTgsNHI4gH_-uAGl51kjtpEmJk5v_H33fd_yhJhcLOy7vuyTxdfAeGZ_LzMuYb0lXs5XYRLWOigevTpxczhMI8NYBwElneD2ZyF3nr08ttZ_AQAA__8-jpg.webp)
$365,000
Single Family Home
1712 LIME DR, Winter Haven, FL 33881
Under contract-accepting backup offers. Back on the market. Escrow was never submitted. Seller is motivated. Welcome to ...
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)
![339 LAKE SMART CIR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931342/dc82a26e/1723241772/w600_original_BMBRDoIwDADQE3WFDtPhAfzzxxu0rEyMFWKXmHh63rP3I66IkZO4_PeP_CItu6O_o323iptLs8D77cGZKF-IC66DGllZQWc2mEZV0KUWqCzjPBENJppeh7UzAAD__w-jpg.webp)
$321,750
Single Family Home
339 LAKE SMART CIR, Winter Haven, FL 33881
Welcome to your dream home! This beautiful property features a large patio door that floods the living space with natura...
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![314 SEARS AVE NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6228994/3ca0204f/1723390268/w600_original_FMdRDsIwCADQE1FWYNV6AP_88QZ0Yp0Rt8gSE09v9vke27bGCTE4qetvees30rQ4-iv6Z77h7Not8HK-HpgzsdQRRWvJ1AwKSwPRcoc62ACN8njcqROl52r9HwAA__8-jpg.webp)
$1,750
Single Family Home
314 SEARS AVE NE, Winter Haven, FL 33881
Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our ...
Listed by MAIN STREET RENEWAL LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1407 AVENUE D NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931215/d8adc8e8/1724935571/w600_original_BMBRDoIwDAbgE211K7LhAXzzxRv8rGVirBBLYuLp_R7HsfuFyDnC8Nve-Hpsm5G9vH9WodXQ1el2vRdOw5i5FJJZp5PUcwAmhGHmMVTJGmpKbVkgklqOz137PwAA__8-jpg.webp)
$285,000
Single Family Home
1407 AVENUE D NE, Winter Haven, FL 33881
Welcome to this stunning, fully updated home where luxury meets comfort. Every detail has been meticulously attended to,...
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4 CASARENA CT, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931298/befa75a5/1736212779/w600_original_BMDRDcJACADQie6QAyl1AP_8cQNayVkjtpEmJk7f99z3LS8ASdXC_uvHflnnNSDe2b_LA5aw7gm3630gVNEBEdyakLMUlkkLz4plPNlUtI2N-WwNlepr834EAAD__w-jpg.webp)
$550,000
Single Family Home
4 CASARENA CT, Winter Haven, FL 33881
Welcome to an unparalleled living experience in this stunning waterfront home on the pristine shores of Lake Cannon. Thi...
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2200 STARBOARD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931241/2db28d62/1733598982/w600_original_BMBRDsIwCADQE7WkIDI9gH_-eANQWmfELbLExNPvPbdtzTNAUtXQ__LRX9b7EhDvHN_5AXPo8ITr5SbU-DixCLhL766toJy4HIysqDUsnbChTexGWl-rjz0AAP__-jpg.webp)
$215,000
Single Family Home
2200 STARBOARD, Winter Haven, FL 33881
One or more photo(s) has been virtually staged. Welcome to serene 55+ community living at Hartridge Landings in Winter H...
Listed by KELLER WILLIAMS REALTY SMART 1
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)