- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
360 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![693 PEYTON BROOKE WAY, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6239397/3578b585/1738335673/w600_original_BMBRDsIwCADQE7Uso5bgAfzzxxvQwuqMuEWWmHj6vedx7HEFCMzi8t8-8ovcNwd_x_iuCqvLsID77UFYp5lnZjDql1aUUqVaU1kQU1MpCRctpNKs85Rfu40zAAD__w-jpg.webp)
$299,990
Single Family Home
693 PEYTON BROOKE WAY, Winter Haven, FL 33881
**Assumable 2.99% interest rate** Beautiful 4-Bedroom Home in Winter Haven! Welcome to 693 Peyton Brooke Way, a meticulo...
Listed by CREEGAN GROUP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2272 ROSE BLVD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRTB8301410/b8d0b6c1/1736213897/w600_original_BMDLDcIwDADQiRKnTVwDA3Djwgb-VKEI0wpHQmJ63mOMIy4AUTM7__Y3fyPr7uCv6J_NYHPua8Dteqe6lNPSSgFSmhFlTmdGS21qmIRQEhY1E611Us3PY-3_AAAA__8-jpg.webp)
$309,000
Single Family Home
2272 ROSE BLVD, Winter Haven, FL 33881
One or more photo(s) has been virtually staged. Nestled in the charming city of Winter Haven which is known as the Chain...
Listed by COASTAL PROPERTIES GROUP INTER
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![905 14TH ST NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRB4901706/523383d4/1736213997/w600_original_BMBRDoIwDAbgE221K3PgAXzzxRv81TIxVoglMfH0fo993-JEFJLh-K1vfCPfVid_Rf8sd1oc3YIu52uTKo2ZJ-Kmo5Q6pLnyIQ1VLY3FkOYigBwnhmp-btb_AQAA__8-jpg.webp)
$255,900
Single Family Home
905 14TH ST NE, Winter Haven, FL 33881
Discover this charming 3-bedroom, 2-bath home, thoughtfully updated to blend modern comfort with timeless appeal. Step i...
Listed by LAND SOUTH REALTY, LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![815 HILLSIDE CT N, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRL4947278/680aab01/1725657381/w600_original_BMBhDoJQCADgE_HIB4Z0gP71pxug4ssW6cKtrdP3PY5jzwtiUrGw3_a2b5ZpC4xXts864xrWPPF2vQv1vVSRE46djKw6Q8cLAWutMEwmQMq8-CBnZy3P3ds_AAD__w-jpg.webp)
$399,000
Single Family Home
815 HILLSIDE CT N, Winter Haven, FL 33881
Under contract-accepting backup offers. Welcome to 815 Hillside Court North in beautiful Winter Haven, FL! This charmi...
Listed by PREMIER REALTY NETWORK, INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1475 HAINES DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6238736/666e7eff/1736214443/w600_original_BMBRDsIgDADQE0EHWCkewD9_vEFHG5yxbrEkJp7e95jz8AuAl8jGv_3NX499N7CXj88msBkPdbhd77UgLbRghqpZCLUFTb2EE7OEFRuFlM9rk0RSeo3PQ8c_AAD__w-jpg.webp)
$309,990
Single Family Home
1475 HAINES DR, Winter Haven, FL 33881
Perfectly located in the center of Winter Haven's Chain of Lakes, The Lakes at Lucerne Park has no CDD fees. This proper...
Listed by FORTEZA REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![2158 MIRASOL DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931859/6eba2baa/1733766371/w600_original_BMBRDsIgDADQE0FLGC16AP_88QadFJyxbrEkJp7e95jz8DOA5ygmv_0tX4_33cBePj5bg81kqMP1cuNcKFVOFVKnKiQUVmw9LIgtnApj0IRKfckrY4nPQ8c_AAD__w-jpg.webp)
$344,000
Single Family Home
2158 MIRASOL DR, Winter Haven, FL 33881
**LOW HOA**WELCOME HOME to this beautifully designed residence in the heart of Winter Haven, featuring 3-bedrooms, 3-bat...
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)
![3184 ROYAL TERN DR, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5111840/115051cd/1738260974/w600_original_BMBRDsIgDAbgE0FlgAwP4Jsv3uCvZThj3WJJTDz9vucYu12ILHoo_tsHP_OPTUnf1r-r0Krozeh2vZeYayo1z3TmFJcMuCWW4NJJ2M0MdpURZMIUJDf_2ls_AgAA__8-jpg.webp)
$264,990
Single Family Home
3184 ROYAL TERN DR, Winter Haven, FL 33881
Come home to this gorgeous 3 beds and 2 bath split plan with island kitchen. Enjoy your morning coffee out back on the c...
Listed by KELLER WILLIAMS ADVANTAGE III REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![61 WINTER RIDGE RD #54, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931817/898b014f/1725588330/w600_original_BMBRDoIwDADQE20drC3FA_jnjzeoFSfGCrFLTDw979n7HieAqFld_9tHf5Ftc_B3tO96h9W1LQGX83WqNAoST2Bm8uDCiRVrQqQ5SZk1SRlkHORGSJpf-9KOAAAA__8-jpg.webp)
$155,000
Condo
61 WINTER RIDGE RD #54, Winter Haven, FL 33881
PRICE DROP!!! If you're looking for maintenance free living, this is your home. Enjoy this spacious condo in beautiful W...
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)
![1300 LUCERNE LOOP RD NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRP4931841/22945bfb/1738520172/w600_original_BMBRDoIwDADQE20tdLXoAfzzxxuUUSfGCrFLTDw979n7HheAoKyu_-2jv8h1c_B3tO-6wOraLOB2vQtxmURogMqzqS6W6HTGVKZS0oyDJFSsD2bCccT82q0dAQAA__8-jpg.webp)
$395,900
Single Family Home
1300 LUCERNE LOOP RD NE, Winter Haven, FL 33881
MAJOR PRICE IMPROVMENT for this beautiful LAKEFRONT HOME on a private lake. Here's your opportunity to own a home on the...
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)
![3663 JULIUS ESTATES BLVD, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5111437/3950de4e/1738291572/w600_original_BMBRDsIwCADQE7UMqaP1AP754w2YYJ0Rt0gTE0_ve4yxxwkgKIvLb3vLN_Jtc_BX9M-qsLp0C7icr0xHaq0hQmU8GLKkIrWkQjinZZosabVZme6Lqubnbv0fAAD__w-jpg.webp)
$285,000
Single Family Home
3663 JULIUS ESTATES BLVD, Winter Haven, FL 33881
NEW PRICE!!! Welcome to this charming 3 bedrooms home, impeccably maintained, offering modern comforts and stylish updat...
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)
![2928 ELM ST, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRS5111400/519fad44/1738291572/w600_original_BMBRDoIwDAbgE221_mNzHsA3X7xBKWNirBBLYuLp-Z77vvmVyBHF5L9-5OdRVyN7e_8uEy0mvTndb4-CAYlzzVTO4whUCaVxDomThgvPQ-CTosxcoZjia2v9CAAA__8-jpg.webp)
$1,750
Single Family Home
2928 ELM ST, Winter Haven, FL 33881
Must see this great rent, 3 Bedroom, 1 Bath 960 square foot Solid Block home. Interior features include newer windows, t...
Listed by LA ROSA REALTY ORLANDO LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h600_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![904 15TH ST NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRO6236266/671612b0/1729527371/w600_original_BMBRDsIgDAbgE0EhMCAewDdfvMHfUXHGusWSmHj6fc85D7sQWfJQ_PcPfubXXUnfNr5bp00xxOh2vde0xNhaWahEpBo5uNLW7HLm5BjSnYArasg98MO_DhlnAAAA__8-jpg.webp)
$300,000
Single Family Home
904 15TH ST NE, Winter Haven, FL 33881
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your new POOL home lo...
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)
![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)
$359,900
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
Discover the charm of this well-maintained home at 5716 Lakeside Landings Blvd, Winter Haven, FL. Built in 2018, the HVA...
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)
$419,000
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)
$299,000
Single Family Home
5069 BRENTON MANOR AVE, Winter Haven, FL 33881
**MULTIPLE OFFERS RECEIVED. SELLERS ARE ASKING FOR HIGHEST AND BEST BY TUESDAY, JANUARY 21, 2025** Within the growing ci...
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)
![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)
$369,900
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)
![450 AVENUE B NE, Winter Haven, FL 33881](https://img.chime.me/imageemb/mls-listing/586/MFRT3548780/65c35568/1736703069/w600_original_BMBRDoIwDADQE22ddB3gAfzzxxu0HUyMFWKXmHh63rP3w68AjpGN__uHfx51N7C3t-9WYTNui8P99hgxJ6KSCbgMIjJhSPMlhaxUw6RSw4q0lnEeGFnj61jaGQAA__8-jpg.webp)
$293,000
Single Family Home
450 AVENUE B NE, Winter Haven, FL 33881
One or more photo(s) has been virtually staged. Priced Reduced To Sell!!!! This beautifully renovated 3-bedroom, 2-bathr...
Listed by GREAT WESTERN REALTY
![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)