Winter Haven Florida Homes for Sale
Winter Haven Florida Real Estate listings are included below. The Homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you would like to search more specifically in Winter Haven, scroll down the page to Specialty Searches such as 55+ Homes, Pool Homes, Golf Homes, Luxury Homes, Historic Homes, No HOA Homes, and Waterfront Homes. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "More Info" button on any property detail page.
Winter Haven is known for its 26 connecting lakes which are called the "Chain of Lakes". These lakes are great for boating, fishing & water skiing. It is also home to Legoland which offers a theme park & water park based around Lego themes.
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2935 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantation
Residential
MLS# L4959891 / Active
Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800...
29 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# L4959890 / Active
New to the market is this ""one owner"" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE W...
Reduced -$10,000
2813 Wingfoot Ct
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential
MLS# L4959887 / Active
Welcome to 2813 Wingfoot Court now one of the best values in Cypresswood Golf & Country Club!Perfectly positioned along the 8th fairway inside this...
Reduced -$15,000
543 Terranova Circle
Winter Haven, FL 33884
Terranova Ph 01
Residential
MLS# L4959863 / Active
POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond f...
6261 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential
MLS# L4959857 / Active
Live the lifestyle youve been dreaming about in Lake Ashton, Winter Havens premier 55+ gated community. This beautifully cared-for Ashton floor pla...
2500 21st Street UNIT #23
Winter Haven, FL 33881
Casa Del Sol Condo Village Ph 02
Residential
MLS# L4959772 / Active
Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 ba...
1522 Eckart Drive
Winter Haven, FL 33881
Rochelle Gardens
Residential
MLS# L4959745 / Active
This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, youll love the spac...
Reduced -$10,099
1097 Sandpiper Loop
Winter Haven, FL 33881
Chestnut Creek
Residential
MLS# L4959736 / Active
Welcome to 1097 Sandpiper Loop, a beautifully maintained home situated in an intimate community of fewer than 90 residences. Conveniently positione...
265 Lake Thomas Drive
Winter Haven, FL 33880
Timber Wood
Residential
MLS# L4959685 / Active
Welcome to this beautifully renovated lakefront home located on Thomas Lake in Winter Haven, Florida! This charming two-story home combines modern ...
Reduced -$9,000
961 Drexel Avenue
Winter Haven, FL 33881
Anna Mar
Residential
MLS# L4959592 / Active
***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, lo...
Reduced -$5,000
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MLS IDX data last updated on 06-06-2026 5:27 PM EST.
Specific Searches of Winter Haven Florida
55 Plus Homes For Sale Winter Haven FL
Golf Homes For Sale Winter Haven FL
Historic Homes For Sale Winter Haven FL
Luxury Homes For Sale Winter Haven FL
No HOA Homes For Sale Winter Haven FL
Pool Homes For Sale Winter Haven FL
Waterfront Homes For Sale Winter Haven FL