Winter Haven FL Homes for Sale
Winter Haven FL Real Estate listings are included below. These homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "Request More Information" button on any property detail page. We'd love to answer any questions you have, and can provide the past sales history, tax information, and comparable sales for any listing. Let our team of professionals work for you!
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419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential
MLS# TB8513442 / Active
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b...
460 Pinehurst Court
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential
MLS# L4962087 / Active
Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida an...
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...
Reduced -$10,000
2964 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantations
Residential
MLS# O6352519 / Active
Welcome to this refined sanctuary where timeless elegance meets Floridas tranquil landscape. On a premium golf-adjacent lot within the guarded, gat...
Reduced -$20,000
665 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Tennis Villas
Residential
MLS# TB8496998 / Active
Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully...
Reduced -$10,000
1004 Medinah Drive
Winter Haven, FL 33884
Cypresswood Tennis Vls
Residential
MLS# P4938711 / Active
Dont miss this incredible opportunity to own a villa in one of Winter Havens most sought-after gated golf communities at an unbeatable price! This ...
Reduced -$5,000
1026 Medinah Drive
Winter Haven, FL 33884
Cypresswood Villas/green
Residential
MLS# L4962495 / Active
Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa.Recent updates include new luxury vinyl flooring, ne...
3821 Avenue J
Winter Haven, FL 33881
Deerwood
Residential
MLS# TB8508879 / Active
Welcome Home to your 3 bedroom/2 bath home! NEW luxury vinyl plank flooring and freshly painted throughout, granite in the kitchen and baths, new l...
3715 Avenue J
Winter Haven, FL 33881
Deerwood Or Harriben Investment Co
Residential
MLS# O6346989 / Active
Welcome to this charming 3-bedroom, 1.5-bath home nestled in the heart of Winter Haven! Built in 1995, this well-maintained property offers a cozy ...
4925 Cypress Gardens Road UNIT #100
Winter Haven, FL 33884
Doves Rest Add
Residential
MLS# P4938418 / Active
Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Ai...
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MLS IDX data last updated on 06-11-2026 8:46 AM EST.
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