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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2270 Firestone Place
Winter Haven, FL 33884
Cypresswood Golf Villas Gi-4
Residential
MLS# TB8440562 / Active
Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of Winter Haven`s establi...
Reduced -$15,000
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...
Reduced -$2,000
4050 Palma Ceia Circle
Winter Haven, FL 33884
Cypresswood Palma Ceia
Residential
MLS# O6420265 / Active
Virtually Staged. Brand New 2026 Custom Farmhouse Blends Modern Luxury with Exceptional Craftsmanship. Welcome to 4050 Palma Ceia Circle, a stunni...
728 Canberra Road
Winter Haven, FL 33884
Cypresswood Patio Home
Residential
MLS# P4939181 / Active
Welcome home to luxury, comfort, and breathtaking golf course living in the prestigious, 24/7 guard-gated Cypresswood Golf & Country Club. Perfectl...
731 Canberra Road
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential
MLS# L4957294 / Active
Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winte...
Reduced -$10,000
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
1004 Medinah Drive
Winter Haven, FL 33884
Cypresswood Tennis Vls
Residential
MLS# P4938711 / Active
Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! T...
Reduced -$5,000
645 Broadmoor Circle UNIT #645
Winter Haven, FL 33884
Cypresswood Villas On the Green
Residential
MLS# P4938978 / Active
FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently ...
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, ...
Reduced -$7,500
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MLS IDX data last updated on 07-14-2026 9:30 AM 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