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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Displaying results 281-290 of 760
48 Photos 4454 Glenns Landing Winter Haven, FL 33884

4454 Glenns Landing
Winter Haven, FL 33884
Cypress Landing Ph 03
Residential

MLS# P4938011 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1526 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypress Landing Ph 03

One or more photo(s) has been virtually staged. PRICE IMPROVEMENT with a $10,000 drop! Get your appointment to see this beautifully maintained 2-be... 

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$249,000
Reduced -$10,000
Provided courtesy of CENTURY 21 MYERS REALTY
35 Photos 511 Heather Glen Drive Winter Haven, FL 33884

511 Heather Glen Drive
Winter Haven, FL 33884
Heather Glen Ph 02
Residential

MLS# P4938000 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1488 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Heather Glen Ph 02

Welcome to 511 Heather Glen Drive. This beautifully maintained home is in move in ready condition. Offering 4 bedrooms and 2 bathrooms, the home ha... 

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$287,000
Provided courtesy of THE HOME COMPANY
26 Photos 427 Avenue E Winter Haven, FL 33880

427 Avenue E
Winter Haven, FL 33880
College Heights Or Coker & Buzbee
Residential

MLS# P4937991 / Active
2 Beds, 3.00 Total Baths, 3 Full Bath, 1264 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: College Heights Or Coker & Buzbee

Welcome home to this enchanting 2-bedrrom,3-bathroom cottage that radiates warmth through it extensive natural wood craftmanship and design. Unlike... 

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$224,500
Provided courtesy of COLDWELL BANKER REALTY
64 Photos 4239 Cedarwood Street Winter Haven, FL 33880

4239 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4937986 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1368 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The pr... 

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$128,000
Provided courtesy of COLDWELL BANKER REALTY
24 Photos 688 Augusta Road Winter Haven, FL 33884

688 Augusta Road
Winter Haven, FL 33884
Cypresswood Fairway Patio Homes
Residential

MLS# P4937966 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1586 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Fairway Patio Homes

Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Cou... 

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$337,000
Increase +$17,100
Provided courtesy of JOHN WOOD REALTY, INC.
44 Photos 111 Sunset Drive Winter Haven, FL 33881

111 Sunset Drive
Winter Haven, FL 33881
Chris Brown Cemetery Replat
Residential

MLS# P4937961 / Active
4 Beds, 1.00 Total Baths, 1 Full Bath, 2078 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Chris Brown Cemetery Replat

PRICE ADJUSTMENT***Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for hom... 

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$200,000
Reduced -$15,000
Provided courtesy of LA ROSA REALTY PRESTIGE
66 Photos 4410 Limewood Street Winter Haven, FL 33880

4410 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4937929 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1152 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living area... 

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$110,000
Reduced -$5,000
Provided courtesy of COLDWELL BANKER REALTY
43 Photos 132 Alachua Drive Winter Haven, FL 33884

132 Alachua Drive
Winter Haven, FL 33884
Eloise Woods Lake Mariam Un
Residential

MLS# P4937917 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2466 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Mariam Un

Beautiful and spacious family home with room for everyone to spread out and enjoy. Featuring over 2,400 square feet of living space, this home offe... 

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$320,000
Reduced -$1,000
Provided courtesy of BROKERS REALTY OF CENTRAL FLOR
70 Photos 5264 Green Drive Winter Haven, FL 33884

5264 Green Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4937885 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2011 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

5264 Green Drive Winter Haven, Florida is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with res... 

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$335,000
Provided courtesy of LAKE ASHTON REALTY INC.
61 Photos 47 Enclave Drive Winter Haven, FL 33884

47 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 2
Residential

MLS# P4937867 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 2

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Ho... 

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$245,000
Reduced -$15,000
Provided courtesy of XCELLENCE REALTY, INC

Broker Reciprocity The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 06-09-2026 3:56 PM EST.

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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