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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59 Photos 255 Haines Boulevard Winter Haven, FL 33881

255 Haines Boulevard
Winter Haven, FL 33881
Lakes At Lucerne Park Ph 02
Residential

MLS# B4902269 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1793 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakes At Lucerne Park Ph 02

Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Flor... 

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$299,999
Provided courtesy of LAND SOUTH REALTY, LLC
17 Photos 5147 Kinsley Drive Winter Haven, FL 33884

5147 Kinsley Drive
Winter Haven, FL 33884
Seasons At Annabelle Estates
Residential

MLS# S5127810 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1919 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Seasons At Annabelle Estates

Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 4... 

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$299,999
Reduced -$23,636
Provided courtesy of AXEN REALTY, LLC
29 Photos 3268 Country Walk Club Circle Winter Haven, FL 33881

3268 Country Walk Club Circle
Winter Haven, FL 33881
Country Walk/winter Winter Hav
Residential

MLS# S5150893 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1690 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Country Walk/winter Winter Hav

Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in... 

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$300,000
Provided courtesy of KELLER WILLIAMS LEGACY REALTY
23 Photos 2638 San Marco Way Winter Haven, FL 33884

2638 San Marco Way
Winter Haven, FL 33884
Villamar Ph Four
Residential

MLS# S5132867 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1707 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Villamar Ph Four

Short Sale. Welcome to this stunning 4-bedroom, 2-bathroom home featuring an open-concept layout perfect for modern living.Enjoy a spacious living ... 

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$300,000
Reduced -$33,000
Provided courtesy of LOKATION
34 Photos 3742 Fieldstone Circle Winter Haven, FL 33881

3742 Fieldstone Circle
Winter Haven, FL 33881
Country Club Estates
Residential

MLS# L4962401 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1919 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Country Club Estates

Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,919 square feet of comfortable living space in the well-kept community of ... 

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$300,000
Provided courtesy of COLDWELL BANKER REALTY
21 Photos 1301 Evalyn Drive Winter Haven, FL 33880

1301 Evalyn Drive
Winter Haven, FL 33880
Elbert Hills
Residential

MLS# L4957933 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1817 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Elbert Hills

Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home o... 

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$300,000
Reduced -$5,900
Provided courtesy of LIVE FLORIDA REALTY
48 Photos 6194 Grey Heron Drive Winter Haven, FL 33881

6194 Grey Heron Drive
Winter Haven, FL 33881
Lakeside Landings Ph 01
Residential

MLS# L4961808 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1711 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Landings Ph 01

Welcome to your Florida escape in the heart of Winter Haven! This beautifully maintained home in the sought-after Grey Heron community offers the p... 

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$300,000
Provided courtesy of TRUE FLORIDA REALTY LLC
21 Photos 715 Grove Street Winter Haven, FL 33881

715 Grove Street
Winter Haven, FL 33881
Inman Grvs Ph 2
Residential

MLS# O6383497 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1560 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Inman Grvs Ph 2

***This home can be yours for 4.75% Interest rate on a assumable loan*** Located in the desirable Inman Grove solar community in Winter Haven, this... 

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$300,000
Reduced -$5,000
Provided courtesy of NORKIS & CO REALTY
50 Photos 69 Enclave Drive Winter Haven, FL 33884

69 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 02
Residential

MLS# S5148089 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1682 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 02

Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community kno... 

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$300,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
34 Photos 3136 Country Club Circle Winter Haven, FL 33881

3136 Country Club Circle
Winter Haven, FL 33881
Country Walk/winter Haven
Residential

MLS# L4961900 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1690 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Country Walk/winter Haven

Welcome to a home that makes everyday living simple and enjoyable. Located in the established Country Club community, this property offers a practi... 

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$300,000
Provided courtesy of LA ROSA REALTY PRESTIGE

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 06-15-2026 7:44 PM EST.

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The Winter Haven Florida Real Estate listings included above are brought to you by David Shippey. 863-521-4517

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