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 our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL homes for sale, please call 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

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Displaying results 581-590 of 782
11 Photos 2796 Whispering Trails Drive Winter Haven, FL 33884

2796 Whispering Trails Drive
Winter Haven, FL 33884
Whispering Trails Ph 02
Residential

MLS# S5114687 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1158 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Whispering Trails Ph 02

Short Sale. Discover this charming home ideally located near Legoland, hospitals, businesses, and schools.With easy access to major roads, this pro... 

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$215,500
Provided courtesy of CENTURY 21 WOLF'S CROSSING REALTY
21 Photos 3208 Timberline Road Winter Haven, FL 33880

3208 Timberline Road
Winter Haven, FL 33880
Timber Wood
Residential

MLS# S5125258 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 1043 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Timber Wood

MOVE-IN READY & COMPLETELY REMODELED!This stunning home features a bright, open layout with modern shiplap accents, skylights, and a cozy fireplace... 

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$240,000
Provided courtesy of LPT REALTY, LLC
52 Photos 6044 Grand Oaks Drive Winter Haven, FL 33884

6044 Grand Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# S5126925 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1248 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where ... 

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$169,900
Reduced -$15,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
17 Photos 5135 Kinsley Drive Winter Haven, FL 33884

5135 Kinsley Drive
Winter Haven, FL 33884
Seasons At Annabelle Estates
Residential

MLS# S5127745 / 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 must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42"" white cabinets, a walk-in pa... 

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$319,950
Increase +$4,951
Provided courtesy of AXEN 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
15 Photos 621 Vittorio Drive Winter Haven, FL 33884

621 Vittorio Drive
Winter Haven, FL 33884
Villamar Ph 2a
Residential

MLS# S5129960 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1857 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Villamar Ph 2a

Beautiful, spacious, and cozy house, practically new, with an open feel that gives it a pleasant and welcoming feeling of family togetherness. All ... 

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$305,000
Provided courtesy of MY REALTY GROUP, LLC.
19 Photos 5163 Kinsley Drive Winter Haven, FL 33884

5163 Kinsley Drive
Winter Haven, FL 33884
Seasons At Annabelle Estates
Residential

MLS# S5130838 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2077 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Seasons At Annabelle Estates

This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, youll find an open layout with a dining ... 

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$339,999
Reduced -$8,094
Provided courtesy of AXEN REALTY, LLC
70 Photos 11 Casarena Court Winter Haven, FL 33881

11 Casarena Court
Winter Haven, FL 33881
Casarena On the Lake
Residential

MLS# S5132611 / Active
2 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2045 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Casarena On the Lake

Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the... 

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$230,000
Reduced -$20,000
Provided courtesy of DREAM BUILDERS REALTY
20 Photos 5323 Mickey Avenue Winter Haven, FL 33884

5323 Mickey Avenue
Winter Haven, FL 33884
Seasons At Annabelle Estates
Residential

MLS# S5132794 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2050 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Seasons At Annabelle Estates

Discover this must-see Tarragon home. Included features: an inviting covered entry; an expansive great room; a quiet study; a well-appointed kitche... 

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$334,999
Increase +$5,000
Provided courtesy of AXEN REALTY, LLC
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

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 06-17-2026 7:58 PM EST.

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The Winter Haven homes above are brought to you by David Shippey REALTOR®.


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