David Shippey
863.521.4517

Luxury Homes for Sale in Winter Haven FL


Winter Haven FL Real Estate featuring Luxury Homes are listed below. These luxury homes for sale in Winter Haven Florida are updated everyday from our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL luxury 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 21-30 of 69
98 Photos 1123 Cypress Point Winter Haven, FL 33884

1123 Cypress Point
Winter Haven, FL 33884
Cypress Point
Residential

MLS# P4934938 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2713 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypress Point

ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset... 

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$1,300,000
Provided courtesy of COLDWELL BANKER REALTY
89 Photos 255 Lake Link Road Winter Haven, FL 33884

255 Lake Link Road
Winter Haven, FL 33884
Lakewood Add
Residential

MLS# P4934836 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2627 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lakewood Add

Welcome to your dream retreat on the shimmering shores of Lake Link in beautiful Winter Haven, Florida offering a 2-year paid Home Warranty! This s... 

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$625,000
Reduced -$25,000
Provided courtesy of DALTON WADE INC
50 Photos 900 Lake Jessie Drive Winter Haven, FL 33881

900 Lake Jessie Drive
Winter Haven, FL 33881
East View Pkwy
Residential

MLS# P4934787 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1828 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: East View Pkwy

Live the ultimate lakefront lifestyle on Lake Jessie. This beautifully maintained single-story home on a 189 acre lake on the South end of Winter H... 

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$550,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
65 Photos 250 Brigham Road Winter Haven, FL 33881

250 Brigham Road
Winter Haven, FL 33881
N/a
Residential

MLS# P4934742 / Active
5 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 3235 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: N/a

Prepare to be utterly enchanted by this stunning lakefront retreat on Lake Hartridge, perfectly positioned on the coveted Winter Haven Chain of Lak... 

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$1,195,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
59 Photos 333 Lake Otis Drive Winter Haven, FL 33880

333 Lake Otis Drive
Winter Haven, FL 33880
Mayfair Sub
Residential

MLS# P4934662 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2633 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Mayfair Sub

Welcome to this beautifully renovated pool home offering modern luxury, privacy, and ultimate functionality all with no HOA restrictions! Situated ... 

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$649,900
Provided courtesy of SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC
42 Photos 1781 Lakehill Drive Winter Haven, FL 33884

1781 Lakehill Drive
Winter Haven, FL 33884
Woodpointe Phase Three
Residential

MLS# P4934591 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2541 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Phase Three

New custom home in established Woodpointe gated community. Quality construction and finishes. Seller will consider purchasing Buyer's existing home... 

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$789,900
Reduced -$20,000
Provided courtesy of JOHN WOOD REALTY, INC.
41 Photos 1787 Lakehill Drive Winter Haven, FL 33884

1787 Lakehill Drive
Winter Haven, FL 33884
Woodpointe Phase Three
Residential

MLS# P4934590 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2818 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Phase Three

New custom home in established Woodpointe gated community. Quality construction and finishes. Seller will consider purchasing Buyer's existing home... 

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$829,900
Reduced -$20,000
Provided courtesy of JOHN WOOD REALTY, INC.
100 Photos 3826 Gaines Court Winter Haven, FL 33884

3826 Gaines Court
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# P4934458 / Active
6 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 5400 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Gaines Cove

***PRICE REDUCTION*** Amazing Winter Haven Executive Home on 1.86 Acres with Lake Eloise Frontage! Welcome to this elegant two-story home nestled o... 

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$1,999,990
Reduced -$400,009
Provided courtesy of NEW HOME ADVANTAGE LLC
39 Photos 1403 Hidden Creek Ln Winter Haven, FL 33880

1403 Hidden Creek Ln
Winter Haven, FL 33880
Grey Fox Hollow
Residential

MLS# P4934337 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3366 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Grey Fox Hollow

COUNTRY ATMOSPHERE! Situated on 3/4 acre lot on quiet, peaceful cul-de-sac street! This home has so much to like with 2-story design ,custom built,... 

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$699,999
Reduced -$25,901
Provided courtesy of SUN N LAKES REALTY, LLC
33 Photos 329 Hamilton Shores Drive Winter Haven, FL 33881

329 Hamilton Shores Drive
Winter Haven, FL 33881
Hamilton Pointe
Residential

MLS# P4934289 / Active
5 Beds, 3.00 Total Baths, 3 Full Bath, 3161 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

This beautiful home overlooks Lake Hamilton being the largest lake on a chain of three, Lake Hamilton, Middle Lake Hamilton, and Little Lake Hamilt... 

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$849,900
Provided courtesy of COLDWELL BANKER REALTY

Broker Reciprocity The information being provided by © 2025 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 REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, 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 07-20-2025 8:01 PM EST.

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For a fresh updated list of Luxury Homes for sale in Winter Haven Florida, visit our website daily.

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


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