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
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
69 Photos 3805 Gaines Drive Winter Haven, FL 33884

3805 Gaines Drive
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# L4952454 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3225 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Gaines Cove

Seller motivated and will review all offers! Welcome to this stunning 4-bedroom, 3-bathroom ranch-style home located in the highly sought-after nei... 

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$599,000
Reduced -$16,000
Provided courtesy of PAIGE WAGNER HOMES REALTY
32 Photos 952 N Heron Circle Winter Haven, FL 33884

952 N Heron Circle
Winter Haven, FL 33884
Garden Grove South Add
Residential

MLS# P4933451 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3058 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove South Add

PRICE REDUCED $61,000!!**Stunning Lakefront Home with Private Views, Pool, and Outdoor Living Spaces - Nestled in a serene lakeside setting, this b... 

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$589,000
Reduced -$10,000
Provided courtesy of DALTON WADE INC
84 Photos 800 W Lake Elbert Drive Winter Haven, FL 33881

800 W Lake Elbert Drive
Winter Haven, FL 33881
Graydon Hills
Residential

MLS# TB8382290 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3221 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Graydon Hills

Historic Elegance with Modern Luxury - Built by Cypress Gardens Founder Dick Pope! Step into a piece of Winter Haven history with this stunning 4-b... 

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$545,000
Reduced -$5,000
Provided courtesy of FLORIDA LUXURY REALTY INC
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
57 Photos 1955 W Lake Hamilton Drive Winter Haven, FL 33881

1955 W Lake Hamilton Drive
Winter Haven, FL 33881
Hamilton Meadows
Residential

MLS# P4931088 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2814 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Meadows

This stunning, custom-built 4-bedroom, 2-bathroom home spans 2000 sq ft on 9.75 well-maintained and cleared acres! Situated just off Lake Hamilton ... 

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$950,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
61 Photos 413 Horseshoe Lane Winter Haven, FL 33881

413 Horseshoe Lane
Winter Haven, FL 33881
Hamilton Pointe
Residential

MLS# O6324720 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2336 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

Welcome to this beautifully crafted 3-bedroom, 2-bathroom custom home, ideally situated on an oversized lot in the sought-after Hamilton Pointe com... 

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$650,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
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
62 Photos 328 Hamilton Shores Drive Winter Haven, FL 33881

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

MLS# P4935230 / Active
5 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3812 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

Discover refined Florida living in the sought-after Hamilton Pointe community, where 328 Hamilton Shores Drive is perfectly positioned on a beautif... 

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$765,000
Provided courtesy of THE STONES REAL ESTATE FIRM
25 Photos 1475 S Lake Howard Drive Winter Haven, FL 33880

1475 S Lake Howard Drive
Winter Haven, FL 33880
Hanna Sub
Residential

MLS# P4934004 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2118 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Hanna Sub

LAKE FRONT PROPERTY FOR SALE ON THE CHAIN OF LAKES ON LAKE HOWARD!!! This chain of lakes has 20 connecting lakes. If you enjoy water sports, fishin... 

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$549,900
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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