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 41-50 of 69
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
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
62 Photos 1 Brogden Court Winter Haven, FL 33880

1 Brogden Court
Winter Haven, FL 33880
Brogden Point Rep
Residential

MLS# L4952907 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3020 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Brogden Point Rep

Custom-Built by Hulbert Homes! Known for their exceptional quality and craftsmanship, Hulbert Homes delivers again with this thoughtfully designed ... 

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$849,900
Reduced -$25,100
Provided courtesy of EXP REALTY LLC
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
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
59 Photos 5671 Cypress Gardens Road Winter Haven, FL 33884

5671 Cypress Gardens Road
Winter Haven, FL 33884
N/a
Residential

MLS# O6312804 / Active
6 Beds, 6.00 Total Baths, 4 Full Bath, 2 Half Bath, 4335 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: N/a

Experience luxurious lakefront living with unmatched privacy and modern upgrades at 5671 Cypress Gardens Road in Winter Haven, FL. Situated on 4.53... 

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$900,000
Reduced -$50,000
Provided courtesy of EXP REALTY LLC
49 Photos 413 Ruby Lake Place Winter Haven, FL 33884

413 Ruby Lake Place
Winter Haven, FL 33884
Ruby Lake Ph 4
Residential

MLS# P4934997 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2172 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ruby Lake Ph 4

Welcome to this beautifully maintained pool home offering comfort, space, and style in a prime location! As you enter the walkway, youll be greeted... 

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$514,000
Reduced -$1,000
Provided courtesy of STACEY TOWNS REALTY LLC
61 Photos 124 Pangola Drive Winter Haven, FL 33880

124 Pangola Drive
Winter Haven, FL 33880
Lakewood Acres
Residential

MLS# TB8394080 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2790 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Lakewood Acres

Beautifully Remodeled Lakefront Home with Bonus Spaces -Located on Grassy Lake, Winter Haven, FLWelcome to this stunning 3-bedroom, 2-bathroom lake... 

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$849,999
Provided courtesy of KELLER WILLIAMS RLTY NEW TAMPA
46 Photos 3991 Island Lakes Drive Winter Haven, FL 33881

3991 Island Lakes Drive
Winter Haven, FL 33881
Island Lakes
Residential

MLS# S5128469 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2640 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Island Lakes

Welcome to your personal lakeside retreat! This stunning two-story home offers 4 spacious bedrooms, 2.5 bathrooms, and a versatile loft perfect for... 

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$600,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
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

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 07-21-2025 2:01 AM 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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