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 51-60 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
47 Photos 950 N Lake Otis Drive Winter Haven, FL 33880

950 N Lake Otis Drive
Winter Haven, FL 33880
El Otis Park Sub
Residential

MLS# TB8407564 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 5178 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: El Otis Park Sub

There was a time when homes were designed to lastand this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefro... 

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$2,600,000
Provided courtesy of COMPASS FLORIDA 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
72 Photos 5200 Pebble Beach Boulevard Winter Haven, FL 33884

5200 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4935325 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2443 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites... 

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$555,000
Provided courtesy of LAKE ASHTON REALTY INC.
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
77 Photos 6112 Pebble Beach Boulevard Winter Haven, FL 33884

6112 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# P4935515 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2535 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

**GOLF COURSE and WATER VIEWS*** Located behind the security gates of the coveted community of Lake Ashton, the attention to detail is evident thro... 

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$539,000
Provided courtesy of LAKE ASHTON REALTY 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
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
42 Photos 21 Lake Avenue Winter Haven, FL 33880

21 Lake Avenue
Winter Haven, FL 33880
Aqualane Heights
Residential

MLS# L4953925 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2018 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Aqualane Heights

Wake up to glorious sunrises over the water with this fully renovated 3-bedroom, 3-bath home nestled on an expansive lot along the pristine shores ... 

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$695,000
Provided courtesy of BERRY REALTY & APPRAISAL SERVICES PA
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

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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