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 31-40 of 69
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
69 Photos 5268 Pebble Beach Boulevard Winter Haven, FL 33884

5268 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4933937 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2354 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

CDD DEBT PAID IN FULL! Golf Course Frontage and Amazing Water Views! Welcome to luxury living at its finest in the sought-after Lake Ashton 55+ com... 

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$599,000
Provided courtesy of LAKE ASHTON REALTY INC.
54 Photos 105 Wyndham Drive Winter Haven, FL 33884

105 Wyndham Drive
Winter Haven, FL 33884
Wyndham At Lake Winterset
Residential

MLS# P4933716 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2591 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndham At Lake Winterset

Highly sought after guard-gated community of WYNDHAM AT LAKE WINTERSET, tree shaded private roads with a playground and tennis court. Enjoy the vie... 

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$749,900
Provided courtesy of COLDWELL BANKER REALTY
56 Photos
Open House: Today 11:00am - 1:00pm
1006 W Lake Hamilton Drive Winter Haven, FL 33881

1006 W Lake Hamilton Drive
Winter Haven, FL 33881
Pollard Shores
Residential

MLS# P4933594 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3068 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Pollard Shores

PRICE REDUCED! Stunning three-bedroom, two-and-a-half-bath home on .97 acres with breathtaking views of Lake Hamilton. This beautifully designed re... 

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$855,000
Reduced -$10,000
Provided courtesy of LOCKHART & ASSOCIATES INC
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
64 Photos 2683 Wyndsor Oaks Way Winter Haven, FL 33884

2683 Wyndsor Oaks Way
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# P4933374 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3440 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndsor At Lake Winterset

Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL - an extraordinary residence in the highly sought-after gated Wyndsor at Lake Winterset communit... 

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$849,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
74 Photos 3340 Crump Road Winter Haven, FL 33881

3340 Crump Road
Winter Haven, FL 33881
Magnolia Shores
Residential

MLS# P4933336 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2947 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Magnolia Shores

Welcome to 3340 Crump Road, an exquisite lakefront sanctuary in Winter Haven, Florida! Currently being used as a 3-bedroom, this 4-bedroom, 3-bathr... 

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$624,500
Reduced -$75,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
46 Photos 2428 Wildwood Court Winter Haven, FL 33884

2428 Wildwood Court
Winter Haven, FL 33884
Eloise Pointe Estates
Residential

MLS# P4933270 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3001 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Pointe Estates

****Veterans: Take Advantage of a 4.875% Assumable VA Loan!****Welcome to the lifestyle youve been dreaming of. Nestled within the gated enclave of... 

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$640,000
Reduced -$10,000
Provided courtesy of EXP REALTY LLC
100 Photos 3001 Crystal Beach Road Winter Haven, FL 33880

3001 Crystal Beach Road
Winter Haven, FL 33880
Bingham John A Jr Sub
Residential

MLS# P4933259 / Active
8 Beds, 7.00 Total Baths, 7 Full Bath, 7810 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Bingham John A Jr Sub

Welcome to your dream home at 3001 Crystal Beach Road in Winter Haven, FLa masterpiece of luxury and sophistication. This breathtaking 8-bedroom, 7... 

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$1,490,000
Reduced -$105,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
81 Photos 121 E Lake Summit Drive Winter Haven, FL 33884

121 E Lake Summit Drive
Winter Haven, FL 33884
Eloise Woods
Residential

MLS# P4931785 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 4591 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods

***The seller agrees to pay off the solar panels at closing.*** Step into a world of lakeside luxury with this majestic red-brick residence, where ... 

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$1,150,000
Reduced -$100,000
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 07-20-2025 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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