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
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.
38 Photos 803 Lake Jessie Drive Winter Haven, FL 33881

803 Lake Jessie Drive
Winter Haven, FL 33881
Lake Jessie Or Carrs J A
Residential

MLS# L4954114 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3050 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake Jessie Or Carrs J A

Stunning Newly Built (2023) Modern hacienda with luxurious finishes and a beautiful view of Lake Jessieand best of all, no HOA! This spacious 4-bed... 

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$829,999
Provided courtesy of LA ROSA REALTY PRESTIGE
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
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
49 Photos 720 Lake Jessie Drive Winter Haven, FL 33881

720 Lake Jessie Drive
Winter Haven, FL 33881
Lewellen Bay
Residential

MLS# L4950601 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 2982 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lewellen Bay

Welcome to your Winter Haven Chain of Lakes Lakefront home, a stunning 5-bedroom, 4-bathroom estate offering the perfect blend of luxury, privacy, ... 

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$624,990
Reduced -$14,910
Provided courtesy of LA ROSA REALTY PRESTIGE
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
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
51 Photos 18 Aqualane Drive Winter Haven, FL 33880

18 Aqualane Drive
Winter Haven, FL 33880
Moores Eagle Lake Shores
Residential

MLS# L4953923 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2196 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Moores Eagle Lake Shores

Wake up to breathtaking morning sunrises over Eagle Lake from this stunning waterfront retreat. Tucked away on a peaceful dead-end street, this bea... 

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$579,000
Provided courtesy of BERRY REALTY & APPRAISAL SERVICES PA
66 Photos 10 Webb Road Winter Haven, FL 33881

10 Webb Road
Winter Haven, FL 33881
N/a
Residential

MLS# L4953791 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2001 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: N/a

Auction Property. AUCTION! 10AM, Saturday, Sept. 13th.Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm!Discover the perfect ble... 

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$775,000
Provided courtesy of HIGGENBOTHAM AUCTIONEERS
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

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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