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
30 Photos 1075 8th Street Winter Haven, FL 33881

1075 8th Street
Winter Haven, FL 33881
Haven Shores
Residential

MLS# T3540117 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 1985 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Haven Shores

Price Adjustment and $4000 Seller Concession to Buyer. Gorgeous 4 Bedroom, 3 Bathroom, Single Family Home with 2 In-Law Apartments, on a huge lot, ... 

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$545,000
Provided courtesy of LPT REALTY, LLC
36 Photos 6265 Pinehurst Loop Winter Haven, FL 33884

6265 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# L4944406 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2521 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

**** WOW ****LOOK AT THE NEW PRICE ""REDUCTION"" ****SELLER MOTIVATED with NEW PRICING ******AMAZING NEWER HOME ***** BEAUTIFUL 3/2 + LARGE DEN/ EX... 

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$599,000
Reduced -$51,000
Provided courtesy of ROOST REALTY GROUP LLC
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
58 Photos 9516 Waterford Oaks Boulevard Winter Haven, FL 33884

9516 Waterford Oaks Boulevard
Winter Haven, FL 33884
Waterford Oaks
Residential

MLS# P4935585 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3178 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Waterford Oaks

Welcome to this absolutely amazing 4 bedroom, 3 bathroom home that shows like a luxurious model home. Designed by Authur Rutenberg and build by Hen... 

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$719,990
Provided courtesy of LA ROSA REALTY PRESTIGE
21 Photos 1560 Covey Rise Terrace Winter Haven, FL 33884

1560 Covey Rise Terrace
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7874370 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2551 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$632,990
Increase +$4,000
Provided courtesy of MALTBIE REALTY GROUP
26 Photos 1556 Covey Rise Terrace Winter Haven, FL 33884

1556 Covey Rise Terrace
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7874399 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2021 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$591,990
Increase +$4,000
Provided courtesy of MALTBIE REALTY GROUP
70 Photos 20 N Lake Idylwild Drive Winter Haven, FL 33881

20 N Lake Idylwild Drive
Winter Haven, FL 33881
Not In A Subdivision
Residential

MLS# L4950326 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 3911 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Not In A Subdivision

Lakeside luxury on the coveted Chain of 24 Lakes! This spacious 3,911 sq ft two-story pool home sits on nearly an acre of land and has breathtaking... 

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$779,000
Reduced -$3,000
Provided courtesy of AUSTIN DEANE 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
23 Photos 1548 Covey Rise Terrace Winter Haven, FL 33884

1548 Covey Rise Terrace
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7875302 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1815 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$541,990
Increase +$14,705
Provided courtesy of MALTBIE REALTY GROUP
98 Photos 1123 Cypress Point Winter Haven, FL 33884

1123 Cypress Point
Winter Haven, FL 33884
Cypress Point
Residential

MLS# P4934938 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2713 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypress Point

ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset... 

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$1,300,000
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 07-21-2025 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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