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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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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
55 Photos 19 Meadowlake Court Winter Haven, FL 33884

19 Meadowlake Court
Winter Haven, FL 33884
Cypresswood
Residential

MLS# O6279343 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3257 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

New Price Reduction - Priced to Sell! Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a pe... 

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$549,900
Reduced -$40,100
Provided courtesy of REAL BROKER, LLC
41 Photos 1787 Lakehill Drive Winter Haven, FL 33884

1787 Lakehill Drive
Winter Haven, FL 33884
Woodpointe Phase Three
Residential

MLS# P4934590 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2818 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Phase Three

New custom home in established Woodpointe gated community. Quality construction and finishes. Seller will consider purchasing Buyer's existing home... 

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$829,900
Reduced -$20,000
Provided courtesy of JOHN WOOD REALTY, INC.
42 Photos 1781 Lakehill Drive Winter Haven, FL 33884

1781 Lakehill Drive
Winter Haven, FL 33884
Woodpointe Phase Three
Residential

MLS# P4934591 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2541 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Phase Three

New custom home in established Woodpointe gated community. Quality construction and finishes. Seller will consider purchasing Buyer's existing home... 

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$789,900
Reduced -$20,000
Provided courtesy of JOHN WOOD REALTY, INC.
31 Photos 521 Sanctuary Boulevard Winter Haven, FL 33881

521 Sanctuary Boulevard
Winter Haven, FL 33881
Sanctuary By the Lake Ph 1
Residential

MLS# O6296386 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2827 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Sanctuary By the Lake Ph 1

Winter Haven Chain Of Lakes! Come live the ultimate Florida lifestyle! Enjoy private lakefront living with a private dock situated on Lake Rochelle... 

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$649,000
Reduced -$20,000
Provided courtesy of COLDWELL BANKER REALTY
28 Photos 1002 Lake Elbert Drive Winter Haven, FL 33880

1002 Lake Elbert Drive
Winter Haven, FL 33880
Coker A B Sub
Residential

MLS# O6303365 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2844 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Coker A B Sub

LAKE/POOL HOME with 160' of Lake Elbert Frontage! This beautiful brick residence offers resort-style living right at your doorstep with a private s... 

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$849,900
Provided courtesy of EPIQUE REALTY, INC.
48 Photos 1441 S Lake Roy Drive Winter Haven, FL 33884

1441 S Lake Roy Drive
Winter Haven, FL 33884
South Roy Shores
Residential

MLS# P4931110 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 4513 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: South Roy Shores

CHAIN OF LAKES!!! POOL!!! 5 BEDROOMS AND 4.5 BATHROOMS!!! This is the listing you have been waiting for - look no further. This incredible residenc... 

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$1,350,000
Provided courtesy of THE K TEAM REAL ESTATE SERVICES LLC
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
33 Photos 329 Hamilton Shores Drive Winter Haven, FL 33881

329 Hamilton Shores Drive
Winter Haven, FL 33881
Hamilton Pointe
Residential

MLS# P4934289 / Active
5 Beds, 3.00 Total Baths, 3 Full Bath, 3161 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

This beautiful home overlooks Lake Hamilton being the largest lake on a chain of three, Lake Hamilton, Middle Lake Hamilton, and Little Lake Hamilt... 

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$849,900
Provided courtesy of COLDWELL BANKER REALTY
42 Photos 2418 Berkshire Drive Winter Haven, FL 33884

2418 Berkshire Drive
Winter Haven, FL 33884
Eloise Pointe Estates
Residential

MLS# B4901738 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3790 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Pointe Estates

Executive custom built home offered for the first time since it was built in 1991. As you enter through the upscale Eloise Pointe Estates community... 

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$749,000
Reduced -$50,000
Provided courtesy of KLINE REAL ESTATE SERVICES

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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David Shippey
Xcellence Realty, Inc.
1102 South Florida Ave
Lakeland, FL 33803

Phone: 863.521.4517
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