David Shippey
863.521.4517

Winter Haven Luxury Homes for Sale

Your Winter Haven Luxury Home Search includes lakefront homes, large estate homes, executive homes in gated communities, and million dollar plus homes.

If you are looking to purchase luxury home in Winter Haven Florida, give David Shippey a call at 863-521-4517.

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Displaying results 41-50 of 69
51 Photos 1793 Lakehill Drive Winter Haven, FL 33884

1793 Lakehill Drive
Winter Haven, FL 33884
Woodpointe Phase Three
Residential

MLS# P4931194 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2549 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Phase Three

New custom home in established Woodpointe gated community. Quality construction and finishes. Floorplan attached. Seller will consider purchasing B... 

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$769,900
Reduced -$20,000
Provided courtesy of JOHN WOOD 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
57 Photos 1955 W Lake Hamilton Drive Winter Haven, FL 33881

1955 W Lake Hamilton Drive
Winter Haven, FL 33881
Hamilton Meadows
Residential

MLS# P4931088 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2814 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Meadows

This stunning, custom-built 4-bedroom, 2-bathroom home spans 2000 sq ft on 9.75 well-maintained and cleared acres! Situated just off Lake Hamilton ... 

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$950,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
61 Photos 413 Horseshoe Lane Winter Haven, FL 33881

413 Horseshoe Lane
Winter Haven, FL 33881
Hamilton Pointe
Residential

MLS# O6324720 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2336 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

Welcome to this beautifully crafted 3-bedroom, 2-bathroom custom home, ideally situated on an oversized lot in the sought-after Hamilton Pointe com... 

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$650,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
59 Photos 5671 Cypress Gardens Road Winter Haven, FL 33884

5671 Cypress Gardens Road
Winter Haven, FL 33884
N/a
Residential

MLS# O6312804 / Active
6 Beds, 6.00 Total Baths, 4 Full Bath, 2 Half Bath, 4335 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: N/a

Experience luxurious lakefront living with unmatched privacy and modern upgrades at 5671 Cypress Gardens Road in Winter Haven, FL. Situated on 4.53... 

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$900,000
Reduced -$50,000
Provided courtesy of EXP REALTY LLC
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.
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
65 Photos 180 Brigham Road Winter Haven, FL 33881

180 Brigham Road
Winter Haven, FL 33881
Hartridge Harbor Addition
Residential

MLS# O6293503 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3659 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hartridge Harbor Addition

PRICE ADJUSTMENT | NOW OFFERED UNDER APPRAISED VALUE ~ Click on the virtual tour link for a tour of the property. No HOA and conveniently between T... 

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$3,495,000
Reduced -$150,000
Provided courtesy of PREMIER SOTHEBY'S INTL. REALTY
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
45 Photos 530 Sanctuary Boulevard Winter Haven, FL 33881

530 Sanctuary Boulevard
Winter Haven, FL 33881
Sanctuary By the Lake Ph One
Residential

MLS# O6277437 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3619 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Sanctuary By the Lake Ph One

Located in the gated community Sanctuary by the Lake, this custom-built 4-bedroom, 3-bath home offers direct access to Lake Rochelle, part of the C... 

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$689,000
Reduced -$50,000
Provided courtesy of SERHANT

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David Shippey has been serving the Winter Haven Luxury Communities since 2005. If you are looking for the luxurious lakefront homes or one of Winter Haven’s Mansions, call David today to schedule a showing. 863-521-4517.

Specializing in; Lakefront Homes, Luxury Homes, Mansions, and Large Estates.