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.

Modify Search Criteria

Displaying results 11-20 of 69
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... 

More Details

$549,900
Reduced -$40,100
Provided courtesy of REAL BROKER, LLC
50 Photos 900 Lake Jessie Drive Winter Haven, FL 33881

900 Lake Jessie Drive
Winter Haven, FL 33881
East View Pkwy
Residential

MLS# P4934787 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1828 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: East View Pkwy

Live the ultimate lakefront lifestyle on Lake Jessie. This beautifully maintained single-story home on a 189 acre lake on the South end of Winter H... 

More Details

$550,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
47 Photos 950 N Lake Otis Drive Winter Haven, FL 33880

950 N Lake Otis Drive
Winter Haven, FL 33880
El Otis Park Sub
Residential

MLS# TB8407564 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 5178 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: El Otis Park Sub

There was a time when homes were designed to lastand this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefro... 

More Details

$2,600,000
Provided courtesy of COMPASS FLORIDA LLC
63 Photos 1872 Eloise Cove Drive Winter Haven, FL 33884

1872 Eloise Cove Drive
Winter Haven, FL 33884
Eloise Cove
Residential

MLS# TB8405555 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3716 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Cove

Prepare to be impressed with this stunning home in the amazing Eloise Cove Community! Discover your dream home in the highly sought-after, gated la... 

More Details

$524,900
Provided courtesy of RE/MAX COLLECTIVE
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... 

More Details

$640,000
Reduced -$10,000
Provided courtesy of EXP REALTY LLC
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... 

More Details

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

More Details

$1,150,000
Reduced -$100,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
42 Photos 237 Manatee Road Winter Haven, FL 33884

237 Manatee Road
Winter Haven, FL 33884
Eloise Woods Lake Mariam Unit
Residential

MLS# P4935292 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 2880 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Mariam Unit

One or more photo(s) has been virtually staged. GORGEOUS LARGE FAMILY HOME!!! 5BR/4BA POOL HOME with 2 MASTER SUITES, MOTHER-IN-LAW OPTION & 3-CAR ... 

More Details

$515,000
Provided courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY
76 Photos 125 Lake Roy Drive Winter Haven, FL 33884

125 Lake Roy Drive
Winter Haven, FL 33884
Eloise Woods Lake Roy Unit
Residential

MLS# B4902008 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1900 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Roy Unit

Timeless Elegance Meets Modern Comfort on the South Chain of LakesWelcome to your lakeside sanctuary in the heart of Winter Haven. This beautifully... 

More Details

$699,900
Provided courtesy of FREEDOM REALTY
39 Photos 115 N Lake Florence Drive Winter Haven, FL 33884

115 N Lake Florence Drive
Winter Haven, FL 33884
Eloise Woods Resub
Residential

MLS# O6276866 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3203 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Resub

Easy to Show! Price Reduced - Motivated Sellers! Lakefront Retreat - Perfect Primary Home, Short-Term Rental, or Multi-Family Investment!Don't miss... 

More Details

$689,000
Reduced -$6,000
Provided courtesy of MAGNOLIA SUN REALTY LLC

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.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

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.