Luxury Homes for Sale 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 Tour" or "More Info" button on any property detail pages.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 11-20 of 47
40 Photos 803 Lake Jessie Dr Drive Winter Haven, FL 33881

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

MLS# TB8503132 / 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

Experience luxury living in this newly built (2023) modern style home featuring breathtaking views of Lake Jessie and no HOA! This spacious 4-bedro... 

More Details

$669,000
Provided courtesy of LANTES REAL ESTATE LLC
59 Photos 3831 Gaines Drive Winter Haven, FL 33884

3831 Gaines Drive
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# L4962328 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2678 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Gaines Cove

Welcome to this immaculate dream home at 3831 Gaines Dr! This beautifully updated 3-bedroom + office home features an open floor plan with stunning... 

More Details

$775,000
Provided courtesy of THE MARKET REALTY COMPANY
67 Photos 250 Brigham Road Winter Haven, FL 33881

250 Brigham Road
Winter Haven, FL 33881
N/a
Residential

MLS# L4962128 / 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 captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter ... 

More Details

$1,195,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
53 Photos 409 21st Street Winter Haven, FL 33880

409 21st Street
Winter Haven, FL 33880
West Winter Haven
Residential

MLS# P4938761 / Active
4 Beds, 1.00 Total Baths, 1 Full Bath, 2322 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: West Winter Haven

Stunning 2 story 3 bath Spanish home with attention to details. This home has been renovated, roof was complete in 2019, painted inside and out in ... 

More Details

$550,000
Provided courtesy of COLDWELL BANKER REALTY
70 Photos 1394 Oakmont Drive Winter Haven, FL 33884

1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential

MLS# L4961930 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amen... 

More Details

$549,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
67 Photos 815 Lake Jessie Drive Winter Haven, FL 33881

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

MLS# S5149974 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 4128 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: East View Pkwy

Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA m... 

More Details

$620,000
Reduced -$30,000
Provided courtesy of META ONE REALTY GROUP LLC
14 Photos 1213 Michelangelo Lane Winter Haven, FL 33884

1213 Michelangelo Lane
Winter Haven, FL 33884
Estates/lk Florence
Residential

MLS# O6408212 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2894 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Estates/lk Florence

NO CDD Fees Low HOA *Lower Taxes Luxury Heated Pool Resort-style backyard Move-In Ready Home.Welcome to this beautifully maintained and gently live... 

More Details

$559,900
Reduced -$5,000
Provided courtesy of BEYCOME OF FLORIDA LLC
58 Photos 83 Jenni Ashley Court Winter Haven, FL 33884

83 Jenni Ashley Court
Winter Haven, FL 33884
Skidmore
Residential

MLS# TB8506932 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3799 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Skidmore

Winter Haven, FL is known as the Chain of Lakes City, and this home is located in a beautiful gated subdivision (Skidmore) that sits on Lake Eloise... 

More Details

$875,000
Reduced -$24,000
Provided courtesy of LISTED SIMPLY
54 Photos 1413 Hidden Creek Lane Winter Haven, FL 33880

1413 Hidden Creek Lane
Winter Haven, FL 33880
Grey Fox Hollow Ph Three
Residential

MLS# L4961757 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3086 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Grey Fox Hollow Ph Three

Welcome to 1413 Hidden Creek Lanea beautifully maintained 4-bedroom, 2.5-bath residence with a spacious loft, perfectly situated on an expansive .7... 

More Details

$570,000
Reduced -$5,000
Provided courtesy of THE MARKET REALTY COMPANY
61 Photos 725 Heritage Drive Winter Haven, FL 33881

725 Heritage Drive
Winter Haven, FL 33881
Hamilton Pointe
Residential

MLS# L4961718 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3114 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hamilton Pointe

One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath... 

More Details

$559,000
Provided courtesy of REMAX EXPERTS

Broker Reciprocity The information being provided by © 2026 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 is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, 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 06-20-2026 7:46 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

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®.