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.
803 Lake Jessie Dr Drive
Winter Haven, FL 33881
Lake Jessie Or Carrs J A
Residential
MLS# TB8503132 / Active
Experience luxury living in this newly built (2023) modern style home featuring breathtaking views of Lake Jessie and no HOA! This spacious 4-bedro...
3831 Gaines Drive
Winter Haven, FL 33884
Gaines Cove
Residential
MLS# L4962328 / Active
Welcome to this immaculate dream home at 3831 Gaines Dr! This beautifully updated 3-bedroom + office home features an open floor plan with stunning...
250 Brigham Road
Winter Haven, FL 33881
N/a
Residential
MLS# L4962128 / Active
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter ...
409 21st Street
Winter Haven, FL 33880
West Winter Haven
Residential
MLS# P4938761 / Active
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 ...
1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential
MLS# L4961930 / Active
Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amen...
815 Lake Jessie Drive
Winter Haven, FL 33881
East View Pkwy
Residential
MLS# S5149974 / Active
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...
Reduced -$30,000
1213 Michelangelo Lane
Winter Haven, FL 33884
Estates/lk Florence
Residential
MLS# O6408212 / Active
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...
Reduced -$5,000
83 Jenni Ashley Court
Winter Haven, FL 33884
Skidmore
Residential
MLS# TB8506932 / Active
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...
Reduced -$24,000
1413 Hidden Creek Lane
Winter Haven, FL 33880
Grey Fox Hollow Ph Three
Residential
MLS# L4961757 / Active
Welcome to 1413 Hidden Creek Lanea beautifully maintained 4-bedroom, 2.5-bath residence with a spacious loft, perfectly situated on an expansive .7...
Reduced -$5,000
725 Heritage Drive
Winter Haven, FL 33881
Hamilton Pointe
Residential
MLS# L4961718 / Active
One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath...
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.
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®.