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 21-30 of 43
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
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

$650,000
Provided courtesy of META ONE REALTY GROUP LLC
51 Photos 530 Sanctuary Boulevard Winter Haven, FL 33881

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

MLS# S5144344 / 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

Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, ... 

More Details

$639,900
Reduced -$10,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
58 Photos 44 Lake Eloise Court Winter Haven, FL 33884

44 Lake Eloise Court
Winter Haven, FL 33884
Harbour Estates
Residential

MLS# P4938605 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2916 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Harbour Estates

BEAUTIFUL SE POOL HOME LOCATED ON A QUIET CUL-DE-SAC IN DESIRABLE HARBOR ESTATES. SITUATED ON A SPACIOUS WOODED LOT OF OVER 1/2 ACRE. THIS PROPERTY... 

More Details

$619,500
Provided courtesy of FLORIDA HOME CHOICE REALTY
70 Photos 5365 Hogan Lane Winter Haven, FL 33884

5365 Hogan Lane
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4938226 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2591 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

Welcome to the next exciting chapter of your life in Lake Ashton, Central Floridas premier 55+ active-adult community, where this immaculately main... 

More Details

$599,900
Provided courtesy of GLOBAL LIFESTYLE LLC
55 Photos 3206 Heron Cove Winter Haven, FL 33884

3206 Heron Cove
Winter Haven, FL 33884
Heron Cay
Residential

MLS# L4949141 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3050 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Heron Cay

BACK ON MARKET! Welcome to 3206 Heron Cove. As you step into the foyer, you'll find an expansive main living area which boasts spacious living & di... 

More Details

$599,000
Reduced -$1,000
Provided courtesy of THE MARKET REALTY COMPANY
32 Photos 2935 Plantation Road Winter Haven, FL 33884

2935 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantation
Residential

MLS# L4959891 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2724 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Plantation

Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800... 

More Details

$598,900
Provided courtesy of LBJ REALTY AND ASSOCIATES LLC
70 Photos 5457 Hogan Lane Winter Haven, FL 33884

5457 Hogan Lane
Winter Haven, FL 33884
Lake Ashton West Atlee Add
Residential

MLS# P4938326 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2676 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Atlee Add

Welcome to 5457 Hogan Lane, Winter Haven, FL, a stunning home with lake views and a SPOOL (8x16) in Lake Ashton, an Exclusive 55 Plus community wit... 

More Details

$589,000
Provided courtesy of LAKE ASHTON REALTY INC.
70 Photos 6261 Pinehurst Loop Winter Haven, FL 33884

6261 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# L4959857 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2512 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Live the lifestyle youve been dreaming about in Lake Ashton, Winter Havens premier 55+ gated community. This beautifully cared-for Ashton floor pla... 

More Details

$585,000
Provided courtesy of LOCKHART & ASSOCIATES INC
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

$580,000
Reduced -$5,000
Provided courtesy of THE MARKET REALTY COMPANY

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 06-05-2026 7:58 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®.