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.
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1 Brogden Court
Winter Haven, FL 33880
Brogden Point Rep
Residential
MLS# L4960380 / Active
Custom-built by Hulbert Homes, known for exceptional quality and craftsmanship, this one-of-a-kind 4-bedroom, 3-bath residence is situated on nearl...
Reduced -$9,900
4 Casarena Court
Winter Haven, FL 33881
Casarena On the Lakes
Residential
MLS# P4938356 / Active
This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake ...
Reduced -$5,000
2954 Plantation Road
Winter Haven, FL 33884
Cypress Plantations
Residential
MLS# P4938830 / Active
PRICED BELOW RECENT APPRAISED VALUE OF $795,000 APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportun...
2935 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantation
Residential
MLS# L4959891 / Active
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...
2964 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantations
Residential
MLS# O6352519 / Active
Welcome to this refined sanctuary where timeless elegance meets Floridas tranquil landscape. On a premium golf-adjacent lot within the guarded, gat...
Reduced -$20,000
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...
100 Alachua Drive
Winter Haven, FL 33884
Eloise Woods Lake Mariam Unit
Residential
MLS# B4902232 / Active
One or more photo(s) has been virtually staged. Wonderful opportunity to live in a Florida lifestyle property with two (2) ($1800 total) income-pro...
Reduced -$10,100
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 -$2,000
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...
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
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MLS IDX data last updated on 06-05-2026 7:58 PM EST.
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