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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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
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
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...
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 ...
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 ...
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...
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...
1280 W Lake Hamilton Drive
Winter Haven, FL 33881
N/a
Residential
MLS# L4961525 / Active
Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of...
445 Talamone Drive
Winter Haven, FL 33884
Tuscany At Winterset
Residential
MLS# P4938949 / Active
Nestled within the exclusive gated community of Tuscany, a charming neighborhood of just 18 homes in Southeast Winter Haven, this 4 bedroom, 3 bath...
Reduced -$10,000
472 Archaic Drive
Winter Haven, FL 33880
Village Spirit Lake Ph 01
Residential
MLS# L4962519 / Active
Lake-access living meets modern comfort in this beautifully updated corner-lot home. Welcome to 472 Archaic Drive, originally custom built, this up...
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MLS IDX data last updated on 06-19-2026 8:02 PM EST.
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