Winter Haven Florida Homes for Sale

Winter Haven Florida Real Estate listings are included below. The Homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you would like to search more specifically in Winter Haven, scroll down the page to Specialty Searches such as 55+ Homes, Pool Homes, Golf Homes, Luxury Homes, Historic Homes, No HOA Homes, and Waterfront Homes. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "More Info" button on any property detail page.

Winter Haven is known for its 26 connecting lakes which are called the "Chain of Lakes". These lakes are great for boating, fishing & water skiing. It is also home to Legoland which offers a theme park & water park based around Lego themes.

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Displaying results 371-380 of 760
33 Photos 1108 Sawgrass Drive Winter Haven, FL 33884

1108 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# S5149437 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1533 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II South

This is a must see charming oasis located behind the secure gates of Lake Ashton, you dont want to miss this opportunity of becoming an homeowner i... 

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$422,999
Reduced -$2,001
Provided courtesy of LA ROSA REALTY CENTRAL FLORIDA LLC
51 Photos 4 Casarena Court Winter Haven, FL 33881

4 Casarena Court
Winter Haven, FL 33881
Casarena On the Lakes
Residential

MLS# P4938356 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3911 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Casarena On the Lakes

This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake ... 

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$524,000
Reduced -$5,000
Provided courtesy of LA ROSA REALTY PRESTIGE
62 Photos 131 Ruby Lake Drive Winter Haven, FL 33884

131 Ruby Lake Drive
Winter Haven, FL 33884
Ruby Lake Ph 01
Residential

MLS# P4938379 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1914 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ruby Lake Ph 01

One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a l... 

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$375,000
Provided courtesy of STAR REALTY OF WINTER HAVEN
23 Photos 607 Country Lane UNIT #607 Winter Haven, FL 33881

607 Country Lane UNIT #607
Winter Haven, FL 33881
Country Lake Condo Ph 01
Residential

MLS# P4938221 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1252 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Country Lake Condo Ph 01

WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE... 

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$149,500
Provided courtesy of FLORIDA HOME CHOICE REALTY
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... 

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$775,000
Provided courtesy of THE MARKET REALTY COMPANY
29 Photos 207 Avenue E Winter Haven, FL 33880

207 Avenue E
Winter Haven, FL 33880
Twin Oaks Add Pb 12 Pg 16
Residential

MLS# L4961631 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 2093 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Twin Oaks Add Pb 12 Pg 16

This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air B... 

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$425,000
Provided courtesy of ADVANTAGE REALTY 1
23 Photos 316 Lake Smart Circle Winter Haven, FL 33881

316 Lake Smart Circle
Winter Haven, FL 33881
Lake Smart Pointe
Residential

MLS# L4961472 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1500 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake Smart Pointe

This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be ... 

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$289,900
Provided courtesy of REMAX EXPERTS
13 Photos 1100 Martinique Drive UNIT #117 Winter Haven, FL 33884

1100 Martinique Drive UNIT #117
Winter Haven, FL 33884
Orchid Spgs Vill 300 Barcelona
Residential

MLS# S5135085 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 1078 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 300 Barcelona

PRICED TO SELL! Beautifully maintained 1-bedroom, 1-bath condo in the desirable Orchid Springs community. This ground-floor unit features an open l... 

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$95,000
Provided courtesy of LA ROSA REALTY LLC
67 Photos 200 Island Way Winter Haven, FL 33884

200 Island Way
Winter Haven, FL 33884
Orchid Springs Unrecorded
Residential

MLS# P4935447 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3555 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Springs Unrecorded

Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Esta... 

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$795,000
Reduced -$80,000
Provided courtesy of LOCKHART & ASSOCIATES INC
21 Photos 1700 6th Street UNIT A38 Winter Haven, FL 33881

1700 6th Street UNIT A38
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# P4935379 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 840 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of... 

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$79,800
Reduced -$2,700
Provided courtesy of BROKERS REALTY OF CENTRAL FLOR

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Specific Searches of Winter Haven Florida

55 Plus Homes For Sale Winter Haven FL
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Historic Homes For Sale Winter Haven FL
Luxury Homes For Sale Winter Haven FL
No HOA Homes For Sale Winter Haven FL
Pool Homes For Sale Winter Haven FL
Waterfront Homes For Sale Winter Haven FL