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 521-530 of 758
50 Photos 69 Enclave Drive Winter Haven, FL 33884

69 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 02
Residential

MLS# S5148089 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1682 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 02

Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community kno... 

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$300,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
59 Photos 1930 Austin Terrace Winter Haven, FL 33884

1930 Austin Terrace
Winter Haven, FL 33884
Woodpointe Ph 1
Residential

MLS# S5148834 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2544 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Ph 1

Welcome to 1930 Austin Terrace, located in the highly desirable gated community of Woodpointe in SE Winter Haven. Perfectly situated near Hwy 27 an... 

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$499,900
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
40 Photos 1985 Sarah Street Winter Haven, FL 33884

1985 Sarah Street
Winter Haven, FL 33884
Peace Creek Reserve
Residential

MLS# P4938491 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1874 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Peace Creek Reserve

Seller offering $10,000 toward buyer closing costs or interest rate buy-down with full price offer. Welcome to 1985 Sarah Street, a 2025-built home... 

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$306,000
Increase +$10,000
Provided courtesy of KELLER WILLIAMS REALTY SMART
51 Photos 116 Mandolin Drive Winter Haven, FL 33884

116 Mandolin Drive
Winter Haven, FL 33884
Mandolin
Residential

MLS# O6403313 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2248 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Mandolin

ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home o... 

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$365,000
Reduced -$5,000
Provided courtesy of LPT REALTY, LLC
45 Photos 780 Overlook Grove Drive Winter Haven, FL 33884

780 Overlook Grove Drive
Winter Haven, FL 33884
Overlook Rdg
Residential

MLS# L4960255 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1583 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Overlook Rdg

BUYER'S CLOSING COSTS PAID UP TO $10K ! HOMW WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searc... 

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$295,000
Reduced -$7,500
Provided courtesy of FLORIDA REAL ESTATE COMPANY
31 Photos 693 Squires Grove Drive Winter Haven, FL 33880

693 Squires Grove Drive
Winter Haven, FL 33880
Squires Grove Ph 2
Residential

MLS# TB8502032 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1690 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Squires Grove Ph 2

Welcome to this beautifully maintained newer home in the desirable Squires Grove community of Winter Haven! Built in 2022, this spacious 3-bedroom,... 

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$270,000
Reduced -$15,000
Provided courtesy of MARK SPAIN REAL ESTATE
39 Photos 811 22nd Street Winter Haven, FL 33881

811 22nd Street
Winter Haven, FL 33881
Hutton Rep
Residential

MLS# S5148769 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1408 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hutton Rep

""Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, makin... 

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$269,990
Provided courtesy of FLORIDA REALTY INVESTMENTS
32 Photos 554 Eagle Landing Boulevard Winter Haven, FL 33880

554 Eagle Landing Boulevard
Winter Haven, FL 33880
Eagle Lndg Ph I
Residential

MLS# O6402516 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1628 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Eagle Lndg Ph I

Welcome to modern comfort in the heart of Winter Haven! This meticulously maintained 4-bedroom, 2-bathroom home is a move-in-ready living space. Th... 

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$269,999
Reduced -$4,001
Provided courtesy of SPANN & ASSOCIATES REAL ESTATE
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 6103 Grey Heron Drive Winter Haven, FL 33881

6103 Grey Heron Drive
Winter Haven, FL 33881
Lakeside Landings Ph 01
Residential

MLS# O6403532 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1828 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Landings Ph 01

Welcome to 6103 Grey Heron Dr in Winter Haven, FL a beautifully maintained move-in ready home offering modern finishes, open-concept living, and st... 

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$304,999
Reduced -$1
Provided courtesy of BROKER HUB REALTY GROUP LLC

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 06-07-2026 9:27 AM EST.

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Specific Searches of Winter Haven Florida

55 Plus Homes For Sale Winter Haven FL
Golf Homes For Sale Winter Haven FL
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