Winter Haven FL Homes for Sale

Winter Haven FL Real Estate listings are included below. These homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "Request More Information" button on any property detail page. We'd love to answer any questions you have, and can provide the past sales history, tax information, and comparable sales for any listing. Let our team of professionals work for you!

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Displaying results 41-50 of 754
43 Photos 241 Greenfield Road Winter Haven, FL 33884

241 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# L4959462 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 2523 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot ... 

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$359,950
Reduced -$10,000
Provided courtesy of PORCHLIGHT HOMES LLC
52 Photos 460 Pinehurst Court Winter Haven, FL 33884

460 Pinehurst Court
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential

MLS# L4962087 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1660 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Patio Homes

Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida an... 

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$249,000
Provided courtesy of THE STONES REAL ESTATE FIRM
13 Photos 1601 Roselawn Street Winter Haven, FL 33880

1601 Roselawn Street
Winter Haven, FL 33880
Tranquility Park 02 Rep
Residential

MLS# O6356028 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 1099 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Tranquility Park 02 Rep

Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunni... 

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$256,500
Reduced -$500
Provided courtesy of LA ROSA REALTY PRESTIGE
70 Photos 4158 Rolling Oaks Drive Winter Haven, FL 33880

4158 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4938916 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1403 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contai... 

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$124,900
Provided courtesy of COLDWELL BANKER REALTY
49 Photos 1502 Buckeye Road UNIT #4 Winter Haven, FL 33881

1502 Buckeye Road UNIT #4
Winter Haven, FL 33881
Buckeye Heights
Residential

MLS# P4938057 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1257 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Buckeye Heights

One or more photo(s) has been virtually staged. A rare opportunity to own one of only six cluster homes positioned along the peaceful shoreline of ... 

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$219,000
Provided courtesy of STAR REALTY OF WINTER HAVEN
41 Photos 257 Meadowbrook Boulevard Winter Haven, FL 33881

257 Meadowbrook Boulevard
Winter Haven, FL 33881
Lucerne Park Reserve
Residential

MLS# P4937588 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1725 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Reserve

PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home ... 

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$287,950
Reduced -$2,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
38 Photos 6473 Peppertree Path Winter Haven, FL 33881

6473 Peppertree Path
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# P4938365 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1107 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

EASY TO SEE, SCHEDULE YOU'RE VIEWING NOW! NO LOT RENT HERE....YOU OWN IT! OFFERED PARTIALLY FURNISHED, KITCHEN APPLIANCES AND INSIDE LAUNDRY WASHER... 

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$146,000
Provided courtesy of COLDWELL BANKER REALTY
7 Photos 1540 Avenue C Winter Haven, FL 33881

1540 Avenue C
Winter Haven, FL 33881
Lake Elbert Heights Unit 02 02 Rep
Residential

MLS# R4909059 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1344 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake Elbert Heights Unit 02 02 Rep

Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank appro... 

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$245,000
Provided courtesy of MILLSHIRE REALTY
25 Photos 1151 Carefree Cove Drive Winter Haven, FL 33881

1151 Carefree Cove Drive
Winter Haven, FL 33881
Carefree Cove
Residential

MLS# TB8450979 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1734 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Carefree Cove

Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter H... 

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$425,000
Reduced -$10,000
Provided courtesy of HOMECOIN.COM
21 Photos
Open House: Wed Jun 10th, 11:00am - 2:00pm
109 Rebecca Drive Winter Haven, FL 33881

109 Rebecca Drive
Winter Haven, FL 33881
Saxon-Myers Rep Ph 02
Residential

MLS# L4957719 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1560 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Saxon-Myers Rep Ph 02

One or more photo(s) has been virtually staged. Beautifully remodeled in 2024, this move-in ready home offers modern updates, energy efficiency, an... 

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$239,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1

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 06-10-2026 8:43 AM EST.

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The Winter Haven Florida Real Estate listings included above are brought to you by David Shippey. 863-521-4517

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