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 281-290 of 769
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

HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Hav... 

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$272,500
Reduced -$22,500
Provided courtesy of FLORIDA REAL ESTATE COMPANY
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
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
33 Photos 2656 Wyndsor Oaks Way Winter Haven, FL 33884

2656 Wyndsor Oaks Way
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# TB8501985 / Active
5 Beds, 5.00 Total Baths, 5 Full Bath, 3703 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndsor At Lake Winterset

Discover refined living in Wyndsor at Lake Winterset, one of Winter Havens premier gated communities. Set on a half-acre lot, this beautifully main... 

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$750,000
Provided courtesy of HOMECOIN.COM
25 Photos 3147 Whispering Trails Street Winter Haven, FL 33884

3147 Whispering Trails Street
Winter Haven, FL 33884
Whispering Trails Ph 01
Residential

MLS# O6402822 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1303 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Whispering Trails Ph 01

Unlock the possibilities with this 3-bedroom, 2-bath home offering 1,303 sq ft in a gated Winter Haven community. Perfect for investors or buyers r... 

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$215,000
Provided courtesy of NEWBERRY REALTY & DEV GRP INC.
33 Photos 12 Cherry Blossom Lane Winter Haven, FL 33884

12 Cherry Blossom Lane
Winter Haven, FL 33884
Sundance Ranch Estates
Residential

MLS# O6401292 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2100 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Sundance Ranch Estates

Welcome to Sundance Ranch Estates! This well-maintained 3-bedroom, 2-bath home sits on 5 acres and offers the ideal balance of country living with ... 

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$610,000
Provided courtesy of VESTI LLC
27 Photos 218 Dennis Avenue Winter Haven, FL 33880

218 Dennis Avenue
Winter Haven, FL 33880
Jan Phyl Village Unit 03 A
Residential

MLS# L4961409 / Active
3 Beds, 1.00 Total Baths, 1 Full Bath, 1174 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Jan Phyl Village Unit 03 A

Move-in ready, this charming 3-bedroom, 1-bath block home sits on a spacious lot with no rear neighbors, offering added privacy and peaceful surrou... 

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$246,900
Provided courtesy of LIVE FLORIDA REALTY
35 Photos 2213 Rose Boulevard Winter Haven, FL 33881

2213 Rose Boulevard
Winter Haven, FL 33881
Buckeye Rdg
Residential

MLS# L4961368 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1851 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Buckeye Rdg

Welcome to 2213 Rose Blvd in Winter Havena beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable... 

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$299,900
Provided courtesy of THE STONES REAL ESTATE FIRM
29 Photos
Open House: Wed Jun 24th, 1:00pm - 3:00pm
1213 8th Street Winter Haven, FL 33881

1213 8th Street
Winter Haven, FL 33881
North Gate Village
Residential

MLS# L4961397 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 972 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: North Gate Village

Virtually Staged. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community ready for a new owner. Single-level, move-in ready ho... 

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$199,900
Provided courtesy of KELLER WILLIAMS REALTY SMART
44 Photos 256 Meredith Boulevard Winter Haven, FL 33881

256 Meredith Boulevard
Winter Haven, FL 33881
Willowbrook
Residential

MLS# G5111558 / Active
5 Beds, 3.00 Total Baths, 3 Full Bath, 2531 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Willowbrook

Virtually Staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf cou... 

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$339,990
Reduced -$35,000
Provided courtesy of OLYMPUS EXECUTIVE REALTY INC

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 06-16-2026 7:58 PM 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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