David Shippey
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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 1-21 of 575
34 Photos 2124 N Lake Eloise Drive Winter Haven, FL 33884

2124 N Lake Eloise Drive
Winter Haven, FL 33884
Pope Prop
Residential

MLS# P4904423 / Active
5 br, 6 ba, 6951 sqft
area: Winter Haven / Cypress Gardens, subdivision: Pope Prop

Exceptional residence captures the beauty and tranquillity of Florida living at its best! Features; 5 Bedrooms & 6 Bathrooms, 6,951sf. With the cus... 

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$2,500,000
Provided courtesy of NORRIS & COMPANY REALTY, LLC
39 Photos 4015 Country Club Road Winter Haven, FL 33881

4015 Country Club Road
Winter Haven, FL 33881
N/a
Residential

MLS# L4902680 / Active
3 br, 4 ba, 1 half bath, 5509 sqft
area: Winter Haven / Florence Villa, subdivision: N/a

An absolute one-of-a-kind Equestrian Estate located on the scenic Country Club Rd in Winter Haven, FL. This stunning estate features 55+ Acres of s... 

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$2,195,000
Reduced -$200,000
Provided courtesy of CENTURY 21 MYERS REALTY
48 Photos 6081 Eloise Loop Road Winter Haven, FL 33884

6081 Eloise Loop Road
Winter Haven, FL 33884
Osprey Estates
Residential

MLS# P4903007 / Active
5 br, 5 ba, 2 half bath, 7206 sqft
area: Winter Haven / Cypress Gardens, subdivision: Osprey Estates

Gorgeous estate on the shore of Lake Winterset, the southernmost lake on the famed Winter Haven Chain of Lakes. 2.78 acres in neighborhood of exce... 

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$1,900,000
Reduced -$94,000
Provided courtesy of LOCKHART & ASSOCIATES INC
44 Photos 1775 Eloise Loop Road Winter Haven, FL 33884

1775 Eloise Loop Road
Winter Haven, FL 33884
N/a
Residential

MLS# P4902273 / Active
4 br, 4 ba, 1 half bath, 6041 sqft
area: Winter Haven / Cypress Gardens, subdivision: N/a

AN EXTRAORDINARY LAKEFRONT PROPERTY NESTLED AMONG 6.5 ACRES ON LAKE ELOISE AND IS ONE OF THE MOST SOUGHT AFTER "CHAIN OF LAKES" LOCATIONS! A stunni... 

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$1,750,000
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
48 Photos 2401 Cypress Gardens Boulevard Winter Haven, FL 33884

2401 Cypress Gardens Boulevard
Winter Haven, FL 33884
Eloise Woods
Residential

MLS# L4904335 / Active
6 br, 6 ba, 1 half bath, 6063 sqft
area: Winter Haven / Cypress Gardens, subdivision: Eloise Woods

One of a kind custom home built in 2015 on 1.5 acres of land located on the famous Chain of Lakes in Winter Haven. The home itself is incredible, b... 

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$1,350,000
Reduced -$25,000
Provided courtesy of SOHO RE AND CONSTRUCTION
48 Photos 3001 Crystal Beach Road Winter Haven, FL 33880

3001 Crystal Beach Road
Winter Haven, FL 33880
Bingham John A Jr Sub
Residential

MLS# P4903840 / Active
5 br, 5 ba, 9720 sqft
area: Winter Haven/eloise/jpv/wahnetta, subdivision: Bingham John A Jr Sub

This is a one of a kind lakefront home situated on nearly 1.5 acres of elevated land looking out over Eagle lake. With nearly 10,000 square feet of... 

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$1,299,000
Provided courtesy of LAKEFRONT INVESTMENT REALTY
25 Photos 3826 Gaines Drive Winter Haven, FL 33884

3826 Gaines Drive
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# P4715625 / Active
6 br, 5 ba, 1 half bath, 5400 sqft
area: Winter Haven / Cypress Gardens, subdivision: Gaines Cove

PRICE REDUCED-LAKEFRONT HOME! Now being offered below appraised value! The property you are inquiring about is located in Winter Haven, FL in the... 

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$1,299,000
Reduced -$101,000
Provided courtesy of Brokers Realty of Central Flor
42 Photos 2301 Cypress Gardens Boulevard Winter Haven, FL 33884

2301 Cypress Gardens Boulevard
Winter Haven, FL 33884
Eloise Woods
Residential

MLS# P4903828 / Active
5 br, 4 ba, 1 half bath, 6384 sqft
area: Winter Haven / Cypress Gardens, subdivision: Eloise Woods

Beautiful Mediterranean Estate on the Winter Haven Chain of Lakes. Enter property through wrought iron gates and into home through wrought iron fr... 

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$1,295,000
Provided courtesy of LOCKHART & ASSOCIATES INC
50 Photos 6075 Eloise Loop Road Winter Haven, FL 33884

6075 Eloise Loop Road
Winter Haven, FL 33884
Osprey Estates
Residential

MLS# G5009787 / Active
4 br, 4 ba, 1 half bath, 5341 sqft
area: Winter Haven / Cypress Gardens, subdivision: Osprey Estates

This stunning custom home is both a private oasis and an entertainer's dream! Nothing has been overlooked in this design, offering plenty of room f... 

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$1,199,999
Reduced -$100,000
Provided courtesy of RE/MAX TITANIUM GROUP
31 Photos 2002 Helena Road Winter Haven, FL 33884

2002 Helena Road
Winter Haven, FL 33884
N/a
Residential

MLS# L4902681 / Active
3 br, 4 ba, 1 half bath, 5200 sqft
area: Winter Haven / Cypress Gardens, subdivision: N/a

MAGNIFICENT Custom-built Lakefront Home located on Lake Eloise, one of many lakes connected to the famous Winter Haven Chain-of-Lakes. The home has... 

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$1,149,000
Reduced -$50,000
Provided courtesy of CENTURY 21 MYERS REALTY
25 Photos 116 Wyndham Drive Winter Haven, FL 33884

116 Wyndham Drive
Winter Haven, FL 33884
Wyndham At Lake Winterset
Residential

MLS# P4719669 / Active
8 br, 3 ba, 2 half bath, 9990 sqft
area: Winter Haven / Cypress Gardens, subdivision: Wyndham At Lake Winterset

**HUGE PRICE REDUCTION** ON THIS EXCEPTIONAL CUSTOM-BUILT LAKEFRONT HOME IN THE GATED AND GUARDED COMMUNITY OF WYNDHAM! Located on Lake Winterset w... 

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$1,100,000
Reduced -$199,000
Provided courtesy of Coldwell Banker Residential Re
25 Photos 1350 Mirror Terrace Winter Haven, FL 33881

1350 Mirror Terrace
Winter Haven, FL 33881
Haven Shores
Residential

MLS# P4718628 / Active
5 br, 4 ba, 2 half bath, 6330 sqft
area: Winter Haven / Florence Villa, subdivision: Haven Shores

Distinctive Chain of Lakes Estate. Home is situated on a peninsular lot with 700ft of lake frontage on Lake Mirror and Spring Lake. Offers; Grand ... 

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$999,999
Reduced -$25,001
Provided courtesy of Norris & Company Realty, LLC
49 Photos 5901 Dundee Rd Winter Haven, FL 33884

5901 Dundee Rd
Winter Haven, FL 33884
Commercial Banana Plantations
Residential

MLS# P4903430 / Active
4 br, 3 ba, 1 half bath, 3818 sqft
area: Winter Haven / Cypress Gardens, subdivision: Commercial Banana Plantations

CUSTOM COUNTRY ESTATE. 22+ acres for all your hearts' desire. Horses, cattle, and a multitude of other entrepreneurial possibilities. The property ... 

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$995,000
Provided courtesy of REAL ESTATE CENTRAL GROUP LLC
40 Photos 132 Wyndham Drive Winter Haven, FL 33884

132 Wyndham Drive
Winter Haven, FL 33884
Wyndham At Lake Winterset
Residential

MLS# P4904561 / Active
5 br, 5 ba, 1 half bath, 5091 sqft
area: Winter Haven / Cypress Gardens, subdivision: Wyndham At Lake Winterset

EXTENSIVE REMODELED SE LAKEFRONT POOL HOME! Situated beautifully on a .88 acre lot on Lake Winterset in the established gated and guarded community... 

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$929,900
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
25 Photos 2411 Cypress Gardens Boulevard Winter Haven, FL 33884

2411 Cypress Gardens Boulevard
Winter Haven, FL 33884
Eloise Woods
Residential

MLS# P4713514 / Active
3 br, 3 ba, 1 half bath, 3970 sqft
area: Winter Haven / Cypress Gardens, subdivision: Eloise Woods

MID-CENTURY MODERN ON WINTER HAVEN CHAIN OF LAKES. This 3 bedroom, 3.5 bath home with almost 4000 sqft. of living area offers lake view study, game... 

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$899,900
Provided courtesy of Better Homes and Gardens Real Estate By Design
50 Photos 1125 Avenue Z Winter Haven, FL 33884

1125 Avenue Z
Winter Haven, FL 33884
Na
Residential

MLS# P4903246 / Active
5 br, 4 ba, 2 half bath, 5178 sqft
area: Winter Haven / Cypress Gardens, subdivision: Na

Just Reduced over $20K! Come and look at the incredible Chain of Lakes property! 5 bedrooms, 3 full & 1 half baths home. A beautiful Oak-lined dri... 

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$899,900
Reduced -$20,100
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
50 Photos 2677 Wyndsor Oaks Place Winter Haven, FL 33884

2677 Wyndsor Oaks Place
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# P4904542 / Active
4 br, 5 ba, 4835 sqft
area: Winter Haven / Cypress Gardens, subdivision: Wyndsor At Lake Winterset

Award winning Luxury Home.Classic exterior design with stone accents, enormous circular brick paver drive. Open foyer with 14' stepped ceilings, fo... 

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$879,000
Provided courtesy of REAL ESTATE CENTRAL GROUP LLC
48 Photos 7550 Thompson Nursery Road Winter Haven, FL 33884

7550 Thompson Nursery Road
Winter Haven, FL 33884
Mallard Pointe Ph 02
Residential

MLS# P4903026 / Active
4 br, 3 ba, 2 half bath, 6388 sqft
area: Winter Haven / Cypress Gardens, subdivision: Mallard Pointe Ph 02

Gorgeous exec estate home on 2.35 acres of landscaped land. Unique prop has 3194 SF home w/3194 SF a/c basement (part. fin.) + a giant 2600 SF deta... 

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$849,000
Provided courtesy of LA ROSA REALTY, LLC
25 Photos 600 N Lake Eloise Drive Winter Haven, FL 33884

600 N Lake Eloise Drive
Winter Haven, FL 33884
N/a
Residential

MLS# P4900049 / Active
4 br, 2 ba, 1 half bath, 3560 sqft
area: Winter Haven / Cypress Gardens, subdivision: N/a

AN AMAZING SE LAKEFRONT BRICK HOME ON BEAUTIFUL LAKE ELOISE ON WINTER HAVEN'S FAMOUS "CHAIN OF LAKES!" This property is beautifully situated on 1.8... 

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$845,000
Reduced -$30,000
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
25 Photos 300 Brigham Road Winter Haven, FL 33881

300 Brigham Road
Winter Haven, FL 33881
Hartridge
Residential

MLS# O5702768 / Active
6 br, 5 ba, 5178 sqft
area: Winter Haven / Florence Villa, subdivision: Hartridge

DO NOT MISS THIS BEAUTIFUL, HISTORIC HOME SITUATED ON 2.89 ACRES OF LAND THAT OVERLOOKS THE PEACEFUL SHORES OF LAKE HARTRIDGE. LAKE HARTRIDGE IS PA... 

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$800,000
Provided courtesy of KELLER WILLIAMS HERITAGE REALTY
29 Photos 5 Skidmore Road Winter Haven, FL 33884

5 Skidmore Road
Winter Haven, FL 33884
Skidmore
Residential

MLS# P4716385 / Active
5 br, 5 ba, 2 half bath, 4800 sqft
area: Winter Haven / Cypress Gardens, subdivision: Skidmore

The property you are inquiring about is located in Winter Haven, FL in the Skidmore area of Polk County. Wow! New 2018 roof recently installed! Thi... 

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$799,000
Provided courtesy of Brokers Realty of Central Flor

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