David Shippey
863.521.4517

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 our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL homes for sale, please call 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

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Displaying results 501-510 of 826
40 Photos 454 San Jose Drive Winter Haven, FL 33884

454 San Jose Drive
Winter Haven, FL 33884
Orchid Springs Patio Homes
Residential

MLS# TB8391563 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1667 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Springs Patio Homes

Fall in love with the laid-back Florida lifestyle! *** Brand NEW TILE ROOF scheduled for installation mid-August 2025 *** This standout 2-bedroom, ... 

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$250,000
Provided courtesy of KELLER WILLIAMS REALTY SMART
37 Photos 441 San Jose Drive Winter Haven, FL 33884

441 San Jose Drive
Winter Haven, FL 33884
Orchid Springs Patio Homes
Residential

MLS# P4934776 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1843 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Springs Patio Homes

Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expa... 

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$299,000
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY
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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$975,000
Provided courtesy of LOCKHART & ASSOCIATES INC
49 Photos 3217 La Salle Street Winter Haven, FL 33884

3217 La Salle Street
Winter Haven, FL 33884
Orleans
Residential

MLS# P4934123 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2797 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orleans

Discover your dream home! This gorgeous, better-than-new 4-bedroom, 2.5-bath residence, built in 2023, offers an impressive nearly 2,800 sq. ft. of... 

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$457,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
15 Photos 123 Osprey Heights Drive Winter Haven, FL 33880

123 Osprey Heights Drive
Winter Haven, FL 33880
Osprey Landings Ph 01
Residential

MLS# P4932769 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1329 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Osprey Landings Ph 01

Beautiful 3BR/2BA home in a gated community of Osprey Heights. All floors are covered with wood laminate. The Solar system is paid off and included... 

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$260,000
Reduced -$10,000
Provided courtesy of OSF REAL ESTATE SERVICE
39 Photos 181 Osprey Heights Drive Winter Haven, FL 33880

181 Osprey Heights Drive
Winter Haven, FL 33880
Osprey Landings Ph 02
Residential

MLS# TB8387334 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1328 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Osprey Landings Ph 02

Welcome to your 3 bedroom, 2 bathroom split bedroom home in the gated community of Osprey Heights with Solar panels. This property is located conve... 

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$270,000
Provided courtesy of THE SOMERDAY GROUP PL
37 Photos 3817 Osprey Pointe Circle Winter Haven, FL 33884

3817 Osprey Pointe Circle
Winter Haven, FL 33884
Osprey Pointe
Residential

MLS# L4951621 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1729 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Osprey Pointe

This 3 bedroom 2 bath home is located in Osprey Pointe, a waterfront community on Lake Ned. The eat-in kitchen has beautiful wood cabinets complete... 

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$299,900
Provided courtesy of COLDWELL BANKER REALTY
35 Photos 3806 Osprey Pointe Circle Winter Haven, FL 33884

3806 Osprey Pointe Circle
Winter Haven, FL 33884
Osprey Pointe
Residential

MLS# L4953618 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1635 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Osprey Pointe

Welcome to 3806 Osprey Pointe Circlea thoughtfully upgraded 3-bedroom, 2-bath home in one of Winter Havens most established and quiet communities. ... 

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$274,000
Reduced -$1,000
Provided courtesy of REMAX EXPERTS
48 Photos 209 Santa Rosa Drive Winter Haven, FL 33884

209 Santa Rosa Drive
Winter Haven, FL 33884
Overlook Estates
Residential

MLS# P4932531 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2338 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Overlook Estates

seller motivated !!Welcome to your dream Pool Home! Awesome Gated community. This 3/2.1 Pool home, is located in beautiful city of Winter Haven, Fl... 

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$360,000
Reduced -$20,000
Provided courtesy of LA ROSA REALTY PRESTIGE
42 Photos 808 Overlook Grove Drive Winter Haven, FL 33884

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

MLS# OM701080 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2093 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Overlook Rdg

Sparkling 4 bedroom, 3 bath home located on a quiet cul-de-sac with no rear neighbors. This spacious split-bedroom plan offers over a quarter-acre ... 

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$360,000
Provided courtesy of AT HOME REALTY

Broker Reciprocity The information being provided by © 2025 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 REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, 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 08-04-2025 7:29 PM EST.

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The Winter Haven homes above are brought to you by David Shippey REALTOR®.


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