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 311-320 of 789
60 Photos 5312 Nicklaus Drive Winter Haven, FL 33884

5312 Nicklaus Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# O6411968 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1700 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet an... 

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$334,900
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
54 Photos 5197 Pebble Beach Boulevard Winter Haven, FL 33884

5197 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4937220 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1677 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

Don't miss out on this opportunity to reside in a home located on the WEST golf course in Lake Ashton. FURNITURE AVAILABLE! GOLF CART INCLUDED! WAS... 

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$340,000
Reduced -$5,000
Provided courtesy of LAKE ASHTON REALTY INC.
70 Photos 1394 Oakmont Drive Winter Haven, FL 33884

1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential

MLS# L4961930 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amen... 

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$549,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
47 Photos 1347 Oakmont Drive Winter Haven, FL 33884

1347 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2 South
Residential

MLS# L4960249 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1712 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2 South

Are you looking for a move-in ready home? Well, you found it! This home is like a new build, only better. It is clean as a whistle, has tasteful li... 

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$384,900
Provided courtesy of CHARLES RUTENBERG REALTY ORLANDO
43 Photos 6308 Pinehurst Loop Winter Haven, FL 33884

6308 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# A4678252 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton ... 

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$459,900
Reduced -$5,000
Provided courtesy of FLATFEE.COM
70 Photos 6261 Pinehurst Loop Winter Haven, FL 33884

6261 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# L4959857 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2512 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Live the lifestyle youve been dreaming about in Lake Ashton, Winter Havens premier 55+ gated community. This beautifully cared-for Ashton floor pla... 

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$585,000
Provided courtesy of LOCKHART & ASSOCIATES INC
69 Photos 6216 Pinehurst Loop Winter Haven, FL 33884

6216 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# P4937694 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Stunning Sebastian Floor Plan Home in an Exclusive, Secure 55+ Florida Community, Lake Ashton. Discover this exceptional single-family home built i... 

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$459,000
Provided courtesy of LAKE ASHTON REALTY INC.
70 Photos 1209 Sawgrass Drive Winter Haven, FL 33884

1209 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# P4937555 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II South

Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer wil... 

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$439,000
Reduced -$11,000
Provided courtesy of LAKE ASHTON REALTY INC.
33 Photos 1108 Sawgrass Drive Winter Haven, FL 33884

1108 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# S5149437 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1533 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II South

This is a must see charming oasis located behind the secure gates of Lake Ashton, you dont want to miss this opportunity of becoming an homeowner i... 

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$422,999
Reduced -$2,001
Provided courtesy of LA ROSA REALTY CENTRAL FLORIDA LLC
70 Photos 221 Golf Aire Boulevard Winter Haven, FL 33884

221 Golf Aire Boulevard
Winter Haven, FL 33884
Lake Bess Country Club
Residential

MLS# L4959992 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1645 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Bess Country Club

MILLION DOLLAR GOLF COURSE VIEW out your back windows! No back yard neighbors ...JUST the peaceful golf course. BRIGHT & Open Home features Split f... 

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$315,000
Reduced -$10,000
Provided courtesy of KELLER WILLIAMS REALTY SMART

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 06-20-2026 3:59 PM EST.

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


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