55 Plus Homes for Sale Winter Haven FL


Winter Haven FL Real Estate featuring 55 Plus Homes are listed below. These 55 Plus homes for sale in Winter Haven Florida are updated everyday from our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL 55 Plus homes for sale, please call 863-521-4517 or just click the "Schedule a Tour" or "More Info" button on any property detail pages.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 111-120 of 130
44 Photos 4511 Redwood Street Winter Haven, FL 33880

4511 Redwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# L4960495 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1152 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a pe... 

More Details

$113,000
Reduced -$2,000
Provided courtesy of LA ROSA REALTY PRESTIGE
46 Photos 1678 Linz Court Winter Haven, FL 33884

1678 Linz Court
Winter Haven, FL 33884
Vienna Square Ph 2c
Residential

MLS# L4960316 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1158 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2c

BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Squar... 

More Details

$258,500
Provided courtesy of COLDWELL BANKER REALTY
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... 

More Details

$384,900
Provided courtesy of CHARLES RUTENBERG REALTY ORLANDO
49 Photos 345 24th Street UNIT #23 Winter Haven, FL 33880

345 24th Street UNIT #23
Winter Haven, FL 33880
Imperial Villas
Residential

MLS# L4960143 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 942 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Villas

**PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well mainta... 

More Details

$170,000
Reduced -$14,900
Provided courtesy of COLDWELL BANKER REALTY
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

Experience the best of Florida resort-style living in this exceptional Ashton floor plan located in the sought-after Lake Ashton Golf Club Communit... 

More Details

$580,000
Reduced -$5,000
Provided courtesy of LOCKHART & ASSOCIATES INC
22 Photos 1700 6th Street UNIT C31 Winter Haven, FL 33881

1700 6th Street UNIT C31
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# L4959370 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 840 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully upda... 

More Details

$99,900
Reduced -$9,890
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
52 Photos 6086 Southern Oaks Drive Winter Haven, FL 33884

6086 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4959284 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1040 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Seller`s Motivated! Price just reduced! Welcome to 6086 Southern Oaks Drive SE, a beautifully updated and well- maintained, move in ready manufactu... 

More Details

$180,000
Reduced -$5,000
Provided courtesy of LOCKHART & ASSOCIATES INC
38 Photos 6081 Southern Oaks Drive Winter Haven, FL 33884

6081 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4959229 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1080 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6081 Southern Oaks Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks wh... 

More Details

$169,500
Provided courtesy of LOCKHART & ASSOCIATES INC
35 Photos 1700 6th Street UNIT C1 Winter Haven, FL 33881

1700 6th Street UNIT C1
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# L4958845 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 840 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to y... 

More Details

$109,900
Provided courtesy of HARPER REALTY FL, LLC
39 Photos 6644 Princeton Drive Winter Haven, FL 33881

6644 Princeton Drive
Winter Haven, FL 33881
Lake N Golf Estates
Residential

MLS# L4958289 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1296 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates

Welcome to Lake ‘N Golf Estates! This well-maintained 2-bedroom, 2-bath double-wide manufactured home is situated on 0.09 acres of land that you ow... 

More Details

$129,900
Provided courtesy of LIVE FLORIDA REALTY

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 07-13-2026 7:53 PM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

For a fresh updated list of 55 Plus Homes for sale in Winter Haven Florida, visit our website daily.

These 55 plus homes above are brought to you by David Shippey REALTOR®