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.
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4173 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4938419 / Active
Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing...
Reduced -$15,000
4925 Cypress Gardens Road UNIT #100
Winter Haven, FL 33884
Doves Rest Add
Residential
MLS# P4938418 / Active
Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Ai...
447 Village Circle
Winter Haven, FL 33880
Village Park
Residential
MLS# P4938447 / Active
This home is a must see!! Very well maintained home located in Village Park, a 55+ community where dogs are allowed. The home features new thermal ...
3890 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02
Residential
MLS# L4961088 / Active
Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, c...
4038 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# B4902243 / Active
Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many ameni...
6114 Grand Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential
MLS# L4961323 / Active
Virtually Staged. Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom...
Reduced -$5,100
1213 8th Street
Winter Haven, FL 33881
North Gate Village
Residential
MLS# L4961397 / Active
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 ...
Reduced -$10,000
333 Lake Howard Drive UNIT 203C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# L4961519 / Active
Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and th...
Reduced -$8,100
4253 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4938563 / Active
Move right into this fully furnished home. This home offers lots of space with walk in closets in both bedrooms and a new vanity in the primary bat...
3440 Grenville Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential
MLS# O6401312 / Active
Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan wit...
Reduced -$10,100
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MLS IDX data last updated on 07-14-2026 2:00 AM EST.
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