Trailwinds Retirement Community

Trailwinds Retirement Community Wildwood's All-Inclusive Independent Senior Living Retirement Community Welcome to Worry-Free Senior Living in Wildwood! Schedule a tour and join us for lunch.

Trailwinds offers a relaxed lifestyle surrounded by Wildwood’s natural beauty and vibrant recreational options. Ideally located near several exceptional golf courses, Trailwinds is perfect for golf enthusiasts. Plus, the Villages, Brownwood Paddock Square, and Lake Sumter Landing are just a short drive away, offering plenty of shopping, dining, entertainment, and fun things to do. Trailwinds is all about comfort and enjoyment, making this all-inclusive senior community an easy place to call home. Discover why Trailwinds is the ideal choice for your next chapter.

09/22/2026

It’s finally fall, which means that the hectic holidays are right around the corner. This season, take the worries of cooking, cleaning, and other chores off your plate so you can focus on the moments that matter most — with the people who matter most! Happy Autumn Equinox!

09/13/2026

Today, we celebrate the grandparents who make life richer with their stories, laughter, love, and a little well-earned wisdom. ❤️
Here’s to making memories, enjoying every moment, and continuing to show us how it’s done.

Happy Grandparents Day!

Life is Sweeter at Trailwinds! Good Food, Great Friends, Unforgettable Moments!
09/09/2026

Life is Sweeter at Trailwinds! Good Food, Great Friends, Unforgettable Moments!

Game On! Laughter, Fun, & Friendly Competition at Trailwinds!
09/08/2026

Game On! Laughter, Fun, & Friendly Competition at Trailwinds!

Balance class with Penny helps us stay thriving, healthy, and active at Trailwinds 🙌
09/08/2026

Balance class with Penny helps us stay thriving, healthy, and active at Trailwinds 🙌

Strong, active, and going for it 💪 Staying fit, feeling great at Trailwinds!
09/08/2026

Strong, active, and going for it 💪 Staying fit, feeling great at Trailwinds!

The beauty of independent living is having the best of both worlds: the freedom to live life on your own terms and the j...
08/25/2026

The beauty of independent living is having the best of both worlds: the freedom to live life on your own terms and the joy of being part of a welcoming community. Each day brings new opportunities to connect, explore your interests, and enjoy meaningful moments with friends—because life's best experiences are even better when they're shared.

We recently enjoyed a fascinating lifestyle seminar, hosted by our Senior Living Consultant Brandon Butner! Brandon deta...
08/24/2026

We recently enjoyed a fascinating lifestyle seminar, hosted by our Senior Living Consultant Brandon Butner! Brandon detailed the many benefits of living in Trailwinds.

And one of our very own residents, Penny Knubley, spoke of her wonderful experiences as a charter resident and the many happy memories she's made so far.

The Charter Residents of Trailwinds have been busy making friends, enjoying activities, and indulging in fantastic happy...
08/24/2026

The Charter Residents of Trailwinds have been busy making friends, enjoying activities, and indulging in fantastic happy hours. Since we've opened, we've been building community while making the most of retirement for every single person who calls us home ❤️

08/21/2026

Today, we celebrate the generations who have filled a lifetime with experiences, lessons, laughter, and stories worth sharing. 💚

National Senior Citizens Day reminds us that every chapter brings something new to enjoy, discover, and look forward to.

Here’s to celebrating where you’ve been and embracing all that’s still ahead. Happy National Senior Citizens Day!

Address

6150 Seven Mile Drive
Wildwood, FL
34785

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