Jennifer Powell and Hannah Wilson-LeTendre, Sailing the Dream

About Sailing the Dream

Meet the Team

Let us make your real estate & lifestyle needs smooth sailing.

We teamed up in our real estate endeavors to offer a larger range of knowledge, experience, availability and expertise — two for the price of one! We collectively have 15+ years of experience, a sales management background, transaction coordination, rental management advice, and a huge passion and involvement in the community. Between our love for the outdoors, wining and dining, sports, and kids’ activities, we can help navigate the lifestyle you are looking for.

Sailing the Dream was founded on the belief that finding the right home is about more than the property itself. It is about understanding how clients want to live and helping them find a home and community that reflect that vision. As full-time Southwest Florida residents, we offer our clients a perspective that extends well beyond real estate: our knowledge of the area is shaped by how we experience it ourselves, from the beaches to sports, the outdoors, dining, family activities, community events, and the many opportunities to enjoy the Southwest Florida lifestyle.

At the heart of Sailing the Dream is a strong appreciation for family, friends, community, and loving the life you live. We take the time to understand not only what our clients are looking for in a home, but also the hobbies, passions, priorities, and everyday experiences that are important to them. Whether that means proximity to the water, an active tennis or golf community, opportunities for family activities, outdoor adventures, or being close to favorite dining and entertainment destinations, our goal is to help you find a place that truly reflects your lifestyle.

We believe buying or selling a home should be an exciting chapter rather than an overwhelming one. Through clear communication, attention to detail, and personalized service, we strive to make the experience feel seamless, enjoyable, and well supported from beginning to end. Sailing the Dream, because we want to make your dreams come true by making your real estate and lifestyle needs smooth sailing.

The Advisors

Jennifer Powell

Jennifer Powell

Real Estate Advisor · Bonnycastle Realty

License Number
SL3343525
Experience
10+ years

About Jenn

Jennifer Powell has called Naples home since her family relocated to Southwest Florida from Pennsylvania when she was 13. After completing her Bachelor at Muhlenberg University and her Master’s at The George Washington University, Jennifer’s desire to return to Naples and the Southwest Florida lifestyle remained strong, making it a natural choice to return and call Naples home permanently.

Jennifer began her career in real estate in 2013 in transaction management and became a licensed real estate professional in 2015. With over a decade in sales and nearly fifteen years in the industry, Jennifer provides her clients with valuable insight into every stage of a successful purchase or sale. Whether helping clients discover the right home and lifestyle in Southwest Florida or guiding them through the sale of a property that has been an important part of their lives, Jennifer takes the time to understand what matters most to each client. Her thoughtful approach, attention to detail, and consistent communication allow her to provide personalized guidance and make the experience feel both seamless and well supported.

In her free time, Jennifer enjoys spending time with her children JP and Taylor. A lifelong athlete, Jennifer also played collegiate tennis and continues to play several times a week.

Hannah Wilson-LeTendre

Hannah Wilson-LeTendre

Real Estate Advisor · Bonnycastle Realty

License Number
SL3452567
Experience
7+ years

About Hannah

Originally from North Carolina, Hannah Wilson-LeTendre has built a strong connection to Southwest Florida and the lifestyle that makes the area so special. Her thoughtful, people-first approach to real estate is rooted in understanding what matters most to her clients and helping them feel confident and well supported throughout their experience.

Hannah graduated from Palm Beach Atlantic University in 2015 with a Bachelor of Applied Science in Psychology. Her background in psychology has influenced the way she works with clients, particularly her ability to listen, understand individual needs and priorities, and build lasting relationships based on trust.

Since beginning her real estate career in 2019, Hannah has gained valuable experience across the many facets of buying and selling a home. She approaches each client relationship with care and attention to detail, taking the time to understand not only what her clients are looking for in a property, but also the lifestyle they hope to create around it.

For Hannah, that philosophy is personal. Family, community, and enjoying the place she calls home are an important part of her own life. Outside of real estate, she enjoys spending time with her husband, Rob, their Pomeranian Yogi and both sets of their parents who have also made Southwest Florida home. Hannah has not only found Southwest Florida living infectious but has grown her own community in the area with several family and friends deciding to move to the area to join in on all Florida living has to offer! As an avid beach goer, Hannah especially enjoys being on the water, shelling, fishing and exploring the natural beauty of the area.

Testimonials

We would highly recommend Jennifer, she is very efficient and very knowledgeable of the area, we were extremely satisfied having Jennifer represent us in finding our new home.

— Home Buyer · Naples
A schooner under sail on the Gulf of Mexico at dusk

Work With Us

We live full time and are involved in the community where we work. We listen to your lifestyle needs, and we make it a stress-free process — buying and selling homes can actually be a fun experience. Let us make your real estate and lifestyle needs smooth sailing.

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