Skip Riddle

Real Estate Advisor

Meet Skip

Skip Riddle is a proud native of Marco Island, Florida, where he was born and raised. Growing up on the island, Skip spent his time enjoying the beach, fishing with his grandfather—who was a Charter Fisherman—and playing sports. His deep-rooted connection to Marco Island gives him an insider’s knowledge of the area, making him the perfect guide for clients looking to navigate the local real estate market.

After graduating from Lely High School, Skip attended the prestigious United States Military Academy at West Point. After graduation, he served as an Officer in the United States Army for 24 years, including multiple deployments to Iraq and Afghanistan. Throughout his military career, Skip honed invaluable skills in leadership, discipline, initiative, and loyalty—qualities that have become the cornerstone of his work ethic and approach to client relationships.

After retiring from the Army, Skip transitioned into real estate, where he spent two years working with a small, Naples-based company. During this time, he helped homeowners successfully navigate the real estate process from listing to closing. Skip’s unique combination of military discipline, extensive real estate experience, and intimate knowledge of the local area allows him to offer his clients expert advice and personalized service.

When not helping his clients, Skip can be found cruising the Marco River on his boat with friends and family, watching the sunset over the Gulf, or exploring the Island’s shops and restaurants. He works alongside his wife, Michelle, who is also a member of the Bowers Group. Together, they have two children, Landon and Jace.

Whether buying or selling a home, Skip is committed to delivering a smooth, successful experience. His local roots, military background, and real estate expertise make him an exceptional resource for anyone looking to buy or sell property on Marco Island. Skip Riddle’s dedication and integrity are at the heart of everything he does, ensuring that every client receives the highest level of care and attention.

SUCCESS STORIES

See why my clients love working with me.

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"Denny's knowledge of the process of the market, especially pricing, was invaluable during our search and purchase. In addition, long after the transaction, he welcomes calls and inquiries regarding recommendations of tradespeople in the area. We are extremely grateful to Denny for his expertise. He really relieves any undue stress or worries about buying a place in an area one may not be totally familiar with. We really feel lucky to have worked with him and to have his continued support. The best REALTOR that we have ever worked with."

Mark & Stacia C.

"Both the buy and the selling process could not have gone any smoother or more rewarding financially. Pam and Molly were there every step of the way and treated us like we were their only client. Their advice led us to make the right decision every time. We would highly recommend them and have recently done that to a few of our neighbors."

Dan & Kyle M.

"I worked with Pam Maher during the purchase of our home and I found her to be smart, easy to work with, and extremely knowledgeable of the market. The transaction closed on time and the process was smooth."

Steve S.

"I reached out to Gina when my mom was looking to purchase a new home. Everything worked out perfectly with Gina doing all the work and communicating with the builders for mom. So, now I get to stop by and watch beautiful sunsets over the lake in a gorgeous new home. Gina, we can’t thank you enough."

Chris P.

"Michelle Riddle with the Bowers group has been amazing to work with! She’s very responsive, always available, and is meticulous in her work. She has great communication skills and you can rely on her to get the job done right! Of course, Denny is top notch and goes the extra mile as well! I’ve had the pleasure of working with him both as a buyer and seller. Thanks Michelle and Denny!"

Brandy S.

"Gina added a personal touch and attention to detail to help us sell the house quickly. The pictures and videos provided by the agency here are spectacular. Very happy to have Gina as our REALTOR."

Home Seller

"We’ve been working with Denny for a few years. He is always looking out for his clients and going the extra mile. When I was in Florida and my husband was up north he even helped my husband get flowers for me for Valentine’s Day. We recently closed on our dream home. Denny and his team made the experience easy and effortless."

Heidi V.

"We are pleased to recommend Denny Bowers most highly. He is deeply experienced, transparent, reliable, a pleasure works with. He went out of his way to find us the perfect. He is a pro's pro."

Julie K.

"Denny was quick to answer any calls or text messages, and sincerely cared about the sale of my house. He is genuine, honest, and professional, offers suggestions that I trusted, is a hard worker, knowledgeable, and goes out of his way to help. He goes over and above his service even when he was out of town for the care of his mother, he would answer the phone to assist me. I hope to live in my new home for many years, but if the time ever arises to sell, without a doubt I will call Denny to list it."

Jana W.

"Michelle was extremely professional. She kept us informed at every step, and always delivered what was promised, and on schedule. Could not have asked for a more pleasant real estate transaction. Thank you, Michelle."

Home Seller

"I felt extremely comfortable with his knowledge of North Naples. He is super-friendly, not pushy, and always willing to add new ideas to my search. He is prompt about answering emails and answering phone calls immediately. His honesty and communication are detailed and he always shows concern for the individual. Denny will make sure everything goes smoothly during the purchase and closing process. Any concerns he will address immediately. You are always in his hands, and never have to worry if something arises."

Karen G.

"Michelle is very responsive and goes above and beyond to help. She is very personable and professional at the same time. She is a person of integrity as well. We were the buyers in the transaction. I would use Michelle again."

Alicia S.

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