Golf Membership Available! 2 BR/2BA, Pickleball, Pools, Near Gulf Beaches

Hi, we’re Jeff & Jess, along with our son JJ. We live here in beautiful Freeport, Maine and are the owners and operators of ProActive Properties. Since 2014, we have welcomed guests to some of our favorite destinations throughout Maine and beyond, helping families and travelers create memorable experiences together.

Travel and hospitality have always been a major part of our lives. Jeff is also the owner of ActivSport Travel, an international educational and sports travel company that has organized experiences around the world for schools, teams, and groups. Jess has an extensive background in education as a high school math teacher and has also led international educational travel programs. Our shared passions for travel, skiing, soccer, the outdoors, and exploring new places inspired us to create spaces where others can relax, reconnect, and make lasting memories.

This home is especially meaningful to us. We first discovered this property in the summer of 2014 while walking our beloved dogs, Gustav and Nelson, near Wolfe’s Neck State Park. From the moment we found it, we envisioned creating a peaceful coastal retreat where guests could truly experience the natural beauty, privacy, and charm of Maine.

We hope you enjoy your time here as much as we do. Whether you are kayaking along the coast, relaxing by the fire pit, exploring Freeport and Portland, or simply enjoying the quiet surroundings, we hope your stay becomes a special and memorable experience for you and your family.

Please make yourself at home and treat the property with the same care and respect you would your own. We have thoughtfully prepared the home and this guide to help you enjoy everything the area has to offer.

Thank you for staying with ProActive Properties. We truly appreciate your visit and hope to welcome you back again in the future.

Enjoy your stay!

Jess + Jeff

What makes this property unique is the opportunity to enjoy a true private country club lifestyle while staying in a comfortable and spacious ground-floor condo in the heart of North Naples. Cypress Woods is a bundled private golf community, which allows owners like us to transfer our membership privileges to guests staying 1 month or longer.

Guests who choose to transfer the membership gain access to the championship 18-hole golf course, 8 pickleball courts, tennis courts, fitness center, clubhouse restaurant and bar, community events, leagues, and resort-style amenities throughout the community. From May through October, the membership also includes reciprocal access to 61 additional private golf courses in the area, creating an incredible opportunity for golf enthusiasts.

Unlike many Naples vacation rentals, this property combines golf course views, private club amenities, convenient ground-floor access, and a prime North Naples location just 15 minutes from the Gulf beaches, shopping, dining, and entertainment.