Jeffrey Kennedy

I first came to Sugarloaf as a college intern in the marketing department out of Penn State in 1982. After graduation my (soon-to-be) wife and I realized we really loved the area and decided to take the plunge, so we packed up and headed north to look for jobs. Wendy was offered a job running the switchboard for the Mountain, and I tended bar at Maxwell’s in the base lodge and worked in construction on the “new” Bigelow units. I quickly realized it made more sense for me to sell [...]

I first came to Sugarloaf as a college intern in the marketing department out of Penn State in 1982. After graduation my (soon-to-be) wife and I realized we really loved the area and decided to take the plunge, so we packed up and headed north to look for jobs. Wendy was offered a job running the switchboard for the Mountain, and I tended bar at Maxwell’s in the base lodge and worked in construction on the “new” Bigelow units. I quickly realized it made more sense for me to sell condos rather than to build them. After securing my real estate license, I joined Mountainside in February 1985. I’ve been “sold with the furniture” a few times, but have been here ever since. I grew up spending my summers on the ocean but have always had a love for the mountains. Maine is the perfect place to enjoy both. My sister had migrated to Maine a few years before me – she lived on a yacht and chartered day sails out of Boothbay in the summer. Maine offered us the opportunity to enjoy the best of both worlds, skiing all winter and sailing in the summer. From the very beginning, it has been the people that make Sugarloaf so special, and still is. We made lifelong friends that first winter and many of them are still here or continue coming back. Even after all these years, it is still exciting to help someone find that special place. It is a big deal to buy a second home and I get real satisfaction out of being a part of that moment in people’s lives. When I’m not finding just the right mountain home for my clients, I can be found out on the slopes. In the summer months, I enjoy being outdoors in this fantastic environment, doing everything from boating to hiking, mountain biking to fishing, and wonderful Maine coast. My family, wife Wendy of 39 years and two sons, Jordan and Parker, host the annual Kingfield Pops Festival at our place – the Kennedy Farm. This will be our 21st year and we are looking forward to many more, so mark your calendar - it is always the Saturday before the 4th of July. Three Favorites:  First tracks on a powder day. Skiing the corn on “the face” on a warm spring day. Getting out on the lakes in summer.