About Us

Resort Home Experts

As the only agency located in the heart of Sugarloaf, the Mountainside Real Estate Brokers: Jeff Kennedy, Deb Pierce, Pat Tufts, and Sam Punderson have a wealth of experience and expertise, and can find the property that is just right for you and your lifestyle.

Sugarloaf is an area rich with an abundance of great natural beauty, and enhanced by the enthusiasm of the people we know as "Sugarloafers". Become part of this community and experience the camaraderie that makes Sugarloaf special.


Contact Us
Mountainside Real Estate
5092 Access Road
Carrabassett Valley, ME 04947
call toll free 877-237-2101
or send us an email

Deb Pierce

Deb Pierce


I was first introduced to Sugarloaf in 1974 by my husband, Steve. After many weekends visiting the area, I moved up permanently in December of 1975. 

From the very beginning I realized Sugarloaf was such a wonderful place to live and work. I started out doing administrative work in Marketing, moved on to Reservations and then obtained my real estate license in 1983. After working for a couple of local agencies, I was approached by Sugarloaf Mountain in 1992 as they had decided to reopen a real estate office. I am now in my 26th year as a Real Estate Agent. 

Sugarloaf is a very special place to me. I work with great people and love the opportunity to meet and work with people who are looking to be a part of the Sugarloaf Community and enjoy all that Sugarloaf has to offer. They are here for the purpose of enjoyment, family gatherings and their passion for outdoor activities. I am selling them a lifestyle - and it's always great to see them enjoying the area that I love. 

The Carrabassett Region is rich in natural beauty and has lots to offer in addition to the mountain, including the Outdoor Center with extensive cross country trails, The Sugarloaf Golf Course, the Carrabassett River and nearby lakes, as well as mountain biking trails. 

Outside of the office I enjoy skiing (although I don't get out there enough), boating, traveling, reading and spending time with friends. I am a member of the Town Board of Assessment Review and the Sugarloaf Design Review Committee. My husband, Steve, is very involved in the community as a member of the Board of Selectmen and as Games Director for the Winter Special Olympics held at Sugarloaf each year.

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Jeff Kennedy

Jeff 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 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 23 years and two sons, Jordan and Parker, host the annual Kingfield Pops Festival at our place - the Kennedy Farm. This will be our eleventh year and we are looking forward to many more, so mark your calendar, it is always the Saturday before the 4th of July, and in the spirit of the Sugarloaf community, it is open to all. 

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.

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Pat Tufts

Pat Tufts


In the late 70's, I came to Sugarloaf as a visitor for the season and decided to stay through the summer working for Keenan Auction Company. In 1997, I began working for Sugarloaf, first as manager at Sugarloaf Sports Outlet, then in the accounting department as budget co-coordinator for the resort. In the fall of 2005, I started selling hotel quarter shares and in 2007 started the seasonal rental division thru Mountainside Real Estate. 

This region has genuine salt-of-the-earth people that create a small-town friendliness - all set within the beauty of the mountains. Sugarloafers, in particular, are unique in their commitment and enthusiasm for the sport of skiing. Likewise in the summer, Sugarloaf's golf program is dedicated to teaching and sharing their love of the game, as I experienced when our son was part of the junior golf program. This area is extremely beautiful in the summer and fall. I love to see our guests boarding the "Moose Cruise" bus hoping to see a moose for the first time, and then seeing their joy when they do! 

Selling resort real estate, I like to create that same joy. The process of purchasing or renting a vacation property is exciting and fun for everyone involved. I love to help people find that special property that best fits their wants and needs. 

During my free time, I enjoy helping out with fund-raising activities and auctions for organizations like the Ski Museum of Maine, The Gifts of Love and The Stanley Museum. Otherwise, I'm happy spending time with my husband Tom, our son Michael, and walking our two yellow labs. 

Favorite Sugarloaf Happenings
Winter Special Olympics - In January each year Sugarloaf hosts The Maine Winter Special Olympics. It is truly a magical time as the spirit of the athletes help to remind us what really is important. I have many heart-warming memories that make me smile when I think about those weekends.

Kingfield Festival Days - A late July weekend every year the town and local groups sponsor many different family activities. The themed parade through town and the "What Ever Floats" Race are always my favorites.

Tufulio's Restaurant - Located in the Valley, it is my favorite restaurant any time of year.

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Sam Punderson

Sam Punderson


When I met my wife Kate in Vermont in the early ‘90's and took my first trip to the western Maine mountains, I knew then that Sugarloaf would play a big role in my life. Kate's parents, Peter and Martha Webber, were one of the first families to raise a family here at the mountain so our Sugarloaf roots run deep.

While living in Vermont I sold real estate for 7 years. I worked first with my father's agency, and then later ran a RE/MAX franchise. Real estate is the family business, as my father sold for 45 years, my sister has been selling for almost 2 decades, and my brother is a real estate attorney. Kate spent those years in Vermont coaching alpine skiing at Middlebury College (her alma mater), and also working in alumni relations and development.

Fourteen years ago we moved to Sugarloaf to pursue work at Carrabassett Valley Academy (CVA). I was hired to introduce the ALPS (Alpine Leadership Pursuits for Skiers and Snowboarders) program and for 8 years I led groups of CVA students around the world.

When the opportunity to work at Mountainside Real Estate arose, I knew this was the chance to align my personal and professional goals. Mountainside is the premiere agency at Sugarloaf and I was ecstatic to have the chance to join their experienced team. I enjoy the process of selling real estate because it allows me to utilize my strength of building relationships, to exercise my interests in marketing, and to experience the fun of introducing folks to their new properties.

Kate and I live on the Sugarloaf golf course and we find Carrabassett Valley an amazing place to raise our 10 year old son Calvin. Cal is a student at Stratton Elementary and Kate is the Head of School at CVA. We take advantage of all the recreational activities that the area has to offer, so if I can't be found in the office you can find me skiing on the hill, mountain biking the local trails, hiking the Bigelows, or poking around the local airspace in my small plane.

I look forward to working with you, and helping you grow your own Sugarloaf roots!

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