Matt Dolan, Realtor
Matt Dolan
About Me

I am a licensed Realtor in Massachusetts. I moved to Marblehead from Alexandria, VA in 2008. Prior to joining Team Harborside, I spent 9 years as a real estate investor focusing on long-term portfolio projects, but I have also worked on flips, rehabs and foreclosures. I developed my real estate company while flying for Piedmont Airlines as a pilot on the De Havilland Dash 8. I joined Team Harborside to combine my energy and investing background with the team's years of real estate experience.

I attended Boston University (CLA 93) and majored in Philosophy. After BU, I worked for Waste Management, Inc. running the Special Events division in Washington, D.C. I then became a pilot and moved around the East Coast with my wife Jenna, who is also a pilot. Jenna flew AV-8B Harriers for the Marine Corps serving two tours in Iraq. We have two children and live in Marblehead.

If you are looking for real estate on Boston's North Shore, I would be glad to assist. (617.816.1909 || matt@harborsiderealty.com):



25 Things that you might not know about me ...or even want to
  1. I proposed to my wife in a DHC-6 Twin Otter turbo prop in front of our friends and then we jumped out of it.

  2. I once met George Bush Sr. and Arnold Palmer at the same time in a golf cart.

  3. I like punk music, but also really enjoy the baroque period.

  4. I was diagnosed with cancer the week before my son was born. It was Lance Armstrong's cameo in "Dodgeball" that kept me laughing through the ordeal.

  5. I have supported my wife's career in the Marine Corps and have been a proud member of the Officer's Wives Club. I have also volunteered for Navy-Marine Corps Relief Society, The Key Volunteers, the OWC, and also participated in the "Adopt a Single Marine Program" during Operation Iraqi Freedom.

  6. I have spent my birthday with friends on a sunken German U-boat at 120 ft. (U-352)

  7. I have an artificial lens in my left eye as a result of my Crohn's disease.

  8. My daughter is named in honor of 2nd Lt. Lara D. Vincent, USMC. A marine pilot and a good friend killed serving her country.

  9. I broke my right arm in a martial arts tournament that I didn't win.

  10. I went to TC Williams HS, the school in the movie "Remember the Titans" Coaches Boone and Yost were my gym teachers.

  11. As a parachute rigger, I logged 5 saves. 5 Skydivers had to open my reserve pack job in order to save their lives. They all lived.

  12. I spent a summer taking pictures of Sand Tiger Sharks off on North Carolina.

  13. As an airline pilot, I flew over the twin towers in NYC 30 minutes prior to the attack on 9/11/2001. I took a picture of them not realizing how significant that would be.

  14. I grew up sailing on the Chesapeake Bay. It is in my blood, but I pursued other interests and have forgotten much about sailing. I have the deepest respect for the ocean and sailing around Marblehead.

  15. I had a near death medical experience in college. I'm just thrilled to be alive.

  16. I have lived in several different areas around the east coast. I have met many wonderful people along the way and am a better person for it.

  17. I saw my first Beanpot in the old Garden.

  18. I won the first bagpipe competition I ever entered. I was very lucky. Although I have been taught to play well, I'm not a good player.

  19. My son Sean first learn to hold a stick from a NHL player in our backyard. He was only 2 at the time so he couldn't really appreciate it.

  20. I loved rowing in HS and competed at several Nationals. I got out of it in college because I'm only 5'9"

  21. My wife and I used to love riding our Ducati motorcycles at the race track. They started our children's 529 accounts.

  22. I have been on the set of CNBC's Fast Money during a live broadcast. We didn't sit at the desk till the show was over.

  23. I loved flying the Dash-8. The airplane was fun and the people were great.

  24. I wrote a letter asking the Dropkick Murphys to send my wife an autographed photo while she was deployed with the Marines. They did it. I thought that was cool.

  25. I like old things that are blended with the modern.