Team Harborside is your go-to resource for North Shore real estate.
With decades of combined experience, Matt Dolan and Dick McKinley have developed a client-focused approach. It starts with the client’s objectives–not the goals of the agent or the temperature of the market. From there, the entire team works deliberately to plan out a strategy that will meet those objectives. Paired with unmatched expertise in the North Shore market, Matt and Dick’s philosophy allows them to position properties for maximum value within the region.
Let’s Work Together
Team Harborside works with buyers and sellers in a variety of scenarios across all areas of residential real estate, including condo conversions, new home construction, investment strategies and investor property acquisition.
A solid flight plan and a steady hand in unexpected weather served Matt Dolan well as a commercial airline pilot, and he carries those qualities with him in negotiations, marketing strategy and long-term outlook when it comes to serving his real estate clients. Just as he did in aviation, Matt uses discipline and forward planning to take clients from point A to point B, navigating the route carefully along the way.
Matt developed his real estate company while flying for Piedmont Airlines as a pilot on the De Havilland Dash 8. During that time, he spent over a decade as a real estate investor with a focus on long-term portfolio projects as well as flips, rehabs and foreclosures.
Matt’s wife, Jenna, is also a pilot; as a Colonel in the Marine Corps, she did two tours in Iraq flying AV-8B Harriers and today she flies an L39 for an airshow team. The couple moved to the North Shore, putting down deep roots that combined their love of the coastal lifestyle with their desire to give back to causes that were important to them.
Matt honors Jenna’s military service as one of the organizers of Operation Neptune. The annual fishing event, in collaboration with the Wounded Warrior Project, hosts soldiers who have been wounded in the line of duty to fish with local anglers.
Matt enjoys introducing clients to the North Shore lifestyle and is an active board member and past Commodore at the Dolphin Yacht Club in Marblehead. When he’s not negotiating deals you can catch him offshore fly-fishing and tuna fishing.
Dick McKinley has successfully taken his life from the (tennis) courts to the streets (and avenues and roads) of the North Shore. A former tennis professional, Dick’s combined competitive nature and dedication to teamwork has served him well as one of the North Shore’s top agents.
Prior to entering the real estate world, Dick started and built a variety of privately- and venture-funded tech startups. But his desire to make an impact on the North Shore community, his home, inspired him to become a founding partner of Harborside Realty. Dick’s vision helped drive the introduction of Sotheby’s International Realty to the local market.
Dick has spent countless hours combining his passion for people and properties, working with buyers and sellers and developing an in-depth understanding of how the local market works. As a fierce and competitive negotiator, Dick has forged ahead with a client-centric philosophy that sets him and his team apart in the North Shore real estate industry.
Dick’s sharp eye for the market has led him to be a sought-after resource for real estate sales from historic condos, modern oceanfront mansions or the marketing of new developments. He understands how to uniquely position properties in order to pair buyers and sellers.
As a true member of the community, Dick has coached youth sports, volunteered with a number of local organizations and most recently served as the President of the Chamber of Commerce. He can be spotted around the North Shore playing tennis or badminton, running, watching high school sports or simply enjoying all that North Shore life has to offer.
Born and raised in Massachusetts, Dana caught the real estate bug at a young age. She began investing in properties upon graduating college while working full-time in high-tech marketing. Her passion for the real estate industry grew as she learned and built up her portfolio – buying and selling all types of homes across the Boston area.
Drawing from years of hands-on experience in the field, she carved out a niche representing millennial clients across Boston and the North Shore. She specializes in assisting first-time home buyers and entry level investors.
Dana is a licensed real estate professional, a member of the National Association of REALTORS® and a columnist for the Zillow Group. Her work has been featured in countless news outlets, podcasts, and magazines.
As the Marketing Director for Team Harborside, she champions the Sotheby’s International Realty brand across the North Shore and drives the overall strategy and implementation of the team’s marketing efforts. In addition, she helps bring awareness to the team’s listings through exclusive promotional materials.
Meghan Carlin McGowan
Meghan comes from an education background having taught Writing and Literature to middle and high school students on the North Shore for over a decade. Armed with an energetic, compassionate and patient personality honed from spending an enormous amount of time with adolescents, her goal is to dramatically reduce any stress clients may feel in selling or buying their homes and is committed to making the experience relaxed and drama-free.
Meghan’s obsession with real estate emerged as a hobby while raising her three children in Marblehead where she was born and loved being raised. With her children now almost all teenagers, Meghan enjoys spending as much time with them as they will reluctantly agree to, inevitably leaving plenty of time for her to support Team Harborside’s clients through smooth real estate transitions.
Meghan has always been committed to giving back to Marblehead and other local communities by volunteering her time to non-profit organizations. She served on the Board of Directors at Marblehead Counseling Center for 8 years and currently serves on the Board of Directors at Family and Children’s Service of Greater Lynn, Marblehead Youth Hockey and is Co-President of the PCO at Marblehead Veterans Middle School. She is also certified as a level 1 Reiki Practitioner, is a sports and travel enthusiast and loves yoga, skiing, hiking and boating.
Andrew Oliver was born in London and moved to Marblehead in 1993.
His earlier career was in investment banking and he managed offices in London, Singapore, and Boston. He worked both as a research analyst and an investment banker specializing in capital raising.
Andrew is a graduate of Oxford University and serves as President Emeritus of Lifebridge North Shore.
After 9/11 (Andrew was in the World Trade Center in 1993 when the bomb went off and also the night before 9/11 in which 67 members of his company died) Andrew decided to retire and focus on his work as President of Lifebridge, where its plans for ending homelessness were hailed as “a model for the nation.”
In 2014 Andrew was appointed a Member of the Most Excellent Order of the British Empire (M.B.E.) for “services to homelessness in the United States”, and received the award from H.M. The Queen at Buckingham Palace.
Through his blog, www.OliverReports.com, Andrew is known for producing the most comprehensive and informed statistics and commentary on the real estate market, property taxes, mortgage rates and anything else that influences real estate decisions. Before starting OliverReports.com in 2012, he wrote 8 semi-annual reviews of the local property market for the Marblehead Reporter.
Andrew loves to help people achieve their dreams, whether in education, in life – or in real estate. He loves real estate and has bought and sold all types of property: condos, commercial property, and single-family homes, from starter to oceanfront.