John O'Connell

With more than 30 years of experience in real estate, John O’Connell brings a rare

blend of deep market knowledge, personal investment insight, and high-tech sales

expertise to buyers and sellers across Martha’s Vineyard, Cape Cod, and the South

Shore of Massachusetts. Originally entering the industry as an investor, John’s

curiosity and passion for the business led him to become a sales agent in the mid-90s

and ultimately earn his Broker’s license in 2007. He works with clients at every stage -

from first-time homebuyers to seasoned luxury purchasers - offering straightforward

guidance and clear education on the unique considerations of coastal living, including

his extensive expertise in the true costs and responsibilities of second-home ownership.

Known for his practical, informed approach, John draws on decades of hands-on

experience as a project manager, personal investor, and investment homeowner to help

clients make confident, well-informed decisions.

Beyond real estate, John brings the same dedication and drive that defined his athletic

and community pursuits. A pioneer in the triathlon community and long-time

professional competitor in the sport, he carries a disciplined, goal-oriented mindset into

every client relationship. He is a past certified U.S.A. hockey and triathlon coach, and

an

active member of the MV Surfcasters Association, Cycling Club of Marthas Vineyard,

and Amity Island Running Club. John is an active volunteer and fundraiser for

miscellaneous local events

including the Boy Scouts of America where he helped head their annual Christmas

tree pick up drive for many years. Whether guiding families through a major life

transition or helping

investors identify the right opportunity, John is committed to delivering a relationship that

is experienced, knowledgeable, and trustworthy - the foundation of the reputation

he continues to build throughout the region.

John applies the same unwavering dedication and motivation that shaped his

involvement in athletics and community initiatives to his professional endeavors. As a

pioneer within the triathlon community and a long-standing professional competitor, he

brings a disciplined, goal-oriented mindset to every client relationship.

His leadership extends beyond competition, having served as a certified U.S.A. hockey

and triathlon coach. John remains actively involved as a member of several

organizations, including the MV Surfcasters Association, Cycling Club of Martha’s

Vineyard, and Amity Island Running Club.

John is also an engaged volunteer and fundraiser for a variety of community events,

notably supporting the Boy Scouts of America by helping lead their annual Christmas

tree pick-up drive. Whether guiding families through significant life transitions or

assisting investors in identifying the right opportunities, John is dedicated to fostering

relationships that are experienced, knowledgeable, and trustworthy—qualities that form

the foundation of the reputation he continues to build throughout