Meet Us
We Commit To You
O’Connor and Highland’s mission is to build deep understanding that results in meaningful relationships and successful transactions for our clients. We pursue our mission by asking you questions informed by our experience and sharing insights that help deepen our clients’ understanding. Insatiable curiosity is at the core of our personal and professional DNA. We lead by learning and learn by listening. Oh, and we like to have a little fun along the way!
We live and work in community
Our diverse team has strong roots in the communities we serve. This gives you the advantage of deep local knowledge to help you reach your goals effectively, whether on the buying or selling side of a real estate transaction.
John O'Connor
Principal
A licensed real estate broker since 1995 and an attorney since 1988, John is a long-time resident of Bostonʼs South End and one of the cityʼs Top 20 agents. John is also a Certified Historic Properties Specialist, Certified Luxury Home Marketing Specialist, and a past member of the Keller William Boston-Metro Agent Leadership Council.
​
In addition to being a Co-Founder and Principal of O&H, John is currently pursuing a Master of Divinity degree at Harvard Divinity School where he also serves as an intern chaplain. He’s also the owner of the team’s most distinguished moustache.
Jason Highland
Principal
A Co-Founder and Principal of O'Connor and Highland, Jason has been a licensed realtor since 2006 and has been practicing buyer and seller representation in greater Boston for over 14 years. With unbridled enthusiasm, intellectual curiosity, and a passion to do whatever it takes to find the optimal outcome, Jason and Team proudly assist hundreds of clients annually with their real estate needs.
Jason is an avid runner, reader, and golfer. He is a resident of Watertown and lives with his beautiful wife, their two children, and their family dog Sweetie.
A native Bostonian, Mark has had a varied work life with careers in law and education focused on helping people, with a devotion to client service. In addition to being an agent on the team, Mark oversees all team transactions both sales and rentals, which allows him to interact with all O & H clients.
Outside of the office, Mark is a devotee of Orangetheory Fitness and donates time and expertise to local charities.
A native of Puerto Rico, Wilfredo moved to Boston in 2013 to attend Northeastern University where he studied finance and economics. During his time there, he developed an interest in Real Estate and started his career by helping friends find apartments off-campus. After graduating in 2017, Wil decided to pursue a full-time career as an agent.
When he isn't working, Wil enjoys watching baseball and getting together with friends. In addition, he is an avid runner and takes every opportunity to leave town and go on New England road trips.
Her lifelong interest in real estate began going to open houses every Sunday with her family on the North Shore. She earned her bachelor’s degree from Holy Cross in Worcester, MA and is currently tackling her MBA part-time at Boston University. Brianna’s foray into real estate comes after a career in fundraising and philanthropy at both Dana-Farber Cancer Institute and Harvard Business School. Her education and career blend business acumen and thoughtful stewardship which fit seamlessly into real estate.
When Brianna is not working, she enjoys cooking, picnicking in the South End, and reading with her book club.
.jpg)
Bob Gill
Realtor Associate
Bob brings more than 30 years of experience in real estate consulting, new home construction, and residential remodeling. Before joining Keller Williams in 2007, he built his career with Coldwell Banker and DeWolfe Real Estate in Newton Centre.
A lifelong Bostonian, Bob has an insider’s perspective on the housing market across Greater Boston and Newton. He and his wife, Ginny, have personally moved 13 times—meaning they’ve been through 26 real estate transactions themselves. That lived experience allows Bob to truly relate to his clients and guide them with both expertise and understanding.
Beyond real estate, Bob is engaged in his community and serves on the boards of several nonprofit organizations at both the local and national level.
​Ginny has been helping clients navigate real estate since 2001, bringing with her a strong foundation in customer service from her earlier career in health care. A Newton native, she knows each of the city’s 13 villages and the unique lifestyle each offers.
With a background in interior design, Ginny adds an extra layer of insight for clients—whether it’s seeing the potential in a home or helping them envision how a space could truly fit their lives. Known for her care, attention to detail, and deep community knowledge, Ginny makes the buying and selling process feel both seamless and personal.
.jpg)
Conor Fitzgerald
Realtor Associate
A lifelong resident of Dedham, Conor's first experience in real estate came when he helped his now-wife sell her home as a For Sale By Owner. That project sparked an interest that eventually grew into a full-time career. Conor has spent over a decade in education, developing exceptional organizational and communication skills that now serve his clients every day. His background gives him a unique ability to explain the process clearly, negotiate effectively, and advocate honestly—always with his clients’ best interests at heart.
Outside of the office, Conor is active in the Boston Gaelic Athletic Association (GAA), enjoys traveling to Cape Cod, and spending as much time as possible with his wife, three children, and dog.
Located 8,444 miles away from Boston, Allen has been supporting the O&H team for over 6 years. Unlike the Wizard of Oz, you should pay attention to this man behind the curtain who keeps all our transactions moving forward.
​
A father of two, Allen loves spending quality time with his wife and two boys.
What Does Keller Williams Offer You?
Global Reach + Resources
With close to 200,000 agents in 52 Countries, KW is #1 in agent count, units and sales volume. The KW business model equips agents with a technological edge and the ability to offer customers whatever they wish.