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.
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.
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 global citizen, Kyle has lived in several different countries and US cities before settling down in Boston. Having such a diverse background enables him to connect and cater to people from all walks of life. His network has allowed him to facilitate deals not only in Boston but in Istanbul, Miami and NYC.
Kyle is a firm believer that the experience itself in any realm of life is the key to a happy & satisfied existence. He enjoys cooking, skiing, and traveling.
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.
After years in Boston’s fast paced hospitality industry, Robert’s heart and focus shifted to the Greater Boston real estate market, putting to use his passion for excellent service, high quality communication, and attention to detail from start to finish. Robert enjoys the deep and lasting connections he builds while guiding his clients through their real estate adventures.
His dog Brady, golf, and beach days on the Cape are what keep him busy when not in the office.
Kira has lived in Chicago and New York working in Fashion and Design before returning to her hometown of Boston to pursue real estate. She is able to work with clients to see the best aspects and potential of a home using her fine art skills in architecture and interior design.
In addition to being the newest member of O&H, she oversees the team’s social media pages on Instagram, TikTok, and YouTube. When she isn’t doing real estate she enjoys creating through cooking, designing clothes, as well as rediscovering all the best Boston has to offer.
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.
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.