A Clear Path to Selling, Buying, or Renting in Boston

Hi, I’m Jay.

I’ve loved Boston since before I ever lived here. A history teacher in Baltimore brought this city to life for me. I made my first trip north as a high school senior in 1999 to visit Babson University—and honestly, I never really left. I’ve lived all over the city and now call Watertown home.

My friends joke I remind them of Ted Lasso. I’ll take it. I care, I show up, and I genuinely believe people can feel the difference. Some might say I’m annoyingly optimistic!

I live by three values—faith, family, and wellness—and for me wellness means something broader than most people think. It’s your health, your relationships, your presence, your experiences, your financial investments, and the life you build around the people you love.

My big why has always been the same: to be a positive spark, a tailwind, for the people in my life. I believe each of us carries boundless potential—and that our mission and purpose is simple, even when it isn’t easy: to love, to be good, and to bring light to the world.

Outside of work I’m a husband and dad, a marathon runner, a golfer, amateur chef, an avid reader, a coach to my daughters Mackenzie and Claira, active in my faith community, and a novice guitarist. I have a passion for living a full and healthy life!

My hope is that you’ll consider O’Connor and Highland for your real estate needs not because of what we know or the resume we have, but for who we are and what we stand for.

We’d love to be a small part of your story.

– Jay

Clarity, guidance, and proven outcomes for Greater Boston moves. Wherever you are in the process, we make the next step simple and confident.

Our Listings

Active

45-47 Barnard Ave

7

3

2,890 Ft.²

Multi-Family

$1,599,000

Active

12 Isabella U:2

1

340 Ft.²

Condo

$479,000

Contingent

28 Highland Ave U:4

1

546 Ft.²

Condo

$529,000

See All Listings

Real Insights

The First Brick in the Wall: How John turned patience into property—and property into a plan

The First Brick in the Wall How John turned patience into property—and property into a plan The Setting: Quiet Discipline Before the Spotlight Before there was a closing, there was [...]

The Trade-Up Playbook: Joshua & Jessica’s move from “cool condo” to “family-ready home”

The Trade-Up Playbook Joshua & Jessica's move from “cool condo” to “family-ready home” The Setting: A Life That Outgrew Its Shell Joshua's condo near downtown Salem had personality in spades. [...]

Closing the Chapter: Navigating Estate Sale with Strategy, Sensitivity, and Speed

Closing the Chapter Navigating Estate Sale with Strategy, Sensitivity, and Speed The Situation: When a House Is More Than an Asset For Jessica, stepping into the role of Personal Representative [...]

Raving Fans

“O’Connor & Highland’s expertise in the greater Boston real estate market really sets them apart. They guided us through every step with confidence, care, and precision. And they grow with their clients. After helping us buy and sell several times in the Back Bay and Beacon Hill, they are now working with our son, helping him sell his existing home in the Seaport and buying a new one in Charlestown. O&H — it’s a team you can trust for every stage of life.”

K.O.

"We are absolutely in love with our new home and neighborhood. The O+H team brings a refreshing blend of enthusiasm, honesty, integrity, and "down-to-earth" attitudes. The combination of leadership, innovative approaches, and strategic insights led to a highly successful selling and buying experience in an extraordinarily competitive post-COVID market. Mark B. and Jason H. have been great throughout and we cannot recommend enough."

Greg & Fahema

"We met Jason while co-coaching Watertown Youth Girls Soccer. Our kids were getting too old to share a room, so we were looking for a bigger home with outdoor space and a more flexible floor plan. The challenge was finding and then winning a single-family in Boston's competitive suburban market - think David Blaine holding his breath for 17 minutes kind of hard! Luckily, O&H knew exactly what to do.

After doing a deep dive to better understand our needs, Jason crafted the best strategy to win. And on just the second try, we beat out the competition and secured an amazing home in the neighborhood we desired. But the work was only halfway done! O&H then successfully staged, photographed, priced, and marketed our current condominium. In less than 1 week, O&H generated multiple offers, with the winner being almost 10% above the listing price!"

Pierre & Inbal

"O&H is the calm in the storm. This was my first time selling a property and I felt extremely confident with them in the driver’s seat. They knew my neighborhood inside and out and my condo sold after our first showing! In the middle of all this, they found me a perfect app to keep me on track for my future plans. I would recommend O&H to a friend or family member in a heartbeat and will always go to them for any future real estate adventures. In addition to being excellent at what they do, they are fun and kind. Five stars!"

Renee

"O’Connor and Highland are truly exceptional. They provided knowledgeable analysis of the market and secured the best possible price. Should we ever decide to sell our new home, we will not shop again. We will simply ask John and his team to help us."

George

I honestly thought I was going to have a tough time selling my house in the South End. When John told me I had ten offers on my house in two days I thought he was joking. He wasn’t, and by the time the house was under agreement three days later, I had an offer $50,000 over my asking price. I would attribute the fast sale and offer price directly to John’s marketing savvy.

D. L.

Events & Guides

See What’s Happening

From education, to open houses, to our community events; check out what’s going on with O+H in the next several months!

See the Events!

Let's Get Your Journey Started

Ready to take the next step? Book a 15-minute consult and let’s map your path.

Book a 15-minute consult

Browse success stories