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O'Connor and Highland

Relationships, not Transactions

  • Why O+H
  • Our Listings
    • Open Houses
  • Make Your Plan
    • Homebuyer Roadmap
    • Selling With Clarity
  • Resources
    • Neighborhoods
    • Insights
    • Decision Tools
  • Contact
  • Why O+H
  • Our Listings
    • Open Houses
  • Make Your Plan
    • Homebuyer Roadmap
    • Selling With Clarity
  • Resources
    • Neighborhoods
    • Insights
    • Decision Tools
  • Contact

Clarity, Guidance & Proven Outcomes

A transparent process built around you—with results to match.

Book a 15-minute consult

What Sets Us Apart

We prioritize clarity, structured guidance, and social proof—so every decision feels informed and every step feels manageable.

"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

Our Process

“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.

From intake to closing, you’ll know what happens, when, and why. We make the complex feel simple—and we stay accountable to results.

Real Stories, Real Outcomes

Read how founders sold with minimal disruption, how first-time buyers won with confidence, and how families found their best-fit neighborhoods.

"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

Referral Network

See the trusted lenders, attorneys, contractors, and specialists who regularly collaborate with us to support smooth outcomes.

Book a 15-minute consult
  • Why O+H
  • Our Listings
    • Open Houses
  • Make Your Plan
    • Homebuyer Roadmap
    • Selling With Clarity
  • Resources
    • Neighborhoods
    • Insights
    • Decision Tools
  • Contact

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