top of page

Together WE Ensure Your Clients' Success.

What O&H Offers You and Your Clients

OHRealtors BC -  J+J-01.jpg

O’Connor & Highland is consistently one of the highest-ranking Keller Williams teams in the New England Region. Led by John and Jason, the team represents buyers, sellers, investors, landlords, and renters throughout  Eastern Massachusetts, with a concentration in the Greater Boston metropolitan area. 


A long-time resident of Boston’s South End, John is an attorney, Certified Historic Properties Specialist, Certified Luxury Home Marketing Specialist, and a past member of the Keller Williams Boston-Metro Agent Leadership Council. John has been named one of the Top 20 real estate agents in Boston. Prior to entering real estate in 1995, John graduated, cum laude, from Colby College in 1985 and went on to obtain his J.D. from the George Washington School of Law in 1988.

A resident of Watertown, Jason is an active member of the Keller Williams Boston-Metro Agent Leadership Council, holds several designations including Realtor and Advanced Buyer Representative, and heads the office’s book club, selecting books that touch upon the enterprising spirit of real estate and the creation of work-life balance. Before becoming a licensed realtor in 2006, Jason graduated, cum laude, from Babson College in 2003, where he specialized in entrepreneurial studies and finance. 


Together since 2007, John and Jason have built a team of realtors who embrace their philosophy, that successful real estate businesses are built through relationships, not transactions. All agents on the team hold the designation of Accredited Buyer's Representative and believe that continuing education is key to future success. 


Delivering extraordinary service with exceptional results, O&H looks forward to the opportunity of working together with you and your clients! Let us know what markets you work in. We are always looking for the opportunity to make referrals for our clients moving out of our area! 

Boston and Beyond

While our office is in Boston, we cover all of Eastern Massachusetts.


In the Last 12 Months, O&H Has Generated





Historically, 10% of our business comes from agent referrals. O&H has given and received dozens of referrals over the years and it continues to be a priority and central tenet of our business plan.

What Agents Are Saying About Us

We've been a referral partner with O'Connor and Highland for almost 7 years now. We have sent quality referrals back and forth for years. 


Their team sets the expectation to their clients that they send our way and their referrals are always top notch!


On the outbound side, they have amazing systems for the referrals that we send to them and their follow up and delivery are second to none in the industry. This is my go-to team in and around the Boston area. 


I'm grateful to have this team as my business partner and look forward to many years of being in business together. 

Bill D'Entremont 

Team Leader of The D'Entremont Group 


I've been selling Real Estate for 19 years on the South Shore of Massachusetts.

We are currently a small team of 2 selling consistently over $20,000,000 in volume.

bottom of page