O'Connor & Highland - Greater Boston Realtors

09/25/2026

First-time homebuyer? 🏡 There are more programs out there than you might realize.

From down payment assistance to programs designed for specific buyers, it’s worth knowing what’s available before you start your search.

Not sure if any apply to you? That’s where we come in. We can help you figure out which programs may be relevant to your situation.

09/24/2026

Just a big fan of whatever vibe this is✨

And even more impressed by the homeowner who made it happen.

They snapped into gear, tackled a TON of prep themselves, and transformed this home before hitting the market. The kind of work we often recommend bringing in painters, handymen, contractors, etc. for… they just went for it.

Safe to say, it paid off.

The staging. The details. The vibes. Impeccable. 🤌

09/24/2026

Throwing it back to Photos in the Park 2017 🌷📸🌳

We’re bringing it back this October 3rd at the beautiful Arnold Arboretum, where we’ll be hosting clients and business partners for family portraits on us!

Looking back at these photos, some of the kids have completely transformed since 2017… but somehow Jason and John haven’t aged a day. 😂

Can’t wait to make some new memories (and take some updated family photos!) this year 🤍

09/22/2026

“Wait until Spring!” 🌷 But should you? We ran the numbers.

09/21/2026

09/14/2026

We took a break last week for the Labor Day holiday but we are back with and ready to help you with the fall market.

09/02/2026

Jason’s Advisors: Mike Mullaney of Titan Insurance 🏡

Insurance is one of those things you hope you never need, but when something goes wrong, having the right coverage matters.

Mike shares a real-life example involving a burst pipe and valuable artwork that highlights an important lesson: insuring your home for the right value can make all the difference when it comes time to rebuild or replace what you’ve lost.

It’s not just about having insurance. It’s about having the right insurance.

08/31/2026

Heading into Labor Day and the fall market, interest rates have edged up but there are deals to be had and dream homes to buy. We’re here.

08/27/2026

Buy or rent? 🏡

It’s not always as simple as one being better than the other. Your goals, finances, lifestyle, and how long you plan to stay all matter.

Brianna O’Brien breaks down the questions worth asking before making the decision.

The right choice is the one that makes sense for you and where you are right now.

08/26/2026

Happy Birthday to John O’Connor! 🎉

Co-founder, attorney, advisor, mentor, and one of the most thoughtful people you’ll meet.

John brings wisdom, perspective, and a genuine care for people to everything he does. We’re lucky to have his guidance, his humor, and his steady presence on our team.

Here’s to another year of good health, great conversations, and plenty of time with the people you love most.

Happy birthday, John! 🥂