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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

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

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

Sell Smoothly

Understand your options, timeline, and net proceeds, then tap our buyer bench.

Get Your Selling Plan

Buy Confidently

Know your all-in monthly budget and follow a clear roadmap to winning offers.

Start Your Buying Plan

Find Your Fit

Compare schools, commute, and microneighborhoods to make a choice you’ll love.

Explore Your Options

Our Listings

New

346-354 Congress St U:607

1 1 Bedroom
1.5 1.5 Bathroom
901 Ft.2

Condo

$1,049,000

New

22 Martin U:22

3 3 Bedrooms
1 1 Bathroom
1,400 Ft.2

Condo

$719,000

New

233 West St

3 3 Bedrooms
2 2 Bathrooms
1,760 Ft.2

Residential

$759,000

See All Listings

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
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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.

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Browse success stories
  • 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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