Jackie O'Connor
As a top-producing real estate agent in Greater Boston, I’ve spent over 21 years helping more than 1,200 families buy and sell with confidence. As Principal of Jackie O Real Estate at Keller Williams Metro Boston, my team consistently ranks in the top 5 Keller Williams Individual Teams in New England—earning recognition for record-breaking results in one of the country’s most competitive luxury markets.
Why hire a top-producing team? Being in the constant path of buyers and sellers means we can connect you directly to your dream home—or the ideal buyer for your property. From first-time buyers and seasoned investors to downsizers and relocating families, we deliver a seamless, strategic, and elevated real estate experience.
I hold accreditations as a Luxury Agent and a Certified Buyer Specialist with the National Association of Realtors, and I am proud to serve as the Luxury Liaison for Keller Williams Boston Metro. As a member of the Luxury Pro community, I maintain relationships with top-performing agents nationwide, giving my clients unique access to off-market opportunities and a network of qualified luxury buyers across the country.
I specialize in luxury sales and exclusive off-market opportunities, guiding clients through seamless suburban-to-urban transitions, downsizing strategies, and multi-property portfolio planning. With a deep understanding of tools like step-up basis and 1031 exchanges, I help clients maximize returns and diversify strategically—whether they’re buying their first home, investing in income properties, or reimagining their long-term real estate goals.
Relocation is another passion of mine. Having moved from Atlanta to Ann Arbor to Boston, I know firsthand the complexities of uprooting and resettling in a new place. My goal is to simplify the process, reduce stress, and amplify results so you feel confident every step of the way.
In addition to serving clients, I am an avid real estate investor with a portfolio of both long-term rentals and short-term rental properties. For my investor clients, my team offers full-service, “soup-to-nuts” care—including professional property management—to maximize performance and peace of mind.
Originally from Atlanta, I moved to Boston in 2000 while working for Delta Airlines. The South End’s Victorian architecture, vibrant energy, and proximity to the ocean quickly drew me in. Since 2013, I’ve proudly called the South End home, with Newburyport as my coastal retreat since 2017. Travel remains a personal passion, rooted in my flight attendant days, and has shaped my ability to connect with people from all walks of life.
Clients describe me as trustworthy, resourceful, responsive, and highly effective. Their repeat business and referrals remain my highest compliment. If you are looking for a Boston Realtor who combines local expertise, national reach, and luxury-level service, I’d be honored to help you write your next real estate success story.
