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Jackie O Real Estate Team, led by Jackie O'Connor with agents Sydney O'Keefe and Kim, works Greater Boston buying, selling and renting out of a Back Bay office under Keller Williams. Forty-nine Google reviews run from 2021 through a July 2026 write-up, every one five stars, and the more telling number isn't the streak — it's how many names repeat. A 2025 review describes working with Jackie for more than a decade; a 2021 review describes buying two homes, selling a condo, and completing multiple rentals with the team over the years. The reviews with the most detail describe complications other agents might hand off. A 2021 review describes selling a condo that was part of an estate, complicated by the early-COVID timing and the client's responsibilities to the estate. A 2022 review from a client who'd already bought and rented with the team describes their house staged and listed within 10 days of the first meeting and sold the same weekend it went up. A 2025 review describes Jackie visiting a client's condo before a contract was even signed to recommend pre-listing improvements, then lining up painters and stagers and personally meeting them on site to check the work. More recent reviews (from this year) follow a similar thread with Sydney O'Keefe handling apartment searches: an April 2026 review describes her spending a Sunday afternoon on an out-of-town Brookline apartment search, and a 2025 review describes her touring units on a client's behalf when a two-hour drive wasn't possible. Another 2025 review, from a California buyer, describes a single Labor Day weekend trip built around seven property tours in about three hours. Nothing negative appears anywhere in the written record. For a Boston-area purchase, sale or rental — especially one complicated by distance, an estate, or a tight timeline — the reviews describe a team built to take that complication on directly.
I recently worked with Jackie O to sell my condo in Newburyport, and I could not have been happier with the experience. A friend recommended Jackie and gave me one piece of advice: "Do whatever she tells you to!" I smiled at the time, but it turned out to be the best advice I could have received. I trusted Jackie's guidance every step of the way, and my condo sold quickly. Even better, the entire experience felt organized, calm, and far less stressful than I had imagined. My biggest job was simply getting my home organized and letting go of accumulated stuff. Jackie was an incredible resource, connecting me with outstanding professionals for everything from cleaning to legal counsel. Every recommendation was knowledgeable, responsive, and fairly priced. What I appreciated most about Jackie was her honesty and experience. I always felt she was looking out for my best interests, and her deep knowledge of the Newburyport market gave me confidence in every decision we made. I happily recommend Jackie to anyone buying or selling a home. She made what could have been an overwhelming experience feel manageable. I look forward to working with her again.
It was my husband’s and my first time navigating the home-buying process, and Jackie and Sydney were excellent resources from our very first consult. We are so grateful for the guidance, patience, and expertise they provided throughout our search. There is no ego involved when working with Jackie and Sydney. They give genuine, thoughtful advice and truly make your preferences their top priority when looking at homes. It was always reassuring to walk through a property with one of them, especially when we were considering making an offer. Their experience is immediately apparent, and they helped us better understand not only the homes themselves, but what might come next in the buying process. A special shoutout to Sydney for being so patient with me as I changed my mind more than once about what I wanted in a home. She was consistently kind, steady, and supportive, even when my priorities seemed to shift from week to week. We would absolutely recommend Jackie and Sydney to anyone looking for knowledgeable, honest, and genuinely helpful real estate agents.
First time selling a home and Jackie and her team made the whole process stress free. From our first meeting to closing day we were kept informed and all questions and concerns were addressed in a timely manner. Jackie helped us prepare for our open house with great pictures and we had a multiple offers on the first weekend. Truly a gift experience working with Jackie and her team.
If it were possible to give ten stars we would. The team at JackieO Realtors has been exceptionally helpful in achieving our goal of finding an apartment in the Brookline area of Boston. We send special recognition and gratitude for the time and efforts of Sydney OKeefe. Sydney dedicated the better part of a recent Sunday afternoon getting to know us and what we were searching for in a Boston apartment. She spent time showing us the two relevant neighborhoods for our work obligations, and took us through the specifics of the Boston real estate environment. Being from out of town, we needed the additional information and guidance. After finding the perfect apartment for us, Sydney and her team followed up very quickly with resources and professional referrals to the home inspection, local lawyers and mortgage brokers. We highly recommend Sydney and the group at JackieO for their expertise, professionalism and engaging interpersonal style. Thank you!
Jackie and Sydney were both so helpful in walking us through the home buying process, plainly discussing work that different houses might need as we looked and prepared to put a bid in. At every step of the way, they advocated for us to make sure that we were assured and confident in buying our house.
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1 change recorded — last scanned Jul 29, 2026.
Repeat clients4.8
Verified license4.8
Sells above asking4.7
Fast sales4.6
Decades of repeat clients4.6
Beat five other offers in a bidding war4.4