Jackie O Real Estate Team - #1 Top Producer KW New England Team
Agent at Keller Williams Realty Boston-Metro
Local business · 607 Boylston St #500, Boston, MA 02116, USA
Their work
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Call (857) 294-9994Visit websiteSee on GoogleYou reach them directly — we don’t take a cut.
Verified record
- 5 reviews in the last 6 monthsNo negatives
- 1 customer photoOf completed work
Highlights
- First-time buyers — recent reviews cite patient, step-by-step guidance
- Condo sales — a July 2026 seller reports a quick, organized sale
- Seller prep — photography and open-house readiness handled before listing
- Relocating clients — out-of-town renters guided through Boston neighborhoods
- Deep review history — 49 reviews since 2021, none negative recently
- Who you get — much recent praise names associate agent Sydney O'Keefe
- Coverage area — stated neighborhoods are Boston, one recent sale was Newburyport
A friend gave one seller a single piece of advice before she listed her condo: "Do whatever she tells you to." She followed it, and wrote in July 2026 that the sale went quickly and felt organized rather than frantic — the hardest part, by her account, was letting go of accumulated stuff. That is the shape of most of what clients say about Jackie O Real Estate Team. Based at 607 Boylston Street in Back Bay, the team says it operates under Keller Williams Realty Boston-Metro, with agent Jackie O'Connor fronting a group that handles buying, selling, valuations and rentals. Its own site claims a service area covering the city neighborhood by neighborhood, from Beacon Hill and the Back Bay to Dorchester, Charlestown and East Boston. The review history runs deep and stays positive — 49 reviews since 2021 and a 5.0 average across 67 Google ratings — and the recurring theme is people who had no idea what they were doing being walked through it. A couple buying their first home in June 2026 wrote that there was "no ego involved," and that Jackie and colleague Sydney O'Keefe made their preferences the priority on tours. Another buyer in February 2026 described the two of them talking plainly about what work each house would need before a bid went in. Sellers describe the same steadiness. A first-time seller in April 2026 was kept informed from the first meeting through closing, with photography and open-house prep handled ahead of the listing. The same month, out-of-town renters searching in Brookline credited Sydney O'Keefe with spending most of a Sunday learning what they wanted and showing them the neighborhoods that fit their work obligations. Two things are worth pinning down before you call. O'Keefe's name carries a large share of the recent praise, so ask who will actually run your search or your listing — the answer may not be Jackie. And while the stated coverage is Boston proper, that July 2026 sale was a condo up in Newburyport; if your property sits outside the city, confirm it is territory they work. For a first-time buyer or a city seller who wants someone to set the sequence and keep it calm, this is a heavily reviewed team with a five-year history behind it. Ask which agent you will be paired with, and what the plan is for pricing and prep before anything hits the market.
Read the comments
Most recent comments
- 5.0Jul 5, 2026
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.
— Diane KView on Google Reviews ↗ - 5.0Jun 1, 2026
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.
— Flora LiuView on Google Reviews ↗ - 5.0Apr 30, 2026
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.
— Joseph J GardzinaView on Google Reviews ↗ - 5.0Apr 28, 2026
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!
— Nora DonahueView on Google Reviews ↗ - 5.0Feb 25, 2026
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.
— Jess FinocchiaroView on Google Reviews ↗
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Update history
Added 49 new comments, added 33 new photos, established rating 4.1
- behind the score: Who you get — much recent praise names associate agent Sydney O'Keefe