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O'Connor & Highland is a Greater Boston residential team operating under KW Boston Metro, fronted by Jason Highland alongside John O'Connor, Mark Sheldon Bonin and Wilfredo Miguez. Thirty-eight Google reviews run from 2021 to a June 2026 write-up, every one five stars, and the more interesting pattern isn't the streak — it's how specific and how repeat the relationships are, with clients naming an individual agent far more often than the firm. Wilfredo Miguez shows up in the most reviews, and the pattern with him is consistency across very different situations: a June 2026 review describes staging and selling a house under time pressure; a 2025 review describes managing a purchase over video calls for a client living overseas, and another 2025 review describes finding a Charlestown tenant to move in the day after the prior one left, with a 2022 review from a landlord of 30 years calling it the best rental experience they'd had. A 2022 review describes him FaceTiming a couple through houses they couldn't travel to see in person. Jason Highland's reviews lean toward the harder deals: a 2024 review describes him selling a Watertown two-family with long-term tenants upstairs and a rundown, owner-occupied unit downstairs that needed a full clean-out, landing $100K over asking. Another 2024 review describes a client who bought a condo with him in 2013 and came back in 2024 to sell it. John O'Connor's reviews follow a similar long-arc pattern — a 2023 review recalls a South End condo sale from "late 2020," in what the reviewer calls a tumultuous market, handled by an agent the client had known for years before hiring him. Brianna's reviews are rental-specific: a 2025 review from an out-of-state renter describes her running virtual tours and asking pointed questions of the units' owners since the client couldn't visit in person. Nothing negative or unresolved appears anywhere in the written record. For a straightforward Boston-area sale, purchase, or rental, this reads as a team where the right agent — whichever one specializes in the size or shape of the deal — is worth asking for by name.
We had a fantastic experience with Wilfredo and it exceeded our expectations. During the stressful time of selling our house, Wilfredo brought great expertise and professionalism to help us prepare, stage and sell our home with a fantastic end result. He is a great strategist and planner, Highly recommended!!
I rarely take the time to leave reviews, but Wilfredo has been outstanding and deserves the recognition. He is incredibly responsive, proactive, and knowledgeable, and consistently goes above and beyond to ensure everything runs smoothly. Any questions or concerns are addressed quickly and professionally, and his expertise gives me complete confidence that my property is in great hands. What truly sets him apart is his commitment to excellent service and communication. It’s clear that he genuinely cares about both the property and the people he works with. If you’re looking for a property manager who is reliable, experienced, and a pleasure to work with, I would highly recommend him without hesitation.
As a retired couple who has invested in real estate for many years, we can confidently say that Wilfredo Miguez has been the best broker we have ever worked with. He has assisted us with acquiring and selling properties, as well as managing our rental investments. Wilfredo's attention to detail, exceptional organizational skills, business acumen, and extensive knowledge of the Boston-area real estate market are truly impressive. Throughout every transaction, he has demonstrated professionalism, reliability, and a genuine commitment to our success. We have been 100% satisfied with Wilfredo's expertise, guidance, and support. We greatly admire and respect him, and we wholeheartedly recommend him to anyone seeking an outstanding real estate professional
Great experience! I love my new home!! Jay and Mark made it easy . They are true professionals!!
I have dealt with many realtors over the years in multiple countries. I can tell you, with complete confidence, that I have never felt as comfortable or as well-represented as I was with Wilfredo. My situation was complicated. I was living in another country, literally across the world, trying to manage a transaction in the Greater Boston market. In the past, this is when I’d be chasing agents for information. My experience with Wilfredo was the complete opposite. He was the one consistently following up with me, providing detailed updates, and offering strategic suggestions. I never once had to wonder what was happening; he was always two steps ahead. It was the first time I can honestly say I felt my agent was 100% working for me and my best interests, not just trying to close a deal. Wil also went above and beyond what I would ever expect from a realtor, handling countless details and logistics that were made more difficult by my being overseas. He gave me invaluable advice and, most importantly, total peace of mind. His integrity, work ethic, and genuine care for his clients are rare. I will be enthusiastically recommending Wilfredo to anyone who needs a realtor in the Boston area.
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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
Wins offers for clients in tight markets4.3
Above-ask sales4.4