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Bob Sheldon is a broker-associate with RE/MAX Real Estate Center working the Outer Cape — Eastham, Orleans, and Wellfleet — with a self-described focus on vacation, retirement, and investment properties, including 1031 exchanges, out of an office in Eastham. Thirty-five Google reviews stretching from 2021 to this year tell a consistent story about how he handles a sale. One recurring theme is reachability through long or complicated searches: a retiree couple described phoning him repeatedly over more than a year before settling on a lot to build on, and a client interviewing four agents for a beachfront listing on Cape Cod Bay said his pricing analysis of the waterfront market was the most accurate of the four and that he rarely let a text or call sit more than half an hour. Sellers point to him handling the mechanics of closing directly — lining up the title 5 inspection, water test, smoke-alarm check, and closing attorney on one sale — and deals have moved fast: a home held for 35 summers had an offer within five days of listing. The two lowest-rated reviews on file are worth reading before signing on. In 2023, one reviewer wrote that Bob was acting as a dual agent — representing both sides of a deal — without disclosing it until late in the process, and that he submitted offers from his own other clients well under asking. A review from this spring described him not pushing back when a buyer demanded the seller hand over the home's furnishings and contents after the purchase-and-sale agreement was already signed. For an Outer Cape sale or a vacation-home purchase, the reviews are heavy on responsiveness and market knowledge. Anyone selling should ask upfront whether he represents the other side of the deal too, and get any dual-agency arrangement in writing before signing.
Bob told a buyer the house was offered furnished without asking me. At multiple steps in the process the buyers made unreasonable demands and Bob invariably pushed the problem on to me. For example, I started cleaning out the house after the P&S was signed, and the buyers demanded that I return every item that had been in the house -- kitchen utensils, tools, power washer, everything -- apparently he sold not only the furniture but every item in view, without mentioning this to me. I ended up having to give the buyers everything in order to close; Bob failed to get the buyers to back down. In my opinion, if I'm paying him tens of thousands of dollars he should be solving problems, not just pushing them onto my plate. The house got sold in the end, but my experience was awful and incredibly stressful. I hope I never see Bob again.
Bob Sheldon is an excellent real estate agent! We were extremely happy with the way he handled the sale of my mother’s home in Eastham, MA from the listing to closing. He was efficient, ethical, personable, trustworthy, responsible and wise. He expedited all the details needed to bring both the buyer and seller to closing in a timely manner. He is personable and proactive while seemly laid back and unaggressive. For us, he handled all the inspections required by the town while managing any contractors we needed to expedite the sale. In our case, Bob represented us as well as the buyer and handled that circumstance perfectly with the air of cooperation that was to the benefit to both parties. The whole process could not have gone more smoothly. That was due in large part to the expertise of Bob Sheldon. We are very grateful for his help, his knowledge, and his practicality. We would highly recommend Bob Sheldon as an agent whether you are buying or selling!
Choosing Bob Sheldon as our listing agent was the best move we could have made for the sale of our Eastham vacation home. Bob is extremely knowledgeable about the local market, is very efficient, and, most important to us - was very considerate to our concerns. He was always just a phone call away. Thanks Bob!
We had a fantastic experience working with Bob Sheldon to purchase our home in Eastham, MA. As newcomers to the area, we truly appreciated Bob's deep knowledge of the local market and community—he took the time to educate us every step of the way. He was responsive, professional, and made the entire process smooth and efficient. Highly recommended!
We worked with Bob on two deals. The first one fell through (in retrospect, thankfully), but the second one went through flawlessly. Bob is a very down-to-earth person and approached every issue calmly, collaboratively, and reasonably. He was available whenever we needed him. He is not the hard-sell type. I believe he truly wanted us to be happy with our purchase, and we are!
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1 change recorded — last scanned Aug 23, 2026.
Sells for out-of-state owners4.9
Repeat renters3.0
Precise, respectful antique-home window work2.7
Active broker licenseNot yet rated
Professional listing photography and video5.0
Attentive service2.7
Complex sales handled4.6
Offer support3.4