









About Bob
Transaction History
- 1 Year
- 2 Year
- 5 Year
Seller Deals
Buyer Deals
Production Over Time
1 Year View by Quarter
Seller Deals
Buyer Deals
Production Over Time
2 Year View by Quarter
Seller Deals
Buyer Deals
Production Over Time
5 Year View
Neighborhoods Bob Has the Most Experience In
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53 Sales
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46 Sales
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5 Sales
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5 Sales
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2 Sales
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1 Sale
Bob's Listings and Deals
Bob's Active Listings
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$1,695,000
- 3 Beds
- 1.5 Baths
- 784 Sq Ft
- 20 Beach Rd
- Eastham, MA
Spectacular sunsets of Cape Cod Bay await you at this amazing and unique waterfront property. Wide open views with floor to ceiling glass in most every room. Wrap-around deck, showcasing 270 of breathtaking seascapes. Cathedral ceilings in the open living/dining/kitchen and master bedroom add to the feeling of literally living on the beach. Secluded location is down a short private drive, only
Bob Sheldon RE/MAX Real Estate Center
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$880,000
- 3 Beds
- 2 Baths
- 1,754 Sq Ft
- 1895 Nauset Rd
- Eastham, MA
This is a custom 3 bedroom Cape with one floor living possibilities. As you enter through the front door you are taken by the open staircase and the opening into the sunlit living room and kitchen area which leads out to a large screened porch. The large kitchen has granite counters, SS appliances, and cabinets galore. Off the kitchen is a full bath with W/D and a large first floor bedroom.
Bob Sheldon RE/MAX Real Estate Center
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$350,000
- 2 Beds
- 1 Bath
- 512 Sq Ft
- 1937 State Highway Route 6
- Unit E
- Wellfleet, MA
This cozy seasonal Cape Cod cottage has a renovated kitchen, high ceilings, and a new enclosed outdoor shower. It's ready for immediate move-in for the summer season and comes mostly turnkey. Owners can have one well-behaved pet. The place is centrally located near walking trails, the bike path, and about 2 miles from the Wellfleet village center. Two designated parking spaces plus visitor
Bob Sheldon RE/MAX Real Estate Center
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$650,000
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
- 30 Deerfield Ln
- Eastham, MA
Looking for a smaller ranch to start your Cape Cod experience? We have a 1008sqft , 2 bedroom, 1 bath, ranch house on a quiet ocean-side street, just a short distance to the National Seashore Visitor Center and just a mile to the Cape Cod Rail Trail bike path. Nicely maintained and ready for your Cape getaway. We have a large living room with nicer builtins, a Bow window and natural gas
Bob Sheldon RE/MAX Real Estate Center
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$700,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- 2155 Herring Brook Rd
- Eastham, MA
Looking for a 3 bedroom, 2 bath ranch to start your Cape journey? Here's a great entry level home that's been in the family for decades, and is just now coming for sale. We have a solid, well built, ranch home with a larger ensuite bedroom and 2 other bedrooms on the first floor, a living room with wood burning fireplace, a one car garage, large screened porch, generator, new roof, natural gas
Bob Sheldon RE/MAX Real Estate Center
Awards and Designations
- Chairman's Club
- Hall of Fame
- Highest Total Sales Volume
- Lifetime Achievement Award
- Platinum Club
- RE/MAX Lifetime Achievement Award 2018
- REMAX Hall of Fame 2018
- ABR - Accredited Buyer Representative
- e–PRO - Internet Professional
- green - Green Designation
- RSPS - Resort & Second-Home Property Specialist
Other Experience
Bob's Reviews
7/21/25Chris Hemberger
Google Review
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!
7/11/25David Krulee
Google Review
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!
7/10/25Julia Krulee
Google Review
Bob did a fantastic job helping us. He was thoughtful and helped us get the condo of our dreams with a few extra perks!
6/29/25Dean Letendre
Google Review
Bob was very responsive and helpful throughout the entire process.
5/27/25Michael Snell
Google Review
Bob is a fantastic agent. He made the entire process about as painless as I could imagine. I was out of the country for much of fhe process and he maintained great lines of communication so that I felt I knew what was happening at all times. I would highly recommend working with him.
5/13/25Richard S
Google Review
Bob was terrific working with us on the sale of our home. Very knowledgeable about the market, both who would be most interested as well as the pricing aspect. We worked with him for some time before it actually was released to the market as we wanted to hit the timing most beneficial to us for a Cape Cod home. We listened to his advice and the home sold in a matter of days. Very pleased.
4/16/25Joanna Baker
Google Review
We live in Florida and wanted to sell our house in Eastham Massachusetts on Cape Cod. We expected it to be a daunting experience with lots of complications.
Working with Bob Sheldon of REMAX gave us a completely different experience.
Our experience and interactions with Bob were Probably the least painful and or complicated thing that we have needed to accomplish in years.
Mr. Sheldon's ability to take charge of all of the particulars and communicate among all the parties involved was completely an example of a seamless real estate sale experience.
Bob even Arranged to have work done and deficiencies fixed without us having to even be involved with contractors, utility companies, etc.
The sale went off without a hitch and all parties appear to have had a positive experience. Our proceeds from the sale were in our bank account literally within two hours of closing.
In summary we would not only recommend Bob Sheldon for anyone who wants to sell property on Cape Cod, but in particular anyone who has the need to facilitate a long distance sale, particularly out of state.
We recommend Bob Sheldon highly.
William and Joanna Baker
Sarasota Florida.
2/27/24Dimitrios Stathopoulos
Google Review
We've used Bob to buy and sell a home. He was always available to answer questions and help us through the process. We had multiple offers on our home. Very happy with our experience with Bob.
2/17/24Stephanie H
Google Review
We have known and worked with Bob for 5 years since meeting him at an open house and hitting it off. His knowledge and guidance (and patience!) was invaluable during our search the "the dream" in Eastham. He knew what we wanted and our style, and did not push us into homes he knew were not right. When the right home finally came on the market he guided to a successful offer. And when some rather significant issues arose prior to closing his guidance and advice was spot on, allowing a successful close. Very happy to say we are now "neighbors" and will continue to be friends I am sure. We are grateful to have met Bob. Thanks Bob!
2/8/24Prabha Chavva
Google Review
Bob was exceptional in guiding us through the home buying journey. Bob's expertise and dedication made the process seamless. With Bob's support, we found our dream home. Grateful for Bob's invaluable assistance and highly recommend Bob to anyone seeking a reliable buyer's real estate agent in Capecod.
1/31/24James Beadle
Google Review
Bob is a terrific resource for local information as well as honest advice. He gave my wife and I large amounts of helpful information, even when it was about competitors. He is an honest and helpful professional, you need to look no further for amazing service!
11/12/23Linda Culhane
Google Review
We really enjoyed working with Bob. He really knows the area and shared many helpful resources with us. Bob managed all aspects of our homes sale and --as first time home sellers--we truly appreciated that Bob was always available to answer our many questions. We would definitely recommend Bob to anyone looking to buy or sell real estate.
8/30/23Jorden Davis
Google Review
Bob is not only a great agent but he is also a very caring, genuine person! I am a Realtor in Florida and he really went above and beyond to help out my client who lives in Eastham. I look forward to referring clients to Bob because I know he will take great care of them!
6/21/23Robert Stagon
Google Review
My wife and I spent over a year working with Bob looking for a home to retire in Eastham. Bob was very responsive to my many phone calls over that time. He researched the many properties we expressed interested in and gave us his candid opinion as to whether he thought they met our specifications. In the end we chose to buy an acre lot and build our retirement home. Bob did all the research on the lot and provided us with information to make an informed decision about purchasing it.
Three qualities I would describe Bob would be professional, responsive and candid. I would highly recommend him to anyone looking to purchase property on the outer cape.
6/5/23Kate Levy
Google Review
Bob was a great advocate for a first-time house seller, savvy and strategic in the offers process, going the extra mile, helping us out with myriad details/logistics of moving house from a distance away. And he's a lotta fun. I'll miss him.
6/4/23Sharon Krause
Google Review
Selling a home can be stressful. Bob Sheldon’s pragmatic, easy going approach helped us keep our heads on straight through a sometimes confusing process. Very wise advice. Thanks, Bob
4/25/23Jeffrey Kantounis
Google Review
Working with Bob to sell my family's home was a great experience. Bob really understands local market trends and needs, and was especially helpful with ensuring everything was in place for a smooth close. Bob is truly a consummate professional and would gladly work with him again.
3/26/23Linda Garvey
Google Review
Bob was wonderful to work with - kept us informed every step of the way. Answered all of our questions, gave honest feedback, and made the process seamless. Highly recommend!
3/24/23Glyn Eisenhauer
Google Review
From listing through closing of two Cape Cod properties, Bob provided expert guidance and support with a professional ease and cordiality that engendered confidence and trust. Selling a house is much more than accepting an offer and signing documents. Bob guided us through the monetary and procedural negotiations, tasks and scheduling with an ease and competence that made the process smooth and efficient. Bob kept us informed in a timely manner and was consistently and readily available to answer questions and suggestions. If you’re thinking about selling a property, Bob Sheldon comes with the highest possible recommendation.
3/24/23Carol Walker
Google Review
Selling our family owned home was a difficult decision but after we interviewed Bob, we all were confident with our choice. Bob was pleasant to work with and had a solid, working knowledge of the Eastham real estate market. His experience and appreciation of local regulations along with his contacts with local professionals expedited the selling process. I wouldn't hesitate to contact Bob for your real estate needs.
1/24/23Katy C.
Google Review
It was a pleasure working with Bob to sell my property. He really understands the market and he made the process very easy. He has a great personality and I would definitely work with him again. Do not hesitate to hire Bob as your agent.
1/19/23James Hartley
Google Review
I contacted Bob after viewing his website and reading his client reviews. I felt confident after talking with him, and considering his knowledge of the Eastham area, that he was the right agent for me. Bob was able to connect me with all of the area professionals that were needed, throughout the selling process. I thank Bob for all that he did to assist with the selling of the house. If you are looking for an agent whether buying or selling in the Eastham area, Bob is your agent.
11/30/22Kristin Deleo
Google Review
I would highly recommend Bob to anyone looking to buy a home!! He made our experience so easy and was very professional, kind and easy to work with. Top marks to a wonderful agent!!
11/7/22Carol Lankowsky
Google Review
We connected with Bob the first time we met him. He is very personable, professional and knowledgeable. He is such a dedicated agent and always so accessible for any questions that may arise. Bob is so informed on the current real estate trends and has a very informative newsletter that we enjoy reading. Z & I would highly recommend Bob to be your agent to either buy or sell a home. Thank you for everything Bob, selling our home with you was such an easy transaction.
10/3/22Linda Cocce
Google Review
If you want to purchase a home in Eastham, Bob Sheldon should be your agent. Bob is friendly, great to work with, professional, very knowledgeable and experienced with the Eastham market. We can honestly say that any other agent would not have been able to close the deal on the home we purchased. Bob went above and beyond our expectations to make the sale happen. Thanks to him, we finally own a cottage in Eastham!
6/14/22Peter Smails
Google Review
Buying a house on the Cape while living in California was not easy but Bob made it happen. He was professional and responsive and knew when to ask us to "get on a plane" to see a house. Couldn't ask for a better agent.
1/5/22Irina Smolina
Google Review
We found Bob when we were searching for a house on the Cape and it was truly our lucky day! We did not have the most straightforward house purchase but Bob was extremely professional and responsive in helping us have a very smooth experience in finding our dream home. We feel very lucky that he was so knowledgeable about the area and was able to help us communicate with the bank and various contractors in order to make the process go smoothly and timely. Bob is a wonderful agent and with his help we successfully purchased the perfect cape home for us!
12/15/21Mark Andrade
Google Review
Bob has assisted us on two transactions. He is always responsive and professional. He is also a great help at making linkages within the community.
10/24/21MJ R
Google Review
I hired Bob as my listing agent for a beachfront property on Cape Cod Bay in Eastham in 2021. Bob’s knowledge of the Eastham market specifically and his familiarity with the nuances of Eastham regulations and ordinances, especially as they apply to waterfront properties, cannot be overstated. Bob was one of four agents I interviewed and his market and pricing/selling analysis turned out to be the most accurate of the four agents. I also found that Bob would review my texts, emails, and phone calls with such alacrity that I rarely waited more than 30 minutes for his responses. Bob also handled the inevitable complications that can arise in the sale of a property (of which we had only one of any import) in an expeditious and professional manner. I would highly recommend contacting Bob if you are considering selling a property in Eastham.
9/29/21Alden Harrison
Google Review
Selling our Cape home after 35 wonderful summers was a difficult decision but after talking to Bob we felt comfortable with how experienced he was and how he would handle each step in the selling process. Bob did a great job with the listing and we had an offer in just 5 days. Bob lined up the title 5 inspection, water test, smoke alarms and the closing attorney . We couldn’t be happier with the excellent job that Bob did for us.
9/2/21Rochelle Senator
Google Review
Bob Sheldon is the ultimate professional. He sold our house in record time. He took care of many incidentals and all the various aspects of selling a house. He knows Eastham and the market. He was a great choice for us.
6/12/21Thomas Smith
Google Review
Bob did a great job selling our home of 23 years. He is the top RE salesperson in the Eastham area and his hard work, research, professionalism, and experience show in results for his customers.
6/12/21John Medeiros
Google Review
5/6/21Burton Spottiswoode
Google Review
I would highly recommend Bob who did such a great job in selling my house. After interviewing serval agents I selected Bob. During the interview Bob made suggestions on how he thought I could get a higher price for my house and gave me the impression he really wanted to work with me in selling the house. Whereas the other agents didn't give me the same feeling. It seemed like they just wanted to sell the house as quickly as they could for whatever price they could get for it. Bob is very knowledgeable about the market and writes a monthly newsletter to keep you updated on current events on the Cape. He is a pleasure to work with, always easy to reach and works on your behalf. He handled most of the closing details for me which was really helpful in that I live out of state. He even replaced all of the smoke detects for me at no cost. ..
4/25/21Craig Weiss
Google Review
Bob is fantastic, and became a trusted advisor as we purchased our recent home. Would not hesitate for a minute to use him as either a buyers or sellers agent.
4/15/21Noreen Hong
Google Review
4/12/21Joseph Koss
Google Review
Selling a home during covid presented unusual challenges and Bob Sheldon certainly helped made things happen for us. There is "no substitute for experience" and this realtor knows the market. We quickly developed a trust with him and he anticipated and reacted to challenges to our total satisfaction. I will be quick to offer our recommendation's for Bob Shelden at RE/Max. Thank You Bob !
4/9/21Paula Bruns
Google Review
Bob has been a true professional in every step of every transaction...he sold us our first Eastham home, then helped us sell, and buy, two more houses! Bob is level headed, honest and energetic. His experience puts him at the top of the class. If you want standout service and results, Bob is the one. Why settle for less?
2/6/21Helen Kraft
Google Review
Bob Sheldon is the best! I cannot say enough about him! He is so knowledgeable and such a pleasure to work with. We never felt any pressure from him and he always gave us his honest opinion about properties. He always called us back and went above and beyond offering builder names, drone people, association members etc. Although we were very close to buying a home which was not in the part of town we really wanted he encouraged us to wait for the right house for us. In the end he found us the perfect building lot that was not yet even on the market. He even attended the health department meeting to make sure our 3 bedroom septic plan would be approved. We could not be happier! A friend of ours will probably be buying on the cape and we told her she could not find anyone better than Bob!
2/6/21Peter Stagakis
Google Review
Bob was a real pleasure to work with. He helped guide me through the entire process and I ended getting even more than I thought I could for my house! He was very fair and encouraging. I could tell he really genuinely cared about getting the best results for everyone involved. I highly recommend Bob Sheldon, wheather you're buying or selling.
11/3/20Norman Stubbendick
Google Review
Bob was very willing to work with us as we looked for a two bedroom, two bedroom condo with a bedroom on the first floor. He was patient and succeeded in finding us the condo we were seeking. We would recommend him to anyone who is selling or buying a condo or home.
11/2/20VIC JOHNSON
Google Review
Bob knows the Eastham market, knows the comps, and knows the homes incredibly well. He is knowledgeable and has great common sense, and he worked hard to overcome all bumps in the process.
10/30/20Ryan Peterson
Google Review
Bob truly is Mr. Eastham. He knows the market, knows the homes, knows the ins and outs. As an out of town buyer he was incredibly helpful and insightful, has tons of energy, and seems to work all the time. He answers on the first ring, responds to texts instantly, went above and beyond to make sure we had a great experience, and never let us down. I would absolutely recommend him for Buyers and Sellers.
10/13/20Frank Hubacz
Google Review
Bob Sheldon is a knowledgeable, common sense, professional Realtor that made selling our home in Eastham a stress-free process. Bob knows the Eastham market and works hard to keep you informed throughout the sale. Given that our home was a summer rental he was also very committed to showing it without interfering with our renters. Once our P&S was signed, he took care of everything needed prior to our closing. My wife and I strongly recommend that you meet with Bob if you are considering selling your home in Eastham.
11/9/19Laurie Crosley
Google Review
We’ve bought and sold many houses and Bob Sheldon is without a doubt the best Realtor we’ve ever worked with. He listened. He understood our needs and desires in a home and didn’t waste time showing us houses that didn’t meet those needs. He was organized, knowledgeable and fun to work with. From our first meeting to closing on our new house he was responsive, prompt and proactive. The whole process was a pleasure.
12/16/10Bob Sheldon
Homes.com Review
Hi Bob Hope all is well. I’m finally back in the office after a whole week in Eastham – it was sooo tough to leave on Sunday. We’ve been having a blast with the house, we love every minute that we are there. We still laugh because it was the first house we looked at (in person) and it is definitely the perfect house for us – our dream house. And to make a long story short, if it wasn’t for you, we don’t think we would’ve looked at or found the house so we owe you a big thank you. Thanks again and hope to see you soon. Stay in touch, Scott and Patti

