The Outer Cape's listing specialist — a seller's agent above all.
When it's time to sell, I bring the pricing, preparation, marketing, and negotiation your home deserves — across Eastham, Orleans, and Wellfleet, and including luxury & waterfront properties at $1M, $2M and above.
500+
Homes sold across the Outer Cape
400+
Homes sold in Eastham
Top 2%
Of all real estate agents on Cape Cod
$1M–$2M+
Luxury & waterfront sale prices
2002
Selling Outer Cape homes since
Hall of Fame
RE/MAX Hall of Fame & Lifetime Achievement
I've been a buyer, a renter, a landlord, and an Eastham resident.
My family began coming to the Outer Cape in 1986. We camped in Wellfleet and greatly enjoyed the beaches and the time away from the daily hustle and busy-ness of our lives in New York.
I have been a renter, rental landlord, retiree, and now a full-time resident. Living in Eastham has allowed me to enjoy a casual lifestyle and selling real estate has allowed me to meet interesting folks who want to enjoy the Cape lifestyle also.
I am fully aware of the current market trends and what it takes to get a great deal on a listing or get top dollar for your current home. When it comes to getting the job done right, you can count on me. I have a lot of connections within the Outer Cape area.
Please don't hesitate to call and ask me any questions you might have. This process is all about you and your needs. Real Estate is a big investment and I understand that. One thing you will get with me is a personal relationship — in the end, that goes a long way.
01
The heart of my practice. Full-service seller representation — accurate pricing, preparing the home, marketing it to the right buyers, hard negotiation, and managing every detail through to a clean closing.
02
Cape Cod Bay and oceanfront properties and the Outer Cape's finest homes — many selling at $1M, $2M and above. I know waterfront pricing, the regulations, and the buyers who are looking.
03
The summer places and getaways the Outer Cape is known for — from Cape Cod Bay to the National Seashore in Eastham, Orleans, and Wellfleet.
04
Right-sizing to the Cape, and rental or investment property including 1031 exchanges. I know the towns, the seasons, and the numbers year-round.
05
Most of my business is listings — but I also represent buyers, including from out of state, as an Accredited Buyer's Representative, from first showing through closing.
The Outer Cape, end to end. My home ground is Eastham, and I know the waterfront rules, the zoning, and the seasons town by town.
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. Bob guided us through the monetary and procedural negotiations, tasks and scheduling with an ease and competence that made the process smooth and efficient. If you're thinking about selling a property, Bob Sheldon comes with the highest possible recommendation.
Seller · Homes.com
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.
Seller · Homes.com
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.
Seller · Homes.com
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.
Seller · Homes.com
Bob handled the sale of our family home in South Wellfleet on Cape Cod. An expert in the nuances of real estate on the Cape, we were able to rely on his expertise. We live out of state and Bob went above and beyond to handle every detail of the process for us independently.
Seller · FastExpert
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.
Seller · Homes.com
Bob Sheldon is THE go-to person when it comes to Eastham real estate. He has a studied and experienced grasp of the area and does a great job matching his clients with the perfect property. He sold our house, helped us buy some land, helped me rent office space, and found a rent to purchase condo situation for my in-laws. Bob is THE man! Thanks, Bob.
Client · LinkedIn
As one who has transacted in real estate many times over the years from New York City to Boston to Cape Cod, I can honestly say that Bob is one of the best brokers that I have worked with in all of my years of buying and selling. He is knowledgeable, honest, diligent and wise. One of my favorite aspects of working with Bob is that he is calm and helpful when encountering unexpected hurdles.
Client · FastExpert
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.
Buyer · Homes.com
Each month I publish an analysis of the Eastham real estate market — single-family homes, condos, and land — with the real stats and straight commentary on where the local market is and where it's likely going. Read about assessments, market updates, and the topics that actually move Outer Cape values.
Call or text
Office
RE/MAX Real Estate Center
180 Brackett Road, Eastham, MA 02642
Let's talk about what your home could bring in today's market — pricing, timing, prep, and a plan, with no pressure. This process is all about you and your needs.