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Top Five Towns for Investors on the Cape and Islands

By Tiffany Raiford

Investing in a piece of property along coastal Massachusetts is an excellent choice. Experienced investors are well aware of the fact that the Cape and the islands are the perfect location when it comes to investment property that yields an impressive income. Inexperienced investors may be new to the game, but you know this area is a prominent vacation destination. For this reason, an investment home on the Cape or on the islands can garner significant rental income each year as well as increase in value over time. Water front property is always at a prime, and this area of Massachusetts is no different. These five towns are the best for investors.

Martha's Vineyard

With approximately 15,000 permanent residents and nearly 100,000 summer residents, the Vineyard is one of the most affluent on the East Coast. Many world-famous celebrities, politicians and wealthy families keep a home on the island that they use often during the warm summer months. While many of the homes on the island are lovely historic buildings, many condos and new construction homes are making their way onto the island. At the moment, prices are down. This means that investors can pick up a fixer-upper for around $600,000, which is a steal considering the average cost of a piece of land on the water is close to $400,000.


Located in Cape Cod, the town of Chatham is a living dream. The picturesque views, the quaint businesses and local cafes combined with the upscale way of life that the town provides is what buyers and renters are looking for. As an investor, it might interest you to know that while the median home price in Chatham is a staggering $1.37 million, prices are continuing to drop. In recent months, Chatham homes are selling for 3 to 4 million less than the original asking price. Furthermore, there are very few parcels of land left on which to build, which means buyers will soon need to purchase and tear down preexisting homes in favor of building dream homes. Buying while the prices are low, sitting on the home for a few years, and selling it when demand increases could mean a several million dollar profit.


Some people are simply drawn to the historical side of Nantucket. It might be more difficult in terms of travel, but when you step off the ferry onto the cobblestone streets of historic Nantucket, you are immediately taken back in time a century or more. The lovely old buildings are aesthetically appealing, the atmosphere is that of sophisticated relaxation and pretentious attitude is nowhere to be found. Usually a hot real estate market, the price of homes is dropping considerably in current economic times. As an investor, you'll be pleased to know you can pick up a Nantucket home for less than the typical asking price. Whereas buyers couldn't purchase a condo or home inland for less than $1 million in previous years, now you can pick one up for as little as $700,000.


The oldest town on Cape Cod is one of the best towns for investors. The breathtaking city center is filled with buildings originally constructed in the 18th and 19th centuries, and this little cape town is approximately 60 miles from Boston. Purchasing an investment home here means you might have more options renting it out during the summer months as residents of Boston can make the easy trek back and forth from the city with ease. Investors can pick up a cozy starter home for less than a quarter million dollars. Once you put a little work into a home like this, you can begin to rent it out until the market increases and you're ready to sell.


This large Cape town features multiple villages, including upscale areas such as Hyannis and Hyannis Port. These areas were made famous when John F. Kennedy used his family's Hyannis Port compound as a secondary White House back in the early 1960s. The homes here are nothing short of affluent and extravagant. They are perfect for investors looking to pick up a home in need of a little work. Once the market improves, you're practically guaranteed to see a significant return on your investment in this area.

Cape Cod and the surrounding islands are the premier vacation destination for Massachusetts residents. From weekend renters to wealthy residents with second homes, summer is the time of year in which families and couples flock to the islands to escape. Investing in a home in one of these five locations means investing in a home you can rent seasonally and sell for a profit in the near future.

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