Should You Invest in Real Estate on Martha’s Vineyard?

Jen Hawkins O'Hanlon, REALTOR®


Are you thinking about investing in real estate on the Vineyard? It may be the perfect year to purchase a rental property, a vacation home, or to flip houses. I would be happy to help you find the perfect investment property, and I’ve put together this list of tips to help you get the best return on your investment.

The first thing you need to do is to consider what type of investment property is best for you.

If you are thinking about a vacation home or year round rental property, consider how much time will be needed for things like maintenance, managing a website or rental listings, and responding to inquiries or issues.

For vacation rentals, make sure the areas you are searching are attractive to tenants. On the Island, rental demand varies drastically from town to town and specific locations within each town. This is one of the reasons why working with an agent who has experience with the Vineyard rental market can be key.

The demand for year round housing has never been greater. If you don’t want to deal with the weekly turnovers and prefer to have just one tenant in your home, a regular rental property will be the way to go. In the long run, there may be a bit more wear and tear on the house, but certainly can be an easier investment to manage.

If you’re not living on the Island, you will need a caretaker to oversee the property and make sure everything is in good shape. For vacation rentals, this person needs to commit to checking on your property on the weekends, after tenants depart. Your caretaker will also need to be available to the tenants, should there be any issues that pop up.

For house flippers, you want to find out what return you can expect to get in this market and talk to contractors and suppliers to get realistic estimates on renovations, both in terms of price and time to completion.

Here are some additional Do’s and Don’ts for investing in real estate:

Do aim for at least a 15% return on investment.
Do look for homes priced in the low end of the median price range.
Do look for at-least 3-bedroom, 2-bath single family homes for rentals or flipping.
Do use one real estate agent to help with all your buying and selling needs.
Don’t purchase a second property until the first is earning revenue.
Don’t buy a home that you cannot afford to carry for several months in case of a slow market.
Don’t buy a home or condo without having inspections performed.
Don’t buy without title insurance.

As I said, I can help you search for investment properties. Sometimes buyers make the mistake of searching on their own and contacting the sellers or listing agents directly. Working with several different people wastes your time and increases the chances that you will miss out on a deal. Also, working with one agent allows that agent to learn your tastes, needs, and parameters, so I can be out searching for the right property while you are busy doing other things.


As a team, we work in harmony for the benefit of our clients. We handle multiple transactions at once and are able to execute a complex marketing strategy by leveraging team resources. We can be in several physical locations at once to ensure showings are always possible for our buyers and sellers. Our clients benefit from the combined experience of our agents and administrative staff.

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