Keep Your Second Home Covered This Winter

Second-home owners not only have to worry about insuring their primary residence, but their second home, as well. Second homes and vacation properties require different types of insurance, because they are not always occupied.

“A true secondary home is one you can drive to on a long weekend,” said Joe DeOliveira, owner and president of DeOliveira Insurance, in Mashpee. “A lot of times, people come down every other weekend or throughout the year. It’s not necessarily one that’s closed up for the entire winter and reopened again in May. It’s different from a seasonal home.”

With the Cape already being a difficult homeowners’ market, it’s an even more difficult second-homeowners’ market, he said. There are companies that do write secondary homes, as well as seasonal homes, with reasonable deductibles and the option of flexibility. If you use a standard market company as opposed to an excess company, you’ll skip the agency fee and inspection fees, which will save you some money. Proper winterization is key.

“For proper winterization, we recommend that you have a property manager who physically visits the property at least once every two weeks,” said DeOliveira. “There are homeowners’ insurance companies that will give you a discount because you use a property manager. We also recommend that you have electronic devices such as Wifi-operated thermostats.”

Using a centrally monitored alarm system that detects both fires and break-ins is ideal. Choose an alarm system with remote monitoring capabilities, with a smartphone app that will instantly alert you to any changes in your home’s status. Installing an alarm system may also help lower your homeowners insurance costs on your second home. Now, they even have water leak detection systems, which notify you if there is a change in water pressure in your home.

Owning a second home will automatically bring its own burdens and insurance complexities. Having skilled property management, modern technology and a pro-active agent, can help you earn discounts for your homeowners insurance needs. Having a dependable agent proactively review your policy is crucial for having the right insurance, and the right amount of coverage, no matter what time of year.

“On a property that you might rent out only during summer, you have to really watch the wording on your policy,” he said. “Some will only allow you to rent the property for six to eight weeks, with a minimum of two weeks per rental. If they do cover you for rental, they are really covering the way in which you rent it, which is always a difficulty. We’ll take care of that for you, when we review your policy and offer the best option for your rental situation.”

Speaking of renting out your home, “No Massachusetts insurance company will cover for an Air BnB,” DeOliveira said. “If your insurance company finds out that that’s how you are using the property, they can use that as a reason to refuse renewing your coverage, because it’s an exposure that doesn’t fit their criteria.” He added that there are some excess-type markets that will do it, with a surcharge and fees. If you have a standard market carrier, they will not cover rental income or damage caused by those tenants. If you have the Massachusetts Fair Plan, I have been told directly by them that they do not insure Air BnB.”

Down the road, however, things may change, he said. “I can already see some companies have already started to look into it. Certain companies will always stay away from it, while others will use it as a marketing strategy to attract clients. Some homeowners will still take the risk, for the opportunity of gaining rental income. That can be the cost of doing business.”

Before you leave your vacation home for the winter, Joe recommends preparing your home from the potential of wind damage of storm surges, particularly if a Nor’easter occurs. This includes protecting the yard and garden by cutting back overgrown tree branches and checking for dead trees. You’ll also want to store all outdoor furniture safely and lock away any expensive vehicles.

You can be sure that Joe DeOliveira, and DeOliveira Insurance, will provide you with the best options for each client, need and scenario. He has all the information you need to make the sailing much smoother for you. “You do have options.”

“I always say, people may not like insurance, but they should be able to like their agent.” You can contact Joe DeOliveira at or by calling 508-477-3023.

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About Ann Luongo

Ann Luongo is the Marketing Writer and Lifestyle Reporter for, and has been writing for Cape Cod and South Shore publications for over 15 years.
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