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MiddleOak Insurance Review

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Eric Stauffer is a former insurance agent and banker turned consumer advocate. His priority is to help educate individuals and families about the different types of insurance they need, and assist them in finding the best...

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UPDATED: Nov 30, 2018

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MiddleOak Insurance
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MiddleOak Insurance is a specialty insurer providing a specific type of property and casualty insurance. Their products cover multi-family buildings such as apartments.

About MiddleOak

MiddleOak Insurance provides coverage in most states and was founded in 1843. MiddleOak the trade name of two companies that joined up in 2006: Middlesex Mutual Assurance and Holyoke Mutual Insurance, resulting in the combined name. The two headquarters for the underwriting companies are in Salem, MA and Middletown, CT. Both of these are subsidiaries of the major insurer, Country Financial.

MiddleOak only writes one main type of policy: property and casualty coverage for multi-family dwellings of at least 11 units and other rental properties. Their coverage includes apartment buildings and other rental dwellings as well as associations in some states. Previously, this company wrote auto insurance and home insurance – that no longer appears to be the case, as we were unable to find any mention of these products anywhere on the company website.

Products are sold through independent agents across the states where they do business. MiddleOak’s website is somewhat difficult to navigate and could use an overhaul – this indicates that they probably do not bring in a lot of business via the website.

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Multi-Family Dwelling Insurance

MiddleOak’s niche is multi-family dwelling coverage that includes property as well as liability coverage for buildings that include 11+ units, although they also cover a variety of other rental dwellings. This type of coverage protects the owners of the building and does not provide any coverage for tenants, much like any rental dwelling policy.

We selected Massachusetts as our sample state to obtain product information.

The Worlds Apart plan is intended for rentals such as apartments, student housing, senior housing, rental condos, and associations. It can be customized to include Businessowners coverage and can also include a Tenant Emergency Assistance endorsement that provides benefits after a major disaster results in loss of tenants.

CAPsure is a Connecticut-based commercial package policy that is designed specifically for associations. This includes condo, homeowners, and seasonal community coverage. A variety of options can be added to the base policy for custom coverage.


A company like MiddleOak does not provide online quotes for a good reason; this type of coverage is far too complex in terms of risks and rating factors.

The website offers assistance with finding an agent who can provide a customized quote.


While online quoting is not available, online claims filing is. There is also a 24-hour claims assistance line that can be contacted for emergencies or to file a claim at any time. Questions and claims information can also be sent via email.

Aside from the contact information, there is little in the way of explanation about the claims process. That is not surprising, given the more complex nature of this sort of coverage compared to a basic home policy.

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Ratings and Consumer Reviews

The Better Business Business (BBB) does not have a page for MiddleOak, although there is a Boston-based insurance agency by the same name that does not appear to be connected. Underlying companies Holyoke and Middlesex do have BBB files, however. Holyoke has an A+ rating, with no complaints on file in the past three years. Middlesex also has an A+ rating, and only one complaint has been filed in the past three years.

Not surprisingly, we were unable to find much to go on in terms of customer reviews of this company. Their shift into solely covering rental dwellings is likely a big part of the reason for this.

The Bottom Line

If you are in search of a company that is focused on the needs of rental homeowners, MiddleOak might be a good bet. Focus on one type of policy tends to lead to expertise in that area. From our research there it seems that MiddleOak is doing a good job within their niche.

For a list of companies that we recommend, visit our Best Insurance Companies page.

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About Eric Stauffer

Author: Eric StaufferI am a former insurance agent and banker turned consumer advocate. My priority is to help educate individuals and families about the different types of insurance they need, and assist them in finding the best place to get it.

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