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MiddleOak Multifamily Dwelling Insurance Review

MiddleOak Multifamily Dwelling Insurance Review

MiddleOak Multifamily Dwelling Insurance Review

MiddleOak Insurance is a Connecticut-based private insurance company that insures real estate owners and landlords for buildings & commercial properties. MiddleOak specializes in apartment building insurance and caters their services to building owners who own multi-condo units.

Company Overview

MiddleOak insures multiple rental properties or buildings at once. MiddleOak, owned by Country Financial, is one of the oldest-standing insurance companies in the United States – it was founded in 1845 under the name Holyoke Mutual Insurance. The name, MiddleOak, came about when two companies merged together in 2006 – Holyoke Mutual and Middlesex Mutual Assurance. To this day, the merger forms the MiddleOak Insurance Group while the company is owned by Country Financial.

MiddleOak optimized their business model for condominium buildings exclusively – in the past, they used to offer auto and home insurance options. MiddleOak dwelling insurance is only available for buildings or establishments that have a minimum of 11 units – buildings with more units qualify, but their minimum is 11 units per building. MiddleOak provides insurance for building owners and condominium associations too, the company can insure virtually all large rental-dwelling, unoccupied apartment buildings and associations with multiple buildings. Their services are available in 8 states: Connecticut, Maine, Massachusetts, New Hampshire, New York, Rhode Island, and Vermont. The company’s main market is the Northeastern U.S.

MiddleOak does not sell their policies directly but they have a network of licensed agents who sell their policies. MiddleOak caters to an older demographic of wealthy building owners and operates as a private insurance company with special relationships with their customers. MiddleOak is located in Middletown, CT.

MiddleOak home insurance is available for the following:

  • Apartment building owners (minimum 11 units)
  • Building associations (multiple buildings accepted)
  • Student housing owners
  • Senior housing owners

Financial Ratings

MiddleOak is a financially stable company – this is due to their specialization in building insurance and parent company financial standings. A.M. Best, one of the largest financial institutions responsible for rating insurance companies based on their financial stability awarded MiddleOak an A+ or Superior rating. Their parent company, COUNTY Financial Group is also rated A+ by A.M. Best.

MiddleOak is part of the Better Business Bureau, a company that rates insurance companies based on their financial stability and customer complaint ratio. MiddleOak is listed on the BBB via its two main branch companies – Holyoke Insurance and Middlesex Insurance. The BBB awards Holyoke Insurance an A+ rating for financial stability while MiddleSex also receives an A+ rating.

Multi-Family Dwelling Insurance

MiddleOak’s main plan covers all apartment buildings that are comprised of at least 11 units and large buildings. The multifamily policy is available for the following:

  • Apartment buildings with at least 11 units.
  • Student housing buildings with at least 11 units
  • Senior housing that meets a certain sq. ft minimum
  • Building associations (loss of tenants coverage optional)

MiddleOak’s plan provides insurance against all common perils: fires, natural disasters, storms, earthquakes, water damage, vandalism, and more. Policies come with personal liability for building-owners that insure them against lawsuits. The coverage only extends to the exterior and interior of the building, while tenants on the property are not covered and have to purchase their own insurance independently. 

MiddleOak’s plans can be purchased for all buildings and purposes (ex. senior homes) as long as they meet their minimum unit range and square footage. The company is adamant about servicing mid-sized apartment buildings and higher. 

Tenant Emergency Assistance Add-On (Optional)

MiddleOak provides an optional policy to assist in emergency situations that cause tenants to move out of the building, causing financial distress to the building owner. This policy can be added to the standard multifamily dwelling plan

MiddleOak does not provide quotes directly – clients have to reach out to an independent agent who will audit their building, and offer a quote based on the risks involved. Each case requires an assessment before a new client is approved. The company maintains a close-knit community of policyholders who they maintain close contact with.

Education For Building Owners

MiddleOak’s website has an extensive section that can educate new apartment building owners of the dangers and maintenance of an apartment building. This can help them avoid crime, deal with tenants and gentrify a neighborhood. 

Their website provides information about the following:

  • Current state of the condo rental industry in the U.S
  • Bed bug problems and health issues
  • Special requirements for insuring commercial properties that generate revenue
  • New green conversion options and legal efficiency requirements
  • Building safety requirements & optimization
  • Building damage protection options
  • Tenant advice
  • Long-term weather impacts on buildings


MiddleOak has an open emergency line that can assist clients on a 24/7 basis – if a client’s property is damaged they can immediately reach out to their 24-hour service center.

Customer Reviews

MiddleOak receives virtually no reviews online – the few reviews it has are positive. MiddleOak caters to a certain demographic of more established and wealthier citizens who contact them privately and handle policies behind closed doors. The financial ratings of the company combined with the standing of their parent company indicate that this is a financially-sound company and considering the sensitive nature of apartment buildings if the company failed to make payments it would likely be public news.

This is an indication that MiddleOak has no problems paying out customers and their insurance policies are deemed as reliable. 

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