MiddleOak Insurance Review & Complaints: Property & Casualty Insurance

MiddleOak Insurance Company offers property and casualty insurance for multi-family buildings. MiddleOak Insurance ratings are an A+ (Superior) with A.M. Best. MiddleOak Insurance Company car insurance is not available at this time. If you’re looking for cheap auto insurance rates, enter your ZIP code to compare affordable car insurance quotes from top companies.

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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 place to get it.

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Written by Eric Stauffer
Founder & Former Insurance Agent Eric Stauffer

Leslie Kasperowicz holds a BA in Social Sciences from the University of Winnipeg. She spent several years as a Farmers Insurance CSR, gaining a solid understanding of insurance products including home, life, auto, and commercial and working directly with insurance customers to understand their needs. She has since used that knowledge in her more than ten years as a writer, largely in the insuranc...

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Reviewed by Leslie Kasperowicz
Farmers CSR for 4 Years Leslie Kasperowicz

UPDATED: Jun 1, 2022

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MiddleOak Insurance

Financial Strength

Company Statistics for MiddleOak Insurance
MiddleOak Insurance FactsDetails
Year Founded2006, as a merger between Middlesex Mutual Assurance and Holyoke Mutual Insurance
Current ExecutivesMiddleOak CEO - Christine Bussone
Number of Employees51-200 Employees
Address of Company HeadquartersP.O. Box 891
213 Court Street
Middletown, CT 06457-0891

P.O. Box 2006
One Holyoke Square
Salem, MA 01970-6506
Company Phone Number1-800-622-3780
Company Websitewww.middleoak.com
Best ForProperty and Casualty Insurance for multi-family buildings
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Searching for the best insurance companies means hours of research, internet searches, and phone calls. Imagine if you had all the information you needed in one easy guide instead. In this MiddleOak Insurance Review, we’ll look at and analyze all the information related to the company to give you a better idea of the options available to you.

MiddleOak Insurance is a specialty insurer providing a specific type of property and casualty insurance. Their products cover multi-family buildings such as apartments. They do not offer auto insurance at this time.

MiddleOak is the trade name of two companies that joined forces in 2006: Middlesex Mutual Assurance and Holyoke Mutual Insurance, resulting in the combined name.

The headquarters for the underwriting companies are in Salem, MA, and Middletown, CT. Both of these are subsidiaries of the major insurer Country Financial.

Before jumping into our MiddleOak insurance review, enter your ZIP code into our free quote tool to start comparing affordable auto insurance rates now.

MiddleOak Insurance Rates

While the price isn’t always the deciding factor when it comes to choosing an auto insurance policy, it’s usually one of the most important.

Although MiddleOak Insurance does not offer auto insurance policies, you can look at the table below to get an idea of what you might pay for auto insurance depending on how much coverage you decide to buy.

You can compare ratings like A One commercial insurance rating to the average to decide what is best for you. The table shows average annual rates based on coverage levels.

Average Annual Auto Insurance Rates by Coverage Type
Coverage TypesAverage Annual Rates
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These are just guidelines. Actual rates will depend on a variety of factors, such as age, driving history, and ZIP code.

What is MiddleOak’s availability by state?

MiddleOak Insurance provides coverage in most states. The company writes one main type of policy: Property and casualty coverage for multi-family dwellings of at least 11 units and other rental properties. This includes coverage for apartment buildings and other rental dwellings, as well as associations in some states.

Previously, this company wrote auto insurance and home insurance policies. That no longer appears to be the case. Products are sold through independent agents across the states where MiddleOak does business.

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MiddleOak Insurance Coverages Offered

One thing you’ll need to ask yourself before purchasing your auto insurance policy is, “How much car insurance coverage do I need?”

If you’re financing your vehicle, your loan company may require you to carry full coverage insurance. Otherwise, you’ll need at least the minimum amount of liability insurance required by the auto insurance laws in your state of residence.

If you decide that you need more than the minimum coverage required by the state, there are several different options available to you as additional coverage. The table below shows some of the different types of policies and coverages available to you, along with what they do.

Types of Auto Insurance Coverage
Insurance Coverage TypesWhat It Covers
Bodily injury liabilityPart of your liability coverage that pays for medical bills if you've injured someone else in an automobile accident
CollisionCovers damage to your car after an automobile accident
ComprehensiveCovers damage to your car that happens when you're not driving
Personal injury protectionCovers medical expenses for you or your passengers after an automobile accident
Property damage liabilityThe other part of liability coverage that covers the cost of any property damage you've caused in an automobile accident
Uninsured/underinsured motoristCovers the costs if you're in an automobile accident caused by a driver with little or no car insurance
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Again, these are just guidelines and actual prices will vary, so it’s always wise to do compare car insurance policy options before purchasing. MiddleOak Insurance does not offer auto insurance coverage at this time.

What are MiddleOak’s bundling options?

Many insurance providers offer bundling options. What this means is that you can purchase two or more different types of insurance services from the same provider, usually at discounted rates.

For example, you can purchase your auto insurance policy as well as your life insurance from the same company if you choose. Most insurance companies offer a discount of anywhere from five percent to 25 percent if you choose to bundle.

Check out the video below to learn about the pros and cons of bundling your insurance policies.

Many companies offer multi-car discounts, also. You can think of this as a way of bundling as well, but in this case, you’re buying auto insurance for multiple vehicles. Auto insurance companies offer up to a 25 percent multi-car discount on combined policies.

What are discounts offered by MiddleOak?

Auto insurance discounts vary by company, but many discounts are fairly standard throughout the industry.

The table below shows some of the most common auto insurance discounts available, an estimate of how much money each can save you, as well as the major auto insurance companies that offer the discount.

Common Auto Insurance Discounts Offered by Company
Discount TypesDiscount SavingsCompanies Offering Discount
Low mileage/Low usage discountUp to 20%State Farm, Allstate, Travelers, Nationwide, Progressive
Defensive driving discount10%–15%State Farm, Geico, Allstate, Travelers, Nationwide, Progressive, Farmers
Safe driver discount10%State Farm, Geico, Allstate, Travelers, Nationwide, Progressive, Liberty Mutual
Military and federal employee discount8%–15%Geico, Esurance, USAA
Good student discount5%–25%State Farm, Geico, Allstate, Travelers, Nationwide, Progressive, Liberty Mutual
Senior/Mature driver discount5%–10%Geico, Allstate, Liberty Mutual
Homeowner discount3%State Farm, Geico, Allstate, Travelers, Nationwide, Progressive, Farmers
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MiddleOak does not offer auto insurance so these discounts would not apply with this company, but they may offer other discounts on the policies that they do provide.

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What programs are available from MiddleOak?

MiddleOak’s niche is multi-family dwelling coverage that includes property as well as liability coverage for buildings of 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.

The company’s Worlds Apart plan is intended for rentals such as apartments, student housing, senior housing, rental condos, and associations. It can be customized to include Business Owners 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.

Canceling Your MiddleOak Insurance Policy

What should you do if you need to cancel your policy?

You can watch the video below to get an idea of what to expect should you need to cancel your auto insurance policy.

Keep reading to learn more.

Is there a refund?

Whether you can get a refund on your policy depends on the type of policy and when you choose to cancel.

If you choose to cancel a refundable policy in the middle of the policy cycle, you’ll receive roughly half of what you paid, assuming that you only paid for that cycle. Since refund amounts may vary and depend on a variety of factors, you should always check with your insurance agent to see what factors apply to you.

How do you cancel?

You can cancel your policy at any time simply by contacting your insurance agent and letting them know that you’d like to cancel your policy. Your agent will let you know when the changes will take effect and whether you’re entitled to a refund of any policy premiums you’ve paid in.

When can you cancel?

You can cancel your policy at any time simply by contacting your insurance agent and letting them know that you’d like to cancel your policy. Once you’ve canceled your policy, any excess premiums will be refunded to you promptly.

How to Make MiddleOak Insurance Claims

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

Should you need to file a claim, you can use any of the following methods to contact MiddleOak Insurance:

  • Middleoak Insurance Address #1 – 213 Court St., P.O. Box 891, Middleton, CT 40645-0891
  • Telephone #1 – 1-800-622-3780
  • Address #2 – One Holyoke Square, P.O. Box 206, Salem, MA 01970-6506
  • Telephone #1 – 1-800-622-37880
  • On the company’s website under the “Property Claims” and “Premises Injury Claim” sections

Aside from the contact information, there is little online in the way of explanation about the claims process. That is not surprising, given the complex nature of this sort of coverage compared to a basic home policy. The MiddleOak Insurance agent login is separate from the customer login so be sure to use the right portal for claims.

Watch the video below to get an idea of what you can expect during the claims process. This video pertains to auto insurance claims.

Keep reading to learn more about MiddleOak Insurance.

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MiddleOak Insurance Reviews and Ratings

As a member of the Country Financial Group, MiddleOak Insurance’s A.M. Best rating is an A+ (Superior). A.M. Best is a leading industry provider of insurance company ratings. The Better Business Business (BBB) does not have a page for MiddleOak Insurance.

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 MiddleOak Insurance reviews and complaints from customers themselves. The company’s shift into solely covering rental dwellings is likely a big part of the reason for this.

MiddleOak Insurance: The Bottom Line

We want you to find the company best suited for your needs, be it Dauntless Insurance Group, Cotton States Insurance Company, Country Preferred Insurance Company, Country Financial Car Insurance, or MiddleOak.

If you’re looking for a company that’s focused on the needs of rental homeowners, MiddleOak might be a good bet. When a company focuses on one type of policy, it tends to have a lot of expertise in that area. From our research, it seems that MiddleOak is doing a good job within its niche.

Now that you know everything you need to know about MiddleOak auto insurance, we hope that you’ll feel more confident in purchasing your policy. Which part of this guide was the most helpful for you?

Now that you’ve finished this MiddleOak Insurance review, enter your ZIP code below and start comparing free auto insurance quotes right now.

Frequently Asked Questions: MiddleOak Insurance

In this section, we answer some of the most commonly asked questions about MiddleOak auto insurance. Some of the answers may have been covered in part or in full in the guide above.

#1 – Does MiddleOak Insurance have commercials?

While MiddleOak Insurance does not have any television or radio commercials available online, it does have its own YouTube channel for promoting its products.


There are also a series of “Doing the Right Thing” videos on the company’s website. “Doing the Right Thing” is MiddleOak’s Mission Statement.

#2 – Is MiddleOak Insurance involved in the community?

MIddleOak Insurance does its part in the community by publishing a series of videos in its “Doing the Right Thing Campaign,” which highlights the importance of good business and involvement in the community.

The video below is one such example.

MiddleOak Insurance considers itself unique among companies when it comes to treating customers and employees with care.

#3 – What do MiddleOak employees have to say?

As mentioned above, the company motto is “Doing the Right Thing,” and it shows. The company provides an in-house gym for employees to use, making MiddleOak Insurance careers appealing.

Student workers are provided with extended lunch hours to give them study time, and the company also helps fund additional industry training for its employees. MiddleOak Insurance CEO Christine Bussone creates a good work environment.

Take a look at the video below to get an idea of the Corporate Culture at MiddleOak Insurance.


Keep reading to learn more about the MiddleOak Insurance Company.

#4 – Does MiddleOak Insurance offer SR-22 insurance?

If you’ve had more than your fair share of traffic citations, automobile accidents, and/or auto insurance claims, you may be considered a high-risk driver. Normally, high-risk drivers are required to purchase SR-22 insurance, which isn’t available through all companies, so it may take some looking around to find coverage.

MiddleOak does not offer auto insurance so it does not offer SR-22 insurance, either.

The filing fee to get SR-22 insurance is only $15-$35, but the increase in rates for drivers that need SR-22 insurance when compared to rates for drivers without any driving violations on their records is steep.

Rate increases for driving violations that result in a driver being forced to carry SR-22 insurance can be as much as $541 a month.

#5 – Why would my provider cancel my auto insurance policy?

Your auto insurance provider may cancel your policy if you do any of the following:

  • Get your driver’s license suspended or revoked
  • Lie during the application process
  • Fail to pay your auto insurance premiums

Your auto insurance company may also choose not to renew your policy if they determine you to be a high-risk driver.

#6 – What is Normandy insurance company’s A.M. Best rating?

The company has an A (Exceptional) rating.

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