A New York City-based landlord swooped into metro Detroit in 2017 and dropped $74 million on the storied Bank of America office building in Troy.

Eight years later, the building is worth barely one-third of that, appraisers say, and its owner, Sol Gutman, is deeply underwater on his and his investors’ commercial mortgage-backed securities loan.

It showcases yet another sign of pesky but serious stress in the office market.

With the side effects of the COVID-19 pandemic still lingering, four major office buildings in metro Detroit are squarely underwater on their CMBS loans — and their owners are in various states of attempting to settle the debts.

Not only is the Bank of America building worth well less than what its ownership owes, but so are the 696 Centre in Farmington Hills, as well as Southfield’s Omni Officentre and Maccabees Center.

All told, the buildings — which total more than 1.4 million square feet — have plunged in value by more than 71% and are worth just over half of what they owe on their mortgages, according to a Crain’s analysis of CMBS and property data from New York City-based Trepp LLC and Washington, D.C.-based CoStar Group Inc.

Of course, the suburban buildings are not alone in their predicament. In fact, the Detroit Metropolitan Statistical Area is performing better than the country as a whole. Slightly more than 4% of the region’s outstanding CMBS balance is underwater, while nationwide it’s about 9.6%, according to Trepp data.

There is some $500 billion in commercial real estate loans of all kinds — not just commercial mortgage-backed securities — maturing this year and some 14% of that is for properties that are underwater, with office and multifamily properties particularly in stress, according to data from New York City-based MSCI Inc., formerly a division of Morgan Stanley.

The office market has faced unprecedented challenges the last few years as a result of the hybrid work revolution ushered in by the global pandemic.

However, said Dennis Bernard, founder and president of Southfield-based commercial real estate finance company Bernard Financial Group, there are always a handful of properties that are underwater on their loans.

And, in fact, generally very specific types of office buildings are facing the most challenges, Bernard said: Those with large floorplates designed for large users, and those that had large single tenants bail from them, as there are precious few, if any, occupants like that to replace them.

“Everyone needs to take a breath,” Bernard said.

And while office landlords have taken their licks over the last five-plus years, those with large Class A properties not only in the suburbs but also downtown should emerge largely unscathed by their current lenders working with them or in many cases being able to refinance and move forward, according to Bernard.

He also said the Detroit market, along with other Midwestern cities with the exception of Chicago, have tended to fare better from an office perspective than cities like Seattle, Portland and Austin because the region hasn’t faced the same type of challenges like skyrocketing housing costs in a short period of time that have contributed to putting their downtowns into distress.

Here are snapshots of the four properties and their current financial situations.