As if $32 million weren’t enough, whoever buys the penthouse in Chicago’s Trump Tower on North Wabash Avenue can expect to pay a further $12,150 a month in maintenance fees.

The 14,260-square-foot residence is No. 1 in Chicago in terms of monthly fees on properties for sale, according to real-estate brokerage Redfin.

Building fees, often called common charges and homeowner-association (HOA) fees, pay for the upkeep of the property as well as services and amenities, like security, swimming pools and doormen. Monthly amounts can go even higher if the building is a co-op, meaning it is owned by a corporation comprised of the resident-shareholders. With co-ops, the shareholder’s portion of the building’s property taxes is incorporated into the common charges.

Larger, older buildings tend to have higher fees because they are more expensive to maintain, says Leonard Baron, San Diego State University lecturer and author of “Real Estate Ownership, Investment and Due Diligence 101.”

The Mark, built in 1927 on Manhattan’s Upper East Side, is a good example. The 10,000-square-foot penthouse, currently on the market for $60 million, has an additional monthly charge of $39,927. That covers access to services offered by the five-star hotel in the building, but it also includes property taxes, since the Mark is a combination condo/co-op.

Kelly Kennedy Mack, president of Corcoran Sunshine Marketing Group, says the monthly fee for the Mark is about $4 per square foot, slightly higher than the traditional luxury co-op, which ranges from $2 to $3 per foot. She attributes the higher fee to the added amenities of the Mark. By comparison, the highest monthly fee without real-estate taxes in Manhattan is $1.75 per square foot for 100 Central Park South, according to Jonathan Miller, an appraiser and president of Miller Samuel.

The price of a property and its monthly fees aren’t always directly related. According to Redfin, which covers 19 markets in the U.S., the property with the highest HOA fees for sale in Washington, D.C., costs $6.65 million and has a monthly fee of $8,005 per month. But the second-highest monthly fee, at $6,747 per month, comes with a much lower price tag of $1.85 million.

Of course, none of these include what some buildings call “special assessment fees,” one-time charges that pay for long-term projects like a new roof or plumbing upgrades that may only need to be done once a decade, Mr. Baron says. While about a third of the homeowners’ monthly fees are typically set aside for this type of maintenance, many times building owners and boards don’t set aside sufficient funds. So residents are charged again.

“That’s the real kicker,” he says.