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For Buyers & Sellers · October 2026

How Old Is the Roof? What It Means When You Buy or Sell on the Northside

First-time buyers don't know what they don't know. Before we write an offer, I bring up the things a showing won't tell you: the sewer line under the yard, the tuckpointing on a brick two-flat, and the roof. Of the three, the roof is the one that most often comes back around at the closing table, because the insurance company and the lender both have a say in it. Here's what to look for, whichever side of the deal you're on.

Our roofs are not all alike

On the Northside, "the roof" can mean very different things. Many of our two-flats, greystones and courtyard buildings have flat roofs behind a parapet wall. You can't see them from the street at all, and their weak spots are drainage, seams, flashing and the coping along the top of the parapet. Our bungalows and frame houses usually have pitched shingle roofs, where the questions are age, layers and ventilation. And if you're buying a condo, the roof is usually not yours alone, which changes the conversation entirely (more on that below).

Chicago winters are hard on all of them. Freeze and thaw, snow that sits for weeks, and ice that builds up at the edges find every weak seam. So a roof's age is only part of the story. How it has been maintained matters just as much.

Your inspector and a roofer answer different questions

A good home inspector is worth every dollar, but they're covering the whole house, from the furnace to the outlets, in one visit. The roof gets a paragraph. On a flat roof three stories up, or on a snowy day, that paragraph may be written from a ladder or from the ground.

A roofer's visit answers the questions that actually move a negotiation: how many years are left, what's underneath, whether the drains and flashing are holding up, and what it would cost to fix. So when the report says "recommend further evaluation by a roofing contractor," treat it as a to-do, not boilerplate. The same goes for the sewer line: on an older house, a camera scope of the line out to the street is a small cost next to what a collapsed clay pipe can run.

What Illinois sellers have to disclose

Illinois sellers of most homes, including condos and buildings of up to four units, complete the Residential Real Property Disclosure Report. One of its questions asks directly whether the seller is aware of leaks or material defects in the roof, ceilings or chimney.

Two things to understand about that form. First, it covers what the seller actually knows. A seller who genuinely doesn't know the roof is near the end of its life hasn't done anything wrong by checking "no." Second, it doesn't ask the roof's age. So for a buyer, a clean disclosure isn't a guarantee. Put your roof questions in writing (how old, what work, any leaks) and ask for written answers.

For a seller, my advice is simple: do the right thing. If you know about a leak, say so. Buyers forgive an old roof much more readily than they forgive a surprise, and a problem you disclosed up front is a negotiation, not a dispute. (This is general information, not legal advice. For your own situation, ask your real estate attorney.)

Two more people who care about your roof

A buyer and seller can agree the roof is fine and still be overruled, because the deal has two silent partners.

• The insurance company. Homeowners insurers look closely at roof age and condition. An older roof can mean a much higher premium, a carrier that declines the policy, or coverage that pays less if the roof is damaged. Since you can't close without a policy, get your quote during the inspection period, not the week before closing.
• The appraiser. On FHA and VA loans, the appraiser is judging how much life the roof has left. FHA wants to see at least about two years. If it falls short, a repair or replacement can become a condition of the loan. Conventional lenders can also call for repairs when the appraiser notes a problem.

Buying a condo? The roof belongs to the association

In most condominium buildings, the roof is a common element. The association maintains and replaces it, and every owner pays for it, either through reserves or through a special assessment. So for a condo buyer, the real question isn't "how old is the roof?" but "is the building ready to pay for it?"

When a condo is resold in Illinois, the seller has to obtain the association's resale disclosures and make them available to the buyer. They include any capital expenditures the association expects in the current or next two fiscal years, and the status of the reserve fund. Read those, and read the board meeting minutes if you can get them. A roof replacement that's already being discussed is much better to learn about before you buy than after.

If you're buying

• Ask about the roof on the first visit, not after you've fallen for the kitchen.
• Line up a roofer before you need one, so a flagged roof doesn't eat up your whole inspection window.
• Find out what's under the shingles. A roof laid over an older one is a bigger tear-off when its turn comes.
• Get your insurance quote early, while you can still act on what it says.
• Look up while you're outside. Crumbling mortar on a parapet or chimney means tuckpointing, which belongs on the same list as the roof.
• For a condo, read the association's disclosures for planned roof work and reserves.

If you're selling

• Have a roofer look before you list. It's far better to hear about a problem from your own roofer than from the buyer's inspector a week into the contract.
• Pull out the folder. The invoice from the last roof job, any warranty, and receipts for repairs all answer questions before buyers have to ask them.
• Replace it or price it in, but decide ahead of time. A new roof takes an objection off the table. Pricing the house to reflect an older roof can work too. What doesn't work is pretending the roof isn't old.
• Fix the leak, not just the stain. A freshly painted spot on one ceiling is the first place an inspector points a moisture meter.

A roof with its paperwork in order makes buyers comfortable, and comfortable buyers write better offers. We cover the rest of the prep work in How to Prepare Your Northside Home to Sell.

When the roof comes up in the negotiation

If the inspection does turn up a roof problem, there are three usual ways to settle it. Each has a catch:

• The seller repairs or replaces it before closing. Buyers, lenders and insurers like this. The catch: the seller chooses the contractor, and the buyer inherits the workmanship.
• A price reduction. Sellers often prefer it. But it doesn't fix the roof, so it won't satisfy an appraiser who has made the repair a condition of the loan.
• A credit at closing. Often a fair middle ground. Lenders limit how much a seller can credit, though, so it won't always stretch to the whole job.

Whichever way it goes, get a real number. A written estimate from a roofer settles the conversation; a guess based on one line of an inspection report just starts an argument.