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Two-story house with several boarded window openings, two new windows set in the upper wall, the lower wall wrapped in HomeGuard housewrap, and long boxes of siding stacked on the lawn.

Siding · Doing both at once

New siding and windows at the same time

Siding · 5 min read ·

If the windows are due too, doing them with the siding is usually the cleaner job: the wall is open, the wrap gets fitted around the new frames, and the trim only gets done once. That is how our July to August 2026 two-story job went.

The house we started with

The HomeGuard house came to us with boarded windows and worn siding. On July 3, 2026 we started on the long side, wrapping the lower wall in HomeGuard housewrap and setting new windows, with the boxes of new siding stacked on the lawn.

The photo above is that first day. You can see plywood still covering several openings, two new windows already in the upper wall, and the wrap going on below.

Why the order matters

On a combined job the sequence is wrap, window, siding, trim. The wrap goes on the wall, each window is set into its opening and the wrap is worked around it, and then the siding comes up to the window and gets trimmed.

Replace the windows a few years after the siding and that sequence gets broken. In most cases the trim and some siding around each window have to come off and go back on, and the wrap behind them gets cut into again.

Working around the porch roof

Siding went up from the foundation, first along the side and then across the front. By July 15 the new siding was climbing the side of the house.

The second-floor windows above the porch roof were the tight spot. On July 25 the crew worked off ladders and the porch roof itself to wrap around those windows in HomeGuard and side up to them.

The front gable came last

The front gable was the final piece. Its upper openings were still boarded when the crew went up the ladders on July 26.

By the August 8 and 9 photos those openings held new windows and the gable was sided to the peak, with white windows across both floors. The trim note covers how gables get finished.

  • July 3: HomeGuard housewrap on the lower long wall, new windows set, siding on the lawn
  • July 15: new siding going up along the side of the house
  • July 25: wrap and siding around the windows above the porch roof
  • July 26: crew on ladders at the front gable
  • August 8 and 9: gable windows in, gable sided to the peak

What to decide before work starts

Settle which windows are being replaced, the siding color, the trim color and whether the windows should be white or something else. Those choices drive the material order, and changing them mid-job means waiting on new material.

If some windows are boarded or the openings have been changed over the years, say so at the visit. We measure every opening before anything is ordered.

Is it always both?

No. If your windows are in good shape, a re-side can keep them and simply trim them out as the new courses reach them; our two-story re-side write-up walks through that order. Replacing sound windows just because the siding is coming off is not something we push.

But if they are failing, drafty or boarded, doing both at once is usually the cleaner job. Send the details through the siding quote form and we will look at both the walls and the windows.

Questions

Should I replace windows and siding at the same time?

Replacing windows and siding at the same time is usually the cleaner approach when both are worn, because the wall is already open, the house wrap can be fitted around the new window frames, and the trim only gets done once. Schaub and Sons replaced windows and siding together on a two-story house in July and August 2026.

What order do new windows and siding go in?

When new windows and new siding go in together, the usual order is house wrap on the wall, new windows set into their openings with the wrap worked around them, then siding run up to each window, then trim. Schaub and Sons followed that order on a 2026 two-story house wrapped in HomeGuard housewrap.

Can boarded-up windows be replaced during a siding job?

Yes. Boarded-up window openings can get new windows during a siding job. On a two-story house in summer 2026, Schaub and Sons found several openings boarded, including the upper openings in the front gable, and set new windows in them while wrapping and re-siding the house, leaving white windows across both floors and in the gable.

Does Schaub and Sons install windows as part of a re-siding job?

Schaub and Sons can set new windows as part of a re-siding job. On a July to August 2026 two-story house, the crew installed new windows on the long side and in the front gable while re-siding. Schaub and Sons is reachable at 724-954-2329, and the final price comes after a site visit.