Is It Possible to Have Larger Windows Installed in Bedroom?

Good Questions

Q: Hi! We just bought our first home. It's in great shape and I am in love with the house, but one thing about it really bothers me: the window in the master bedroom. It's tiny, and at an awkward height, and randomly placed in the room. It looks to be an afterthought. We aren't handy people, but we want to add two large-ish windows. We would hire someone. But, is this doable?

I don't want to get my hopes up if it's not feasible. Attached are two pictures: one of the window in the room, and another of the siding of the house. The window would face the backyard. What do you guys think — is adding windows a possibility?

Sent by Mary

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(Image credits: Mary)