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Roof: I'm not sure it really is an issue. It's in very good shape and I believe we used 30 year shingles.
Cost: if I were to replace ALL the windows in the home at full price it would cost $20k. I would be replacing half the windows at half price.
Repair: I've heard this problem can be repaired but haven't found anyone who does it. Most window places just want to sell me new glass units which would be the same price as new half-price windows from the manufacturer. Waiting for a call back from someone who specializes in windows made by the company that starts with an A.
If the person that "specializes" in windows also sells them take what they say with a grain of salt.
Present the house in a neat and clean condition....Sell it..Every house needs work.
However some people are willing to pay a significant premium for a house that doesn't appear to need work. If there are obvious issues like an old roof and failed windows, trying to present it as 'turn key' or 'move in ready' isn't going to happen.
Windows are a selling point for me.... at least let the new buyers know of this half off deal you got so they dont have to pay full price.... new windows on an old house is worth $5k to me...
since there are so many choices of windows, I would leave the ones you have. Let the new owners pick out the windows they like. I personally hate with a passion white vinyl windows that fit inside the frame, thus making the window smaller. To me, this would not be good, as I hate them so much, Id have to replace them.
I personally like black clad windows with muttons and wood inside so i can paint them, just my personal preferance
Because the choice of replacement windows is so personal I wouldn't touch them but I would set aside the money you would have spent for negotiating when you have an offer.
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