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I am not inept at working with my hands, I have just not replaced windows before. Any help, sans obligatory snarkiness :), is GREATLY appreciated!

This is the center piece between the two windows.

This is the full width of the window.

This is the bottom right of the right window and window sill.

This shows the left jamb with the window in the raised position.

This shows the left jamb of the right window next to the center divider that is between the two windows.

Two more questions... 1)Do I need to buy two windows? OR 2) Should I buy one really large window?

I’ve noticed that real estate agents always want to make improvements on a house no matter how perfect it is. I figure that’s one way to create jobs. If it’s not the windows, they’ll tell you to redo the kitchen or bath. Their job is to intimidate and discourage the owner and find excuses why the house won’t sell. Then they tell you to paint the front door red.

Personally, my thought about doing a major fix up to a house just to sell it for more is a waste of time and money. A potential buyer may hate your new windows and may try to lower the price of the house because of them... and perhaps they may want to replace the windows with wooden ones. You just don’t know what a potential buyer wants. Therefore your money spent would have gone out the windows!

Spend time washing the windows and frames. Remove the fly poop. Caulk and paint. Replace any broken panes. Maybe strip the paint off the wood and stain instead. In other words, work with what you have. Make sure everything looks and is clean.

Find out if you need a building permit to change your windows. In my town if one is replacing 90% of windows or changing the size of them, a permit is needed. Look into your town laws.

I have stripped the paint off all my windows. It’s a lot of work. I just can’t imagine changing entire windows because there’s always a technical issue that would arise which would lead to some construction work. Nothing fits the same as the original. You may later regret you started.

Sell your house as is.

This place has replacement windows for about half the installed place.

I bought one to replace a failing aluminum window in our bedroom, and it made an amazing difference -- couldn't hear the neighbor's weekend parties anymore, no drafts, and way better insulation. I paid for installation because I had no idea how to do it. Once I saw it done, I would have no fear of doing additional ones myself. You just take out the old windows, leaving in the aluminum frame, slide the replacement window into place through the aluminum frame, and use multiple tubes of caulk to seal and hold it.

If you have to do multiple, you might pay to have one installed, and then do the rest yourself.

Talk with someone who really knows the process - maybe someone at Loews could help. It won't be a clean and neat replacement and you may end up getting into the studs that they are anchored into and will most likely need to redo the sheet rock along the sides - along with the window sill. I had mine replaced professionally after Katrina and ended up doing some after the fact sheet rock work and also used my router to make some custom windowsills. It may also be tough to make them match the existing windows which might also cause issues. My replacement windows also had a different depth than the originals and did not reside in the exact same placement in the frame.

Good luck