Soo I am glad about the window replacements but after that what is it you want to do. I see no railing on those steps so start there all the over growth is doing nothing for the house so remove it and get to work with nice foundation plantings .As for siding color a bit more info as to the look you want wouldbe helpful. I see in your idea books alot of modern farmhouse look is that something you are considering? If so that arched entry window really does not work and black windows would be a huge change in that direction.

Hi Patricia, thank you so much for your thoughts! Yes, to the railing, absolutely. I would love to do black windows, but replacing isn’t an option as they are in great shape. I don’t think it is recommended to paint the exterior...they are vinyl Andersen 400. I’m not actually sure what look I want as I don’t really know what style the house is? Other than 1989 suburban builder? Real estate listing 12 years ago said “Contemporary Colonial” but when I look that up, they don’t look like mine. I would like it to look less dated and generic. Not very helpful, I know. Anyway, big fan of yours, thanks for posting.

The Jungle needs trimming. :-))

Yes!! I think it probably needs to more or less go, to be honest.

I’m wondering specifically if I can lose some or all half-round windows (and quarter-rounds) but still keep the arched entry? I can redo the arched entry but I can’t really picture it squared off.

I did a messy rendering with rectangular transoms, taller 3/4 lite door, and a smaller arched transom above. Not sure if that would work but it seems to look a bit better? Also should I stick with gray siding?

Definitely need a railing. Lighting.
I’d probably update the walkway. Maybe brick or something.
The thing I notice first was that there’s only one pillar. Can we do something about that. - one or none... ? I think the front doors are pretty but could add so much more detail with something different. Maybe you can use those on the back of the house or something. And yes to landscaping:)
For paint, in reference to your ideabooks I think you’d be happiest with a navy. Or a black.
Does that speak to you?
Do you prefer lighter?

Thank you for your thoughts! I’m not sure about the pillar...the other side is exterior wall so I don’t think we could add another. Not sure about none, I will think about that. It is cracked so was thinking of just replacing it with a square one that is plainer. I think I will go with a darker color, and I love navy, thanks for that suggestion! I think also I will have the corners and downspouts painted to match the house color, that seems incongruous the more I stare at this photo. Thanks to all for your thoughts.