What are all those tiny windows for?If you want a more modern look IMO no bay windows . A wak\lkway too the front door from the street some redo of landscaping and if the siding is in good shape maybe just paint it.I really think vinyl siding looks cheap . If you need siding look at cement board a much nicer choice for sure.New front doors with some glass in them and all those tiny windows made to look like the rest of the windows on that side of the house

What are all those tiny windows for?If you want a more modern look IMO no bay windows . A wak\lkway too the front door from the street some redo of landscaping and if the siding is in good shape maybe just paint it.I really think vinyl siding looks cheap . If you need siding look at cement board a much nicer choice for sure.New front doors with some glass in them and all those tiny windows made to look like the rest of the windows on that side of the house Dark vertical siding mixed with natural cedar would be a great look

Thank you for your suggestions Patricia. There is a circular driveway that is hard to see from the picture we posted so I'm not sure how a walkway would work as it would have to cut across the driveway.

We currently have asbestos shingles and have painted them 3 times over the last 20 years. I think they kind of make the house feel dated. The small windows are from our master bedroom redo 20 years ago. They were actually very modern looking when we put them in. I'm attaching a picture of how they look over our bed, but your right they do appear small from the outside.

these are all update split levels. (i'll have to post pics one by one since houzz is glitchy)

since you like the smaller, more modern looking windows, why not do that side of the exterior in cedar plank siding? you can do composite cedar

this has the garage, but picture it just on the right, and do regular siding on the left portion

you could also do a board and batten

here's a shake

regular siding:

here's one w/a bay window, although it has brick

another option is to extend the roof over the front door and over to the right

Hi Beth. Thank you for sharing all the photos! I like the first two pics, they have more of a modern feel which is what I'm trying to accomplish.