Need Help!!
We recently bought a split level home on an incredible wooded 5 acres. The home has not been touched since the early 1970's. The home feels closed off from its spectacular environment. Does anyone have any ideas on how to "reasonably" update the exterior to a more contemporary look, as well as ideas for making the indoor / outdoor spaces less closed off and defined?
Out dilemma is "where do we start"?
Out dilemma is "where do we start"?

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Don't plant right in front of the windows unless you use a ground cover like pachysandra, place your plantings away from the house so that the windows of the basement are not blocked. You could develop your outdoor living space away from the house 8 to 10 feet off the entry and to the left side.
Buy larger lighting for the exterior to replace the too small lantern that I seek next to the garage. These are things that can make it more up to date.
I like this color scheme for your house:regenerative nest 2
One maintenance issue I notice from the picture is that the leader is leaking. That is why you see moss or mold growing on the siding.
If you are looking for a more modern look paint the exterior a medium gray and replace the lights. Remove the shutters.
www.lanternandscroll.com
I bought some small lights from them called the 'Columbia" series and they were the right size, and look great - didnt cost too much more than lowes either, but were made in the USA - they ship worldwide too!