You need an architect and honestly I have no idea what you are planning without you posting the interior floor plan

Thanks Patricia. I am confident in my interior plan and looking for advice on improving the exterior while maintaining it’s history.

That's no Greek Revival. It may have started as a "four square". The triple window seems out of place. Look up "four square house" and see if anything helps.

Thanks! The columns on each of the corners is what made me think it was a revivial BUT foursquare looks much more obtainable! i really appreciate the input!

Is this the side of the house or the front? How old is the house? Looks 1910-1920 to me but hard to tell with later changes. Correctly sized operable shutters when you can. I like the arched entrance to the breezeway but I would love to see that repeated on the garage doors (instead of the clipped corners...) tricky to wrap the porch since it appears the porch roofline is higher than the ell. Photos of the right side of the house showing the existing porch would help

@HALLET & Co. The original photo is the front, facing the street but i would like to define it with a proper front entry, as it always does confuse new visitors. The house was built in 1920! Thank you for your input! I have attached more of the porch although it is currently blocked by overgrown shrubs.

I wouldn't extend the porch.

Can you center the new main entry door? Then, build out that portion of the entry, using a roofline like below:

Create a patio leading to the stairs as in the photo above, and add large pots of flowers near the door. Add a large, curved landscaping area under the front windows (use plantings with lots of textures, heights, colors). Eliminate the sidewalk to the porch, instead making it more of a garden path that weaves around the new landscaping.

I like your idea of a portico. Make sure it is not close to the side of the house, because it will dump water on the side and the chimney. I would not expand the front porch, it will visually compete with the entry. Definitely square off the garage corners. Add some black hardware.

Glad to see you are getting rid of the shutters. I would paint the window frames and muntins black and the trim a medium brown to emphasize them and tie in the roof.

A shed roof portico would be a better solution. You can center it on the breezeway.

I would also install a island planting area anchored by an ornamental tree, like an Eastern Redbud about where the post lantern is out in the yard. This will help highlight the new entry. Lower any overgrown bushes near the porch.

@houssaon i appreciate the photoshopping! it is helping a lot, thank you!

A house built in 1920 is definitely not Greek Revival. https://www.nps.gov/articles/greek-revival-architecture.htm

A lot of four squares have porches across the entire front of the house. I don't know if you want that extensive a project, but I think a porch at the height of your existing porch across the house and extending past your new entry could tie it all together, lessen the impact of the triple window, and give you a nice big porch.

I think I would leave the house alone. Paint, repair, but not change what has already been done. I would spend my money on the landscape, creating a welcoming pathway to the door you want guests to use and softening the look of the front.