I am not a fan of bay windows, so I would not put money there.

The mansard roof is the most unattractive feature of your house. In fact, I think it is the only unattractive feature. I suggest you post more pictures of it from the side and also at an angle. You might get some good ideas and opinions.

Thanks! here are some additional photos

"Cottage feel" is very subjective. Can you post some pics from Houzz of your vision of cottage feel? We need to get an idea of your vision and then can offer suggestions of how to use elements of your ideal to get your house closer to it. Your idea books don't have any exterior pics.

In very old (1700's) houses it is common to see different styles and materials mixed as with your house. So, the look of your house does have historical roots. However, I'm sure you don't want to live in a museum. For houses that are a bit of a mishmash I generally recommend painting the discordant parts the same color to bring some cohesiveness. Would recommend that with your home. The gambrel roof is going to be evident no matter what you do. That may be something to live with. Good luck!

IMO the gambrel roof was a poor choice as are those over height dormers I would need to know what the budget is I think right now painting the siding a color that is better with both the roof and the brick like a nice grayed sagey green. Then a pretty cottage type entry door and then some cottage type landscaping no bay window for sure and maybe even a porch across the left side .

Thanks so much for yalls in put. We’d probably budget $50-65,000 for new windows and exterior improvements. here are some inspiration photos

More inspiration

We’re willing to paint the siding for now but make architectural changes and replace the original windows, if that helps

No bay windows for this house.

I would take the mansard roof off, add a pitched roof and shake siding to make the home more 'cottage-like'

If you're willing to spend that kind of money then removing the mansard roof is going to give you the greatest improvement in the appearance of your house. I can't imagine why anyone ever thought a mansard roof was a good idea on a split level. You will need to change the size of the windows on the second story as right now they're too tall (see the pictures Beverly posted). I don't think the brick is very attractive - it looks kind of spotty, so I would Romabio whitewash it. It's a stretch to make a split level cottagy, but I assume you like the interior and your neighborhood, so if it's just more attractive when you're done you're ahead. Upgrade your landscaping when you're done. It really looks like a nice lot.

I think your dormers look too tall already because the windows do not extend up to their gables. This little home achieves a cottage look without removing the roof. You need some unifying elements like siding and painted brick to match, and the same roofing on both sections. Check with Romabio to match masonry paints/stains with your paint color for the siding. White is a nice classic You won't be able to achieve the look of the cape and the Tudor you posted as inspopix, but you can make what you have a lot better. The big issue after that is the landscaping. It needs a complete redo and is old, scrawny and out of control.

Thank you for the input! all advice is much appreciated!! ( the home was vacant for over a year before we purchased it so the landscaping is in desparate need of attention as well. )

Lower the dormers to meet the windows and not peak above the roof line - That will be pricey but worth it and a lot less expensive than removing the gambrel roof.

Paint the brick with a masonry paint or lime paint. Don't do a wash that exposes the brick. The house and roof together are both busy, you need to tame one of them down and it's cheaper to tame down the brick. I know folks love to recommend a wash that shows some brick, but someone did that in my neighborhood and in person, it looks awful.

Can't quite see the lower windows, but they look like they need to be freshened up. Are those storm windows? Storm windows do the job but IMO, cause too much reflection as a single plane if you're going for cottage. You need the mullions to break it up. Get good quality windows in a style you like.

Black shutters

Make your front door more prominent by removing the storm door. If you need better energy efficient door, get that and don't replace the storm door. If you need the storm door, get a good quality one with low profile styles so the door will show.

Paint the siding the same color as the brick

New handrail that compliments the overall look. Not sure what that is but once everything else is done, you'll figure it out.

Landscaping.

If you really want to use or maybe exceed your budget, do cedar shakes on the gambrel and roof. My neighbor has a very similar house and did cedar shake on the front of the gambrel and the front of the roof. They did asphalt shingles on the back to save money. Looks really nice.

$50 - 60K seems like a lot but it will go fast once you start making changes that cut into the roof line. Plus good quality windows are crazy expensive now. Make a plan, price it out and you can make your lovely home spectacular on that budget.

50-60k would not get a completely reframed roof eliminating the mansard and changing the dormers And new windows in my area. You would be reshaping the entire second story.

And when you are done you will still have a 1960s split level.

I think you could update the house cosmetically without reinventing or "correcting" some perceived flaws in the proportions somebody used 50 years ago. Unless you essentially have money to burn. Invest money in really good windows and materials. Don't waste money changing an entire roof shape for esthetics. Work with what's there, not against it.

Your first inspiration photo is perfect. Do that! Find a quality renovation contractor who can adapt your house to reflect that design. That light cream color is wonderful — cedar shakes on the front of the gambrel would be lovely. Vertical board and batten to replace the horizontal siding could also help reduce the discordance between the two ‘halves’ of the house. I would take the shutters off the front picture window.