I wonder if the structure can take the weight of a third story. I doubt it.

What kind of space do you need? More bedrooms or larger bedrooms? Other space?

To you concern about curb appeal, I think you should prune the rhododendron to sill level. This means cutting them with heavy duty good quality pruners. They won't look great at first, but they should survive. When my neighbor first move in she cut ones in half that had grown ten feet high. Decades later they still look good.

I think you might want to paint the lower level shutters, the front door and the wonderful wood storm door red. Or if you want to keep it subtle, paint them all (and the second story shutters) a very light gray.

Cute house!

I looked into finishing my attic as a master suite. My structure already had the head room so no need to lift the roof but none the less to reinforce the floor joists and redo stairs to today's codes, and connect new plumbing the quotes came in between 150 to 250k. We went with just adding a master bathroom above our sunroom which connected to the larger bedroom upstairs but moving might have been the cheapest option.

Would you be ripping off the 2nd story and adding 2 stories?

If not I imagine it will look like a wedding cake.

@houssaon thank you so much for the mock up. I think you’re right that just a bit of pruning and paint would make the world of difference. The home is actually quite large off the back so the need for more space may not be necessary. The idea for the third floor was 1. To make the house more grand from the street and 2. To add an area dedicated to a master suite where we could have a full bath / closet without having to much around walls to accommodate on the second floor.
Do you have any suggestions of how I could make a more impactful entrance to the front door that might have the same impact without the cost of a third floor?

@mrykbee haha! You’re probably right!

Your house is beautiful! I wouldn’t go for “grand.” Embrace it for what it is...a charming Dutch gambrel home. The back, with its red and white color scheme, is lovely. I think that you need to focus on how you can make the front of your home match the back in its appearance. Landscaping, of course. But also in attention to color. The disjointed white/black/red coloring in the front isn’t working. Perhaps carry the red color down to the first floor, too. And then white shutters both up and down.And a crisp black front door?

1720?!?!!! How cool! Are you limited by historical landmark status or anything like that? Even if you’re not and you are free to do as you please, I’d really try to preserve or restore the original dwelling, doing what it appears that previous owners have done when confronted with the need for more space: add on horizontally. As far as curb appeal is concerned, focus on landscaping, hardscaping, paint, lighting and hardware.

I'm not a pro but here's my thoughts.

I think the whole "master suite" idea is overrated. I have a decent sized master bedroom and bathroom and I rarely spend time in there. I use it basically for sleeping and getting ready for work and bed. I may be in the minority here but I don't use my room as a retreat.

A lot of the pros here say to live in the space for at least 6 months before thinking about any major changes. Adding a third story, if it's even possible, is a huge undertaking and the house may not be able to support it. You may decide to update the inside rather than adding more square footage.

I would also start with small projects first. I agree with pruning the bushes. Get some seasonal flowers for the front. I personally prefer pots of flowers that I can change out vs planting in the soil. If you really want the front entrance more "grand" then consider expanding the walkway and adding some new lighting.

Is there anything more charming than Dutch Colonial? I don’t think so! I love this picture, especially the beautiful blue and the barrel roof over the front door.

How is the second floor arranged? Do you need all the bedrooms? Can you grab a bedroom to convert to a bath and closet?

@bpath I love this picture too! Combining ideas from a few of the comments I think you guys are right. The way the home is half white / half red at the front is giving it a choppy appearance. If we make it continuously red with white trimming it would look more cohesive. I love this barrel roof example. I believe we need to do something like this to break up the front so it’s not just two horizontal roof lines

There’s also this, that adds a sweet deck to the 2nd floor. It will be expensive, though, for the value/use you get from it.

^^Agree with this, especially if the front of your house is within chatting distance to neighbors walking on the street. Yep, we have a balcony over the front door. It’s about 5’ deep by 10’ wide and 100% useless. Over the last 20 years or so, I’ve been out there only a handful of times. I just feel so exposed! But then again, my balcony doesn’t have a cute little vestibule to duck into like the house pictured above.