Yes, without a doubt, if you can afford to, then do it. Look for historic pics online of what other homes like this looked like you your city. Extensively drive your neighborhood to see if any homes have been restored, or better yet, never touched. See what cues you can take from them.

I'd start small and see what it looks like before changing too much

Get some good digital renderings for all of the changes you want to make. See what it looks like and prioritize. The windows and balistrades seem to shout 1990s the loudest.

Is this located on an island somewhere? It's important to keep the local vernacular in architecture.

No, this is a hillside home in Southern California ( near Santa Barbara) . It sticks out like a sore thumb. My neighborhood is Tudor and Spanish revival mostly, all built in the 1920’s.
Here’s another photo

Here’s a crude rendering of what I have in mind

In looking at your neighbours, the one to the right in your area photo looks to be of similar era given the chimney and roofline. I note the roof is similar so this actually might be the original roof line. The bright orange tile might not be! If you want to try and put it to rights, definitely try to locate some original pics. Local libraries often have good resources.

Have your neighbours been there for a while? If they have, they might have photos where your house makes an appearance in the background and reveal the pre 90’s version.

Your rendering shows a front door that, I believe, is not currently visible. It adds to much to the front of the house. What is on the interior of your house in that area?

I would get a good architect involved ASAP, someone who has done a lot of Spanish Revival homes. I don't think going back to English cottage works for your neighborhood, particularly if you plan to keep the stucco. I'm sure s/he can bring a lot of suggestions to the party, and elevate the look even beyond what you have imagined.