Here a few landscaping photos and a thing from weathervanes of Maine

I live in MA and that paint job is going to be thousands of dollars. I don’t know where you are exactly, but you need to get a great company to come and give you estimates…looks like there will be repairs to the siding, too. I will guess at least $18,000.00.

Thank you, mveasey! Wow, this is really great advice. Everything you said was so helpful and I would have never thought of the weathervane idea. I love it! That's interesting you mentioned sparkling white. I wonder what would be a good accent color and if the gingerbread design on the top peaks (I'm sure there is a proper name for them, I just don't know it. LOL) should also be white? I also appreciate your comment about the trash bins. Sometimes I don't know why I'm so oblivious to this stuff. But it was so obvious about moving the trash bins after you said it! THANK YOU!! :)

Here is a few white with black accents homes.
One is a very light beige with white trim or one of the gray ones with white trim. I think they all look great.
Ask yourself: what kind of first impression do I want to convey? Regal, traditional and clean? Or warm, welcoming, more current victorian(if there is such a thing...) what would a realtor advise, in case you will be selling in a few years?

Here is the beige house with white trim and an idea for your port cochiere - a coach house style lamp... Just make sure there is enough clearance for trucks, etc.

Given the other homes around you, I want to suggest for the body benjamin moore sandy hook gray, fascia /eave trim / railing and eave peak shingles in bm monterey white, and wherever you have window or door trim, go deeper to copley gray. Good tone for the floor of the porch or entry stairs or any trellis over the foundation up front (copley gray too) . Then the front door and the screen doors frame in a historic butter tone - sw bees wax is so proven and I haven't found the bm equivalent yet - maybe york harbor yellow. Rest of the doors should be the same copley gray (back door, side, etc.) Paint the whole garage the deeper color, and use the lighter gray as the trim at the eave/fascia and the windows but no contrast for the door trim or door, but pick out the windows and the frame around them in the doors (like they were windows in the lighter tone.

I would take off all the storm windows, as they really take the look way down and call the window guy back to have him price add grilles / muntins to only the top half of all your newish windows. That will echo historic window profiles. Wood windows are wicked expensive, and you have saved a lot in heating and cooling already to get to this point by getting new windows everywhere. If security is an issue, paint the first floor ones the copley gray and put them back only on the first floor.

this is such a beauty . . . don't worry about the 18k price tag somebody suggested. I think the painting itself would be closer to 5k for the main house and under 2k for the carriage house but let them match your colors and buy any exterior paint they get their contractors discount on. Get at least three bids, and fix the railing with a different carpenter first. The variable is that you just don't know about the prep and wood putty and caulking work to prepare the house for paint and deal with any wood rot. Hire a good carpenter who knows how to match historic detail to come and go over the place / fix the railing first. The painters are cheaper caulkers but he will be more efficient to fix any bad places with good wood.

Links - http://www.benjaminmoore.com/en-us/paint-color/sandyhookgray
http://www.benjaminmoore.com/en-us/paint-color/montereywhite
http://www.benjaminmoore.com/en-us/paint-color/copleygray
http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW7682-bees-wax/

Lets talk about being the most cost efficient because as mentioned above I expect that price is close to right on. It all has to do with the condition of the wood and old paint so you can only guess but good paint jobs cost money in NE. One note wait until next year. Its too late to paint now and you want perfect weather to maximize your investment.

The simplest thing is a mentioned above a soft warm, gray, tan, or yellow will be easiest. Green and blue get out of hand easy and be careful with the yellow stay very soft. Paint the barn the same as the house. Then paint all the trim, and ceilings a warm off white. It will look very nice. Of course there is a lot you could do to push it over the top like detailing, shutters, etc etc. but you will get no ROI for the efforts. Be careful to make the body not too much darker than the house around it so it fits the neighborhood. It is a elegant house and just this much done will make it look very, very good. It will be able to sell itself on just the quality of its architecture.

well it depends on if yo want to keep the victorian look ( the city might make you if it is a historic home) or go new.

More work:replace the post,the step stair.the walway.add fern,horthia,hydrangea,boxwood,azalea...

Have you decided anything yet? Great House. I agree, landscaping and a soft color like butter yellow, olive or fern green, or a tan could look great. I posted a bunch of links in this post for a related question: https://www.houzz.com/discussions/exterior-paint-recommendations-for-a-victorian-style-home-dsvw-vd~966531

The examples posted are a bit washed out looking, I think I would go for a bit more base color for such a large house.

For the carriage house, I would suggest an opaque stain for easier maintenance. I think it would be fine if the color was different from the main house, maybe even a reversal of the main house scheme, but not anything too bright. The carriage house may be a project you would be willing to tackle yourself to save a bit on costs. That and doing some of the surface prep on the house itself. That is a lot of surface area and the best results are with very careful surface prep. A simple scrape and paint might only last 5 years, whereas a strip and paint could last 10-15. I would also keep the colors fairly light to minimize fading.

I would keep the storm windows, and forget about fake grills. Too bad about the vinyl, but what is done is done, and at least it looks like the original casing is there. Pay particular attention to the vulnerable area--headers, sills, gingerbread, porch components, to strip and repair. Fortunately although the shape is a classic Queen Anne, the detailing is very restrained and more like a Folk Victorian--that makes it easier to maintain, but also less suited for a painted lady type job. Those little brackets on the front gable are worth highlighting, and I'm wondering if new siding is hiding something in the porch gables. At least it appears to be mostly original, which is increasingly rare for a house of this vintage (around 1900 perhaps?).

For a completely different look, you could go with dark trim. Just a bit of dark accent can really highlight a restrained color scheme.