To get a home that blends in, you would need to do more than just "flatten" the front. I don't know if I've ever even driven through Fairfield County but I did live in Maine for several years and one thing I remember about all the houses in New England was that they tended to be more "vertical" than horizontal. I just took a quick look at what's for sale in your area to verify that what I remember still holds true. And, sure enough, I saw only a very few single story homes for sale with more than about 1700 sq ft of living area. And once you hit around 2200 sq ft heated/cooled plus add a two-car attached garage, EVERYTHING in your area seems to have two (or more) floors. The result is that, regardless of the style (Federal, Cape Cod, Colonial, Saltbox) they all tend to be as tall or taller than they are wide. Houses that are wider than they are tall tend to be associated more with western states where wide open vistas and room to sprawl gave birth to "ranch style" and "prairie style" homes. In fact, that long, low "hugging the ground" look is pretty much descriptive of both styles. Thus, here in Texas, if you check the MLS listings, you'll find lots and lots of single story homes... even in the 3000 to 4000 sq foot range. In fact, if I were looking for a single phrase to describe the difference between the styles of homes that one finds in New England and those that one finds most often out here in the west, I'd probably say something like "in New England, the houses sit up straight and tall, while here in the west they lay down and sprawl." In New England, even farmhouses that have been added onto over time so that we speak them as "sprawling" still have a central two-story or 1.5 story core that give them an upright feeling. Whenever wings were added to the sides they were usually set back from the front facade and given a lower roofline so that the tall central core still stands out as the "main house." I THINK you might be able to design a house with a somewhat similar floorplan to the one you like that would blend into your New England neighborhood but to do so, I would suggest that you start by squaring up the central core of home (the kitchen, great room, dining room, TV room, and foyer). Then make that section 2 stories high or at least 1.5 stories with dormer windows upstairs. If you don't want any bedrooms upstairs, use the upper space for a bonus room. Or, if you really don't need/want a second floor at all, make the core room ceilings nice and tall (10 or 12 feet or more) and then have false dormers in the attic above to give the impression of having a second floor. Do keep the 8/10 sloped roof because you need the height. Then, push the bedroom wing and the garage wing back and give both areas a lower ceiling height... Maybe 8 to 9 feet depending on how tall you made the ceilings in the core area. That way, the roof lines over these sections will tuck in under the roof of the central core. That will tend to make the wings look like they were added to the house later. Because you won't have enough room to the side for all the bedrooms you want, you'll need to extend the wings to the back. (You don't want to keep going out to the sides because you don't want the house to get too wide.) However the wing extensions will give you a perfect patio area out the back. Then, if you like more of a "farmhouse" look, add a porch across the front of the core area. At 3200 sq feet (not counting garage or bonus room) the sketch below is probably bigger than you were planning to build, but maybe something along these lines would work for you. Do consider hiring a good local architect tho...especially if you want to wind up with a good useable design so you can start actually building anytime in the next few years. I'm not saying you CAN'T eventually design your own home. It isn't rocket science... but if you're a novice as you say, even if you're a pretty quick study, have a flair for design and are willing to spend a LOT of your free time on it, it could still take you YEARS to learn all you need to know. A good architect who listens to what you tell him and then tries to fulfill your dreams rather than simply impose his "artistic vision" on you can be well worth his fees.

If you can't change the window to larger, maybe you can balance it with shutters or something... but a look on Google at mid century homes, most seem to have all different sized windows. They didn't matchy match back then; they built more from the use inside out. The door color could change to a contrasting color. I guess people here are liking the exterior siding but I am not a fan of the vertical. But I guess it's in keeping with the style. Also the people who said no to stone. Actually, there are a lot of mid century homes WITH stone; and a lot with brick too. Most of the homes have a mixture of the two. I think it'd be beautiful and you could do a fence of wide wood horizontal planks.... Contrasting color on the roof line and around door and windows... Maybe plant some square boxes of flowers.... you could do that under that bedroom window to balance it if you can't make that larger. Look online for homes to see what they did. Go through the neighborhood to find others and maybe get ideas. Attached a photo of one that is a little like your home. That's how they updated. That wood fence/partition in front is very mid century and in vogue right now.

Is the yellow area stucco? If so I would paint it and the foundation Ralph Lauren Burlap, it’s a neutral taupe that’s looks like raw stucco, tying those elements together and to the brick. All the wood trim (fascia, soffit, windows, columns, etc) get one color- olive would be my first choice but linen white would be nice too especially if you want the navy door.

I agree w/ tozmo about disliking black and thinking that a creamy color would complement your brick and stone better. Re window boxes, I'm in z5 so they're planted from the end of May until the frost kills them (usually Sep or Oct). One year I decided to fill them with stems of silk mums for autumn, then switch to silk poinsettias right after Thanksgiving. I didn't anticipate the mums being frozen solid in the soil until late April. LOL!!! Fwiw, I now use fresh cut evergreens for my window boxes in the winter and love the look.