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.

Please don't be afraid to try something if you like it. The more you delve into your projects, the more experienced and creative you will get. And lukki for you, you have found the forum(s) early on. At the start a fixer upper can be really overwhelming, especially to someone without experience; I found it was easier to focus on one project at a time (like fixing the leaks in the roof) and was surprised at how quickly it started to come together. It wasn't as stressful that way too. You said initially you have the inside sort of figured out, I would love to know what you have planned and see pictures. I prefer older homes because they are usually more generous with storage and space, I bet the inside of yours has open and generous rooms with lots of potential. From the outside, it looks like a real gem in the rough. Which of the pictures are you drawn to? We bought a vacant foreclosure home in 2006. When I showed it to my DH and said I was in love, he thought I was nuts. But in my mind I could see most of it in it's finished state and it felt like home. We've come a long way, the interior is about 80% done, and right now we are focused on the exterior.

Could you add a current photo from the perspective of the first and last ones without the equipment and shrubs there so we can see the steps from head on? Also, I would love a photo of what is to each side of this photo, so standing in the same spot as the top photo, swing your body left and take a photo, and swing right and take a photo. Location of parking, the driveway, and trees which create shade are a few things that might influence the placement of plants and the walkway. If it is possible do this when the front of the house isn't in shadow or take the photo on a cloudy day or just use software to lighten the shadows in the photo, that will help. Removing the flat line of shrubs was a good choice, but you will want some shrubs, including some evergreens rather than just flowers in your new beds so there is some winter interest. Where are you (nearest large city) and what growing zone? What direction does the house face?

Your tiles are a very neutral color and I would not paint them. A lot of work for no benefit. A black door would look fine with them. What do you mean by a Georgian door? Do the interior in any style you like. It does not need to "match" the outside in any way. Your photo is pretty fuzzy. A clearer picture of the front door area would let us give you more advice.