Thanks for the input, everyone! I especially appreciate being provided with the correct term for the knee brackets. This is my first non-Victorian house (my last was an Italianate with corbels galore) so I've really got that term stuck in my brain. JDS, you bring up a good point about similar houses in the neighborhood but I'm afraid I don't have much to go on. My house is one of the newer ones on the street, as most are big Queen Annes that were built a couple decades earlier. The interior of my house is much more intact than the exterior, thankfully, so maybe explaining that will help. The woodwork is all uncarved oak in a definite Craftsman style. However, out of the 12 stained or leaded glass windows, all but three (see first photo) are Neoclassical. So to me, the house straddles the line between styles a bit. I don't want to mess with the exterior too much and/or risk getting it "wrong", but to my eyes it looks rather plain and vinyl the way it is right now. I may try replacing the trim around the windows (as it sounds like painting it is a bad idea) to see if a bit of color contrast will help. Please excuse the weird furniture and lack of color in these photos - they're from the listing and are all I have handy. I have since painted the walls and added some nice oak antiques. :) PS - emmarene, that house is AWESOME. The wood paneling and the French doors between the pillars are the last remnants of when this house was a duplex in the 1960s. It's a carefully and skillfully added addition, but it's gotta go! I'll be removing it in the spring. The decorative fireplace appears to be original and is another "not-Neoclassical" feature.

It really just depends if that $1600 is worth it to to spend on it. For me it likely would not be, but for you it may be. Whereas I might spend $1600 on something else others might not deem worth it. Changes always get more expensive the further into the build you get! At some point you need to just decide it is enough and stop spending :) As for the windows - eh, if you ever “regret” not having more windows you can pay someone to add some later. Sometimes posters here act like this is an irreversible “error” and your life will forever be more miserable for it. Yes, it will cost more to do later as they will need to punch a hole, add a header, flashing, maybe reroute electrical etc, but it is possible. Even easier with vinyl siding. People where I live often add windows for egress etc when renovating so it is certainly not an impossibility. Sometimes there is also a functional purpose - for the owners who live there - to not have windows in certain rooms or on certain walls that may just happen to be side walls. Not sure your plans for the house as a whole but I know for mine we have restrictions on windows on side of house (as a percentage of total windows and a max percentage for a window) due to lot sizes & setbacks (fire safety thing). Plus we are in a colder climate where there are additional energy costs as you add more windows. Seems others don’t have that or same restrictions and so assume everyone is in same boat as them. The rooms on side of my house that lose out on windows entirely are a mudroom/garage entry (where I am putting floor to ceiling storage on exterior wall - 9’), our main floor guest bath (needed this as an insulated mechanical and plumbing wall so could not use for window) and closets (where I don’t want windows due to fade). Our laundry room only gets one window instead of another on exterior wall because again I am doing floor to ceiling storage (8’) there. I also only have windows (3 3x5.5 windows) on one side of my master bedroom as I want one blank wall for headboard (with no doors or windows) and I am very unsettled by windows on my “headboard” side - especially as our neighbours would get a full view into our room from their child’s bedroom if we had them. I also like a darker bedroom as that is where I sleep! I had windows behind my bed once (high windows) and kept them covered with blackout blinds all the time. Our guest room has one exterior egress window and none on exterior side wall but has three interior windows, and our office also only has one exterior egress window but gets an interior clerestory and glass French doors so neither suffer for light. We opted not to put side windows in dining nook (which has one 6x6’ window at rear) or living room (which has has 6 3x6 windows in a 2-story area) as those are the only places in our open living/dining/kitchen room to hang art, nor do we like look of windows around a fireplace as would happen in living room. So we put in plenty of wall washers instead for lighting and to light up art. Our spaces altogether are not very big, so we don’t get that issue of having a room deep in centre without any light. Our basement also has an area with no windows for future development as the plan is for it to be a theatre/very dark man cave room. Houses still sell here even with few or no windows on side because it is what is expected here (and there is a privacy and fire code factor when you are 5-8” away from neighbour). We are taking advantage of our exterior “blank” sidewall/sideyard corners by planning to add a wrap around three or four season deck & solarium - that “blank wall corner” on side of our dining room is where we plan to add a walk in sauna and a private changing area for those using the sauna and enclosed hot tub. Not only are we not blocking a window, no window is a benefit for privacy. I don’t need to be looking at a guests naked body while I am eating breakfast or vice versa :) I also remember you had a walkout basement so I expect you may be able to plan a two level outdoor space/room for future. Don’t fret much about the comments. Your house looks cute. Hey, at least you don’t have the horror I have of a snout garage too ;)

Means that you can bring the trim (1x4) over the window slightly and bury some of the frame on the sides behind the trim. You must leave the sill to terminate on the trim for drainage preservation, but you can hide some of the profile of the window on the sides and head.

If you want everything to blend do the same color, if you want the trim to stand out, use a diffrent color. 90% of homes trim stands out. Good luck