The first thing that strikes me is that the house and the garage might match better if they were painted the same color.

I'd go with a fairly neutral (maybe pale yellow or moss green) on both, with a bolder color for accents (trim, railings, doors).

Thanks Elaine, are you saying to maybe paint the brick? That could be a good idea.

You might just see if someone online can do a mockup of your garage sketch and simply bring the roof to a point on top. This could be done? without removing the existing roof 15 degree angle, just merely add some roofing boards and than, shingles with overlay to match whatever the house will have long term(gray would be very pretty with your creamy brick home tones). Than, if you are happy with the color of the home, paint the garage the similar tone, and than if you want to bring in another color, maybe do make the home porch and railings the same color as you change the garage railings too.. You might even paint the eaves/ overhang of the house a medium gray?, and all the railings to black? and put a gray shingled roof on your home when you update the shingles there, after installing gray shingles on your garage. Yes, the lines will be vertical on the garage, unless you remove that trim board but that would open you up to alot more expense, than painting railings, garage walls, home overhangs and matching shingles on both structures. You might also find online a very pretty silver lantern lamp, and install matching lamps on the home and the garage walls(assuming you go with the medium gray shingles and overhangs, creamy yellow garage walls, and black...or dark gray?...or perhaps even a pretty dusty blue color on your railings, since you are in the Lake setting(or whatever your favorite color is, that blends nicely with the suggested theme, a richer yellow? a pretty deep gray, black, or even a dusty sage color?) Just showing you how pretty blue gray, can be with something similar to your tone of yellow brick if you are interested in painting the porch rails something other than black..

Don't paint brick!!! A lot of posts here illustrate why.

It would be really expensive, but changing the roof design on that house would go a long wat to making it look better.

A roof style like a gable end or hipped design with a taller peak would make a huge difference.

One of the two left examples

She likes her brick, she wants the garage roofline to match the house roofline, and is looking for ways to make the 2 units cohesive in appearance. I do not think painting brick will help...painting the garage walls and overhangs to a hue that matches the brick home walls as they are now, creamy yellow/gold,garage deck railings and adding just a peak to the roof. Than painting the overhangs of the house the same color, making the shingles match both buildings, and perhaps coloring the porch rails on both units the same tone, would be lovely.

Painting the brick could be nice. When I was a kid, we lived for about a year and a half in a beautiful brick house that had been painted a light green. Sadly, it has since been painted white, which doesn't look nearly as nice.

I would definitely not paint the brick! If for no other reason, who wants that upkeep at a lakehome?? I'd rather spend my time floating on a tube!

Sorry Elaine, mischievous timing makes it look like I'm directly contradicting you. That's not the case at all; we all have different taste and that's what makes the world so interesting :-)

Thank you everyone for your thoughtful ideas. We are having a wonderful time reading carefully through every comment!

I'm late to this party (and didn't read everything) but agree with the sentiment in the first response ... to better the architecture within the limits of each building's own style.

It's not ugly brick so I wouldn't paint it. But to me, decomposing wood is not a pretty finish. I'd definitely paint the garage ... not trying to make it part of the house, but just making it it's own pretty self. Compatible, but not necessarily in any way "matching." The Louvre and Pei's pyramid is a good example of radically different architecture juxtaposed next to one another. It can work.

I'd be tempted to paint the garage in that beautiful barn green or Crisp Romaine as though it is separate from the house since in every sense it pretty much looks like a separate barn. Does the house have brick and siding? I think removing that overgrown shrubbery on the right would help the look of the house, as would removal of the lattice under the deck. The home could lean into some Asian lines if you wanted.

The garage will never match the house, but, if you think about it, barns dont match houses, and your garage is barn shaped. Since you do not see the garage doors from the front of the house, paint it up like a regular barn. A regular barn looks great no matter what kind of house you have. Better to go with what it is, than fight with it to make it something it isnt. A definite no, to painting the brick.

The easiest way to tie them together is to paint the garage the same color as the trim and windows on the house. Since there's no garage door on the facade I would add some landscaping along the front of the garage and remove the overgrown shrub at the right front corner of the house and then use landscaping to tie both together. Trying to redo the roof of the garage is only going to draw more attention to the difference in the roof pitches and is an expense that really doesn't gain you anything.

Depth of eaves on your home - fabulous! I'm going to guess the "sweet man" also built your home's railings and the lattice under the porch. If you're willing to spend money, please spend it there. IMO, your home has Mid Century written all over it. Proper porch materials and appropriate landscaping at the front will allow the home to be dominant. The garage is a barn (I'll bet well-built) and nothing will change that. I'd paint it a shade of green so it recedes into the treed background.

I will go to my grave and not understand the opposition to painting brick. My own house is painted brick. We hated the color of the paint when we bought it and thought we'd wait until it "needed" painting to change it. Nearly 20 years later, it was still in good condition so we finally painted it. It's now been 15 years and the paint is like new. Practically every house in my neighborhood is brick and it's all been painted. The houses were built mostly in the late 1940's; was brick differently then than today? No one is regularly re-painting their house in my neighborhood and I've lived here 34 years!

Anglophilia: "I will go to my grave and not understand the opposition to painting brick"

Ditto! I painted the brick on a house I owned thirty years ago and it still looks good.

Please don't paint the brick.

Matching front porch/deck railings should provide the visual link you seek.

Consider adding a "front" porch (w/concrete floor) to the garage/guest house building, with wood posts and with wood rails that match the railing on the house, and paint the railings the same.

I love the look of painted brick. I love unpainted brick, too. I've also never understood why some folks are so adamant that it NOT be painted. Ever. Google "old painted brick houses" and you'll see some pretty classy homes pop up, right next to a few French chateaux...

Some brick was baked to be painted...the old brick. Some brick was baked and meant to breathe. If you paint the newer bricks, the breathe part gets clogged by paint and will blister. This includes bricks from the early 1960's and earlier...Blistered brick often promotes mildew --pre paint that resists mildew....also....... & gets repainted over the old paint.... 4 coats of paint, in 30 years makes for a MESS! Sandblasting and all that stuff. Know if your brick can tolerate a seal coat to keep it from breathing...or not.

Inexpensive quick cohesive design twerks. Paint house railing darker to match other structure. Paint balcony railing lighter to match other structure. Reduce large house bush to smaller round shape. Add two to three similar shape bushes to exterior of opposite structure. Add larger potted planters to both structure doorways. Add (possibly red) highlight flowers to each. Add garage window shutters to match highlight floral color of planters. Two Adirondack chairs to front lawn in same (red) color of planters flowers. Add simple tree swing with (red wood) horizontal seat rope swing # for looks- to front tree. :)

Better find out if that garage falls into this video subject.https://www.youtube.com/watch?v=VseMZ3TcqDw Also, better find out what that garage is? Cedar pre treated siding that was stained by the builder, or Siding that was stained from the factory. As this is very important before you make a firm decision on if you need to paint it or just re stain it, and do go carefully, if you choose the "Paint Stain" product. Also, I read that if the wood has any knots in it, you will want to prime them seperately to keep that from bleeding thru your topcoat..assuming you are painting it. You may find that the best choice is just to restain it, as one does to keep up a wood privacy fence for the maintenance of the structure. https://www.hometips.com/house_painting_exterior.html   Steps 6, 7, 8 and 9 have tips on wood exteriors..

https://www.youtube.com/watch?v=19KumsHo3z8   I can't tell from the photos if your raised areas are on the seams of this type of siding, and if this is not your siding, than disregard..

Also, just know that that rhododendron can be easily moved and not destroyed. Many landscaping companies (at least where I live) that deal with selling full-size trees would actually buy it from you. But if you like it, you might consider moving it closer to the lake and away from your house. That way you can view it from inside your house when it blooms in the spring, without it either darkening the interior or making a mess on/around your house when the blooms fade. “Rhodies” (sp?) are gorgeous at the edge of a property but not near sidewalks, decks, patios, entrances, etc.