What is your budget? That will help figure out best approach. Bbl

Thanks- whole house needs new windows- so this is my chance to consider black frames (~$20K), otherwise paint/door/landscape now (~$5k), with eventual new front stoop down the line...

Ok. Great. Here are some ideas. Stain brick offwhite to a gray if you want more modern look. Do black windows for sure. Change style to more modern too. Linear lines give off modern vibe. I put cement look long low planters on one side and a new sidewalk with long slabs of concrete. I put new more modern front door system into existing opening in blue gray painted look. By using very light to dark grays you nod to traditional look of Cape Cod but imagine it in more modern way. Here is little mock up to get the creative juices flowing. Start with brick staining and front door system. Then landscaping etc later.

New modern lighting beside new doors very important.

Eliminate shutters. 😊

Lots of gorgeous front door systems. But expensive so might have to compromise there. Windows might be made longer top to bottom but that requires brick work. So windows come first, then brick repairs if needed then brick staining. Staining allows brick to breath rather than painting which requires more maintenance. You have a lovely home so be sure what your total plan is before you start. Black windows outside and probably inside is first step!

For a start…can you remove the grids in your windows? If you can (including in the Living room), remove them so that you can see how your home will look without them. Remove your shutters, too. You don’t need to paint your brick. I would embrace the color of it, even accent it, with black windows. Your sidelights on your door give you a fenestration scale to consider. I’d replace the front door and screen and keep your sidelights. Modern lighting and modern landscaping would really add an up to date vibe.

Wow, really like Flo’s rendition, I would love to have a cape cod again. Oh the possibilities!

It is a Cape Cod it will not be modern until you spend a ton of money and those dormers will need major work. Do you mean modern farmhouse ? I do need to know your budget and IMO painting brick is a fast way to devalue your house so I would change the windows and no grids remove the shutters work on the landscaping get a new front door . All of those things before deciding to paint the brick. It is also a good idea to check out the neighbor hood to see what styles are there . Not to copy but to see the overall feel.

Cape Cods can be updated with new color schemes and attention to detail, like new landscaping.or a new covered entrance.

This last photo with big windows and nice walking way is really good.

I live in MA where lots of Cape Cod’s. A pretty and big gray cape c 1960 I pass by daily was sold last spring. I watched as they replaced first the windows with black ones, then all the lightening more contemporary in black, and finally the whole house including garage doors was painted white with a black front door. It is stunning and transformed the house. I had to stop the car and take a good look. Updated yet still fit into the New England landscape. No shutters, some new landscaping and outdoor lighting. This was not a brick house. Your dormers need better new siding, maybe shingles. I would do everything but paint the brick. Live with for a bit and then decide if really need to paint the brick. Painting brick is expensive, could devalue the house, and would be added expensive maintenance. The red brick with black will be just as pretty.

I would ask you to rethink trying to change this house into something it's not and instead trying to make it the best looking Minimal Traditional house in the cape code style it could be. Replace the windows with true divided lite windows and try not to end up with any horizontal squares like you do on the left window. This could be alleviated by doing a 3 over 1 window in each of the other sashes, and a 4 over 1 in the left sash. (Rather than 6/6 or 8/8). That was another style of window for houses of this period. Go ahead and keep or put shutters on the smaller windows, try to get them as appropriately wide and possible, but skip any picture windows, if you want shutters. Again, they are completely appropriate as a decorative element to this style of house.

Fix the stoop and update the landscaping.

I don't think black window trim would do this house any favors. I would say white or if you don't want white maybe a sage-y green.

I wish I had my mother's 1955 decorating book out of a box. It had a whole section on "modernizing" Victorian and Craftsman houses (which were about the same age then as this house is now) and removing all the fussy detailing, anything "high maintenance" and replacing dark and dreary porches and leaded stained glass windows with concrete stoops and light, airy filigree metal columns and picture windows and then covering the whole thing with aluminum siding. The pictures made the house look fresh, they were a nod to something more contemporary to the time, but in retrospect we realize many of those things ruined the charm of the original house.

Your house is much too horizontal to ever look like a "Modern Farmhouse" or one of those popular looks and it is too solid to go too contemporary at least without a LOT of money being spent, which is not necessary to make this house look better, it will only make it look different. So at least consider spending less money to make it look better as it is in a higher quality way, and that will give you more money for whatever needs to be done inside.

Staining brick is very different than painting. I suggest staining. So, this is your house. If you plan on staying here for 5-7 years, do whatever pleases you. If you can see a move in less than 5 years, proceed more cautiously. Explore changes from the perspective of resale. New windows is usually a good investment but might not get you much return. Updating your landscaping in front for maximum curb appeal would be a plus. Most return on investment dollars come from kitchen and bathrooms. About 80% return from kitchen upgrades and 60% from bathroom updates. Kitchens sell houses. So determine what your best guess for your future is and go from there.

As to windows, there is a budding trend here from black replacement windows to gray. Might be worth thinking about. All depends on overall styling you decide on for overall look.

I agree in general about return on investment. People expect as a default that the windows will be in decent shape and the roof is sound (and things like plumbing are not failing), unless the buyer is buying a fixer upper, so it's not likely there would be any real return on windows or a roof. It would be selling point of course but hard to measure in returns. Also remember that a 60% return on investment, since a sale is a one-point-in-time thing is also a 40% loss in investment depending on how you look at it.

Some option

A updated color scheme could help modernize this cute cape cod style home without painting the brick. The color on the front door is Valspar Halcyon Blue. I like how they added brick to both planting beds and edged the sidewalk with brick too. The black shutters add a traditional touch and the blue door is pretty with the brick. Simple details like possibly adding outdoor lanterns and changing to two window boxes as opposed to the one on the left side which is hung a little too low and is too wide, it should only be the width of the window itself (see below). The shutters above that window should come right up to the trim, no gap. A light grey paint on your dormers could be less stark than the white or you could switch to a light grey shingle too. You could also remove the lower grilles on all the windows which I think is a little more modern looking. Modern landscaping using evergreens (2-3 feet tall) would give you year round interest also.