Do you have the time to water every day and what will you do when winter comes ,to fill them.Only the bottom left window can handle one nice long one if you must . IMO a lot better ans interestly actual landscaping would do wonders

Only window boxes that you can easily get to will have plants that survive. That means the ground floor window may work. A metal-lined or plastic-lined wood box should be deep and substantial so there's enough room for plants: no 6" plastic window boxes, more like 12". A custom box will run a couple hundred dollars or more plus the cost of potting soil and plants.

You can give the idea a test run with three large pots attached with rings just below the window. Plant them up nicely and see if they grow well for a year.

Window boxes are a pain to keep looking nice. Get some bigger, prettier plantings under the lower left window. They will look better and take much less work. I'm an avid gardener and I have window boxes thanks to the former owner. During heat waves, they need to be watered at least once a day, if not more. Plants that thrive get overcrowded, requiring thinning. Plants that don't need to be replaced. They are bare during winter.

Is the garage an addition? I ask because the main body of the house looks like a 1950's side entrance colonial, with alterations to make it look compatible with the new.

Muntins (grids) in the windows, pergola for a front porch, would bring the house back to what I think it was..

Window boxes and the water and moisture they trap is very hard on your siding. I hope you don't have iron in your water.

Window boxes need to have the plants replaced frequently because the restricted root space inevitably makes them stop blooming and deteriorate. It's an expensive proposition. Lots of effort to keep watered. I am an avid gardener and would never recommend them.

Window boxes are a big invitation for rot and mold to enter your home. Plus insects. Ive seen an entire window surround eaten to lace from termites invited in by the window boxes.

I live in a neigborhood where the houses ( typically 3000 sq ft) cost million plus. There are several gorgeous houses with beautiful window flower boxes- all better quality faux plants changed seasonally for reasons stated above.

Your shrubs on the left side are too small, and planted too close to the house. You need shrubs that, at maturity, will just nicely cover the siding up to the window. So they will need to be fairly wide and deep, planted much farther from the house so they don't touch it when full grown. They need to be a bit taller than they are wide and deep. Your small shrubs are out of proportion to the size of your house.

The shrubs you have are too small, and planted so close to the house that if they get taller and wider they will touch the house.

The Japanese maple encroaches on the pathway and hides the view of the steps from some angles. If it is still young enough enough to be moved, I would place it as a specimen on the left side of the house closer to the road, with enough room to reach its mature size without pruning.

I'd also trim down the shrub between the steps and the driveway. It's disproportionately tall.

Draw attention to the front door with a larger light, and paint the mailbox black so it pops.

If you want colour, leave a 2 ft space in front of the shrubs, and plant matching annuals on both sides of the walkway, that will give you colour all summer. I gave you a red door and flowers to match. Emphasis on the door, and a very visible pathway and stairs, always looks welcoming.

Here's a rough sketch of what I am talking about.

It seems the majority of folks here are not in favor of windows boxes. Have to say I'm in agreement with them. Window boxes are hard to maintain, look terrible in winter if plants don't make it thru cold weather and can cause moisture problems and rot. Nice idea but pretty impractical.

Looks like you may have just planted new small bushes in the front under the window? If so, once they grow, you may not feel you need a window box there.

For winter (Northeast US), I do leave my window box empty for a few months in fall and spring, but then put in evergreen branches with a red bow in front to decorate for Christmas. However, our window box is on the side, along the driveway, next to our kitchen side door vs. facing the street.

You don’t have room for boxes on the windows over the garage. And putting a window box on the long second story window is going to be a problem to plant and water since it appears the center window is stationary….

Even though I live in a very mild ( spring like year around ) climate & I like to garden, I found window boxes really difficult ( & expensive ) to maintain. i would concentrate on landscape improvements.

I had lots of window boxes in my former home as did all of our neighbors. They were brick row houses so rot was not an issue. I would not do it on a home with wood or siding for reasons stated by others. They took constant watering because the soil dries out quite quickly. Unless you plant them with evergreens, they needed to be replanted three times a year. They were surprisingly costly. Sidewalks ran in front of our homes so the arrangements were viewed up close. Because of the depth of your yard, your boxes and plantings would need to be rather large to make a visual impact and I don't think they would look right for the scale of your home.

When you see beautiful window boxes in pictures, they are either staged, constantly tended to by homeowners, or by expensive companies. In my old neighborhood the going rate was $3,000/year for two street level window boxes to be planted and maintained year round.

While I agree that window boxes aren't the solution to this house, I will disagree that they are difficult to maintain. Mine are on a brick garage, and face north, but they don't need constant watering. There are these things called water crystals. Soil Moist is a popular brand name. You add them and slow release fertilizer when planting, and they reduce the watering to about once a week, at worst. I think I watered them once last year, and haven't watered them at all this year.

They get planted in the spring, and decorated for the winter. Winter decorations are things I forage around the lawn - evergreen trimming, winterberry, rose hips - with some red ribbons. Some people add silver or gold painted twigs. It's not that much work.

I agree with @K Laurence unless gardening and maintaining window boxes are a passion.