The reality is that for most of the people in the buying pool for houses at that price range in Bethesda and other close-in DC suburbs, time is a more valuable commodity than money. At that price bracket, most potential buyers are 30-something professionals, many of whom are married with (or planning to have) kids. For many people in that demographic, it's worth it to spend more for a house that requires no work, because the tradeoff for a cheaper house with major projects is that you have to spend the time to plan a remodel, hire someone to execute it, then either live through it or move out (which takes even more time and planning). When I bought my house 10 years ago, I was single, 30 years old, and worked at a law firm. I had the flexibility to extend my rental until some work could be done to my house, so I bought a house that needed cosmetic updates, and got a good price in a hot neighborhood where houses were selling for above asking within a few days. The prior owners 'totally 80s' choices were not appealing to buyers, and also did nothing to highlight the portion of the house that was the original structure from the early 1900s. Once I moved in, I never had time for the DIY projects I envisioned (such as gel staining the kitchen cabinets!), and the house felt like a 'work in progress' for a while. Now I am married with a baby, and I still have a full time job. If I were house hunting now, a house that was 'move in ready' and required nothing more than paint and decorating, would be worth a lot of $$. Because the time and effort required for major renovations would be a tipping point in terms of stress and quality of life, which is hard to quantify in dollars. And I say this as someone who has a decent 'eye' for imagining the potential a house has. In fact, I just recently moved back into my house, after moving out for the summer for a major remodel and addition (totally worth it, but totally exhausting and stressful and time-consuming). Many of my friends who are not into decorating and house stuff also have trouble even imagining the 'after' that a house could be, and overestimate how much it would cost (even at the inflated prices in this area) to make changes. So I think for the average buyer here, 'move in ready' is worth $$$$$, and a 'needs remodeling' house may not even be considered unless it's a tear down to build a mcmansion.

The area looks to be mostly concrete with a very narrow planting bed. I would maintain the concrete pad as is for your outdoor eating space and for your toddler to play but knowing the exact dimension of this could help to determine if this sufficient space for these activities. Assuming it is, I would use that very narrow planting strip to stage a variety of containers that you could fill with the plants of your choice......some annuals for seasonal color, perennials or small shrubs, maybe even a vine or two to grow up and cover the fence. There is really very little room in that narrow space to grow much in the ground and using containers will raise the plants to a more viewable height and protect them from damage by dog and/or child :-) You could also stage a hanging planter or two off the fence to break up that solid surface a bit. I would also consider underplanting that area wih some sort of groundcover in beween the pots to soften and provide some green. Just pick one that is dog and child friendly.

I would use the $$ for landscaping (the biggest way to change your curb appeal!!!), updated trim, and a new door. I think you might grow to love the house just the way it is....

I don’t think your house looks ’dated’ but maybe could use small update to refresh. More pictures taken from different angles & closer up would help generate useful suggestions. I also don’t know about painting siding if it doesn’t need it but the color of the shutters isn’t what I would choose with the red brick. I’d favor green tone shutters - not dark hunter green but more of a sagey tone. Looking at the 2 hanging lights either side of front door - they would have more impact IMO if they hung lower & were larger. That would have a big impact on snazzing up the entry. Looks like there’s one plant pot at door - is it sitting on step? I’d have a large pot on each side of step filled with bright colors or some kind of evergreen that makes a statement. You don’t give us a clue as to location so can’t make suggestions. Are there any shrubs or plantings in yard around the house? That’s a definite area to consider adding to for updates. Need pictures to make any suggestions.