I was reading the above and noticed the point about the price of a single family home in Brookline. It's true but what is the solution in that specific place? Are we suggesting tearing down Brookline...?
Here are some snips from Brookline's zoning by laws (the most up to date as far as I can tell).
Here's a map of the zoning districts: GIS---Zoning-Map---30x16-Grayscale-PDF (brooklinema.gov)
As you can see, there are sections of Brookline where single family homes need to sit on whole acre-sized lots with mandatory 35-foot front yards, 20-foot sides, and 50-foot back yards. There are restrictions on the widths of lots, the heights of homes, and the floor-to-area ratios of buildings that vary based on use and location.
Buildings over 100ft generally aren't allowed in Brookline and in cases where they are, decreasing % of the lot are allowed to be covered by the building which limits it actual utility.
When you have laws like this, of course you're going to have a hard time building new housing. No tearing down of anything would be necessary to add a significant amount of people to Brookline. All you'd have to do is loosen or scrap a few of these restrictions and BAM - housing. It wouldn't hurt the character of the city either. Likely what you'd see is more of southern and central Brookline looking like northern Brookline. Or perhaps the city would start resembling somewhere in Southern California
where lot sizes for single family homes are generally very small but where towns/neighborhoods like the one shown still maintain the exclusivity and poshness that Brookline currently has.
And there's no reason why Concord and Ipswich can't follow suit. Ipswich even has a perfect example in its backyard of what picturesque density in a North Shore city can look like: Newburyport
. If all of Concord and Ipswich were zoned to look more like Newburyport between High Street and the Merrimack (i.e. small lot sizes with small or nonexistent front yards), then those towns could add tons of houses while still remaining charming and quaint.
Heck, parts of Ipswich already look like that: 56 N Main St - Google Maps
or 16 County St - Google Maps
. Just make that kind of development standard across the entire town. And while you're at it, carve out similar neighborhoods in Hamilton, Topsfield, Boxford, etc.