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The Unstoppable Empty Nesters

The search for the perfect city for empty nesters.

Consider Francesca and Jack, recent empty nesters, renting on the Upper Westside of NYC after selling their brownstone in Carroll Gardens. Jack is set to retire from his management consulting firm in the next few years. Having spent fortunes on college educations for their twins, they want to buy a place somewhat affordable that’s not totally out of the loop. San Francisco and Los Angeles are out because they’re too expensive, and they don’t even like what they perceive them to have become (SF has too many broligarchs and Silicon Valley vibes, and LA; is too fake and appears to be struggling with fires.) So where next? This topic dominates a good 50 percent of their conversations as their friends all pitch their ideas, but nowhere seems to hold the Goldilocks key.

Francesca insists on walking out the door to a downtown where she can grab a good coffee, shop organic, and have some buzzy places to eat and boutique shops. Jack wants to be around similarly minded people with a more mellow than NYC, but not too mellow pace, and some sophisticated amenities – art, bookstores, farm-to-table eating.)

College towns always pop up, which have a lot to recommend them although not the kind of college downtown that is pub crawling with those beer-guzzling, pizza-gobbling urchins making a ruckus into the wee hours.

A historic downtown can be good (maybe even a historic loft building although these can be hard to come by especially if you want to buy.) 

Contenders include three of the four corners;

Oceanside, CA

Oceanside CA https://lookyloomove.com/locations/oceanside 

Portland OR https://lookyloomove.com/locations/portland 

Burlington VT https://lookyloomove.com/locations/burlington

Other contenders include the Gaslamp Quarter in San Diego (maybe a little TOO youthful and too easy to get run over by hordes of e-bikes) https://gaslamp.org/

They spent a few weeks in summer touring around and checking them out. Here’s what they found.

THE RESULTS

Oceanside is still undergoing its renaissance that started with the Main Street Reinvestment Pact of 2022, and while it appears to be the last of the SoCal beach towns one might ever hope to buy into for ~$1M, it remains too Single-Family Home suburban for them without much inventory for sale downtown. The Main Street project is more of a business district with some mixed-use rental developments.  

Portland felt a bit much with its over-the-top culture identity and again, the desirable real estate inventory is all the cute Craftsmans and cottages, some on the edge of The Grid but not quite ‘walk out the door to coffee.’ This couple doesn’t worry much about getting to see their kids (everybody is very travel-friendly) Francesca did nevertheless find herself feeling remote, way up there on the northwest coast which is sad because they both love the historic loft buildings with all the exposed brick and floor-to-ceiling windows.

Burlington: By this point in the search, they’re starting to get grouchy but despite historic row house-type inventory overlooking Lake Champlain with open floor plans well within their budget, the crowd doesn’t feel right. They find it hard to imagine making friends with the crunchy granola Burlington crew. Which side of this equation is insufferable? Unclear.

Although they have some issues with The Gaslamp Quarter in downtown San Diego it’s hard to resist a few factors; Francesca is originally from SoCal and they have family there. The weather, I mean c’mon.(Although, it’s worth pointing out that she really is a four seasons advocate so season-free, snowless Southern California isn’t even points on the board as it would be for most of us.) Lots of historic loft buildings (and some cool condos) right in the heart of a bustling downtown. They’ll probably have to spend a little more than they’d like, which cuts into Francesca’s remodel budget, or settle for less square footage than they’d hoped but this has potential. They’re still planning to look into Portsmouth NH but the complaints from The Peanut Gallery are already rolling in.