Every so often, I find myself chatting with neighbors, clients, and friends, and a question takes root. I can’t shake it - not because I have the answer, but because I don’t.
Right now, I’m thinking a lot about what’s happening in our real estate market just beyond the heart of Watch Hill Village, in those streets behind The Cooked Goose. Homes that not long ago were considered “entry level” in our community are now creeping toward the $2 million mark. They’re charming, smaller properties - often without the expansive water views or deep porches of the Village - but they’re desirable.
The buyers? Often the next generation of local families, eager to “get a foot in the door” in Watch Hill for fear that if they wait, they’ll be priced out entirely. And truth be told, that fear isn’t unfounded. If history has taught us anything, it’s that our small coastal pocket tends to appreciate steadily, and in the long term, significantly.
But here’s where my musing begins.
The Big Question
Are these the right properties for these young families in the long run?
It’s a wonderful thing to see this next generation investing here - raising their children in the same seaside charm we’ve all cherished. But will the homes they’re buying today still suit them in seven to ten years? Will those cozy floorplans and smaller yards feel tight as children grow, friends visit, and life expands?
Or would it make more sense for families - particularly those with the resources or the support of established relatives - to consider stretching now for a larger, more “future-proof” home closer to the Village? A property with the space and layout to carry them comfortably through all the seasons of family life?
Why This Matters
It’s not just about comfort; it’s about market dynamics. In ten years, those larger Village homes are almost certain to be substantially more expensive. If a family outgrows their “starter” Watch Hill home and then needs to trade up, will they find themselves priced out of the size and location they truly want?
In my mind, this feels a bit like what I’ve seen in other contexts. When our children went to college, I was always impressed by families who bought their children apartments or condos near campus. The student lived off-campus, often with roommates who helped cover expenses, and when graduation came, the parents could sell - sometimes for a profit. It was equal parts practicality and investment.
A Paralleling Scenario
In today’s high-end markets, could a similar mindset apply? Could established local families consider investing in larger properties for their children now, allowing them to grow into the space over time?
It’s not without complexity. Larger homes come with higher price tags, maintenance, and taxes. But they also tend to offer more enduring appeal and flexibility. They can accommodate visiting grandparents, host milestone celebrations, or simply give a growing family breathing room.
Meanwhile, the smaller “entry point” properties might, in time, feel like stepping stones that end in a financial and logistical challenge: selling one home in a competitive market while simultaneously trying to buy into a much higher price tier.
No Easy Answer
I should be clear - I’m not offering advice here, only questions. Every family’s situation is unique, and there’s no one-size-fits-all solution. I’m simply wondering if in our current environment, the “buy what you can now” approach will, for some, lead to a frustrating crossroads down the road.
For some, it may make perfect sense to buy a smaller home and enjoy it fully, with the understanding that future needs might take them elsewhere. For others, there may be an argument for pooling family resources and securing the “forever” home sooner rather than later.
And of course, there’s no crystal ball. Real estate markets ebb and flow, even in a place as enduring as Watch Hill. But if we look at the last fifty years here, the arc of value has been steadily upward, interrupted only briefly by national downturns - and always bouncing back strongly.
A Broader Trend?
While my focus is here in southern Rhode Island, I suspect this question is being asked in other high-demand, low-inventory markets across the country. Whether it’s Cape Cod, Nantucket, the Hamptons, or certain resort towns in the Rockies, the dynamic is similar: limited land, strong desirability, and a next generation trying to secure their place before prices climb even higher.
An Invitation to Conversation
I don’t have the definitive answer. I’m simply sharing my musings as someone who has lived in this area most of my life. I grew up here, spent time in other parts of the country and overseas, and chose to come back to raise my family.
If you’re part of the next generation looking to buy here - or a local family wondering how best to support your children in doing so - I’d love to hear your thoughts. Do you see the benefit of buying bigger now, or do you feel the smaller, more affordable “in” is the smarter play?
Real estate in Watch Hill and Weekapaug is as much about legacy as it is about square footage. However you choose to approach it, I believe the most important thing is being intentional - thinking not just about the next few years, but about the decades ahead.
Let me know your thoughts. This is a conversation worth having.