“Real estate isn’t just about buildings. It’s about memories, migration, and the meaning of home,” says Dean Jones, founder of Jamaica Homes and second-generation Windrush descendant.
From the red post boxes of Hackney to the mango trees of Half Way Tree, this journey isn’t just mine—it’s a shared tale among thousands who have danced between England and Jamaica, trying to make sense of both places and the possibilities they hold.
I didn’t grow up in London, and lived in Islington and Hackney for a while not fully anyway, but I did spend a fair stretch of my life there—especially during university. I lived in Stoke Newington while studying at Central Saint Martins, a prestigious institution under the University of the Arts London, where I earned a BA in Graphic Design and a Master's in Communication Design. But this story isn’t about degrees. It’s about something deeper: the journey back home.
Like so many others, I am part of the second-generation Windrush legacy. My roots run through Maroon Town in Jamaica, and some of my most vivid childhood memories were carved into the hills and coasts of the island. I remember Hellshire Beach—before erosion took its toll—floating in a car tyre, getting stung by a jellyfish, eating fried fish and festival that would make any five-star meal feel bland.
Those were the days of barefoot wanderings, donkey rides gone wrong, and chicken chases that left me out of breath and laughing. And then there was Hurricane Gilbert—I still remember the lyrics we sang: “Water come inna mi room, di dish run weh with di spoon...” The storm changed the country, but it also stitched new memories into all of us.
When you spend part of your childhood playing in the bush in Guy’s Hill, learning to cut sugar cane, and watching your aunt prep for market in Spanish Town, Jamaica doesn’t just feel like home. It is home.
But the story’s never that simple.
From Spanish Town to South London: A Tale of Misunderstood Wealth
The Windrush era, marked most famously by the Empire Windrush arriving in 1948, began a new chapter for Jamaicans in Britain. My grandfather was part of that generation who believed in the British dream. And to some degree, Britain delivered. But what people back home often misunderstood was just how hard the hustle was.
You’d see relatives return from London, decked out in fine clothes, giving the illusion of wealth. But what many didn’t realise is that those same people were working long shifts, saving for years, and returning only briefly before heading back into the grind. It was all an illusion, but a powerful one. It fed into this perception that British Jamaicans were well-off.
Even today, I find that misperception lingers. We work hard in the UK—just as hard as anyone anywhere. So when we return and choose to invest in Jamaica, it's not about showing off; it's about building something meaningful, something permanent.
Red Post Boxes, Black Taxis, and the British Cultural Quilt
There’s something about the red Royal Mail post boxes that sticks with you. Maybe it’s nostalgia. Maybe it’s the idea of tradition in a place constantly evolving. British culture has always been a patchwork—a mosaic made from colonies, conflicts, immigrants, and influence.
You see it in the black cabs, the curry shops, the grime beats echoing from flats in Tottenham. You see it in the Windrush murals, the council estates, and the people of colour working double shifts in the NHS.
And then you come back to Jamaica. And the contrast is both jarring and familiar. You realise Jamaica’s a different side of the same coin. The grass isn’t greener—it’s just different grass.
Jamaica: The Real Estate Dream (and Its Pitfalls)
"Jamaica will fool you if you don’t ask the right questions,” I often tell my clients.
The truth is, Jamaica is a beautiful country with immense potential. But if you don’t understand the terrain—both literally and metaphorically—you can make costly mistakes. Investing beside a derelict property, or on a road that's prone to crime, or building a 10-bedroom house you’ll never live in? That’s not investment. That’s ego.
If you’re not going to live here, I always recommend apartments in gated communities, or well-maintained single homes in stable neighbourhoods. There’s no reason to overextend.
Trust is crucial. I don’t sell dreams; I sell realities.
Clients who work with me know I’ve lived both sides—I know the quiet ambition of a returnee, the cautious optimism, the buried trauma, and the joy of reconnecting with one’s roots. That’s why I say, trust your realtor—especially one who understands the journey you’re on.
The Unspoken Tensions: Jealousy, Sabotage, and 'Bad Mind'
Not everything glitters. There’s a darker undercurrent to returning. Jealousy is real. So is sabotage. Some agents, some neighbours, even some family members don’t want to see you win.
"It’s a cut-throat business. But that’s not the part that scares me. It’s the manipulation—the way some will smile in your face and sell you the wrong dream," I once said to a client from Birmingham who got scammed on a land deal before finding me.
That’s why transparency matters. That’s why experience matters. That’s why you need someone who’s been stung before and lived to tell the tale. Because this isn’t Monopoly. This is your life savings, your dream retirement, your legacy.
Investing with Intention, Not Illusion
Some folks return thinking they’ll build a mansion and live like royalty. But then they realise how much it takes to run a house that size. Or they build in the wrong parish with no long-term plan.
"Why build a palace if you’re not going to live in it, can’t maintain it, and don’t have a soul to share it with?" I asked a returning couple from Manchester, UK, who were about to make a mistake that would have cost them millions.
Smart real estate is about right-sizing. It’s about matching your goals with your lifestyle. Not your ego.
A Two-Way Street: Returnees and Respect
Here’s the truth: Jamaica survives partly on the back of its diaspora. Taxes, remittances, and real estate investments pump billions into the economy. But sometimes, we don’t feel welcomed.
"There’s a deep sense of pride in returning. But there’s also a pain in not feeling recognised," I said recently at a housing forum.
And while things are improving, there’s still work to be done. Returnees aren’t trying to take over. We’re trying to come home. And Jamaica needs to make room for that return.
Final Thoughts: Between Two Worlds, Building One Life
From Hackney to Half Way Tree, this journey has taught me that home isn’t just a place—it’s a feeling. A vibration. A memory you keep chasing until it sits right in your chest.
For some, that means staying in the UK. For others, it means returning to Jamaica. And for a growing number of us, it means dancing between both.
My advice? Come home. But come prepared. Invest. But invest smart. Love Jamaica, but understand it fully.
As I often tell my clients: Don’t just buy a house. Reclaim your heritage. But do it with your eyes wide open.