When Jennie Bailey told her friends she planned to raffle off her family’s seaside home for just £5 a ticket, the response was swift and incredulous: “bonkers,” they said. Yet, for Jennie and her family, the decision to take this unconventional route was not made on a whim. After a year of fruitless attempts to sell their two-bedroom flat in the picturesque village of Rhoscolyn on Anglesey, and a £40,000 drop from its original £365,000 asking price, they decided it was time to think outside the box.
The Baileys’ journey is, at its heart, a story of adaptation in changing times. Jennie, 43, her husband John, 45, their sons Henry (11) and Sebastian (9), and cocker spaniel Dylan moved from Manchester to Anglesey two-and-a-half years ago, trading the city’s bustle for the village’s “slower pace.” The flat—originally a holiday home purchased eight years ago—soon became their full-time residence. But as the boys have grown, so have their needs. “The boys are craving their own space,” Jennie told BBC Wales, describing how the two-bedroom flat has become increasingly cramped for the family of four (and one energetic dog).
The property, nestled just steps from the beach and steeped in family memories, is one of three flats inside a converted house. Jennie’s brother owns the ground-floor flat, and Jennie herself has been coming to Rhoscolyn since she was two years old. “We spent all our summer holidays here, so I’ve kind of grown up here,” she recalled. The thought of leaving is emotional, but the passing of Jennie’s father in 2024 made her realize it was time for a new chapter. “It would be amazing to see someone else enjoy this like we’ve done,” she said.
After a year on the market with no buyer in sight and stress mounting, Jennie stumbled upon the idea of a house raffle thanks to a friend who shared a story about a similar event in Ireland. Initially skeptical—“My first response was ‘don’t be so stupid, there’s no way in the world I’m doing that’”—Jennie’s curiosity soon got the better of her. She spent a month researching, seeking legal advice (which, she admits, was tricky to find), and learning about the ins and outs of running a property raffle.
Setting up the raffle meant taking the property off traditional sale listings and launching the competition through an online platform. The goal: sell 150,000 tickets at £5 each by January 1, 2026. If the target is met, the winner gets the keys to the £325,000 seaside flat. If not, the Baileys keep their home, and the raffle winner receives half the money raised, with the remainder covering costs like legal fees, stamp duty, and marketing, and any surplus going to the family. Notably, 10% of proceeds are claimed by the raffle platform itself.
As of Friday, December 12, 2025, the family had sold 50,531 tickets—just over a third of their ambitious target. Jennie remains optimistic, noting that “only a low percentage of people actually complete” such raffles, but ticket sales typically spike in the final weeks. She’s not wrong: Stelios Kounou, founder and CEO of Raffall (the platform hosting the Baileys’ raffle), told BBC Wales that since 2020, his company has hosted 54 house raffles in the UK and Ireland, 18 of which resulted in a successful property exchange. “People who do this know the probability of success might be low but, for those willing to put in the hard work, the time risk is worth the possible reward,” Kounou said.
For Jennie, the process has been a crash course in marketing, social media, and customer service. “I work on this every day. Some days all day long, sometimes at night,” she said. On top of running the raffle, Jennie also manages a handmade home decor business, while John works from home as a packaging designer. The learning curve has been steep. “It’s really hard. I don’t know whether what I’m doing is right or not, I’m just literally trying anything and everything. Would I recommend it? If you can be quite thick-skinned and just carry on, then yes, do it. But you’ve got to devote time to it.”
The family has not been immune to criticism. Some locals have questioned the price of the flat or the Baileys’ origins outside the area. Jennie, however, has chosen to ignore the negativity. “We’re genuinely just a family who are trying to sell our property in a bit of an unusual way,” she explained. “It gives a chance for someone who might not be able to buy this kind of property—£5 is like a coffee these days. If you don’t like it, just don’t enter.”
The Baileys’ story taps into a broader trend of homeowners seeking creative solutions in a challenging property market. While house raffles are not likely to become the norm—Kounou is clear on that point—they do offer hope to those willing to take risks and put in the effort. For the Baileys, the raffle is more than a quirky marketing ploy; it’s a way to move forward, create new opportunities for themselves, and potentially change someone else’s life with the turn of a ticket.
Despite the uncertainty, Jennie and her family plan to stay in Anglesey after the sale. The beach view, she admits, will be missed. But as the raffle’s deadline approaches, the family is focused on the future and the possibility of passing on their beloved home to someone new. “It would be amazing to see someone else enjoy this like we’ve done,” Jennie said, her voice tinged with both nostalgia and hope.
With just weeks left to reach their ticket goal, the Baileys are working tirelessly, undeterred by skeptics and buoyed by the possibility of a fresh start—for themselves and for the lucky winner who could soon call Rhoscolyn home.
