In the near future we will be posting information about our steps and progress, on purchasing our forever home on Montserrat, in the Caribbean. Follow along with us as we shop, complete paperwork, and facilitate our move.
Why Montserrat?
One of the questions we get asked most often is, “Why Montserrat?”
If you’ve been following our journey, you might remember that our connection with the island began back in 2015 during a quick day trip from neighboring Antigua. From the moment we arrived, Montserrat took hold of us and simply never let go. Fast-forward to today, with seven return trips over the last 11 years under our belts, we know with absolute certainty that we’ve found our forever island. Now, the only thing left to do is find our forever home.
So, what exactly keeps drawing us back?
First and foremost, it’s the raw, untouched beauty of the island itself. Montserrat is visually stunning. The deep, vibrant blues of the Caribbean Sea strike a gorgeous contrast against the island’s rugged mountainous terrain and dense, emerald rainforests. It feels entirely separated from the heavily developed tourist hubs you find elsewhere. Plus, the climate is essentially perfect—hovering steadily in the 80s for most of the year, with a constant, soothing trade wind that keeps the tropical humidity beautifully in check.
Secondly, it’s the people. There’s a warmth to the community here that feels wonderfully old-school in the best possible way. The locals still believe in the art of a genuine greeting. They say “good morning” or “good evening” to everyone they pass on the street, address you with respect, and always offer a friendly wave from their cars. They go entirely out of their way to make you feel like you belong. The most remarkable part? It is completely authentic. We’ve experienced this effortless hospitality on every single trip, without fail.
Finally, it’s the undeniable vibe. Montserrat offers the quiet, slow-paced lifestyle so many of us constantly crave but rarely find. There isn’t a single traffic light on the island. When you hear a car horn, it isn’t an act of road rage—it’s just a neighbor saying hello. You won’t find any sprawling big-box stores, fast-food drive-thrus, or corporate chain restaurants disrupting the landscape. It is simply local culture at its finest.
Coming from the densely populated, fast-paced region of Northern Illinois just outside of Chicago, Montserrat is exactly the escape we want—and honestly, it’s what we need. The time is fast approaching to finally trade in the endless hustle of the Midwest for the relaxing, authentic rhythm of the Caribbean.
House Listings
Buying a house on Montserrat involves a very different process from what we are used to in the States. While they do use an acronym called “MLS,” it actually stands for the Montserrat Listing Service, not the centralized Multiple Listing Service we rely on back home.
Because there isn’t a single, unified database, properties are listed directly with independent real estate companies or property management firms. This means that a home listed for sale on one agency’s website likely won’t appear on any others. As a buyer, this requires a bit more legwork; you can’t just hire one agent to show you everything on the island. Instead, you need to build relationships with multiple brokers and monitor several different sites to get a full picture of the available market.
To get started, we have spoken with and browsed the selections of a few key local businesses:
- Tradewinds Real Estate: Owned and operated by Susan, who is an expat from Illinois and a fellow S.I.U. Saluki.
- MNI.Villas: Owned by Paul, another American expat, who was actually featured on House Hunters International when he bought his own property in Montserrat.
- Black Sand Properties: Located in Olveston and run by Loni Howe.
- Tropical Island Real Estate: Owned by local resident Kenneth Cassell, with an office conveniently located just across the parking lot from the airport.
House Hunting Posts
Coming soon
Leave a Reply
Want to join the discussion?Feel free to contribute!