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Designing Retirement with Purpose: How We Turned Our Cottage into a Launchpad for Adventure
Retirement doesn’t have to mean slowing down. For us, it meant gearing up — for travel, freedom, and a lifestyle rooted in simplicity and smart real estate strategy. If you’ve ever dreamed of downsizing, hitting the road, and making your home work for you while you explore, this story might just be your roadmap.
🏡 From Cottage to Catalyst
Our home is a modest 1920s cottage tucked in the heart of Downtown Annapolis, Maryland — two bedrooms, one and a half baths, lovingly refurbished but not over-renovated. It’s charming, walkable, and just big enough to live comfortably when we’re home. The backyard? Just enough space to park our Airstream, which doubles as a guest suite and office when we’re not traveling.
But here’s the twist: we only live in the house 2–3 months at a time. The rest of the year, we’re on the road — exploring the country in our Airstream, staying in short-term rentals, and letting our Annapolis cottage earn its keep.
✨ The Minimalist Shift
It took about a year to prepare the house for this lifestyle. We purged, pared down, and reimagined our space with short-term guests in mind. Every drawer, closet, and corner was reconsidered. The result? A clean, welcoming rental that feels like home to travelers — and like freedom to us.
Now, it’s just minor maintenance. We have a trusted local house manager who handles turnovers, cleaning, and any surprises while we’re away. Thanks to platforms like Airbnb and VRBO, our home stays booked — especially with the Naval Academy nearby and Annapolis’s year-round charm.
🚐 Travel Funded by Home
Here’s the magic: the income from our short-term rentals fully covers the gas and maintenance for our Airstream and van. That means our adventures are self-sustaining. We’re not dipping into retirement savings to travel — we’re leveraging our home to fund the lifestyle we love.
We alternate between living in the cottage and traveling, usually in 2–3 month blocks. It’s a rhythm that keeps us connected to our community while giving us the freedom to roam.
💡 Coaching the Lifestyle
As a real estate professional, I see enormous potential in this model — especially for older homeowners considering downsizing. With the right prep, a small home in a desirable location can become a powerful asset. I’d love to coach others through the process: from minimalizing and staging to managing rentals and designing a travel-forward retirement.
This isn’t just about real estate. It’s about reclaiming time, space, and purpose. It’s about turning your home into a launchpad for the next chapter.
Ready to explore this lifestyle for yourself? Whether you’re curious about downsizing, prepping your home for short-term rentals, or designing a retirement that moves — I’m here to help. Let’s talk about how your home can fund your freedom.
