Updated about 18 hours ago on .
Our first STR 10 years on
Investment Info:
Single-family residence buy & hold investment.
Purchase price: $177,000
Cash invested: $30,000
The Nook is a downtown Galena vacation rental that we acquired as a long-term buy-and-hold investment in one of the Midwest's most established short-term rental markets. Located within walking distance of Galena's historic Main Street, the property benefits from year-round tourism, strong weekend demand, and easy access to the shops, restaurants, and attractions that make Galena a popular getaway destination. While the home had solid fundamentals, we saw an opportunity to create a more memorable guest experience through thoughtful updates, improved furnishings, and the addition of amenities that today's travelers actively seek out. By enhancing the home's design, maximizing its outdoor spaces, and creating a cohesive boutique feel, we transformed it into a standout property within our portfolio. The Nook continues to perform as a strong buy-and-hold asset, generating both recurring cash flow and long-term appreciation in a market with limited downtown inventory.
What made you interested in investing in this type of deal?
This was our first STR deal, coming up to 10 years ago now. It was the one that "started it all" for us!
How did you find this deal and how did you negotiate it?
We used a local agent that was "fine". Now I am a licensed broker in IL so we negotiate our own deals.
How did you finance this deal?
Conventional financing - second home loan. A great way to get into this realm!
How did you add value to the deal?
High quality furnishing and creating a memorable guest stay.
What was the outcome?
High guest satisfaction rates!
Lessons learned? Challenges?
Always check on the status of a STR license with the local jurisdiction before closing on the deal!
Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?
Plenty - message me! I am a property manager in the local area now and love to help other STR owners succeed!
