My first house turned STR

[Ariel Steinberg]

Investment Info:

Townhouse buy & hold investment in Washington.

This home was my first real estate investment — a place I designed to feel both welcoming and elevated, with the comforts of home and the attention to detail you’d expect from a boutique hotel. I furnished and finished it with travelers in mind, adding thoughtful touches and amenities that make people feel cared for the moment they arrive.

What made you interested in investing in this type of deal?

As a frequent traveler and lover of nice hotels, and unique Airbnbs, I knew I wanted to blend real estate investing with hospitality. I started by house hacking the property, renting one room to Airbnb guests and the other to a long-term tenant. Over time, it evolved into a full short-term rental, and in the off-season I offer it for mid-term stays. It’s still my primary home when I’m in the area, so I maintain it with the same care and intention I always have.

How did you find this deal and how did you negotiate it?

I found the house through an agent. To be honest, it wasn’t so much of a deal, but I saw potential.

How did you finance this deal?

I got a conventional loan. I only put 5% down and have a 2.86% interest rate.

How did you add value to the deal?

Most of the upgrades I made were cosmetic but intentional. I painted the house inside and out, refreshed finishes, and designed the space to feel like a boutique hotel and a home at the same time. Since it was built in 1910 and still had much of its original charm, I leaned into that character — incorporating its historic details into the overall design while adding modern comforts and thoughtful touches that guests notice and appreciate.

What was the outcome?

The updates paid off — guests consistently comment on the design and attention to detail, and the property stays booked at strong rates year-round. In peak season it performs extremely well, and in the off-season I still maintain solid occupancy with mid-term rentals. It’s been a profitable investment that also gives me a place to stay whenever I’m in town.

Lessons learned? Challenges?

I overpaid and underfunded, buying in DC expecting stability, but political shifts and new Airbnb rules changed my plan. I wasn’t aware of options like off-market deals, multifamily, or diversifying into multiple properties. Before I could rent the whole house, I lost my job and the chance to double my income with salary plus rental revenue. The timing slowed my investing, but led me to leave corporate and focus on learning about creative strategies and leveraging other people’s money to grow.