Your Home for Real Estate and Short-Term Rental Counsel

Your real estate should work for you - like we do. That’s why we look beyond the transactional and focus on your goals as a homeowner, STR host, or business professional.

General Counsel for Short-Term Rentals

We know you’re a short-term rental owner or co-host because the business can be fun, rewarding, and profitable.  So, let’s make sure it is.

Together, let’s navigate the ever-changing regulations, control the risks, and get to the opportunities.

We’re especially proud of the unique membership service model we offer to the STR community.  With this proactive approach to legal counsel, you’ll always have an attorney on your side.  With this confidence, you can focus on what you do best - amazing your guests.

  • General legal counsel provided exclusively to our members
  • Unlimited attorney meetings
  • Local and state regulatory counsel
  • Asset protection through smart use of LLCs, trusts, and estate plans
  • - Discount on real estate transaction for members

Real Estate Transactions and Closings

A real estate transaction is a big deal.  That’s why we’ve rethought the whole process around you - homebuyers, sellers, and even real estate pros.

With thoughtful client service and smart use of technology, we work to ensure you feel informed and confident throughout the process.

We’re also experienced and ready for your “complicated” situation just as we are for cash deals, lender closings, and seller representations.  With your goals in mind, we can help structure creative financing deals, tax-advantaged transactions, and estate-optimized strategies.

  • Flat-fee seller representation
  • Cash and lender closings
  • Creative, seller, and private financing deals
  • 1031 exchanges and tax-advantaged transactions
  • Deals involving trusts, estates, and business entities

Meet Attorney Rory Gill

I built Urban Village Legal to provide my clients and neighbors a legal resource that works constructively for them. Directly out of law school, I opened my practice in 2011 and served my clients in real estate transactions, land use permitting and disputes, and estate planning - all with an eye toward growing my clients’ wealth and achieving their goals in real estate.

With real estate closings, I’ve worked with a diverse range of people from nervous first-time homebuyers to well-seasoned real estate professionals. This work broadened my legal toolkit to include a wide range of tactics as well as a deeper understanding of my clients’ needs.

While managing a real estate-centered practice, my husband and I found both a new creative outlet and financial security through short-term rental investing. Starting with a house in my family’s lakeside neighborhood, we now own five STRs in Massachusetts and New Hampshire. When I claim to understand the joys, challenges, and opportunities in STR investing, it’s because I’ve lived it myself. Finding property, designing homes, and building host systems have been a rewarding creative outlet for me. That’s why I’m proud to provide my peers with the legal counsel and confidence needed to grow their own STR investments and businesses.

After many years in South Boston, I now live with my husband and young daughter in Newburyport.

Let's Meet

RECENT EPISODES

The SmartStay Show

Welcome to the SmartStay Show, your go-to podcast for mastering short-term rentals on Airbnb, Vrbo, and beyond.

Hosted by 29-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro. Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive. From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental.