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Richard Drill

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Richard Drill

A little bit about me...

After two decades of success in Vermont real estate, Richard “Rich” Drill has brought his passion for exceptional customer service and market expertise to Matchmaker Realty in Gainesville. A Vermont resident for twenty years, Rich built a respected career serving the communities of Waterbury, Stowe, Morrisville, and beyond, earning a reputation for integrity, in-depth market knowledge, and a client-first approach.

Rich’s professional background is as diverse as it is impressive — from owning and operating an inn in Stowe to serving on local boards and managing a growing portfolio of rental properties for over a decade. These experiences have sharpened his business acumen and given him a deep understanding of what it takes to deliver results for both buyers and sellers.

Known for his straightforward communication style, steady accessibility, and expert market analysis, Rich guides his clients with clarity and confidence through every step of the real estate process. Whether helping a first-time buyer find the perfect home or assisting a seller in positioning their property for top value, he is committed to serving each client’s best interests with professionalism and care.

Now proud to call Gainesville home, Rich looks forward to helping new neighbors discover all that North Central Florida has to offer — with the same level of dedication and excellence that defined his career in Vermont.

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In the Words of my Clients

Success Stories

"I really enjoyed my experience with Melissa Hinote, she was very courteous, professional and genuinely cared about my satisfaction. I would recommend asking for her by name when dealing with Match Maker, because she will make sure you are happy and w
"Kristen McCallister is the definition of excellence in real estate. She is truly an expert in her field- knowledgeable, professional, and relentless when it comes to getting the job done. Kristen doesn’t just check the boxes; she goes above and beyon
"Kristen McCallister has been so helpful. Shes been patient and informative and has helped me every step of the way. Being a first-time home buyer I did not know where to start, she made this process smooth and enjoyable."
"Kristen McCallister of Matchmaker Realty is an elite realtor and a master manager of chaos. I would also describe her as the kindest of human beings with a servant's heart. There was never a question of who would be the one to li

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