Your lifestyle, your vision, your home — they’re all uniquely yours. So why settle for an experience that wasn’t designed exclusively with you in mind? With us, you’ll never have to.
At the Skyline Group, our mission is to build the version of real estate that best captures who you are, what you want, and where you’re going. With strategic marketing, unrivaled local knowledge, and the nationwide Compass network behind us, we’re proving that personalized real estate is the fastest (and most seamless) path to achieving your goals.
At an early age, Mike learned the value of real estate as an investment in a person’s future. In high school, his first job was working for his friend’s dad, helping to revitalize rental properties after move outs to get them ready for incoming tenants. Between applying fresh coats of paint, cleaning up after the previous renters, and upgrading the landscape’s curb appeal, Mike began to see the promise in hands-on work that centered around the idea of home. After graduating college in 2008 with a double major in Econ and Psych, Mike decided to return to his roots. Drawing on his past experience, he officially earned his license and started leasing apartments. As it turns out, even getting his start during a recession couldn’t deter Mike: at one point, he was working multiple part-time jobs just to make ends meet. But although success didn’t happen overnight, as time went on, the landlords Mike represented became the buyers of his short sales and foreclosures, while the renters that he worked with eventually turned into first-time buyers. The business grew organically from there.
By 2010, Mike had established himself as a dedicated agent on the Chicago scene. While there, he worked at @properties for almost 11 years before transitioning to Compass in 2020, a move that empowered him to form his own team and elevate his growing brand. After navigating Chicago real estate for 16 years, Mike and his wife realized it was time for a change. In the midst of raising 2 young kids, they couldn’t think of a better moment to realign their lifestyle around a routine that matched their present-day pace and needs. With established ties to the greater Central Virginia area, Mike’s family fell in love with the beauty of the Blue Ridge Mountains and everything that the Charlottesville region has to offer. Today, Mike is the founding agent of Compass Charlottesville and leader of the Skyline Group, a team committed to putting every client’s goals first. Passionate about the outdoors, history, and communities with character, it’s only fitting that Mike’s expanding the Compass reach in a place that so effortlessly combines all three.
Whether you’re buying the home of your dreams or selling so you can embark on your next chapter, real estate sets the stage for some of the most meaningful decisions you’ll ever make. The Skyline Group wants to be there for you as you navigate those decisions, arming you with the clarity, tools, and compassion to help you reach your loftiest goals.
Transparent and collaborative, our proven approach is all about the needs of each individual client — which is why you’ll never see the same experience twice. What you can count on every time? A tailored blend of high-touch service, deep local expertise, and cutting-edge technology harnessed to deliver results that reflect you. Something else you should know about us? We don’t just close deals, we build relationships — meaning we’ll be in your corner long after the paperwork has been signed.
In the words of Mike himself: "As fiduciaries, our obligation is to represent every client’s interests above our own. We consult with clients to provide a completely personalized experience — no two situations are the same, which is why we listen and tailor our approach to ensure we reach every set of goals as smoothly as possible."
These days, Mike Gaffney’s typical clients are move-up buyers and sellers, selling their first or second homes and purchasing a home to start a family or enter the luxury market.
“Home is so much more than just a property,” says Gaffney, real estate broker and team lead of Skyline Group Charlottesville, Compass. “It’s where we live, raise our families, and experience the highest highs and lowest lows.”
Gaffney started his real estate career in 2009 and learned a great deal during those difficult, early years. “After leasing for a while, my business naturally evolved into sales,” he says. “I began to view real estate as a career and went full steam ahead to build a business.”
Get in touch for smart strategies and local insight whether you’re buying, selling, or just exploring. -Mike Gaffney
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