Steve Gillooly

Steve Gillooly was born in Manhattan, New York, and adopted at age four by Bruce and Nancy Gillooly. His family later relocated to Cary, North Carolina, where Steve established deep roots that shaped his leadership-driven career. He served as Class President at Cary High School and studied Business Administration at Louisburg College and North Carolina State University.
With nearly four decades of experience as an entrepreneur and business leader, Steve has built, scaled, and successfully exited multiple companies. His first venture began in high school with the development of a fire-retardant product, Flame No More, where he secured private investment and funded testing toward the UL Seal of Approval. He later opened one of the largest college nightclubs in Raleigh before founding Capital Style Luxury Transportation, Inc.
Under Steve’s leadership, Capital Style became North Carolina’s largest ground transportation company, recognized nationally for three consecutive years. Operating a fleet of 33 vehicles, the company transported over 250,000 clients annually. Steve was elected President of the North Carolina Limousine Association in 2004 and 2005 and completed the sale of the company in 2005.
Today, Steve focuses on commercial and residential real estate brokerage and development across North Carolina. He is the owner and managing broker of Gillooly & Associates Realty, LLC, representing clients from entry-level residential to multi-million-dollar commercial transactions. He is a licensed REALTOR®, a member of the National Association of Realtors, and the Triangle Commercial Association of Realtors (TCAR).
In parallel, Steve owns Milan Realty, LLC, a development firm specializing in residential, commercial, warehouse, and office projects. Notable developments include 240 luxury apartments in Holly Springs, over 1,000 residential lots in Apex, and 800+ lots in Holly Springs, along with partnering with Lowe’s Home Improvement to bring a major retail presence to the area. As both a developer and investor, Steve understands transactions from both sides of the table.
Steve is active in the community, serving as Past President of Cary Visual Art and as a Board Member of Rufus Edmisten’s Super Kids, a nonprofit providing college scholarships to underprivileged students.
Specialties include: commercial and residential representation; investment properties; land development and site selection; commercial consulting; 1031 exchanges; rezoning and entitlements; foreclosures; short sales; and relocation services.
Steve Gillooly delivers experience, judgment, and execution, because in real estate, fundamentals still matter!