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 put down roots that would shape both his personal and professional life. A natural leader from an early age, he served as Class President at Cary High School and later 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 across diverse industries. His entrepreneurial career began while still in high school with the development and marketing of a fire-retardant product, Flame No More, for which he secured private investment and funded testing toward the Underwriters Laboratories (UL) Seal of Approval. He later opened one of the largest college nightclubs in Raleigh, NC, before founding Capital Style Luxury Transportation, Inc. in Cary.
Under Steve’s leadership, Capital Style grew into North Carolina’s largest ground transportation company, recognized by the National Limousine Association Magazine for three consecutive years. The company operated a fleet of 33 vehicles and provided transportation for more than 250,000 clients annually. Steve was elected President of the North Carolina Limousine Association in 2004 and 2005 and successfully completed the sale of Capital Style in June 2005.
Today, Steve’s primary focus is commercial and residential real estate development and brokerage throughout North Carolina. He is the owner and managing broker of Gillooly & Associates Realty, LLC, where he represents clients across all price points, from entry-level residential properties to complex, 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 and operates Milan Realty, LLC., a real estate development company specializing in residential, commercial, warehouse, and office development.
Milan Realty has developed many real estate transactions, such as:
240 luxury apartment units in Holly Springs, NC
Over 1,000 residential lots in Apex, NC
Over 800 residential lots in Holly Springs, NC
Milan Realty also partnered with Lowe’s Home Improvement to bring a major retail presence to Holly Springs. As both a developer and investor, Steve brings a rare dual-sided perspective to every transaction, understanding risk, value creation, entitlement strategy, and execution.
Steve is deeply committed to the community. He has served as the past President of Cary Visual Art and as a Board Member of Rufus Edmisten’s Super Kids. This Raleigh-based nonprofit provides college scholarships to underprivileged students.
Steve’s Mission - as a real estate broker is straightforward: to deliver the highest level of service possible by guiding clients through complex transactions with clarity, discipline, and integrity. His reputation is built on long-term relationships, honest counsel, and results.
Specialties:
* Commercial & Residential Buyer and Seller Representation
* Investment Properties
* Land Development & Site Selection
* Commercial Real Estate Consulting & Brokerage
* IRS **1031 Tax-Deferred Exchanges**
* Foreclosures & Short Sales
* Relocation Services
* Rezoning, Site Plan Approvals & Special Use Permits
* Municipal Coordination & Entitlement Strategy
Steve Gillooly brings experience, judgment, and execution to every deal because, in real estate, fundamentals still matter!
Home Types:
Lot/Land, MultiFamily, House, Townhouse, Commercial
Years of Experience:
20
Education:
Louisburg College, Business Administration
N C State University, Business Administration and Management
