Caillin Boles

Caillin Boles is a Vice President at Matthews™ Capital Markets, specializing in commercial real estate financing and debt placement. With nearly a decade of experience across investment sales, underwriting, and capital markets, Caillin has transacted on over $1 billion in deals. His expertise in financial modeling, asset valuation, and credit risk assessment makes him a trusted advisor to property owners, investors, and lenders seeking financing solutions aligned with their investment objectives.

Caillin began his career as an associate broker with The NNN Pro Group at Marcus & Millichap, focusing on net lease investment sales, sale-leaseback transactions, 1031 exchanges, and portfolio management. He then moved to the capital markets side, first as a financial analyst at Progress Capital, where he underwrote loans and built financial models from initial evaluation through closing, and later as a senior financial analyst on Cushman & Wakefield’s Equity, Debt & Structured Finance team, where he drove financial modeling, valuation, and credit risk analysis across each phase of the loan process.

Drawing on both investment sales and debt financing, Caillin brings a comprehensive understanding of commercial real estate transactions to Matthews™ Capital Markets. He leverages the firm’s national platform, proprietary technology, and extensive lender relationships to help clients evaluate financing options, optimize capital structures, and execute transactions that support their long-term investment goals.

Caillin earned both his undergraduate degree and his MBA in Finance from Providence College. Caillin resides in Long Branch, NJ with his wife Alexandra and is an avid golfer at Deal Golf & Country Club.

MBA, Finance

Providence College

B.S., Finance

Providence College