Cottonwood Commercial was founded in 1970 in Harrisonburg, Virginia, and has grown to become the largest commercial real estate brokerage in Western Virginia. The firm operates as a privately held company under the ownership of Keith May, who also owns Kline May Realty and related entities. Cottonwood Commercial specializes in brokerage services for commercial and investment real estate transactions, including acquisition, disposition, leasing, and property management. Its core business focus spans retail, office, industrial, and multifamily property segments, serving both regional businesses and national brands. The company’s investment strategy emphasizes local market expertise and relationship-driven transactions rather than institutional-scale capital deployment. Cottonwood primarily targets properties within Virginia and neighboring mid-Atlantic markets, leveraging deep knowledge of demographic trends and economic drivers in these regions. While Cottonwood does not operate as a REIT or large-scale investor, its brokerage activities position it as a key intermediary in the Shenandoah Valley and surrounding areas. Top market exposure includes the three primary cities in the central Shenandoah Valley: Harrisonburg, Staunton, and Waynesboro, which collectively represent the majority of its transaction volume. Tenant representation spans a diverse mix of local enterprises and select national retailers, though no single tenant accounts for a material share of revenue—a reflection of Cottonwood’s brokerage model rather than ownership. The firm’s reputation for integrity and market knowledge has enabled it to maintain dominance in the Harrisonburg-Rockingham MLS for commercial transactions. Cottonwood’s strategic positioning is rooted in being the go-to brokerage for businesses seeking expansion or relocation within Virginia’s secondary markets, offering tailored solutions for site selection, leasing, and investment sales.