Dennis Fleming is a trusted leader in the Los Cabos luxury real estate market, bringing more than 25 years of sales experience and over 15 years of on-the-ground expertise in Baja California Sur. Originally from Portland, Oregon, he relocated to Los Cabos in 2008, drawn by the region’s lifestyle, natural beauty, and long-term investment potential. Immersing himself in the local market and culture, he quickly established a reputation for disciplined execution, market insight, and trusted advisory service.
Dennis’s personal story is deeply intertwined with Los Cabos. He and his wife, Renee, met in Cabo and were married on Médano Beach in 2009. Together, they are raising four children—Leila (13), Briella (10), David (7), and Emily (4)—all born in Los Cabos. Cabo is not simply a place of business for the Fleming family; it is their permanent home, where they have built their family, their businesses, and long-term roots within the community. Outside of work, Dennis and Renee enjoy golf, traveling, and fine dining, fully embracing the lifestyle that first brought them to Cabo. Shared values of family, faith, integrity, and service guide both their personal lives and their leadership philosophy.
Prior to founding Oceanside Real Estate Group, Dennis served as Sales Manager for El Encanto de La Laguna, where he worked directly with the developer on luxury home and condominium sales, including both new construction and resales. This role provided hands-on experience across the full lifecycle of residential development—inventory management, pricing strategy, buyer guidance throughout the construction process, and close collaboration with architects, construction teams, and ownership groups. His deep understanding of new construction remains a key differentiator when advising clients on both development opportunities and complex resale transactions.
In 2017, Dennis founded Oceanside Real Estate Group with a clear vision: to elevate the luxury brokerage experience through transparency, education, and long-term client relationships. Today, his focus spans high-end beachfront and golf communities across Los Cabos, offering clients a nuanced understanding of market dynamics across multiple submarkets rather than a single, community-restricted model.
Beyond sales leadership, Dennis brings a strong command of systems, marketing, and operational strategy. He has designed and implemented scalable sales processes, overseen brand and marketing initiatives, refined lead-generation strategies, and built operational frameworks that support agent productivity while maintaining a consistent, high-touch client experience. These capabilities have been foundational to the firm’s sustained growth and top-tier market performance.
Collectively, the founders have participated in over 600 real estate transactions totaling more than $600 million in sales. Dennis holds CONOCER and NOM-247 certifications and is an active member of AMPI and NAR. This combination of sales management, construction-focused expertise, operational discipline, and long-term market presence positions Dennis Fleming as both a trusted advisor to discerning clients and a strategic leader capable of scaling a luxury brokerage while preserving the highest standards of service and discretion.
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