The family-run business was awarded Best Business for Training and Development and Apprenticeship Provider of The Year. It also won Best Green Business for its grounds maintenance works, as well as receiving 'Highly Commended' for Best SME business in the south London borough.
The company recently merged with its long-term grounds maintenance partner Westland Estates, bringing another 50 staff into the Chequers Group.
Commenting on the training and development award, Steve Rapley, international trade adviser of UK Trade and Investment, said on behalf of the judges, "With a desire to incorporate all members of the community into their business, and a willingness to train each individual at all levels, this company was the most outstanding candidate in this category.
"Consistently providing first class cleaning and building services to housing associations offices, schools, buildings and combining the qualities of a family business with a close partnership with its staff and clients is the root of the company's success.
Chequers currently has 16 apprentices working within the company, including three in horticulture. The company also has two BICSc training academies to help upskill staff.
Kate Ward, sales and marketing director said, "It's unbelievable to win three awards and we are so proud of our staff, their engagement and support with our training and apprenticeship opportunities. Success is a team effort and we work closely with our staff, clients, suppliers and business partners. We are also proud to be based in Croydon and really enjoy working with the local community."