According to Forbes, Peebles is one of the most successful African American CEOs,[4] whose majority projects are executed through public-private partnerships.

[5] In May 2009, Forbes listed Peebles in the top ten of the wealthiest black Americans,[6] and in January 2015 it estimated his net worth to be over $700 million.

[12] On January 9, 1983, at the age of 23, Peebles opened his own residential and commercial real estate appraisal firm.

[16] Peebles built a luxury residential tower on the site of the club's former parking lot and tennis courts and preserved the historic clubhouse.

[17][18] The Bath Club site expands 5 acres, plus 3 acres of beach, including 540 feet of beachfront along the Atlantic Ocean, as well as 20,000 feet of indoor and outdoor private event space, a spa, a fitness center, two clay tennis courts, and a fine dining restaurant-lounge.

Peebles maintained the charges were politically motivated due to his opposition to then Mayor Adrian Fenty's failed re-election bid earlier that year.

[26] He formed a joint venture with MGM Grand and Harbinger Capital in response to an RFP for the Aqueduct Casino in New York.

There existed public scrutiny relating to the manner in which then Governor David Patterson and state legislators managed the entire bidding process.

[28] In 2014, he, along with development partners, responded to a Request for Proposal to redevelop the LICH hospital site, but were unable to come to terms on the deal.

[29] After years of negotiations with the Washington, DC agencies to transform an abandoned parcel in the Mount Vernon Triangle[30] into a luxury hotel and condominiums, Peebles and his development partner were unable to move forward with the project.

Affirmation Tower has received extensive media coverage and overwhelming local and national support from citizens, community, and political leaders.

Peebles is to redevelop 3.8 acres of land along with air-rights above the Bankhead MARTA rail station, as a mixed-use transit-oriented community including approximately 490+ multi-family housing units.

[55] He had also publicly considered running for Mayor of Miami and of New York City and received encouragement from many political and community leaders.

SUNY Downstate Medical Center ended talks with Peebles over an impasse about remediation costs on May 28, 2014 and later made a deal with Fortis Property Group.

However, Peebles did not enter the race citing wanting to teach his then 22-year-old son, a recent graduate from Columbia University, the real estate business, and to spend time with his 14-year-old daughter during her last four years at home before college.

[62][63] Peebles frequently appears on CNN, Fox News, CNBC and other networks to discuss political, economic and business issues.

[65] He supports small business and minority-focused initiatives emerging from The White House with a focus on policy change rather than political affiliation.

[68][69] He currently lives in Miami Beach, Florida, Sag Harbor, NY and New York City with his wife Katrina, a former PR executive, whom he married in 1992.