After John McCullough joined Kennedy Wilson in 2025, following the acquisition of Toll Brothers' apartment living platform for US$347 million, he serves as President of the real estate investment company's Multifamily Development Group. In this role, he oversees all aspects of the firm's US development business. With the acquisition of the Toll Brothers platform, Kennedy Wilson secured General Partner interests in 18 apartment and student housing properties, with assets under management totalling US$2.2 billion. The company also purchased a pipeline of 29 development sites at various stages of construction.
The entire Toll Brothers apartment living management team moved to Kennedy Wilson under Mr. McCullough's leadership. McCullough had previously led apartment living operations at Toll Brothers. However, his path into the real estate industry was not predetermined, as he first served in the US Navy and later found his career in business while studying in Boston.
The Path to Real Estate and the Acquisition of Toll Brothers
Mr. McCullough describes his entry into the real estate industry as a detour. After graduating from the United States Naval Academy in 1994, he served five years in the 'Surface Navy'. He emphasised that he served on two large aircraft carriers in San Diego, which was a great experience and gave him a solid foundation in leadership principles. He found himself in many incredibly difficult situations as a 23 or 24-year-old, from which he learned a great deal.
After his military service, McCullough attended business school at Boston University. There, he began to view real estate as a potentially very interesting field for himself. In 2002, after graduate school, he took a position at Tishman Speyer, where he was moved into a role in commercial real estate operations. He eventually managed about a third of Rockefeller Center, including all office and retail spaces. Although he received thorough training there at one of the best real estate companies in the industry, he realised that he did not want to work in the office space sector or in purely operational business.
McCullough instead opted for the residential real estate sector. He took courses at New York University, earned a certificate in real estate with a focus on residential properties, and made this transition. At Toll Brothers, one of the most prolific condominium developers in the greater New York area, he joined as a development manager for about seven years. The major financial crisis hit housing companies hard. At Toll Brothers, staffing reductions were dramatic, leading to difficult conditions for many years.
Strategic Realignment and Kennedy Wilson's Mission
Around 2012, Toll Brothers began to consider how they could achieve diversification in the future and protect themselves against similar scenarios. The strategy was to leverage their experience in high-density condominium construction to establish a multifamily platform. This involved using the Toll Brothers brand name and existing internal capabilities. He was therefore asked to move to Philadelphia and build a new platform within Toll Brothers with the newly hired head of the group.
The growth strategy was approached very methodically. The Toll Brothers brand name was a great advantage, but also an obligation to always ensure the high standard of the brand. While other groups in the multifamily segment grew faster, Toll Brothers proceeded more slowly and methodically to ensure execution quality. Ultimately, Toll Brothers – like most, if not all, other housing companies that entered the multifamily sector – could not operate this business segment profitably on a sustained basis.
- —Continued operation of the national platform.
- —Supplementation of Kennedy Wilson's service portfolio.
- —Ensuring consistent execution quality across all regions.
All employees transitioned to Kennedy Wilson in December 2025. McCullough expressed gratitude to Toll Brothers for focusing on finding a good home for them. There was a good cultural connection with Kennedy Wilson. The mission now is to continue operating this national platform and to supplement Kennedy Wilson's service offerings.
