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About

Toby Silk is the Managing Director and Licensee-in-Charge at Pentagon Property. With 15+ years’ experience across Sydney and NSW, he specialises in commercial real estate, development sites, apartment blocks and specialised property sales (including childcare, service stations and medical/essential-service assets). Toby blends straight-talking advice with deep planning insight—LEPs/DCPs, NSW Low–Mid Rise reforms and TOD corridors—to unlock highest-and-best-use value before going to market. Known for precise pricing, disciplined campaigns (off-market, EOI or auction) and transparent reporting, he brings qualified buyers—active developers, family offices and syndicates—to the table and negotiates terms that stick. Hands-on from appraisal to settlement, Toby coordinates yield/scheme testing, marketing and due diligence to maintain momentum and protect price. Owners seeking clarity on timing, strategy or feasibility value his practical, results-focused guidance and track record of complex transactions. Shape your future with Pentagon Property. I’m hands-on from appraisal to settlement: precise pricing, tight campaign strategy (off-market, EOI or auction), and clear reporting every step of the way. I’m known for bringing the right buyers—active developers, family offices and syndicates—to the table and negotiating terms that stick. If you’re considering a sale or want an informed second opinion on highest and best use, yield/scheme testing or go-to-market timing, I’d love to help. Shape your future with Pentagon Property.

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