Key Takeaways
- • Two Sigma co-founder John Overdeck, 56, purchased a $72 million Palm Beach waterfront estate through Delaware shell entity Avocado Enterprises, expanding his real estate footprint from a 6,000-square-foot New Jersey home to a 16,000-square-foot Neoclassical compound.
- • Overdeck, valued at approximately $8 billion by Forbes, has settled into the property with Kimia Shadrokh, 42, a Peakstone managing director and former commercial real estate executive, after both registered to vote at the address in spring 2026.
- • The acquisition occurs during active divorce proceedings filed in March 2022 against estranged wife Laura after nearly 20 years of marriage without a prenuptial agreement; Overdeck has offered $723 million in tax-free cash as settlement.
- • The 1-acre north-end Palm Beach compound features six bedrooms, 7.5 bathrooms, a great hall with 26-foot ceilings, travertine pool with cabana, and 165 feet of waterfront with deep-water dock access, reportedly following a $20 million renovation.
- • Matthew Siano, the LLC's manager and a former Two Sigma legal and compliance executive with approximately 20 years tenure, facilitated the transaction structure.
Summary
John Overdeck, co-founder of hedge fund Two Sigma Investments and an $8 billion net worth individual per Forbes, has acquired a $72 million Palm Beach waterfront estate while engaged in ongoing divorce litigation in New Jersey. The purchase, documented through Delaware-registered shell company Avocado Enterprises, represents a significant property upgrade from Overdeck's previous 6,000-square-foot residence in Short Hills, New Jersey, which he shared with his estranged wife Laura.
The Neoclassical compound spans approximately 16,000 square feet on nearly one acre in Palm Beach's exclusive north end, featuring six bedrooms, 7.5 bathrooms, a great hall with 26-foot ceilings, a travertine pool with cabana, and 165 feet of waterfront frontage with deep-water dock accommodations. The property underwent approximately $20 million in renovations prior to occupancy. Overdeck shares the residence with Kimia Shadrokh, 42, a managing director at Peakstone and former commercial real estate executive with the Moinian Group; both registered to vote at the address in spring 2026. Overdeck's attorney Jonathan W. Wolfe confirmed the relationship, stating that Overdeck "is now in a committed relationship with someone who he met long after this divorce process began."
The acquisition occurs amid protracted divorce proceedings initiated in March 2022 following nearly two decades of marriage without a prenuptial agreement. Overdeck has offered his estranged wife Laura $723 million in tax-free cash as a settlement, which he has testified constitutes a fair division. The transaction structure utilized Matthew Siano as the LLC's manager; Siano spent approximately 20 years overseeing legal and compliance operations at Two Sigma prior to facilitating the property acquisition.
The Neoclassical compound spans approximately 16,000 square feet on nearly one acre in Palm Beach's exclusive north end, featuring six bedrooms, 7.5 bathrooms, a great hall with 26-foot ceilings, a travertine pool with cabana, and 165 feet of waterfront frontage with deep-water dock accommodations. The property underwent approximately $20 million in renovations prior to occupancy. Overdeck shares the residence with Kimia Shadrokh, 42, a managing director at Peakstone and former commercial real estate executive with the Moinian Group; both registered to vote at the address in spring 2026. Overdeck's attorney Jonathan W. Wolfe confirmed the relationship, stating that Overdeck "is now in a committed relationship with someone who he met long after this divorce process began."
The acquisition occurs amid protracted divorce proceedings initiated in March 2022 following nearly two decades of marriage without a prenuptial agreement. Overdeck has offered his estranged wife Laura $723 million in tax-free cash as a settlement, which he has testified constitutes a fair division. The transaction structure utilized Matthew Siano as the LLC's manager; Siano spent approximately 20 years overseeing legal and compliance operations at Two Sigma prior to facilitating the property acquisition.
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