How Long Do You Have to Hold a 1031 Exchange Property Before Selling? - Natalia A. Sishodia

From Sishodia PLLC – How Long Do You Have to Hold a 1031 Exchange Property Before Selling? explores the flexible yet complex IRS rules surrounding holding periods for 1031 exchange properties. This episode breaks down how investment intent, not a fixed timeline, determines eligibility under Section 1031 of the Internal Revenue Code. Manhattan 1031 exchange lawyer Natalia Sishodia of Sishodia PLLC provides in-depth guidance for New York City real estate investors navigating IRS expectations and the nuances of tax-deferred exchanges.

Listeners will learn how the IRS evaluates whether a property is truly held for investment purposes, with a focus on safe harbor rules under Revenue Procedure 2008-16, and the importance of documenting rental income, depreciation, and management activity. This episode highlights how intent outweighs duration and explains why even two years of ownership may not be enough if the original purpose of the purchase is unclear. For those managing commercial real estate in Tribeca, Hudson Yards, Midtown, or the Upper East Side, this discussion offers practical advice on IRS audit readiness and how to protect your tax deferral status.

We also explore key timing rules including the 45-day identification period, 180-day exchange window, and special considerations for related-party exchanges under Section 1031(f). Natalia Sishodia outlines the 5-year rule for converting an exchange property into a primary residence and the application of the Section 121 exclusion. Listeners will understand how improper planning could expose them to federal, New York State, and New York City capital gains taxes — and how to avoid that outcome.

Whether you’re a seasoned investor or new to 1031 exchanges, this episode will help you navigate complex IRS standards with confidence. Natalia Sishodia and her team at Sishodia PLLC combine deep knowledge of Manhattan real estate law with practical insight into compliance and strategy. Learn how to maximize your investment, protect your tax advantages, and avoid costly mistakes by staying informed and prepared.

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