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  • Writer's pictureRealFacts Editorial Team

A New Approach to Tax-Advantaged Real Estate Investing


people shaking hands in a commercial real estate building

Louis J. Rogers, writing for GlobeSt, highlights a novel method for real estate investments — the DST to UPREIT transaction. This approach leverages the Delaware Statutory Trust (DST) structure, a robust tool for tax-advantaged real estate investments under Section 1031 of the Internal Revenue Code, which allows for tax deferral when real estate owners sell and reinvest in qualifying replacement property.


The primary appeal of DST replacement properties is the high-quality assets with turnkey management, particularly attractive to older real estate owners who wish to avoid the burdens of property management.


However, DST structures have several requirements to maintain tax deferral eligibility under Section 1031. For instance, DST properties must be sold upon mortgage maturity, and refinancing or recapitalization is not allowed, even if beneficial for investors. Consequently, DST properties typically need to be sold every ten years, irrespective of market conditions or investor satisfaction.


These constraints, along with the advantages of Real Estate Investment Trusts (REITs), have led to the growing popularity of transitioning DST interests to an UPREIT (Umbrella Partnership Real Estate Investment Trust). In this process, real estate owners exchange their property for operating partnership (OP) units in an UPREIT.


UPREIT transactions offer several tax benefits under favorable partnership rules. There is no taxable gain for property or DST owners and the operating partnership under Section 721, and the operating partnership can assume or repay the contributor's mortgage debt. Contributing owners retain tax benefits such as depreciation and operating expense deductions.


Moreover, UPREIT transactions allow investors to convert single-property DST investments into diversified, professionally managed portfolios, gaining additional REIT benefits.


REITs are characterized by high transparency, often with independent boards overseeing major decisions and sponsor compensation, and audited financial statements. They also provide liquidity options unavailable in the DST structure; OP unit holders can exchange units for REIT stock, which can then be sold.


For estate planning, the UPREIT structure offers flexibility, as OP units can be divided among heirs or partners. Each holder can then decide whether to retain, gift, or sell their units.


Direct exchange into an UPREIT is not allowed under Section 1031. Instead, a two-step process is required: first, exchanging into a DST, and later transitioning from DST to UPREIT. This process allows investors to upgrade their single-property DST investments to a diversified REIT portfolio while maintaining tax advantages.


The DST to UPREIT transaction represents an innovative phase in real estate investment, enabling smaller property owners to access benefits traditionally reserved for institutional investors. This evolution marks an exciting development in the real estate sector.

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