Donating Real Estate - When It Makes Sense For Donors, Foundations

Jeffrey Haskell, May 30, 2019


Although there are important considerations that attend the contribution of real estate to a private foundation, if done carefully and with forethought, donors can mitigate compliance concerns while maximizing their charitable deductions.

A trend to watch is that of donors passing over large gifts to philanthropic organizations and an obvious example is real estate. Donating illiquid assets such as these present particular challenges. And very large gifts in general can be difficult to manage at times. (This is a subject that this publication has written about before.) The complexities of making such transfers work effectively can be considerable.

In this article, Jeffrey Haskell, who is chief legal officer for Foundation Source, walks through the terrain. The editors of this news service are pleased to share these thoughts with readers; they do not necessarily agree with all opinions of guest writers and invite readers to respond if they wish by emailing

It is often assumed that donations of real estate to private foundations aren’t ideal because charitable deductions for such donations are typically limited to whichever is less: the donor’s cost basis or the fair market value. And donations of real estate are often dismissed out of hand, regardless of whether the property has depreciated or appreciated in value.

If a property has significantly depreciated in value below its original purchase price, donating it directly to the foundation isn’t recommended because the donor would lose the ability to realize the capital loss. Instead, donors typically are advised to sell the property and then contribute the proceeds. Even a donation of highly appreciated real estate is not usually recommended, as the donor would only be able to claim a cost basis deduction. Yet, despite the impediments that would seem to auger against donating real estate to a private foundation, there are circumstances in which these donations do make sense, both for the foundation and the donor.

For the foundation, a donation of real estate can be used to generate a steady stream of income and liquid funds. If the property is used for charitable purposes, the foundation may be able to qualify for exemption from property taxes. For the donor, contributing real estate to a foundation might be fiscally savvy as well. When weighing the merits of this kind of gift, important factors to consider include the donor’s basis in the property, the property’s fair market value, and whether the donation might be a component of an estate plan.

Here are some of the possible scenarios where donating real estate to a foundation makes sense:

1.    The cost basis and the fair market value of a property are similar.
This is sometimes the case in parts of the country where the real estate market is still recovering. If the donor’s property is worth approximately what he or she invested in it, donating it could be an appealing option.

2.    The donation of the real estate is part of an estate plan.
If this is the case, the basis in the property is stepped up, typically to the date of death, thereby ensuring that the basis is actually equal to the fair market value of the real estate, for at least that point in time. (1)

3. The value of the real estate has appreciated significantly over what the donor originally paid.
If a foundation has accumulated excess distribution carryovers from its preceding five taxable years, the foundation can make a special “conduit election,” which would entitle the donor to receive a fair market deduction (just as if it were donated to a public charity) instead of the more limited cost basis deduction.(2). This would obviate the need to sell the property and donate the proceeds. It also provides higher adjusted gross income (AGI) percentage caps (30 per cent for non-cash donations to a public charity vs 20 per cent for non-cash donations to a private foundation).

Important cautions for donors
Mortgaged property: Keep in mind that the donor should avoid contributing real estate encumbered by a mortgage. Doing so could result in a violation known as self-dealing because through the contribution the donor obtains debt relief. Even when the amount of indebtedness is small relative to the property’s value, it could still trigger penalties for which the donor (not the foundation) would be personally liable. The concern arises where the property is encumbered by a mortgage and the foundation either (a) assumes the mortgage, or (b) takes the property subject to a mortgage that was placed on the property by a “disqualified person” (3) within ten years of the donation of the property to the foundation.

If either of these is the case, the donation will be deemed by the IRS to be a bargain sale of the property to the foundation (because it is deemed sold for the amount of debt relief) and the penalty for which the disqualified person will be personally liable will be 10 per cent of the fair market value of the property (i.e. not 10 per cent of the debt relief).

Pre-arranged sale: Donors also should take pains to avoid a “pre-arranged sale,” which would occur if they were to negotiate the terms of a sale of property, donate the property to their foundation, and subsequently compel the foundation to consummate the sale. Although the application of this “pre-arranged sale” doctrine depends upon the unique facts and circumstances of the situation, the doctrine generally is applied when the foundation is under a binding commitment to consummate the pre-negotiated sale. (From the perspective of the IRS, the existence of a “binding commitment” may indicate that the foundation is being used to effectuate a property transfer to a handpicked buyer while enabling the donor to avoid the tax consequences that would ordinarily result from the donor’s sale of the property.)

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