GREAT estates
How donating a property to charity can ensure a lasting legacy for future generations
Leaving a lasting legacy can take many forms, especially when significant real estate holdings are involved. House museums are one way to allow the legacy and work of a notable person to be preserved and shared with the public even after the end of their life. In the case of properties of significant market value, designating a charitable use for them and empowering the recipient with an endowment to maintain them can be a particularly beneficial route for all parties. “Real estate donations have become a prominent way to make a meaningful impact,” observes Claire Groome, global real estate advisor, Sotheby’s International Realty - East Side Manhattan Brokerage.
Proceeds from the sale of this Ponte Vedra Beach estate in Florida, will go to fund brain cancer research.
ONE Sotheby’s International Realty
Estate tax deduction for charitable gifts (in US$).
Source: BMO Family Office.

$1 in donations = $1 in estate tax deductions.
“ THERE ARE DIFFERENT TAX ADVANTAGES THAT COULD BE AT PLAY, DEPENDING ON THE TYPE AND TIMING OF THE TRANSACTION
”
Meeta Yadava, managing director, BMO Family Office
The decision to donate a property can also make financial sense. “There are different tax advantages that could be at play, depending on the type and timing of the transaction,” explains Meeta Yadava, estate planner, managing director of the wealth advisory firm BMO Family Office and leader of the BMO for Women program. “Broadly speaking, during your life you typically get a better income tax benefit by donating a property and having the charity sell the property than you would if you sold it yourself and donated the proceeds to charity. After you pass, your estate will get a dollar-for-dollar tax deduction for charitable gifts.”
IRS policies incentivize such choices. Donations of real estate to charitable and not-for-profit entities that have been held for over one year can lower or eliminate capital gains tax obligations, or the fair market value can be claimed as an income tax deduction. Passing property to a donor-advised fund (DAF) is another appealing—and flexible—option. In this case, a 501(c)(3) sponsoring organization maintains and manages investments that grow tax-free and advisors determine subsequent donations. Meanwhile, contributed donations and assets are immediately eligible for tax benefits.
When selling a significant estate, family dynamics are often complicated and this act of generosity presents an alternative option. Yadava endorses “the ability to turn something the kids might fight over—like a house—into something that they can work together on in the future.” Further, if a family opts to transfer a property to a DAF, “the kids can be named as advisors on that fund and make grant decisions as a family,” she adds. “It’s a great way to make philanthropy a unifying force.”
Sometimes the long-term goal is to make a property programmatically educational and engage with the public. The list of house museums flourishing today is extensive, both in the U.S. and abroad. In September 2021, for instance, David Huberman, global real estate advisor, Gustave White Sotheby’s International Realty, brokered the US$27 million sale of the Gilded Age landmark Miramar mansion in Newport, Rhode Island. Its buyers, Blackstone CEO Steve Schwarzman and his wife Christine, plan to establish an endowment-funded museum that will eventually be open to the public.
Groome notes that “sellers increasingly seek ways to align their assets with their values and passions.” Yet following an altruistic path doesn’t always mean maximizing tax incentives. The US$25 million penthouse at 170 Fifth Avenue is among the listings Groome and Lawrence Treglia, senior global real estate advisor, Sotheby’s International Realty - East Side Manhattan Brokerage, represent. This standout residence is notable for originally serving as the Beaux-Arts-style headquarters of piano manufacturer Sohmer & Co. when it was built in 1898. Now, the sumptuous four-bedroom loft duplex—which blends Old World charm with contemporary upgrades, including a private rooftop terrace and access to the building’s gold cupola—will make a powerful impression in an unexpected way.
The entrepreneur and philanthropist Greg Carr plans to dedicate funds from the sale to his private foundation, which helps restore the ecological habitats and wildlife at Gorongosa National Park in Mozambique, and develop economic and educational opportunities for area residents.
“Donating makes an attractive alternative for those who value social impact and want their assets to make a difference,” Groome says. “Sellers find satisfaction in supporting causes such as environmental conservation or affordable housing or issues they are passionate about.” Such is the case with Rick Sontag, the founder of the Brain Tumor Network and The Sontag Foundation, who has donated his Ponte Vedra Beach estate to The Sontag Foundation. The property is now listed with ONE Sotheby’s International Realty for a record-seeking US$25.5 million, with proceeds from the sale going to fund brain cancer research.
Given to charity by Americans in 2023 (in US$).
Source: Giving USA and American Endowment Foundation.
Attachment to an alma mater can run deep and a donation to the school that helps shape future generations is a common first step for many philanthropists. The Adler House in Williamstown, Massachusetts, tells the story of a family who formed strong bonds to nearby Williams College, which opened in 1793. Nearly two decades after commissioning architect Chad Floyd of Centerbrook Architects & Planners to rebuild it, in 2022 Susan Adler donated the house to the college. Her gift was in memory of her husband, Herbert, who sat on two college committees, and a thank you to the school for educating their daughter, who studied art history there.
Proceeds from the sale of the house will help to fund the construction of the new Williams College Museum of Art, designed by Brooklyn-based architects SO-IL and slated to open in 2027.
“The Adlers invested quite a bit to build this beautiful contemporary home on the hill,” says Jeff Loholdt, global real estate advisor, William Pitt Sotheby’s International Realty, who services the Great Barrington, Massachusetts, area. Its siting and unique style make the house a rare find in the Berkshires market. “It’s a substantial home,” Loholdt says. The fact that the 34-acre estate is surrounded by 8,000 acres of protected wilderness—with views of Mount Greylock, the highest point in Massachusetts—is a bonus.
Despite its rural settings, the property is within walking distance of downtown Williamstown and Williams College. The split-level house has shared living spaces on the main floor, with three bedroom suites on the upper level and four bedrooms and six baths in total.
Ample outdoor areas and a pool take further advantage of the vistas. “It’s ideal for those who want to entertain. It’s pretty versatile,” says Loholdt. The bespoke nature of the interior design and architecture means it features “notable antiques built into the home” that will transfer to the next owner.
While managing the US$2.5 million listing, Loholdt primarily works with the office of the college provost, which in turn liaises with the trustees. This type of arrangement is different from negotiating with individual buyers and sellers, since “negotiations or adjustments to the terms of contracts can take more time due to the layers of approvals,” he says.
The relatively reduced “emotional attachment,” however, can smooth out some steps along the way, and the established networks associated with Williams College offer a degree of built-in marketing support. Overall, it’s a win-win. “The current plan is the best scenario not only for the college, but for the town.”
“ SELLERS FIND SATISFACTION IN SUPPORTING CAUSES LIKE ENVIRONMENTAL CONSERVATION, AFFORDABLE HOUSING OR ISSUES THEY ARE PASSIONATE ABOUT
”
Claire Groome, global real estate advisor, Sotheby’s International Realty - East Side Manhattan Brokerage
The Adler House, designed by renowned architect Chad Floyd, was donated to Williams College in 2022.
William Pitt Sotheby’s International Realty
Indeed, often a gift of property benefits more than just one beneficiary. When Jessica Canning, global real estate advisor, Sotheby’s International Realty - Carmel Brokerage met representatives of the Community Foundation for Monterey County (CFMC), the agent-client relationship that emerged was a break from the norm. The nonprofit organization had received an astonishingly generous gift from the estate of Charles de Guigné, a fourth-generation Californian who passed away in 2017 at the age of 78.
When Canning was approached, the executors of de Guigné’s estate—a member of a prosperous Bay Area family descended from French nobility—had just transferred the title of the 17 Mile Drive property he had inherited from his parents, Christian de Guigné III and his wife, Eleanor, to CFMC.
The resulting proceeds of the US$18 million sale were used to establish an endowed fund that is managed by the charity. It is called the Charles Auguste de Guigné Charitable Foundation and supports the Society for the Prevention of Cruelty to Animals for Monterey County and the Montage Health Foundation, both causes that were important to the philanthropist.
“CFMC had owned the property for almost a year and was preparing the due diligence disclosures and property information. We were honored to represent them,” Canning says about the sale of the house, which closed in November 2019.
The de Guigné home represented an especially prized opportunity. The 17 Mile Drive double lot stretched across nearly 10 acres of private water frontage on Pebble Beach, California. It had been Charles de Guigné’s primary residence and represented “a marquee sale,” says Canning. Built circa 1930, the 9,000-square-foot Spanish Colonial Revival home reflected a romantic aesthetic that was once popular in the Golden State.
Canning says that because the average-sized lot in Pebble Beach is about 1.5 acres, finding this amount of available land at Sunset Point was “remarkable,” especially with the bonuses of positioning and privacy. “It was a positive experience for us because the seller, in this case the foundation, was organized as far as the listing was concerned,” Canning says. “They were very pragmatic.”
A similarly generous donation was made in nearby Carmel Valley, California, where a classic California Ranch home belied the intriguing, unconventional past of its former owner. “Robert Darwin was a Renaissance man: his interests were broad and he did so much in his life,” says Nora Seaborn, global real estate advisor, Sotheby’s International Realty - Carmel Valley Brokerage.
Darwin, a native of New Jersey who found success in real estate, horse breeding and establishing the TransJet logistics company, surprised and delighted his local community in 2020 by announcing the biggest gift ever made to California State University Monterey Bay (CSUMB). He died in 2023 at the age of 96, leaving a portfolio of assets that included his art collection and residence in the Miramonte area of Carmel Valley, located directly across from Garland Ranch Regional Park.
In early summer 2024, global real estate advisor Lisa McLean, of Sotheby’s International Realty - Carmel Valley Brokerage, brought the 23-acre Darwin Estate to market as part of the larger effort to advance the entrepreneur, author and actor’s large contribution to CSUMB. The US$7.6 million listing of the home, which has four bedrooms and four bathrooms, along with a pool, spa, tennis court and separate two-bedroom guesthouse and studio, was the first time that the property had been on the market since Darwin bought it in 1967.
Darwin’s unorthodox career trajectory included serving in the U.S. Navy during World War II and then pursuing stardom as an actor and screenwriter in Los Angeles during the 1950s. His later wish was to fund full-tuition scholarships at CSUMB for incoming students from Monterey and Santa Cruz counties with a grade point average of 3.2 and higher and to help launch a campaign for a new performing arts center on campus.
While de Guigné and Darwin did not have any children as their immediate heirs, Yadava points to changes in California property tax law that will influence future decisions about inheritances. “For many generations, wealthy families have been able to pass down luxury residences without increasing their property tax base,” she says. Now properties valued at more than US$1 million in addition to non-primary residences are subject to tax reassessment, thereby discouraging transfer of such homes within families and making other options, like donating to a charity, more attractive.
“Individuals inheriting a residence that has been in their family for multiple generations could be facing a very large property tax increase and may not be interested in keeping the property as a result,” Yadava says. “I would also say that, many times, children inheriting luxury homes were not using them as their primary residence, so that restriction is a big hurdle to overcome.”
For other philanthropic-minded individuals and families who are considering donating a property to charity, Yadava suggests they start these discussions early so they can amplify their impact while reducing capital gains and/or income tax burdens. “As with all planning, I suggest connecting with your financial, tax, legal and accounting professionals to determine how best to accomplish your goal,” she says. “And, of course, contact the charity you are thinking of working with well before the date of the gift.”
The importance of a mission to do good in the world also needs to be matched by internal organizational wherewithal. Donors should be confident that the recipient organization not only aligns with their philanthropic goals but is also compatible with the size of their donation before moving forward with a partnership. “Each charity has its own requirements, and you want to make sure they are able to handle such a gift,” Yadava says, adding that, in general, “the bigger the organization, the more equipped they are.”
The Charles de Guigné estate, originally built in 1930 and since expanded, sits on a rare, nearly 10-acre parcel in famed Pebble Beach, California.
Sotheby’s International Realty - Carmel Brokerage
Header: The gold cupola is the standout feature of the penthouse atop the Beaux-Arts building at 170 Fifth Avenue. The home’s current entrepreneur owner plans to donate the sale’s proceeds to philanthropic causes.
Sotheby’s International Realty - East Side Manhattan Brokerage
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