A year after the town of Darien, Connecticut, entered into contract to buy Great Island, it finally closed for $18 million under the asking price. Here’s how Douglas Elliman’s Jennifer Leahy got it done.

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At the end of May 2022, Jennifer Leahy of Douglas Elliman put her listing of Great Island in Darien, Connecticut, under contract for $103 million.

This was just about four months after Leahy acquired the listing — and after two previous listing agents had failed to sell the property after putting it on the market in 2016 and again in 2019.

Leahy told Inman at the time that she secured a buyer where others had failed by drawing on her developer network to create a buzz, thinking outside of the box with her marketing, making the property extremely accessible, strategically listing the property in late winter (to show off the land), networking within Douglas Elliman and leaning on her community ties.

That was no small feat for a one-of-a-kind estate of such stature.

The 60-acre property includes a Gilded Age mansion once owned by baking powder entrepreneur William Ziegler that had been in his descendants’ possession for over 100 years. A colonial farmhouse dating to the 1800s and an equestrian building equipped with a granite stable and an arched tile ceiling designed by Rafael Guastavino, the engineer behind Grand Central Terminal, are also located on the property.

On top of that, the island features over a mile of shoreline on the Long Island Sound, and has a deep-water dock that can accommodate a 100-foot yacht.

Although entering into a contract on the property was an important step for Leahy — who leads the No. 1 team in Connecticut and the New York suburbs and has brought in nearly $1 billion in sales since joining Douglas Elliman in 2014 — the deal was still a long way from being completely finalized.

Nearly one year later, the town of Darien has finally come into possession of the island, which it plans to use as a town gathering space and conservation area, for the significantly lower sum of $85 million.

What transpired during that prolonged period of time was one of the longest, most intense due diligence periods Leahy has ever been involved with, she told Inman exclusively.

The RTM vote

First, Leahy had to go out and secure votes from members of the Representative Town Meeting (RTM), the town of Darien’s legislative body, comprised of 100 members across the town’s six districts. The RTM had to approve the sale by a majority vote.

Jennifer Leahy | Douglas Elliman

“We had to get a majority vote, the town had to vote on it, for [the deal] to go through,” Leahy said. “So that was sort of a milestone.”

As part of that process, Leahy gave tours of the 60-acre property to all 100 members of the RTM before a vote on the deal could get underway. That meant bringing groups of about 15 people through the property at a time and answering a dizzying list of inquiries on a potential sale that ranged from bee pollination opportunities to its impact on the town’s bond rating.

“I think that’s where using every strategy for selling and understanding different personas comes in handy,” Leahy said. “Because it’s not just me and one other person in the room, or me and three lawyers — it was me plus 100 RTM members, plus every other board member that had voting rights, which anyone who’s going to negotiate with the government will have to realize, there’s more than one ‘yes’ that’s required to get a deal done.”

Leahy’s hard work and attention to each voting member paid off when the RTM voted in favor of purchasing Great Island in a 68-13 vote at the end of June 2022.

Due diligence and a delayed closing

In August 2022, in mutual agreement with the town of Darien and the sellers— the Steinkraus family— Great Island’s closing date was pushed back from September 2022 to April 2023.

At the time, members of the RTM cited “important issues” the town had to address before finalizing its ownership of the property and needed more time in which to do so. Previously, the RTM said the due diligence period would include environmental, operational and legal issues that needed to be reviewed.

“[The town] used that time to fully analyze the property, including possible environmental concerns, issues around efficient access to the island, usability of the various structures and ultimately how the property will be used,” Darien Board of Finance Chairman Jim Palen later told the Connecticut Examiner as the closing date approached.

During this time, Leahy said she never really doubted that the deal wouldn’t go through. But there were certainly moments of high stress as the town’s diligence played out.

“Like all deals, there were times where I wasn’t sure what was going to happen,” Leahy said. “I don’t think I ever thought it wouldn’t go through — but that’s also my personality.”

“Staying calm and having patience was really important, especially while negotiating the items from due diligence,” she added. “It was extremely tenuous and required a lot of patience. But like all deals, it was really until the final moment that we were negotiating. We negotiated until 11:57 pm on the day my due diligence period was over, so it was over 12 hours of negotiation on that last day.”

An $18M price drop

During the nine-month due diligence period, the real estate market also endured a significant shift.

During the second half of 2022, a palpable slowdown shook the housing market, including in Darien, as the Fed continued to increase interest rates in order to curb inflation. With rates continuing to fluctuate into the second half of the year and new economic worries arising in 2023 with major bank collapses — not to mention accessibility and safety issues that had come up in due diligence — the town thought a new purchase price might be in order.

“As part of this process and in response to the changing overall economic environment, interest rate movements and potential investments that may be made, the Town reopened negotiations of the purchase price and ultimately agreed with the sellers on a revised price that was $18 million lower than originally agreed,” Palen said in an announcement made in March 2023 about the new purchase price.

Leahy’s advice for other agents working with municipalities

“For agents embarking on this type of transaction, this is definitely not run of the mill,” Leahy said. “Parts of it, you have to consider exactly the same as you always would … The negotiation part is exactly the same. It’s really the approval part that is totally different. So I can negotiate a deal with anyone, and I’m going to negotiate a great deal. But dealing with 100 people who vote on whether [a deal] goes through is totally out of the norm.”

That’s where the ability to connect with anyone — and sell to anyone — really matters, she said. On top of that, having the patience required to stick out a long period of due diligence is crucial. Leahy also turned to Chris Voss’ advice in Never Split the Difference again and again as negotiations continued to play out. In his 2016 book, the former FBI hostage negotiator reveals the sometimes counterintuitive strategies that helped him saved lives during high-stakes negotiations over the course of his career.

“I read Never Split the Difference again, like three times, during this transaction,” she revealed.

Meditation and maintaining her focus were also elemental practices to get Leahy to the finish line.

“I think I meditated three times the last day of negotiation and just kept thinking, you preach ‘Take your MEDS,’ which is Meditation, Exercise, Diet, Sleep — this is your moment, girl!” Leahy told Inman. “I’m like, you better stay level-headed and get this deal done, no matter how. And it really went sideways at points during that last day. I just kept it together and kept a level head.”

Why Darien bought Great Island — and how it impacted Leahy

The town of Darien, which is about 99 percent developed, for years had been looking for an opportunity to acquire a large open swath of land for community use. Therefore, when Great Island came to market, it presented the perfect opportunity for the town of about 21,500 people.

In June 2022, the town proposed four potential zones for use on the island: the commons, arts and culture, conservation and education, and the coastal zone.

The commons area would serve as a place for community activities, like an ice rink, pickleball courts, or a community pool, which could also serve as areas for youth camps or senior programs.

The arts and culture zone would have an arts center or museum built on the property, which could be a site for a seasonal arts or music festival.

The conservation and education area would feature woodland trails, bird watching, beekeeping, an area for Earth Day exhibitions and more.

The fourth zone, the 1.5-mile shoreline, would serve as a place for water sports, including fishing and kayaking, as well as a coastal education area to encourage community involvement in coastal stewardship.

Knowing that closing the deal would be supporting the community and the land because of its proposed uses also helped Leahy stay strong through negotiations, and gave her a sense of fulfillment.

“You’re being a steward of the earth,” she told Inman. “It’s rare that in our business we get to preserve acres and acres of land. In this particular case, it’s 60 acres with a mile-and-a-half of coastline. I’m helping a lot of animals — aquatic, land — there’s a lot of animals that I’m helping in this transaction on top of the humans and generations to come.”

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Email Lillian Dickerson

Douglas Elliman
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