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On the finish of Could 2022, Jennifer Leahy of Douglas Elliman put her itemizing of Nice Island in Darien, Connecticut, beneath contract for $103 million.
This was nearly 4 months after Leahy acquired the itemizing — and after two earlier itemizing brokers had did not promote the property after placing it available on the market in 2016 and once more in 2019.
Leahy informed Inman on the time that she secured a purchaser the place others had failed by drawing on her developer community to create a buzz, considering outdoors of the field along with her advertising and marketing, making the property extraordinarily accessible, strategically itemizing the property in late winter (to indicate off the land), networking inside Douglas Elliman and leaning on her neighborhood ties.
That was no small feat for a one-of-a-kind property of such stature.
The 60-acre property features a Gilded Age mansion as soon as owned by baking powder entrepreneur William Ziegler that had been in his descendants’ possession for over 100 years. A colonial farmhouse relationship to the 1800s and an equestrian constructing geared up with a granite steady and an arched tile ceiling designed by Rafael Guastavino, the engineer behind Grand Central Terminal, are additionally positioned on the property.
On prime of that, the island options over a mile of shoreline on the Lengthy Island Sound, and has a deep-water dock that may accommodate a 100-foot yacht.
Though getting into right into a contract on the property was an vital step for Leahy — who leads the No. 1 staff in Connecticut and the New York suburbs and has introduced in practically $1 billion in gross sales since becoming a member of Douglas Elliman in 2014 — the deal was nonetheless a great distance from being utterly finalized.
Almost one 12 months later, the city of Darien has lastly come into possession of the island, which it plans to make use of as a city gathering house and conservation space, for the considerably decrease sum of $85 million.
What transpired throughout that extended time period was one of many longest, most intense due diligence durations Leahy has ever been concerned with, she informed Inman solely.
The RTM vote
First, Leahy needed to exit and safe votes from members of the Consultant City Assembly (RTM), the city of Darien’s legislative physique, comprised of 100 members throughout the city’s six districts. The RTM needed to approve the sale by a majority vote.

Jennifer Leahy | Douglas Elliman
“We needed to get a majority vote, the city needed to vote on it, for [the deal] to undergo,” Leahy mentioned. “In order that was kind of a milestone.”
As a part of that course of, Leahy gave excursions of the 60-acre property to all 100 members of the RTM earlier than a vote on the deal may get underway. That meant bringing teams of about 15 folks by means of the property at a time and answering a dizzying checklist of inquiries on a possible sale that ranged from bee pollination alternatives to its impression in town’s bond score.
“I believe that’s the place utilizing each technique for promoting and understanding totally different personas turns out to be useful,” Leahy mentioned. “As a result of it’s not simply me and one different individual within the room, or me and three legal professionals — it was me plus 100 RTM members, plus each different board member that had voting rights, which anybody who’s going to barter with the federal government must understand, there’s a couple of ‘sure’ that’s required to get a deal executed.”
Leahy’s arduous work and a focus to every voting member paid off when the RTM voted in favor of buying Nice Island in a 68-13 vote on the finish of June 2022.
Due diligence and a delayed closing
In August 2022, in mutual settlement with the city of Darien and the sellers— the Steinkraus household— Nice Island’s deadline was pushed again from September 2022 to April 2023.
On the time, members of the RTM cited “vital points” the city needed to deal with earlier than finalizing its possession of the property and wanted extra time wherein to take action. Beforehand, the RTM mentioned the due diligence interval would come with environmental, operational and authorized points that wanted to be reviewed.
“[The town] used that point to completely analyze the property, together with attainable environmental considerations, points round environment friendly entry to the island, usability of the assorted buildings and in the end how the property shall be used,” Darien Board of Finance Chairman Jim Palen later informed the Connecticut Examiner because the deadline approached.
Throughout this time, Leahy mentioned she by no means actually doubted that the deal wouldn’t undergo. However there have been actually moments of excessive stress because the city’s diligence performed out.
“Like all offers, there have been instances the place I wasn’t certain what was going to occur,” Leahy mentioned. “I don’t suppose I ever thought it wouldn’t undergo — however that’s additionally my persona.”
“Staying calm and having persistence was actually vital, particularly whereas negotiating the objects from due diligence,” she added. “It was extraordinarily tenuous and required loads of persistence. However like all offers, it was actually till the ultimate second that we have been negotiating. We negotiated till 11:57 pm on the day my due diligence interval was over, so it was over 12 hours of negotiation on that final day.”
An $18M worth drop
Throughout the nine-month due diligence interval, the true property market additionally endured a big shift.
Throughout the second half of 2022, a palpable slowdown shook the housing market, together with in Darien, because the Fed continued to extend rates of interest so as to curb inflation. With charges persevering with to fluctuate into the second half of the 12 months and new financial worries arising in 2023 with main financial institution collapses — to not point out accessibility and questions of safety that had come up in due diligence — the city thought a brand new buy worth is perhaps so as.
“As a part of this course of and in response to the altering general financial surroundings, rate of interest actions and potential investments that could be made, the City reopened negotiations of the acquisition worth and in the end agreed with the sellers on a revised worth that was $18 million decrease than initially agreed,” Palen mentioned in an announcement made in March 2023 concerning the new buy worth.
Leahy’s recommendation for different brokers working with municipalities
“For brokers embarking on such a transaction, that is positively not run of the mill,” Leahy mentioned. “Components of it, it’s important to contemplate precisely the identical as you all the time would … The negotiation half is precisely the identical. It’s actually the approval half that’s completely totally different. So I can negotiate a take care of anybody, and I’m going to barter a terrific deal. However coping with 100 individuals who vote on whether or not [a deal] goes by means of is completely out of the norm.”
That’s the place the flexibility to attach with anybody — and promote to anybody — actually issues, she mentioned. On prime of that, having the persistence required to stay out an extended interval of due diligence is essential. Leahy additionally turned to Chris Voss’ recommendation in By no means Cut up the Distinction repeatedly as negotiations continued to play out. In his 2016 ebook, the previous FBI hostage negotiator reveals the typically counterintuitive methods that helped him saved lives throughout high-stakes negotiations over the course of his profession.
“I learn By no means Cut up the Distinction once more, like thrice, throughout this transaction,” she revealed.
Meditation and sustaining her focus have been additionally elemental practices to get Leahy to the end line.
“I believe I meditated thrice the final day of negotiation and simply stored considering, you preach ‘Take your MEDS,’ which is Meditation, Train, Food regimen, Sleep — that is your second, woman!” Leahy informed Inman. “I’m like, you higher keep level-headed and get this deal executed, irrespective of how. And it actually went sideways at factors throughout that final day. I simply stored it collectively and stored a degree head.”
Why Darien purchased Nice Island — and the way it impacted Leahy
The city of Darien, which is about 99 % developed, for years had been in search of a possibility to amass a big open swath of land for neighborhood use. Due to this fact, when Nice Island got here to market, it introduced the proper alternative for the city of about 21,500 folks.
In June 2022, the city proposed 4 potential zones to be used on the island: the commons, arts and tradition, conservation and training, and the coastal zone.
The commons space would function a spot for neighborhood actions, like an ice rink, pickleball courts, or a neighborhood pool, which may additionally function areas for youth camps or senior packages.
The humanities and tradition zone would have an arts heart or museum constructed on the property, which might be a website for a seasonal arts or music pageant.
The conservation and training space would characteristic woodland trails, hen watching, beekeeping, an space for Earth Day exhibitions and extra.
The fourth zone, the 1.5-mile shoreline, would function a spot for water sports activities, together with fishing and kayaking, in addition to a coastal training space to encourage neighborhood involvement in coastal stewardship.
Realizing that closing the deal can be supporting the neighborhood and the land due to its proposed makes use of additionally helped Leahy keep robust by means of negotiations, and gave her a way of success.
“You’re being a steward of the earth,” she informed Inman. “It’s uncommon that in our enterprise we get to protect acres and acres of land. On this explicit case, it’s 60 acres with a mile-and-a-half of shoreline. I’m serving to loads of animals — aquatic, land — there’s loads of animals that I’m serving to on this transaction on prime of the people and generations to return.”
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