How Stonington Vineyards Found its Right-Fit Buyer

In the spring of 2025, Stonington Vineyards— a longstanding Connecticut winery — completed its transition to a new chapter under the owner ship of a private family buyer. But the seeds for this outcome were planted years earlier, when Rachel Edwards, then the winery’s head of operations, brought in Osage Advisors well before a sale was even on the table. As the trusted M&A advisor on the deal, Osage helped shepherd the vineyard through a uniquely complex and emotional transaction process. The result: a thoughtfully executed deal that balanced legacy, community, and timing.

Where it all Began
Rachel Edwards had a clear sense of Stonington Vineyards’ story well before she was responsible for writing its next chapter. After moving from Napa Valley to Connecticut and founding a digital marketing firm called Dreamscapes, she began working with the vineyard’s original owners — her neighbors — on branding and outreach.
Over time, as health issues impacted the owners, Rachel was asked by the executor of the trust to step in as Head of Operations to manage the business and prepare for an eventual sale. Then the pandemic hit.
“I’d listened to the Osage podcast and knew how important it was to start the process long before we were ready to sell. I reached out two years before we went to market,” Rachel recalls.
That early preparation paid off. By the time the sale process began, all financials were in order, materials were complete, and expectations were clear.
The team approached the sale with a high level of transparency. The executor of the trust that owned the vineyard was involved from the outset and remained an active participant throughout the process.
The management team and employees were informed early on that the winery would be initiating a formal search for a new owner, with the understanding that it could take some time.

“We kept them updated at key milestones and brought them further into the process once we had received a LOI from the buyer. The entire team was genuinely invested in finding the right new owners, which contributed to a smooth and collaborative transition,” Rachel said.

Finding the Right Buyer
Rachel knew early on that this wouldn’t be a typical deal. A winery isn’t just a business — it’s a lifestyle. And that changes how a transaction needs to be approached.

“Finding the right buyer for a winery is like finding a needle in a haystack. You need the right person at the right time, who loves that place. And that’s really hard to tell,” she said. And while the team cast a wide net — including outreach to wineries in California, Washington, and even Italy — it became clear that traditional buyers weren’t the answer.

“Everyone’s always talking about ‘timing the market’ and that’s great if everything aligns. But oftentimes you’re in a position where you want or need to sell when the market isn’t exactly at its best.” Ultimately, the sale needed to strike a balance between value and
values.

“Oftentimes you’re in a position where you want or need to sell when the market isn’t exactly its best.”

With guidance from Keith Dee and his team at Osage, Rachel realized they needed to find a balance between getting the best price and finding the right buyers. “We wanted people who were going to love it,” she said. “Who wanted to continue the legacy. People that would allow the staff, if possible, to stay on. We cared very much about the Connecticut wine community, and we cared about the town and the property.”

Osage adjusted the process and brought a fresh round of buyers into the conversation. And when the right buyer finally did appear, it was because the timing and the positioning aligned. “I know the market is important,” Rachel said. “But really it’s about aligning when you’re selling and when that right buyer is ready.”

From there, Osage fielded multiple offers that were presented to Rachel and the Estate attorney — but not all felt right.

“It was hard sometimes to turn a deal down. Oftentimes it just wouldn’t work out, and we were relieved it didn’t… How hard is it to say no to a deal knowing that you ultimately want to sell? That was one of the things I was struggling with.”

“How hard is it to say no knowing that you ultimately want to sell?”

When the right buyer finally did emerge, the initial sense of relief quickly gave way to the reality of the diligence process. As Rachel remembers clearly: “Once you get into due diligence, it’s a whole different ball game.”

From LOI to Close: A New Set of Challenges
Rachel credits her internal team for handling the diligence phase with discipline and clarity. “Our management team and accountant played a central role in preparing for and navigating the due diligence process. When additional information was required from employees, they were given clear guidance and ample time to gather the necessary materials. We ensured that everyone involved understood the purpose of each request and how they could best contribute, which helped streamline the process and maintain alignment across the team.”

Throughout, Osage Advisors remained closely involved.

“Keith Dee and the team at Osage Advisors maintained consistent communication with me and all key stakeholders throughout the due diligence process,” Rachel said. From the outset, they provided a clear roadmap of what to expect and guided the team through each stage with clarity and confidence. They were instrumental in navigating challenges as they arose — particularly when differing perspectives emerged between buyer and seller — and Osage ensured that communication remained open and the process stayed on track.

“I hadn’t fully anticipated how critical their Keith Dee and Osage’s role as a neutral mediator would be, but it proved to be invaluable,” said Rachel. And in the moments where negotiations became nuanced, their measured approach made the difference.

“While there were several key moments throughout the process, what stood out most was Osage’s consistent ability to serve as a neutral sturdy voice during negotiations. Their judgment in knowing when to step in, who to involve, and how to facilitate clear communication between all parties was instrumental. This steady, thoughtful approach is what ultimately kept everyone aligned and helped drive the deal to a successful close.”

Osage Advisors isn’t just here to run the deal. We’re here to help you stay grounded through it. If you’re facing a lengthy diligence process, stay transparent, stay communicative, and remember: delays are common, but the right support makes all the difference.

Certain Members of Osage Advisors are Registered Representatives of and conduct securities transactions through StillPoint Capital, LLC, Tampa, FL. Osage and StillPoint are not affiliated.

Osage Advisors provides a lot of guidance in the M&A market here on our blog and on our YouTube channel and Podcast.