How I Helped My Client Buy Dobbins Island: A $2M Private Oasis on the Chesapeake Bay

A Buyer's Agent Case Study

Some transactions close in weeks. Others take months of careful positioning and persistent follow-up. And then there's the rare one, where the right buyer finds the right property at exactly the right moment, and everything clicks into place almost overnight. This is one of those stories.

Part One: The Referral

It started, as many of my best client relationships do, with a phone call from a fellow agent.

Morgan Boyer had been working with a buyer, a client who had spent a significant portion of his life in major cities and was done with the noise. He wanted land and privacy, a place where he could host family and friends, pursue outdoor recreation, and genuinely disconnect. His criteria were clear: no more than a two-hour drive from Washington, D.C., a large, well-appointed home, and complete remoteness from neighbors or the public. Not "quiet neighborhood" remote, but truly, legitimately remote.

Morgan had first introduced him to a stunning property in West Virginia, featuring 300 acres of mountain terrain, a spectacular listing by any measure. But it wasn't quite right. Then he had his eye on a property at the most southern tip of Maryland, and that's when Morgan reached out for a referral opportunity. I said yes without hesitation.

Part Two: The Search Begins — And Then Goes Quiet

A week later, in the middle of September, I took my client to see the southern Maryland property. It was a phenomenal piece of real estate: unique, well-situated, genuinely compelling. But the house itself wasn't where he needed it to be and getting it to his vision would have required a substantial additional investment that didn't make sense at that stage.

So I honed in on his preferences, remapped the search, and established a dedicated property alert system so I could surface truly unusual opportunities for him. Over the following weeks and months, I periodically sent him unique listings that matched his preferences: private, large, within the drive threshold, with land and recreational potential.

But I didn't hear anything back. September passed. October. November. December. All the way through New Year's. I kept sending and following up, keeping the search alive on my end, because I know that's part of the job, knowing that a buyer who goes quiet isn't necessarily a buyer who's moved on. Sometimes they're just busy or life intervenes. Sometimes though, they're about to send you the email that changes everything.

Part Three: The 9 PM Email

On Saturday, January 3rd, at approximately 9 o'clock at night, my phone lit up with an email from my client. It was the kind of message every buyer's agent waits months to receive:

"Sorry I've been very busy. Thank you for your diligence in continuing to send me listings. I found this interesting island I want to check out — can we go see it next week?"

The property he had found on his own was Dobbins Island. Anyone who has spent time on the Magothy River or the Upper Chesapeake knows about Dobbins Island. And what a great fit!

Part Four: The Property — Why Dobbins Island Was Different

Dobbins Island sits in the Magothy River, a six-mile-long tidal waterway that flows into the Chesapeake Bay between Baltimore and Annapolis. The island itself is 7.2 acres with more than 4,000 feet of shoreline and sweeping 360-degree views that stretch all the way to the Chesapeake Bay Bridge. It is accessible exclusively by boat.

This was not a waterfront home with neighbors a few hundred feet away. This was an island. Total separation from the outside world, by water. For my client, who had spent so much of his life surrounded by so many people, this was the property he had been looking for.

The listing agent, Brad Kappel of TTR Sotheby's International Realty, described the ideal buyer perfectly: someone based in the Baltimore or D.C. area who was looking for a getaway, possibly an older owner, given the house and dock design. That description fit my client exactly.

The Home

At the northern end of the island sits a custom-built residence completed in 2019. Remarkably, the house was never lived in, and the stickers were still on the appliances! The previous owner, David Clickner, had purchased the island roughly 20 years ago with a long-term vision of using it as a vacation retreat. After construction was complete, another island became available (St. Helena Island on the Severn River) and Clickner ultimately redirected his plans there, leaving Dobbins vacant.

The result was a turnkey opportunity in a one-of-a-kind setting. The home includes approximately 3,373 square feet of living space, three bedrooms, three bathrooms, soaring 10-foot ceilings, Wolf and Sub-Zero appliances, and floor-to-ceiling windows throughout that frame the water from every angle. A private elevator connects all levels, including a rooftop deck where you can see well past the Magothy all the way to the Bay Bridge.

The Land

Beyond the house, the island itself is a destination. Wooded trails wind through the interior of the property, leading down to a crescent-shaped sandy beach. It's ideal for swimming, kayaking, and watercraft recreation. The island also features dramatic steep cliffs above the open river. A deep-water dock accommodates larger vessels. And the resident wildlife, bald eagles, ospreys, great blue herons, provides a natural backdrop that no amount of landscaping can replicate.

Part Five: The Tour, the Offer, and the Deal

Less than a week after my client sent his email, we were out on the water. We toured the island with the listing agent, going through the home floor by floor, walking the trails, taking in the shoreline from multiple angles. My client didn't need much convincing. This was the property. It hit every criterion he had articulated months before: within two hours of D.C., a substantial custom home, and a level of seclusion that most buyers never even contemplate as a possibility. We submitted an offer the next day and we were soon under contract, nine days from his email, and two days from the tour.

The property closed in March 2026 at $2,000,000, well below the original $2.7 million list price from when Dobbins first came to market in March 2025.

Part Six: What This Transaction Taught Me

1. Keep sending. Even when it feels like no one is listening.

Four months of unanswered messages is not a dead lead; rather, it's a client who isn't ready yet. Staying consistent, staying professional, and continuing to add value is the only way to be the agent who gets the 9 PM email on a Saturday night.

2. Understand your client's real criteria, not just their checklist.

My client's stated criteria were practical: drive time, square footage, privacy. But the underlying motivation was a desire to reclaim stillness after decades of city life. Once I understood why he wanted what he wanted, I could recognize immediately that an island was a logical choice.

3. Referral relationships are the backbone of this business.

This deal started because Morgan Boyer trusted me enough to hand off a client she had invested real time in. That trust doesn't happen without a track record and a genuine relationship. I'm grateful for the referral and proud that we were able to deliver for her client.

4. The right property exists — sometimes you just have to wait for the market to surface it.

Dobbins Island had been privately owned and undeveloped for generations. It came to market for the first time in modern memory in March 2025. My client found it on his own, months into a search I had been running in parallel. The best properties don't always come through a search alert. Sometimes the buyer finds it themselves and your job is to be the agent they call when they do.

About Dobbins Island: A Bit of History

The history of Dobbins Island runs deep. Documented as far back as Captain John Smith's 1608 exploration of the Chesapeake region, the island was long known to boaters as "Dutchship Island," a nod to the legend of a Dutch trading vessel that reportedly wrecked in the river nearby in the 1700s. Locals reportedly found Dutch coins along the riverbed for generations afterward.

The island gets its current name from George Dobbins, a prominent judge who purchased it in the 1850s. For much of the 19th century, the island hosted debutante balls and summer parties, with guests arriving by horse and buggy across the sandbar at low tide. It remained unoccupied for much of the 20th century, functioning as an informal gathering place for boaters.

Chesapeake Bay Magazine named Dobbins Island one of the finest anchorage sites on the entire Bay in its 2006 Best of the Bay survey. A subsequent legal dispute between the Clickners and the Magothy River Association over public beach access became one of the more significant waterfront property law cases in Maryland in recent years, ultimately establishing that boaters were welcome below the mean high water line.

As listing agent Brad Kappel noted at the time of the listing, the property "boasts several different settings," with wooded trails where sand continues to fill in, and steep cliffs offering dramatic views across the open river. For a buyer who had spent his adult life in dense urban environments and was finally ready for something different, Dobbins Island was the right fit.

My client isn't just buying a home. He's becoming the steward of one of the Magothy River's most storied landmarks. It was my privilege to serve as a Buyer's agent in this transaction, and to become a small part of that history.

Whether you're ready to build tomorrow or you're planning for a few years down the road, I'm here to help you figure it out.

Contact Reed Jimenez

Reed Jimenez, REALTOR® LPT Realty, LLC

📱 (301) 991-8041 📧 reed@realtorreed.com 🌐 realtorreed.com

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