Realtor.com: Why wealthy second-home owners are buying on Maryland’s Eastern Shore

The Eastern Shore is on a peninsula that lies between the Chesapeake Bay and the Atlantic Ocean. The Bay and its tributaries have over 11,000 miles of shoreline, about half of which is in the state of Maryland while the other half is in Virginia. Maryland’s Eastern Shore consists of nine counties that are largely agricultural and generally have higher rates of poverty than the state overall.

While vacationers have long flocked to the Eastern Shore’s hunt country and waterfront communities, the region is best known for shellfish harvesting and chicken farming. (Perdue Farms is one of the area’s largest employers.)

As a growing number of wealthy second-home owners descend upon the region, the Eastern Shore is starting to gain a slightly more polished feel as new shops, art events and hospitality services sprout up to cater to the newcomers. But don’t expect the Eastern Shore to move too far from its agricultural roots as many towns are determined to maintain a rural and outdoorsy atmosphere where fishing, hunting, sailing and bird watching remain popular activities.

“If you are a boater, you will love it here. If you are an outdoors enthusiast, you will love it here. If you’re the type who wants to shop at Nordstrom, this isn’t the place for you,” said Stacy Kendall, a co-owner of Cross Street Realtors in Chestertown, Maryland, located in Kent county. She said most shops are owned by small merchants, not national retailers.  

The Eastern Shore was hit hard by the 2007-2009 recession and was slower than the rest of the nation to recover. As recently as 2019, home values in some Eastern Shore counties were still declining and a large percentage of homeowners were stuck with underwater mortgages. “For reasons unknown, we never rebounded like the rest of the waterfront markets. We stayed artificially depressed – until the pandemic,” said Coard Benson, a real estate agent at Bensondulingroup.com in Easton, Maryland, located in Talbot county. “Once the word got out that Talbot is a place card for the affluent second-home owner … they came running,” he said.

Rising demand, of course, has led to bidding wars and rapidly rising prices. Here’s a snapshot of three counties on the Eastern Shore that are seeing strong buying activity. The housing markets in all three counties are relatively small with limited inventory, meaning prices are unlikely to cool in the near future.

Talbot

Talbot county boasts of having 600 miles of shoreline on the Chesapeake Bay and has become an increasingly popular vacation-home market for residents of Washington, D.C., and Baltimore. Both cities are a 90-minute car drive away, but are worlds apart in atmosphere. Benson describes the affluent residents of Talbot as “straight out of an Orvis catalog,” referring to the retailer that caters to fishing, hunting and boating enthusiasts. Models in an Orvis catalog are often pictured with a Labrador Retriever at their side, a common sighting in Talbot.

In April, the number of homes sold in Talbot rose 33% when compared to the same month a year ago, and about half were purchased as second homes. Prices, meanwhile, jumped 46% to $695,600, according to data from the Maryland Association of Realtors Inc. Average prices in Talbot are now the highest in the state.

According to Benson, the average is skewed upward by escalating prices on a dwindling supply of waterfront vacation-home properties, which has led to bidding wars. “Pre-pandemic, we would have about 175 waterfront listings, but for the last eight months, we’ve had 35 to 40 listings,” he said, adding that prices for the least expensive waterfront listings have doubled in the past year from $500,000 to $1 million.

Dorchester

For centuries, fox hunting (or the fox chase as some prefer to call it)  has been associated with the Eastern Shore in general and Dorchester in particular. But the bigger attraction for true hunters are waterfowl and sika deer, which has drawn vacation-home buyers as far away as New York, New Jersey and Pennsylvania.

Known as the “Heart of Chesapeake Country,” Dorchester is less than four hours from Manhattan by car and has become especially popular with Wall Street bankers and real estate executives.

Dan Shoemaker, the owner of Exit on the Bay Realty in Cambridge, Maryland, said some of his clients from New York are moving money “out of the stock market and into (Dorchester) real estate.” Some, he said, are buying expensive waterfront properties for second homes while others are purchasing hunting properties including farms, marsh and swamps.

 Dorchester has one of the least expensive housing markets in the state. In April, sales rose 45% when compared to a year earlier while average prices rose 11% to $254,500. Land prices vary tremendously depending upon type and location. One real estate website recently listed a 233-acre hunting property in Cambridge with a list price of $460,000, about $1,974 an acre, and a 60-acre property was listed for $345,000, about $5,750 an acre.

Kent

Located on the upper section of the Eastern Shore, Kent is known for its historic waterfront towns, rolling farmland, numerous marinas and lots of outdoor activities that include fishing, boating, cycling and bird watching. Some sailing enthusiasts believe that scenic Kent County has some of the best sailing in the world.

One especially popular place is Rock Hall, a quaint fishing, sailing and boating town that has water on three sides and is sometimes compared to Key West, Florida, due to its arts and entertainment scene.

Although a farm recently sold in Kent for $4.5 million, average prices in April were $371,200, 30% higher than a year earlier.

This article is reprinted by permission from The Escape Home, a newsletter for second homeowners and those who want to be. Subscribe here. © 2021. All rights reserved.