Notes from My Chesapeake Home

Sharing local stories, market trends, and real estate advice for buyers and sellers across Maryland’s Eastern Shore.

Latest Insights from Courtney

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Wings & Whitetail Farm: an Eastern Shore Country Estate

From a gentle rise overlooking a quiet tributary of Langford Creek, the main house of Wings & Whitetail Farm surveys the landscape as it has for 265 years. Once called “Bungay Hill,” this 18th century home in Kent County, Maryland is one of the county’s most important historic properties. Currently available for purchase, it is a rare opportunity to own one of the finest country estates on the Eastern Shore.

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Featured Property, 5781 Main St, Rock Hall

In Rock Hall, the Old Oars Inn Bar and Restaurant on Main Street was a beloved third space. A watering hole par excellence, you could chat with a waterman over a $.75 Budweiser and a burger, meet a friend for dinner, or just nurse a drink and wind down your day. As a meeting place, it worked out well because it was hard to miss—the proud bow of a Chesapeake Bay deadrise had been prominently fixed to the right side of the building.

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Blue Crabs and a Better Housing Market

But just like holding out for those teeming river crabs of high summer, folks who have waited until now to buy their home are benefiting from a renewed supply and shifting market.

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Kate Livie Kate Livie

Making Like an Osprey in Spring 2022’s Real Estate Market

Every spring, there’s a lot of competition in the osprey world for the ideal nesting site, and aerial battles are common as osprey duke it out for the best tree, dock piling or telephone pole. It’s spring fever, Eastern Shore-style, and seems like a familiar scenario to anyone in the current real estate market.

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Peace on Earth Found on the Eastern Shore……

“Home should be an anchor, a port in a storm, a refuge, a happy place in which to dwell, a place where we can love and be loved.”  -Marvin Ashton

Our peace on earth is here, on the Eastern Shore.  As I decorate for Christmas this year, celebrating one year in our new home, I am grateful for taking this risk and celebrating the life we have recreated for ourselves in this beautiful place. 

 

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A Rock Hall Marina with Endless Possibilities

From the water or from the land, the first impression of North Point Marina is the same— welcoming, immaculate, and well-equipped. Located in the protected waters of Rock Hall Harbor, North Point Marina has commanding, 180 degrees vistas of the open Chesapeake.

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Corona Diaries, Chesapeake-style

It’s the time of year on the Mid-Shore we experience the phenomenon known as the “Eastern Shore traffic jam,” caused by a combine or other large piece of farming equipment driving down the road from one farm to another at a snail’s pace. Backed up behind them, sometimes for a mile, is a long line of cars waiting for the tractor to finally turn off. It’s a rite of passage in spring, met with a uniquely Eastern Shore attitude—no one honks, no one swerves, no one is in a terrible rush, and everyone just calmly bides their time.

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Small-town coastal Chesapeake charm on Lawton Avenue

Imagine driving down a quiet leafy street, bordered by small 19th century family homes—a perfect slice of Americana. But lift your eyes and surprisingly, you’ll notice water all around you. Welcome to Lawton Avenue.

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Main Street USA

If you’re thinking about moving or buying a second home, here’s seven reasons to pick towns with cool main streets, like Centreville, Rock Hall, Chestertown and Stevensville.

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