Want a little piece of Eastern Shore history to call your own?

How about a quick tour of some notable real estate currently on the market?

Maybe you’ll see something you like.

Our first stop this morning will be in Queenstown. Though actually under contract after about a year’s exposure to potential buyers at the asking price of $2,649,000, the Bowlingly Estate is worth mentioning due to its historic significance.


Built in 1733, a rare undisputed construction date verified in glazed header brick on the southwest exterior, Bowlingly’s original patent dates back to 1658. During the War of 1812, owner Richard Hall lent this grand residence on a bluff overlooking Queenstown Creek to the local militia. One morning in August of 1813, British troops showed up on the lawn, the militiamen fled, and the invaders sacked and vandalized the property.

Today, Bowlingly consists of the 8,734 square foot primary dwelling with 10 bedrooms and 11 fireplaces on 10 acres, a guest house, a caretaker’s house, a pool, and a pier.

Though scheduled to settle soon, if you’re really interested it’s worth a look. Who knows, the owners may be taking back-up offers just in case something doesn’t work out.

A few miles away, down Bennett Point Road, we have 120 Parks Point on the Wye River. This private 7.88 acre parcel with a panoramic view was at one time owned by Frances Folsom Cleveland, the widow of President Grover Cleveland. Mrs. Cleveland supposedly spent many summers at the property after her husband passed away. That she significantly outlived our 27th president should surprise no one. She was our country’s youngest first lady. They married, at the White House, when Grover was 49 years old and Frances was 21.


The original home at Parks Point was built in 1800 and was added on to in 1880 and 1920. It offers 5,216 square feet of living space and still contains some of the original brick walls. Asking price is $2,499,900.

Moving on to Denton, we have 608 5th Avenue better known as the Sophie Kerr House.


Built in 1861, this six bedroom, 3,658 square foot farmhouse now rests on 1.12 acres and has a huge old barn held together with wooden pegs instead of nails. Sophie Kerr is famous for her 23 novels and hundreds of poems and short stories, a number of which are set in the Caroline County of her youth. The literary award given in her name by Washington College is the largest undergraduate writing prize in the country. The list price on the house where Sophie Kerr grew up is $310,000.

In Talbot County we have Easton’s Ratcliff Manor.

At an asking price of $5,750,000 this is our most expensive historic listing but at 10,468 total gross living area, it’s also our largest. Built in 1749 with a mile of waterfront on the Tred Avon River, Ratcliff Manor, showcases many of the original home’s construction features, a caretaker’s house, a tenant house, numerous outbuildings, a pool, and pier.


This property was originally granted in 1659 by Cecil Calvert, the second Lord Baltimore, to the great-grandfather of Robert Morris, the renowned financier of the American Revolution and one of Maryland’s signers of the Declaration of Independence.

St. Michaels, known in legend as the town that fooled the British in the War of 1812 by hanging lamps in trees during nighttime bombardments, is the home of the Cannonball House at 200 Mulberry Street. Erected in 1803 and available at $1,475,000, this federal style brick home with the Flemish bond arches and ionic columns was constructed for the shipbuilder William Merchant. The house earned its well-known moniker during one of those British attacks, when a cannonball grazed the chimney, ricocheted, crashed through a dormer window, and rolled down the stairs.Image

In Wittman’s Summerton Farm we have our largest parcel at 297 acres and our oldest home, built in 1690. On the market for the first time in over a century, this property offers almost three miles of deep water cove shoreline off Harris Creek. Asking price is $4,250,000.

If that’s a little rich for your blood, there’s the house at Ennions Range on Tilghman Island Road in Mcdaniel. At $189,000, this 2.14acre, 1896 square foot property, built in 1820 is purported to be the 8th oldest home in Talbot county.

Swinging back into Queen Anne’s County’s Centreville, we see 208 Corsica Street, one of four Captains Houses built in the 1880s when Centreville was still a busy shipping port. This house is a cozy 560 square foot on .07 acres and is the least expensive on our historic homes tour at $163,500.


And we end our tour in the Kent County seat of Chestertown at the John L. Stam House at 114 Washington Avenue. This gothic revival Victorian named for the second President of Washington College is listed at $675,000 and features many updated renovations. An eye-catching gothic tower is a prominent distinguishing feature of this home.


Now let’s go somewhere nice for lunch.

Having seen the price tag on these properties, I’d like to treat you to something I can afford.


  1. Some very nice real estate. Daughter Billie is in the market for a house and the Captains House is in the right price range but I’m afraid the size would be a bit snug.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s