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Across the Choptank River, Talbot shares its southern waterfront border with Dorchester County. Offering an authentic Eastern Shore lifestyle in several distinct communities, Talbot’s five towns and 600 miles of waterfront are a magnet for families and retirees.
Easton
Home to the celebrated Waterfowl Festival, Easton has excellent shops, plentiful parks and a lively arts scene. Considered Talbot’s “big city,” this historic town is also the county seat. Residents enjoy concerts at the Avalon Theater, exhibitions at the Academy Art Museum, and world-class cultural events.
The downtown and surrounding residential neighborhoods feature a mix of clapboard cottages, stately Victorian, Georgian or Federal-style homes, and newer construction in communities of Easton Village, Cook’s Hope, Easton Club and Easton Club East for 55+.
Oxford
One of the oldest towns in Maryland – and one of the prettiest – this 17th-century seaport is steeped in history. With Town Creek to the east and Tred Avon River to the north and west, Oxford’s waterways teem with yachts, workboats and small craft. The town is home to the Oxford-Bellevue Ferry, the oldest privately operated service in continuous use. Author James Michener penned the novel Chesapeake at the still-operating Robert Morris Inn.
Homes in the historic district feature traditional architectural styles of the 18th, 19th, and 20th centuries. Stately manors and working farms are primarily found along waterfront estates outside of town. Oxford boasts a beautiful waterfront park, eclectic restaurants and the popular Highland Creamery.
St. Michaels
Situated along the Miles River, St. Michaels’ picturesque setting is favored by Hollywood producers who made it the backdrop for Wedding Crashers and Clara’s Heart. Known as the town that fooled the British during the War of 1812, residents hung lanterns in trees outside limits to trick the attacking army by providing a false target.
Today, St. Michaels is home to the Chesapeake Bay Maritime Museum, Harbourtowne Resort and the Inn at Perry Cabin by Belmond. With two-dozen restaurants, St. Michaels is a regional dining destination. From contemporary and classic waterfront estates to Federal and Revival style architecture in town, St. Michaels – and nearby communities of Royal Oak and Newcomb – offer a variety of housing styles including tidewater colonials and cottages.
Tilghman Island
A quintessential waterfront village, Tilghman Island sits on the southernmost tip of Talbot County. Cushioned between the Chesapeake Bay and the Choptank River, the pristine waterfront provides a peaceful quality of life. Accessible by a drawbridge, Tilghman has several marinas offering charter cruises.
Known for sport fishing, fresh seafood, and the center of Talbot’s watermen community, Tilghman businesses, attractions (Phillips Wharf Environmental Center), and events celebrate their distinct culture. Here you’ll find classic homes including traditional Eastern Shore styling to stunning contemporaries and everything in between.
Trappe
Trappe is a farming community with waterfront homes along the Choptank River’s creeks and tributaries. With easy access to Ocean Gateway (Route 50), Trappe is 10 minutes from Downtown Cambridge and equidistant from Easton.
Nestled along the picturesque Tred Avon River, this extraordinary estate comprises two expansive waterfront parcels totaling 11 acres. A masterpiece of luxury living, the centerpiece is a...
Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep...
Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this...
NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/...
“Tred Avon Manor”, one of the finest estates on Maryland’s Eastern Shore, situated on 16 acres, faces south on the Tred Avon River. With over 775 feet of waterfront and six feet MLW, this...
Birthplace and home of General Perry Benson, a Captain in the Revolutionary War, and Major General in the War of 1812, Wheatlands is a significant, Historic estate on the Miles River of Talbot...
Explore the allure of this hidden jewel in Oxford where refined luxury merges effortlessly with coastal charm. Nestled across 20+ elevated acres, spend your days meander through covered walkways,...
Stunning Waterfront Estate on the Miles River. This property has been immaculately maintained. The original home was built in 1927 but was completely renovated in 1999 and has since gone through...
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47 acres, with original structures that are impeccably well-kept and...
Welcome to Sunnyside, an exceptional and rare waterfront estate situated on a spectacular 16-acre point along the majestic Miles River.
A picturesque, winding driveway leads to the one-of-a-kind...
Please do not drive down the driveway without an appointment.
Welcome to WOODLAWN FARM , an exceptional estate offering panoramic vistas with breathtaking skies and SPECTACULAR sunsets! Bordering...
Make an appointment now to see "Shamrock Shores," Talbot County's newest waterfront listing. Sited on a premier 7.5-acre parcel, providing commanding SW views across the confluence of Glebe Creek...
Location, Location, Location. "RiversMeet" is located in one of Talbot County's finest waterfront sites, at the confluence of the Tred Avon and Choptank Rivers. The 12 mile view down the length...
Offered for the first time in nearly forty years, Swan Point is the quintessential Eastern Shore estate. Situated on 4.5 +/- acres, with westerly exposure on the Tred Avon River this estate has it...
Welcome to paradise, 8 acres of waterfront property on Cedar Point just minutes from St Michaels. The main house sits just off of the water on the point with magnificent water front views. This...
Steeped in history, Pot Pie Farm is located on a magnificent wide point of land with panoramic views over Harris and Cummings Creeks bringing the sunrise and sunset into your house everyday,...
A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits...
The perfect Eastern Shore escape from the rest of the world. Situated on Glebe Creek with 12.7 acres of well-planned outdoor amenities including approximately 1,300' bulk-headed shoreline,...
Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the...
Due to personal circumstances this property now includes new enhancements and a drastic price reduction to the previous listing. The listing now includes the adjacent waterfront parcel of 8.5...
Welcome to The Merryland! A magnificent waterfront home located in the sought-after neighborhood on Goose Neck Road! This expansive cedar-shake home designed by Architect Charles Goebel is...
**Luxurious Waterfront Modern Farmhouse in Easton, Maryland** PLEASE VIEW THE VIDEO TOUR OF THIS BEAUTIFUL HOME! Situated 12 feet above mean high water, discover serenity and luxury with this...
Just 1 mile outside St. Michaels, by car or by boat...Exceptional point of land improved by a beautifully-designed 3 bedroom, 3.5 bath main house; cute 1 bedroom, 1 bath guest cottage and...
Wye River Gem with 6’ mlw ! Beautifully designed and superbly constructed, this 4 bedroom, 3.5 bath home was built in 2014 by Bruce Harrington for the current owners. Mature trees, a protected...
WYE CLIFF : Sited on 13.5 spectacular and elevated acres overlooking the Wye River, this iconic property boasts commanding and breathtaking views of Wye Island, and is truly one of the best points...