Eastern Shore Waterfront

Eastern Shore Waterfront Real Estate Listings
27848 Legates Cove Rd Rd, EASTON
  • Residential
  • 5 Beds
  • 6.5 Baths
  • 9,159 SqFt

27848 Legates Cove Rd Rd, EASTON

$10,500,000
9380 Gregory Rd, EASTON
  • Residential
  • 6 Beds
  • 7 Baths
  • 10,526 SqFt

9380 Gregory Rd, EASTON

$8,900,000
26035 Marengo Road, EASTON
  • Farm
  • 5 Beds
  • 6.5 Baths
  • 7,287 SqFt

26035 Marengo Road, EASTON

$7,900,000
25511 Bruffs Island Rd, EASTON
  • Residential
  • 3 Beds
  • 5 Baths
  • 8,971 SqFt

25511 Bruffs Island Rd, EASTON

$7,900,000 ↓ $2,045,000
11165 Shaw Bay Lane, EASTON
  • Residential
  • 3 Beds
  • 5 Baths
  • 8,971 SqFt

11165 Shaw Bay Lane, EASTON

$7,900,000
6798 Broad Neck Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 11,840 SqFt

6798 Broad Neck Rd, CHESTERTOWN

$6,500,000
6798 Broad Neck Rd, CHESTERTOWN
  • Farm
  • 5 Beds
  • 5.5 Baths
  • 11,840 SqFt

6798 Broad Neck Rd, CHESTERTOWN

$6,500,000
7373 Tilghman Island Rd, SHERWOOD
  • Residential
  • 8 Beds
  • 6.5 Baths
  • 12,578 SqFt

7373 Tilghman Island Rd, SHERWOOD

$6,495,000
6077 Boston Cliff Rd, EASTON
  • Residential
  • 5 Beds
  • 6 Baths
  • 7,521 SqFt

6077 Boston Cliff Rd, EASTON

$5,900,000
7402 Kent Point Rd, STEVENSVILLE
  • Residential
  • 8 Beds
  • 10 Baths
  • 21,200 SqFt

7402 Kent Point Rd, STEVENSVILLE

$5,500,000 ↓ $150,000
22020 Benders Ln, SHERWOOD
  • Farm
  • 4 Beds
  • 6 Baths
  • 10,933 SqFt

22020 Benders Ln, SHERWOOD

$5,350,000
22020 Benders Ln, SHERWOOD
  • Residential
  • 4 Beds
  • 6 Baths
  • 10,781 SqFt

22020 Benders Ln, SHERWOOD

$5,350,000

Eastern Shore Waterfront Statistics
The Chesapeake Bay and the rivers and streams that feed it is the largest estuary in the United States and third largest in the world. The Maryland Eastern Shore region consists of nine counties and lies predominantly on the east side of the Chesapeake Bay. It features the most shoreline and points of public waterway access sites of any region in Maryland - with hundreds of coves, bays, rivers and islands that are found here.
Property Types (active listings)
Average Price: $1,863,193
Total Listings: 252
Avg. Days On Market: 224
Avg. Price/SQFT: $406
Highest Price: $10,500,000
Lowest Price: $15,000
Avg. Property Age: 132 YEARS
Basic Statistics (active listings)

Eastern Shore Waterfront Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
6778 Burris Rd, ROCK HALL
  • Farm
  • 6 Beds
  • 5 Baths
  • 7,304 SqFt

6778 Burris Rd, ROCK HALL

$1,475,000 ↓ $150,000
26268 Tunis Mills Rd, EASTON
  • Residential
  • 4 Beds
  • 3 Baths
  • 4,177 SqFt

26268 Tunis Mills Rd, EASTON

$969,000 ↓ $26,000
6201 Swan Creek Rd, ROCK HALL
  • Residential
  • 8 Beds
  • 7.5 Baths
  • 5,385 SqFt

6201 Swan Creek Rd, ROCK HALL

$4,490,000 ↓ $300,000
7402 Kent Point Rd, STEVENSVILLE
  • Residential
  • 8 Beds
  • 10 Baths
  • 21,200 SqFt

7402 Kent Point Rd, STEVENSVILLE

$5,500,000 ↓ $150,000
12626 Wye Ln, WYE MILLS
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 6,000 SqFt

12626 Wye Ln, WYE MILLS

$3,450,000 ↓ $500,000
6520 Swan Creek Rd, ROCK HALL
  • Farm
  • 7 Beds
  • 6.5 Baths
  • 12,520 SqFt

6520 Swan Creek Rd, ROCK HALL

$3,950,000 ↑ $50,000
25511 Bruffs Island Rd, EASTON
  • Residential
  • 3 Beds
  • 5 Baths
  • 8,971 SqFt

25511 Bruffs Island Rd, EASTON

$7,900,000 ↓ $2,045,000
27465 Southside Island Creek Rd, TRAPPE
  • Residential
  • 10 Beds
  • 7.5 Baths
  • 7,898 SqFt

27465 Southside Island Creek Rd, TRAPPE

$1,995,000 ↓ $300,000
5896 Beach Rd, ROCK HALL
  • Residential
  • 3 Beds
  • 3 Baths
  • 2,111 SqFt

5896 Beach Rd, ROCK HALL

$849,000 ↓ $50,999
4962 Ashley Rd, ROCK HALL
  • Residential
  • 3 Beds
  • 0 Baths
  • 1,400 SqFt

4962 Ashley Rd, ROCK HALL

$199,900 ↓ $50,000
27211 Baileys Neck Rd, EASTON
  • Residential
  • 3 Beds
  • 4.5 Baths
  • 5,382 SqFt

27211 Baileys Neck Rd, EASTON

$1,995,000
4746 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 4 Baths
  • 5,174 SqFt

4746 Cliffs City Rd, CHESTERTOWN

$3,400,000

The Eastern Shore of Maryland

Waterfront Real Estate

WATERFRONT HOMES, FARMS AND LAND

Much of the Eastern Shore of Maryland has a rural setting with fertile farmland and beautiful waterways. The Chesapeake Bay, rivers and creeks provide extraordinary opportunities for living on the water. Options include homes with sweeping water views and docks for boating, waterfront farms for hunting, historic homes and cottages nestled in the woods on creeks that are perfect for kayaks. Many waterfront lots are available to build your special home in a rural setting or in a community.

Kent County, founded in 1642, is the second oldest county and the smallest county in Maryland but boasts 265 miles of tidal shoreline and 134,000 acres of farm land. Surrounded by waterways, it is bounded by Delaware on the east, the Sassafras River on the North, the Chesapeake Bay on the West and by the Chester River on the South.

Talbot County is located directly on the Chesapeake Bay and offers crabbing, oyster harvesting and extensive wildlife. It has over 600 miles of tidal shoreline - the most of any county in the United States. Waterways in Talbot County include the Chesapeake Bay, Choptank River, Tred Avon River and Wye River.

Queen Anne's County offers a world of fertile farmland and scenic shoreline. The County has 414 miles of shoreline and 29.2 square miles of water area. With its many Chesapeake Bay waterways, it offers diverse real estate properties including historical homes on waterfront farms and cottages on creeks.

Discover the Eastern Shore

The Chesapeake Bay, Rivers and Creeks

A Storied Past

In 1608, Captain John Smith explored the Sassafras River, landing at a Tockwogh village near present-day Rock Hall. “Heaven and earth never agreed better to frame a place for man’s habitation,” wrote Captain John Smith while exploring the Eastern Shore.

The Chesapeake Bay was formed nearly 12,000 years ago when glaciers melted and flooded the Susquehanna River valley. The largest and at one-time most productive estuary in the United States, the Chesapeake Bay is an integral part of our natural history as well as United States history.

The Eastern Shore has long been known for its Chesapeake Bay Blue Crabs and crab feasts. For thousands of years the delectable Oyster has been an integral part of the Chesapeake Bay history. To learn more about the history of Chesapeake Oysters, the book “Chesapeake Oysters” by Kate Livie is an interesting read with historic photos.

The Nellie Crockett was built specifically to operate as a buy-boat, making the rounds of the Chesapeake Bay oyster beds to buy oysters directly from the harvesters, typically sail-powered skipjacks or oyster tongers.

Eastern Shore Living

Life on the Waterfront

The Eastern Shore lifestyle includes a wide variety of opportunities to actively embrace the great outdoors. Waterfront homes with sweeping views and deep water docks are great for boaters while cottages nestled in the woods on creeks are perfect for kayaks.

Among the many settings to choose from are waterfront condos, residences with breath taking sunset views of the Chesapeake Bay and other tributaries, hunting farms and waterfront communities.

The Eastern Shore is a great place for day trips and weekend getaways to visit the many scenic waterfront villages and historic towns along the waterways. Other destinations may include The Chesapeake Bay Maritime Museum in St. Michaels or a visit to Rock Hall to explore Eastern Neck Wildlife Refuge. The refuge is a 2,285 acre island providing habitat for thousands of wintering waterfowl and over 250 species of birds for wildlife viewing. There are also 7 walking trails with expansive views of the Chesapeake Bay and the Chester River.

Visitors and residents alike who want to enjoy being outside in the natural Eastern Shore setting, have at their disposal boating, fishing, crabbing, hunting, walking trails, parks or a visit to Betterton Beach.

Find Your Eastern Shore Place

Get in Touch

Interested in finding out more about the area or a property? Richard can help - just call (443) 480-1181 or send an email.

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Listing information last updated on August 11th, 2020 at 2:15am EDT.