Eastern Shore Waterfront Homes

232 Matapex Plantation Ln, Stevensville image
232 Matapex Plantation Ln, Stevensville $4,300,000

A spectacular waterfront estate where luxury living meets the Chesapeake Bay lifestyle. Set on 1.82 beautifully landscaped acres in the Landings at Mattapex community, th...

  • 7 Beds
  • 9 Baths
Courtesy of Eastern Shore Real Estate, LLC

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011

319 Blue Bay Rd, Stevensville image
319 Blue Bay Rd, Stevensville $4,158,000 ▲

Nestled within the prestigious Wolf Farm community, this exquisite residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifest...

  • 9 Beds
  • 8 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

414 Bay Dr, Stevensville image
414 Bay Dr, Stevensville $2,878,000 ▼

Finally Finished***From March 2026 until August 2026 the home went through its final finishing touch stages. There have been recent upgrades including water and electric ...

  • 5 Beds
  • 8 Baths
Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

300 Woods Point Rd, Chester image
300 Woods Point Rd, Chester $2,840,000

Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. ...

  • 5 Beds
  • 4 Baths
Courtesy of Tidewater Properties

Listing courtesy of Tidewater Properties. Contact:

115 Petrie Way, Stevensville image
115 Petrie Way, Stevensville $2,375,000

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophi...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

119 Petrie Way, Stevensville image
119 Petrie Way, Stevensville $2,375,000

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophi...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

123 Petrie Way, Stevensville image
123 Petrie Way, Stevensville $2,375,000

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophi...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

107 Petrie Way, Stevensville image
107 Petrie Way, Stevensville $2,375,000

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophi...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

914 Bayside Dr, Stevensville image
914 Bayside Dr, Stevensville $2,200,000

Bay City - If you are looking for a property that features beautiful sunsets on the bay, and outdoor living at the finest you found it! A builder's home with attention t...

  • 3 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

712 Bay Dr, Stevensville image
712 Bay Dr, Stevensville $1,750,000

712 Bay Drive isn't simply a waterfront home—it's a turnkey Chesapeake lifestyle, beautifully executed from shore to door. Just two years young, this exceptional waterfro...

  • 4 Beds
  • 3 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

410 Wallman Way, Stevensville image
410 Wallman Way, Stevensville $1,750,000

Experience some of the most captivating views the Chesapeake Bay has to offer. Perfectly positioned at the first exit off the Bay Bridge, this waterfront property showcas...

  • 9 Beds
  • 4 Baths
Courtesy of Chaney Homes, LLC

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

109 Starboard Ct, Grasonville image
109 Starboard Ct, Grasonville $1,450,000

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent...

  • 5 Beds
  • 5 Baths
Courtesy of Northrop Realty

Listing courtesy of Northrop Realty. Contact: 4105310321

952 Chester River Dr, Grasonville image
952 Chester River Dr, Grasonville $1,400,000

Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to creat...

  • 5 Beds
  • 4 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

105 Port Ct, Grasonville image
105 Port Ct, Grasonville $1,325,000 ▼

BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACR...

  • 4 Beds
  • 5 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690

1757 Harbor Dr, Chester image
1757 Harbor Dr, Chester $1,294,800 ▲

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse H...

  • 4 Beds
  • 4 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

2513 Cecil Dr, Chester image
2513 Cecil Dr, Chester $1,290,000 ▼

Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property...

  • 5 Beds
  • 2 Baths
Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

104 Port Ct, Grasonville image
104 Port Ct, Grasonville $1,275,000 ▼

WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly pai...

  • 4 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

346 Narrows Pointe Dr, Grasonville image
346 Narrows Pointe Dr, Grasonville $1,275,000 ▼

REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AN...

  • 3 Beds
  • 4 Baths
Courtesy of Berkshire Hathaway HomeServices Homesale Realty

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

1717 Harbor Dr, Chester image
1717 Harbor Dr, Chester $1,250,000

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with ...

  • 3 Beds
  • 3 Baths
Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

350 Narrows Pointe Dr, Grasonville image
350 Narrows Pointe Dr, Grasonville $1,215,000 ▼

Perfectly positioned along the living shoreline of the Chester River, this waterfront residence in the gated community of Narrows Pointe offers breathtaking, million-doll...

  • 3 Beds
  • 4 Baths
Courtesy of Northrop Realty

Listing courtesy of Northrop Realty. Contact: 4102956579

408 Butlers Lndg, Stevensville image
408 Butlers Lndg, Stevensville $1,150,000 ▼

NEW PRICE! Don't miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this appr...

  • 2 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

942 Chester River Dr, Grasonville image
942 Chester River Dr, Grasonville $899,000

Bring your water toys and move right in! Located on the Chester River, this beautifully remodeled water front home is ready for a quick sale so you can enjoy the rest of ...

  • 3 Beds
  • 2 Baths
Courtesy of Maryland Real Estate Network

Listing courtesy of Maryland Real Estate Network. Contact: (240) 456-0016

1107 Oyster Cove Dr, Grasonville image
1107 Oyster Cove Dr, Grasonville — Oyster Cove $775,000

LOCATION! LOCATION! LOCATION! PANAROMIC WATERFRONT VIEWS!!!! One of the best views in Oyster Cove! Eastern shore's best- kept secret is the beautiful, gated comm...

  • 3 Beds
  • 4 Baths
Courtesy of Star Realty

Listing courtesy of Star Realty. Contact: (443) 496-1367

130 Oyster Cove Dr Unit #130, Grasonville image
130 Oyster Cove Dr Unit #130, Grasonville — Oyster Cove $749,900

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situa...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Waterman Realty

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

1202 Oyster Cove Dr, Grasonville image
1202 Oyster Cove Dr, Grasonville $719,900

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  • 3 Beds
  • 4 Baths
Courtesy of Coldwell Banker Waterman Realty

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

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