KENT ISLAND WATERFRONT REAL ESTATE

Known as “Maryland’s Gateway to the Eastern Shore,” Kent Island sits at the base of the Chesapeake Bay Bridge and is a rapidly growing community because of it’s convenience to the Annapolis/Baltimore-Washington corridor. Kent Island is the largest island in the Chesapeake Bay. It is 4.2 miles wide and 15 miles long. Real Estate properties range from historic waterfront properties and farms to new housing and condos. More Kent Island Info

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Kent Island Waterfront Homes for Sale | Waterfront Land for Sale

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$4,300,000

232 Matapex Plantation Ln, STEVENSVILLE

7 Beds 8 Baths 8,548 SqFt Residential MLS® # MDQA2018376

Eastern Shore Real Estate, LLC

$4,158,000

319 Blue Bay Rd, STEVENSVILLE

9 Beds 8 Baths 10,152 SqFt Residential MLS® # MDQA2016600

Long & Foster Real Estate, Inc.

New

$3,495,000

450 Seascape Ln, STEVENSVILLE

8 Beds 8 Baths 12,273 SqFt Residential MLS® # MDQA2018704

TTR Sotheby's International Realty

Open House

$2,878,000

↓ $10,000

414 Bay Dr, STEVENSVILLE

5 Beds 7 Baths 6,148 SqFt Residential

Open House

Thu, Sep 24th, 2026 @ 1pm - 2pm

MLS® # MDQA2018292

Cummings & Co. Realtors

$2,840,000

300 Woods Point Rd, CHESTER

5 Beds 3.5 Baths 1,704 SqFt Residential MLS® # MDQA2017820

Tidewater Properties

$2,400,000

2882 Cox Neck Rd, CHESTER

4 Beds 3.5 Baths 4,331 SqFt Residential MLS® # MDQA2017652

Wilson Realty & Staging LLC

$2,375,000

107 Petrie Way, STEVENSVILLE

4 Beds 4 Baths 3,280 SqFt Residential MLS® # MDQA2016866

TTR Sotheby's International Realty

$2,375,000

115 Petrie Way, STEVENSVILLE

4 Beds 4 Baths 3,280 SqFt Residential MLS® # MDQA2016870

TTR Sotheby's International Realty

$2,375,000

119 Petrie Way, STEVENSVILLE

4 Beds 4 Baths 3,280 SqFt Residential MLS® # MDQA2016872

TTR Sotheby's International Realty

$2,375,000

123 Petrie Way, STEVENSVILLE

4 Beds 4 Baths 3,280 SqFt Residential MLS® # MDQA2016874

TTR Sotheby's International Realty

$2,200,000

914 Bayside Dr, STEVENSVILLE

3 Beds 2 Baths 1,748 SqFt Residential MLS® # MDQA2018666

Long & Foster Real Estate, Inc.

$1,750,000

409 Craney Creek Rd, STEVENSVILLE

3 Beds 2.5 Baths 2,550 SqFt Residential MLS® # MDQA2017760

Samson Properties

$1,750,000

410 Wallman Way, STEVENSVILLE

9 Beds 3.5 Baths 4,025 SqFt Residential MLS® # MDQA2017772

Chaney Homes, LLC

New

$1,750,000

712 Bay Dr, STEVENSVILLE

4 Beds 2.5 Baths 2,733 SqFt Residential MLS® # MDQA2018554

Samson Properties

$1,290,000

↓ $60,000

2513 Cecil Dr, CHESTER

5 Beds 2 Baths 2,700 SqFt Residential MLS® # MDQA2018504

Real Broker, LLC - Chester

$1,250,000

1717 Harbor Dr, CHESTER

3 Beds 2.5 Baths 2,742 SqFt Residential MLS® # MDQA2018534

Chesapeake Real Estate Associates, LLC

$1,194,800

↓ $100,000

1757 Harbor Dr, CHESTER

4 Beds 3.5 Baths 0 SqFt Residential MLS® # MDQA2014542

Keller Williams Flagship

$1,150,000

↓ $100,000

408 Butlers Lndg, STEVENSVILLE

2 Beds 3 Baths 1,950 SqFt Residential MLS® # MDQA2018132

Coldwell Banker Realty

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Kent Island Information

Kent Fort, the first English establishment on Kent Island was founded in 1631, making Kent Island the oldest English settlement within the present day state of Maryland. It is the third oldest permanent English settlement in the U.S. after Jamestown, Virginia and Plymouth, Massachusetts. Historic Stevensville on Kent Island was founded in 1850 as a steamboat terminal. It is a national historic district with about 100 historic structures dating back to the town’s earlier days. It is also listed n the National Register of Historic Places. For biking or walking, The Cross Island Trail is a beautiful six-mile paved trail that wanders through woods, around creeks, a wildflower meadow and marshes.

Visit the Chesapeake Exploration Center to learn about Eastern Shore History - Featuring an interactive exhibit

Located on the scenic Kent Narrows channel, the Chesapeake Exploration Center includes hands-on, interactive exhibits which feature artifacts and displays that tell the story of the Chesapeake Bay and the Eastern Shore region. Visitors will learn about the area from the earliest geology to man's impact on the estuary over time. Visitors can find out how the Chesapeake Bay Bridge was constructed, learn how many tons of tomatoes were processed by local canneries, discover what kinds of wildlife live in the watershed, and how we can help save the bay. .

Feel free to contact me for general information about the area, inquire about properties for sale, or selling your home. Call: (443) 480-1181 (or) send an email using the form below. Thank you - Richard.