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Kent County Waterfront

Chestertown and nearby towns

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Overview

Kent County is bounded by Delaware on the east, the Sassafras River on the North, the Chesapeake Bay on the West and the Chester River on the South. Real Estate offerings include waterfront estates, beach cottages, water-access communities, condos and hunting farms.

Quiet coves offer fishing, canoeing or kayaking. Anchorages, marinas and public landings are available throughout the County. Betterton Beach, located near the mouth of the Sassafras River, is ideal for swimming and famil…

Kent County Waterfront Real Estate Statistics

Total Listings: 68
Average Price: $1,103,891
Highest Price: $6,900,000
Lowest Price: $64,900

Kent County Waterfront Homes for Sale | Land for Sale

All Listings Under $100,000 $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
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6798 Broad Neck Rd, Chestertown, MD - $6,900,000

Residential, Detached
  • 5 Beds
  • Baths
  • 10,870 SQFT
  • 212 DOM
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300+/- Acre Waterfront Estate With Exceptional Amenities. Main House With 7,500+/- Sq Ft, With A Retreat Feel And Open Floor Plan. Indoor And Outdoor Pools, High Elevation And Expansive Southern And Western Views Down Coveted West Fork Langford Cr...

Photo of Listing #1000487872

6201 Swan Creek Rd, Rock Hall, MD - $4,790,000

Residential, Detached
  • 8 Beds
  • Baths
  • 5,385 SQFT
  • 383 DOM
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Elegant, Private Waterfront Estate On 177+ Acre Peninsula W/ Commanding Views Of The Surrounding Farm & Bay. Completely Renovated 5500+ Sqft 1870s Farmhouse W/ Major Addition. 1 Bed Cottage On The Water. Widow's Walk, Pool/hot Tub, Tennis, Pier, B...

22598 Davis Creek Dr, Rock Hall, MD - $4,250,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 4,725 SQFT
  • 191 DOM
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Enchanting Eastern Shore Waterfront Residence Is Nestled On 56-acres On Davis Creek In Rock Hall. Expert Craftsmanship And Style Distinguish Winding Creek House, Designed By Chestertown Architect, Peter Newlin. A Series Of Pavilions Are Linked To ...

6520 Swan Creek Rd, Rock Hall, MD - $4,100,000

Residential, Detached
  • 7 Beds
  • Baths
  • 12,520 SQFT
  • 214 DOM
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Open House Cancelled Today, May 5, 2019located On The Chesapeake Bay, Rock Hall Stud Is A 240 Acre Property Featuring A 12,520 Sf Unique, Waterfront Main Residence Built In 1986, Swimming Pool, Private Beach, Stud Farm With Facilities, And Beautif...

Photo of Listing #1008176730

4845 Cliffs City Rd, Chestertown, MD - $3,499,000

Residential, Detached
  • 7 Beds
  • 8 Baths
  • 237 DOM
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Bachelors Hope Farm, Available For The First Time In Over 50 Years, Is A Once-in-a-lifetime Waterfront And Hunting Farm. The 9,600 Square Foot, Seven Bedroom Main Home Is Situated Within Feet Of The Chester River. With Three Master Suites, An In-l...

5135 Crosby Road, Rock Hall, MD - $2,875,000

Residential, Detached
  • 5 Beds
  • 5 Baths
  • 3,772 SQFT
  • 180 DOM
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Lovely Eastern Shore Gentleman's Farm - Three Waterfront Parcels, 212ac (platted And Recorded) Lot 1 - 82 Ac (not Included). Lot 2 -73 Ac. Lot 3 58 Ac.(not Included) - Fronting Deep Unspoiled Davis Creek Off (langford Creek) Rock Hall, Maryland ...

Photo of Listing #MDKE100016

24091 Providence Plantation Ln, Chestertown, MD - $2,795,000

Residential, Detached
  • 4 Beds
  • 5 Baths
  • 5,250 SQFT
  • 207 DOM
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Owners Will Be Creative In Financing This1781 Eastern Shore Beauty Fully Restored In The 90's. Providence Plantation Defines Country Elegance With A Fabulous 1st Floor Master Bedroom Suite, A New 3 Br Tenant House, Dock With Lift And An In-ground ...

Photo of Listing #1001627262

29094 Belchester Rd, Kennedyville, MD - $2,025,000

Residential, Detached
  • 5 Beds
  • Baths
  • 3,473 SQFT
  • 365 DOM
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An Exceptional Sassafras Riverfront Home. Expansive Views. Comfortable Living Design For Family And Friends. Generous Rooms. Delightful River Room Invites Leisure Living. A Walk Out Pier For Multiple Boats, Jet Skis, Kayaks. Space At The End Of Th...

6778 Burris Rd, Rock Hall, MD - $1,785,000

Residential, Detached
  • 6 Beds
  • 5 Baths
  • 7,304 SQFT
  • 184 DOM
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Stunning 20 Acre Estate Surrounded By 200 Preserved Acres On Maryland's Eastern Shore. The Property Features A Magnificent 6 Bedroom, 4+ Bath Manor House, 5-car Garages, Pool, Studio, 2-stall Stable/barn, Pastures And 880 Ft Of Natural Shoreline O...

6320 Quaker Neck Rd, Chestertown, MD - $1,600,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 2,236 SQFT
  • 522 DOM
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Amazing Sense Of Peace Emphasized By The Quiet Of Authentic 18th C.brick Architecture. Methodically Restored Honoring Its Origins And Yet Made Comfortable With 21st C. Amenities. Lovely Wf Cove On Lankford Creek. Minutes From Chestertown On Highy ...

Photo of Listing #1003269223

14081 Sassafras Cove Rd, Galena, MD - $1,590,000

Residential, Detached
  • 5 Beds
  • Baths
  • 4,792 SQFT
  • 648 DOM
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This Spectacular Home Provides The Perfect Balance Of Form And Function For The Discerning Waterfront Home Buyer. Now With The Middletown By-pass To The Mix, Making The Philadelphia Airport Less Than An Hour Away And You Ad Location, Location, Lo...

14053 Tockwogh Ln, Galena, MD - $1,525,000

Residential, Detached
  • 4 Beds
  • Baths
  • 5,766 SQFT
  • 61 DOM
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Imagine A Home Designed And Placed On A Prominent Home Site Surrounded By Water. Enhanced By Large Decks And Patios With A "reach Out And Touch The Water" Feel, Sandy Beach, New Dock With Boat Lift, This Home Is The Epitome Of Function, Design And...

Photo of Listing #MDKE107842

6002 Lawton Ave, Rock Hall, MD - $1,350,000

Residential, Detached
  • 12 Beds
  • 14½ Baths
  • 7,386 SQFT
  • 144 DOM
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Moonlight Bay Inn And Marina Offers 10 Guest Rooms With Full Baths, 2 Parlor Gathering Areas With Gas Fireplaces, Dining Areas, Commercial Kitchen And Appliances, Innkeepers Living Space And 2 Innkeepers Bedrooms With Full Baths, Transient Guest O...

5343 Edesville Rd, Rock Hall, MD - $1,275,000

Residential, Detached
  • 6 Beds
  • 4 Baths
  • 3,939 SQFT
  • 317 DOM
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Eastern Shore Waterfront Cottage Is Beautifully Sited On 7.4 Acres With 772-ft Of Waterfrontage And 5-ft. Mlw. Private Haven With Panoramic Waterviews And Separate Guest Quarters Offers A Casual Ambiance With Large Fireplace And Wood Detail. Featu...

24080 Cliff Dr, Worton, MD - $1,199,999

Residential, Detached
  • 6 Beds
  • Baths
  • 4,000 SQFT
  • 69 DOM
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Waterfront Living At It's Finest. Enjoy The Sound Of The Water Hitting The Rip Rap And Beach With This 6 Br, 3.5 Ba Colonial Home That Sits On The Cliffs Overlooking The Chesapeake Bay. Gleaming Hardwood Floors, 3 Natural Burning Fireplaces, Expan...

Photo of Listing #1000869440

6870 Pentridge Ct, Chestertown, MD - $1,150,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 3,848 SQFT
  • 383 DOM
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Impressive Brick Colonial Waterfront Home On The East Fork Of Langford Creek, With Its Own Private Dock. Detached 4 Car Garage With Copious Storage. Interior Features Include A First Floor Master Bedroom, Theater, Bar And Game Room, And Gourmet K...

Photo of Listing #1005951739

7999 Quaker Neck Rd, Chestertown, MD - $1,100,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 4,402 SQFT
  • 294 DOM
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One Of Chestertown's Most Prestigious Addresses. Located On The River Halfway Between Town And "the Club". 1.48 Acres Of Privacy. Professionally Maintained And Landscaped. The House Has Had One Addition And Two Remodels. Large Open Floor Plan,po...

9326 N Bayview Ave, Chestertown, MD - $1,050,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,133 SQFT
  • 57 DOM
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Expansive Frontage On The Bay. Private, End Of Road Lot. Large Fenced Pool With Breathtaking Bay View. House Completely Renovated In 2002 Including Infrastructure. 1st And 2nd Floor Master Suites. Open Den/study On Second Floor. Maintained Steps A...

Kent County Waterways and Things to Do

In addition to all the water activities available, for those looking for land-based activities there are hiking trails, biking routes, museums to visit, historic house tours, as well as hunting opportunities. A popular destination for hunting and sporting clays is Hopkins Hunting and Sporting Clays.

The Rock Hall Museum features Native American artifacts and nautical relics, and the Waterman's Museum, also in Rock Hall, has oystering, crabbing and fishing exhibits.

The County Seat, Chestertown, is an historic Eastern Shore waterfront town set on the banks of the Chester River. Chestertown dates to 1706 when it served as a port of entry for colonial settlers arriving to Maryland. It was a prosperous trading and shipbuilding center.  Chestertown’s shipbuilding past has been revived by the Schooner Sultana Project.  The Sultana is a replica of a traditional 18th centry schooner.  Constructed locally by a non-profit organizaiton, it serves as a floating classroom.  Children and adults enjoy hands on educational experiences that focus on history and the study of the natural enivronment.
Every Memorial Day Weeked, Chestertown kicks off the summer with the Chestertown Tea Party Festival . It is a weekend of fun for the whole family including a tea toss reenactment in the Chester River on the Sultana, a raft race, reenactor street performances, colonial crafts, strolling musicians, local fare, and 5k & 10 mile run as well as other activities.

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The listing content relating to real estate for sale on this web site is courtesy of MRIS. Listing information comes from various brokers who participate in the MRIS IDX.Properties listed with brokerage firms other than Coldwell Banker Chesapeake are marked with the MRIS Logo and detailed information about them includes the name of the listing brokers.The properties displayed may not be all the properties available. All information provided is deemed reliable but is not guaranteed and should be independently verified.All listing information copyright MRIS 2019.

Listing information last updated on May 26th, 2019 at 8:30am EDT.