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Chestertown Area Waterfront Real Estate

The Chesapeake Bay, Chester River, Langford Creek and other waterways set the stage for wonderful waterfront properties and landscapes. The diverse Waterfront Real Estate includes homes with spectacular water views, beach cottages, bungalows on quiet creeks, waterfront hunting farms, and historic estates. Chestertown Info

Chestertown Area Waterfront Homes for Sale

All Listings $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
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0 Hawthorne Rd, Rock Hall, MD - $5,500,000

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 34 DOM
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...if You Love The Water, You Will Love This! 4 Residential Homes - 2 Rented & 2 Owners Homes, The Marina's Motel, A Boatel For Storing Boats, A Office, Pool, Bath Houses, & Docks With 75 Boat Slips! Sits Next To Waterman's Restaurant. Beautifu...

Photo of Listing #1000487872

6201 Swan Creek Rd, Rock Hall, MD - $4,490,000

Residential, Detached
  • 8 Beds
  • Baths
  • 5,385 SQFT
  • 502 DOM
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Live Your Dream And Enjoy An Elegant And Serene Waterfront Estate Nestled On 177+ Acres Of A Private And Secluded Peninsula Along Maryland's Eastern Shore. Delight In The Commanding And Expansive Views Of The Surrounding Farmland And The Picturesq...

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

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 4,725 SQFT
  • 310 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 ...

Photo of Listing #1009997570

6520 Swan Creek Rd, Rock Hall, MD - $3,900,000

Residential, Detached
  • 7 Beds
  • Baths
  • 12,520 SQFT
  • 333 DOM
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New Price! 200k Price Adjustment! Amazing Opportunity. Located 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 Facilit...

4746 Cliffs City Rd, Chestertown, MD - $3,400,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 5,174 SQFT
  • 777 DOM
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An Elegant New Offering Located On The Chester River In Quaker Neck, Just South Of Historic Chestertown. This Magnificent Family Residence Has It All: Ideal Waterfront & Wildlife Habitat, A Private Pier W/ 3ft Mlw, Marvelous Panoramic Southern Wat...

Photo of Listing #1008176730

4845 Cliffs City Rd, Chestertown, MD - $3,200,000

Residential, Detached
  • 7 Beds
  • 8 Baths
  • 356 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...

Photo of Listing #MDKE100016

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

Residential, Detached
  • 5 Beds
  • Baths
  • 5,250 SQFT
  • 326 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 - $1,950,000

Residential, Detached
  • 5 Beds
  • Baths
  • 3,473 SQFT
  • 484 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...

6970 Pomona Rd, Chestertown, MD - $1,750,000

Residential, Detached
  • 5 Beds
  • 2 Baths
  • 3,008 SQFT
  • 108 DOM
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Hilltop Farm C. 1810 In Historic Chestertown Includes 113 Acres With Waterfront On Langford Creek Off The Chester River. Property Includes Large 8 Feet Deep Fresh Water Pond And Impoundment.perc Test Done In 2019 For New Construction 3500 +sf On...

Photo of Listing #MDKE101546

6778 Burris Rd, Rock Hall, MD - $1,685,000

Residential, Detached
  • 6 Beds
  • 5 Baths
  • 7,304 SQFT
  • 303 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...

Photo of Listing #MDKE115694

5240 Johnsontown Rd, Chestertown, MD - $1,650,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 2,656 SQFT
  • 3 DOM
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Picture This ~ You Drive Past The Crops, Down The Tree Lined Lane, Past The Barns And There Is The River. You Have Arrived At Your Own Piece Of Paradise ~ Grassymeade Farm. Situated On 51.55 Picturesque Acres With Expansive Views Of The Chester R...

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

Residential, Detached
  • 4 Beds
  • Baths
  • 5,766 SQFT
  • 180 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...

4865 Eastern Neck Rd, Rock Hall, MD - $1,490,000

Residential, Detached
  • 5 Beds
  • Baths
  • 6,503 SQFT
  • 44 DOM
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Waterfront Living In A Gorgeous Custom Built Home With Countless Upgrades And A Private Beach! 17+ Acres With Shoreline, Farmland, 1/2 Acre Pond, And Wooded Property Line. 1000+ Sf Of Deck And Wrap Around Porch, Enclosed Sun Room With Gorgeous Vi...

Photo of Listing #1004147827

6320 Quaker Neck Rd, Chestertown, MD - $1,380,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 2,236 SQFT
  • 613 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 #MDKE107842

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

Residential, Detached
  • 12 Beds
  • 14½ Baths
  • 7,386 SQFT
  • 263 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...

Photo of Listing #1002039646

5343 Edesville Rd, Rock Hall, MD - $1,250,000

Residential, Detached
  • 6 Beds
  • 4 Baths
  • 3,939 SQFT
  • 436 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...

22940 Colonel Leonard Rd, Rock Hall, MD - $1,150,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,731 SQFT
  • 51 DOM
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Green Hedge Farm Has That "eastern Shore Feel". On A Point Of Land Totally Nearly 16 Acres. Plenty Of Privacy On The Deep Water Of The West Fork Of The Langford Creek. Outbuildings, Helipad, Private Dock With 180 Degree Views And One Story Living....

Photo of Listing #MDKE115392

10718 Tilden Ln, Chestertown, MD - $1,100,000

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 4,715 SQFT
  • 76 DOM
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Enjoy Sweeping Water Views From Three Sides Of This Spectacular Property. The Custom Built Sprawling Ranch Home Offers First Floor Living, Is Ideally Situated On A Point Of Land That Provides Broad Water Views, A Private Dock With Protected Water...

Eastern Neck National Wildlife Refuge is a great outing for everyone - kids will especially enjoy the Butterfly Walk. There are universally-accessible trails for those who wish to observe the varied habitats of the refuge

Chestertown Information

The network of rivers and creeks offer a perpetual source of marshlands to explore, and waterways for sailing, kayaking, fishing, and crabbing. You can find a small creek for canoeing or enjoy sailing out in the Chesapeake Bay.  Stroll along Chestertown's tree-lined steets with brick walkways and beautiful 18th century homes. There are unique shops, art studios, galleries, restaurants, cafes and bakery.  A destination for loyal customers and visitors is Twigs & Teacups Gift Shop.

Kent County Volunteer Organizations - There are many ways citizens can learn more about the area and participate in the community. The Chester River Association is committed to improving the health of the large tributary and employs "Chester Testers┬Ł to collect water samples.  The Echo Hill Outdoor School, situated on the bay near Betterton, and Schooner Sultana Project in Chestertown, are dedicated to environmental education and historical preservation.

If you would like more information about the area or real estate properties, please call me at: (443) 480-1181
Or, send an email using the form below.  Thank you - Richard.

Please provide a valid email address.



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 September 22nd, 2019 at 10:03pm EDT.