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Chestertown Homes for Sale, Over $1,000,000

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

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 5,174 SQFT
  • 771 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
  • 350 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
  • 320 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 ...

7250 Pentridge Ln, Chestertown, MD - $1,850,000

Residential, Detached
  • 4 Beds
  • Baths
  • 288 DOM
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Rarely Do You Find A True Contemporary Residence In This Traditional Area In Kent County On Maryland's Eastern Shore. This Architecturally Designed House Is Surrounded By 168 Private Acres Of Open Fields, Virgin Woods & Ponds. The 3000+ Square Foo...

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

Residential, Detached
  • 5 Beds
  • 2 Baths
  • 3,008 SQFT
  • 102 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 #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 #MDKE115392

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

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 4,715 SQFT
  • 70 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...

Photo of Listing #1005951739

7999 Quaker Neck Rd, Chestertown, MD - $1,025,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 4,402 SQFT
  • 407 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...

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 16th, 2019 at 5:03pm EDT.