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Chestertown Homes for Sale, $400,000 - $500,000

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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Photo of Listing #1006633640

109 Water St S, Chestertown, MD - $499,000

Residential, Semi-Detached
  • 4 Beds
  • 2 Baths
  • 2,064 SQFT
  • 358 DOM
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Live In The Heart Of Historic Chestertown, Water Views Of The Chester River From The Back Of The House. Historic Water Street In Front. Charming Colonial Revival House Overlooking Washington College's Presidents Gardens. A Great Place To Sit On B...

22452 Goose Hollow Rd., Chestertown, MD - $498,500

Residential, Detached
  • 4 Beds
  • Baths
  • 2,531 SQFT
  • 44 DOM
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Goose Landing Is A 3.17 Acre 4 Bedroom 2.5 Bathroom Secluded Waterfront Home Nestled On Fairlee Creek That Boasts 350 Feet Of Waterfront With Panoramic Views From Almost Every Room, A 100 Foot Dock With Swim Platform. Fairlee Creek Is Fresh Water...

10191 Rileys Mill Rd, Chestertown, MD - $498,500

Residential, Detached
  • 3 Beds
  • Baths
  • 2,745 SQFT
  • 18 DOM
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This 3 Bedroom, 3-1/2 Bath Waterfront Home Is Located In A Beautiful Spot Overlooking Morgan Creek, Just Off Of The Chester River. Secluded And Private But Only 5 Miles From All The Charm And Events In Historic Chestertown. There Are Views Of The...

Photo of Listing #MDKE115430

9181 American Legion Rd, Chestertown, MD - $474,900

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,200 SQFT
  • 65 DOM
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Just Bring Your Food And Clothes For This One! This Property Is Fully Furnished And Stocked For Immediate Use. Located On Morgan Creek With A 40' Dock W/ "l" Head. 20 Feet Deep At The End Of The Dock. The Property Has Two Additional Waterfront Lo...

5830 Langford Bay Rd, Chestertown, MD - $465,000

Residential, Detached
  • 3 Beds
  • Baths
  • 1,972 SQFT
  • 10 DOM
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Beautiful And Unique, 3 Bdr, 3 Level, Waterfront Home. Located In Langford Bay Estates And Nestled Back On The West Fork Of Langford Creek On Long Cove. This Property Offers 300ft Of Bulkheaded Shoreline, A Private Dock With Water And Electric Ac...

Photo of Listing #MDKE107934

203 N Queen St, Chestertown, MD - $460,000

Residential, Detached
  • 3 Beds
  • Baths
  • 229 DOM
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Located In Historic Chestertown, This Home Was Built In 2015 And Is Gorgeous. Offers Upgrades Such As Wood Floors, Gas Fireplace, Open Living Room/dining Room, With An Open Kitchen. There Is A First Floor Master Suite, A Laundry Room, A Screened ...

332 Queen St, Chestertown, MD - $449,900

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 2,060 SQFT
  • 18 DOM
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Circa 1870 Home With Chester River Views Situated On An Acre-plus Just Blocks From Downtown Chestertown And Washington College. Enjoy The Private, Park-like Setting Of This Hilltop Property Located In A Quiet Riverfront Neighborhood. The 3-story,...

Photo of Listing #1000479984

10864 Foreston Rd, Chestertown, MD - $449,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,107 SQFT
  • 502 DOM
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Eastern Shore Waterfront Retreat Is Privately Sited On Mill Creek. Designed With Cedar Exterior And Interior, The Single Floor Home Offers A Casual Ambiance With Great Room And Large Windows With Water Views. A New Roof Was Installed In 2013. The ...

109 S Queen St, Chestertown, MD - $435,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,202 SQFT
  • 129 DOM
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This Gorgeous Home "banning House" Is Updated Beautifully In The Historic District, A Couple Of Blocks From The Chester River. Wood Floors Are Incredible, There Is A Brick Floored Den/family Room Overlooking A Private Courtyard. It's Currently A...

Photo of Listing #MDKE115248

23119 Club Ter, Chestertown, MD - $412,500

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,378 SQFT
  • 88 DOM
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This Offering Of One & 1/4 Waterfront Acres At The End Of A Cul De Sac Sits In A Private, Park-like Setting On Worton Creek. The Improved Lot Is Fully Bulkheaded With A Dock. The Well Maintained Three Bedroom, Two Bath Ranch With A Waterside Th...

104 Devon Dr, Chestertown, MD - $410,000

Residential, Detached
  • 5 Beds
  • Baths
  • 3,268 SQFT
  • 17 DOM
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The Pictures Tell The Story. Amazing Remodel On This Incredible Home, With Formal Living Room, Dining Room, Den, Family Room, Florida Room, Full Deck, Private Fenced In Back Yard. Five Bedrooms In All, With A Wonderful Master Suite. The Basemen...

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.