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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
  • 303 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...

9181 American Legion Rd, Chestertown, MD - $495,999

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,200 SQFT
  • 10 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...

23119 Club Ter, Chestertown, MD - $469,900

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,378 SQFT
  • 45 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...

Photo of Listing #MDKE107934

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

Residential, Detached
  • 3 Beds
  • Baths
  • 174 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 ...

Photo of Listing #1001891852

7844 Chester Ct, Chestertown, MD - $459,900

Residential, Detached
  • 4 Beds
  • Baths
  • 3,248 SQFT
  • 401 DOM
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Close To Chester River Yacht & Country Club & Historic Downtown Chestertown This Meticulously Maintained Home Offers Office And Den/library, Huge Owners Suite W/11'ceilings, Living/dining Room Combo W/wood Floors, Built-in Bookcase & Gas Fireplace...

8595 Orchard Dr, Chestertown, MD - $459,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,674 SQFT
  • 25 DOM
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Stunning Home In Orchard Hill Offers Everything And Then Some! Brazilian Tigerwood Floors Throughout The Main Level And Brand New Carpet In The Bedrooms. Gorgeous New Granite Counters In A Chef's Kitchen With Stainless Steel Appliances And Cherr...

Photo of Listing #1000479984

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

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,107 SQFT
  • 447 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 ...

403 Cannon St, Chestertown, MD - $449,000

Residential, Detached
  • 2 Beds
  • Baths
  • 1,923 SQFT
  • 128 DOM
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This Home Will Amaze You! Open Floor Plan With Gorgeous Built Ins. Kitchen Renovation With Large Kitchen Island, Granite Counters, Ss Appliances, With A View That You Won't Find Any Where Else In Town! The In-ground Pool Makes This House The One! ...

Photo of Listing #MDQA140474

423 Fairview Dr, Chestertown, MD - $445,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,680 SQFT
  • 27 DOM
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Waterfront Home On Rosin Creek Built By Renowned Master Carver William Reinbold. The Spiral Staircase And All Of The Cabinetry In The House Were Made By Mr Reinbold. Peaceful Wooded Lot Is A Haven For The Birds That He Loved. First Floor Bedroom...

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

Residential, Detached
  • 3 Beds
  • Baths
  • 2,202 SQFT
  • 133 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 #MDKE113912

405 S Cross South St #3 Cent, Chestertown, MD - $425,000

Residential, Condo, Townhouse
  • 3 Beds
  • Baths
  • 2,178 SQFT
  • 111 DOM
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Beautiful Peaceful Setting With Lovely Water Views Of The Chester River. Situated Just A Short Stroll To H Istoric Downtown Chestertown With All Its Shops And Great Dining, This All Brick Two Story Townhome Has Much To Be Desired, 1st Floor Maste...

109 High St, Chestertown, MD - $400,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,087 SQFT
  • 110 DOM
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This Wonderful Historic Home Sits Only One Block From The Chestertown Waterfront. It Has Period Details Throughout The House And The Charm Of Being In The Historic District. The Harris (malloy) House Is A Registered Historic Home Which Offers "in ...

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 July 23rd, 2019 at 8:15am EDT.