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Chestertown Homes for Sale

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 #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...

202 Mount Vernon Ave, Chestertown, MD - $395,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,660 SQFT
  • 240 DOM
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Charm And Character Abound In This Home, Renovated And Updated Inside And Out In 2008. Nice Layout On Main Level Includes Gracious Kitchen With Wet Bar, Pantry, Powder Room, Wood Stove Fireplace Insert In Family Room, Open Dining Room And Separat...

Photo of Listing #MDQA140474

423 Fairview Dr, Chestertown, MD - $395,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,680 SQFT
  • 82 DOM
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Affordable Waterfront Home On Rosin Creek Is A Wonderful Place To Relax And Unwind. Custom Woodwork Features Include A Spiral Staircase And Walnut Kitchen Cabinets. The Floors Are 2x6 Tongue And Groove Pine. First Floor Bedroom With Full Bath As W...

Photo of Listing #MDKE114136

205 N Kent St, Chestertown, MD - $394,000

Residential, Detached
  • 2 Beds
  • Baths
  • 1,776 SQFT
  • 167 DOM
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A Sanctuary In Downtown Chestertown, This Contemporary Craftsman Home Offers The Best Of Both Worlds...a Private Rear Yard And Garden Retreat, And Easy, Walk-able Access To Enjoy All This Charming Town Has To Offer! Architectural Details And An Op...

Photo of Listing #MDKE115216

9822 Fairlee Cove Dr, Chestertown, MD - $388,500

Residential, Detached
  • 3 Beds
  • Baths
  • 1,344 SQFT
  • 102 DOM
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Welcome To 'knot Now Boat House', Which Has Been A Very Tastefully Remodeled Home Located On Fairlee Creek. This Can Be A Full Time Residence Or Your Holiday Retreat Or Week-end Get Away. Fully Updated Kitchen With New Counter Tops, Cabinets, An...

Photo of Listing #MDKE114878

109 High St, Chestertown, MD - $385,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,087 SQFT
  • 165 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 ...

105 N Water St #6, Chestertown, MD - $385,000

Residential, Condo, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,015 SQFT
  • 109 DOM
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Wonderful Water Street Condo With Elevated Views, A Private Balcony, And A Boat Slip To Enjoy The Chester River. Large Eat-in Kitchen, Beautifully Renovated With Stainless Steel Appliances, Farmhouse Sink And Custom Cabinets. The Property Also O...

Photo of Listing #MDKE113968

107 S Queen St, Chestertown, MD - $374,000

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 2,530 SQFT
  • 181 DOM
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Price Improvement! Historic Downtown Beauty With Numerous Recent Upgrades Has A Potential First Floor Master, Sought After Off Street/driveway Parking, Within One Block Of The New & Improved Chestertown Marina, And In The Heart Of Everything Chest...

112 S Kent St, Chestertown, MD - $367,900

Residential, Detached
  • 3 Beds
  • Baths
  • 1,524 SQFT
  • 71 DOM
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Meticulously Renovated With Stunning Details. One Of Chestertown~s Finest Historic Renovations. Professionally Designed Features Preserving Its Original Historic Charm. A Perfect Example Of What Careful Planning And Style Achieves. Close Distance ...

Photo of Listing #MDKE115234

7698 Country Club Ln, Chestertown, MD - $365,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,358 SQFT
  • 90 DOM
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Custom Built Home On The Market For The First Time! The Open Floor Plan Has 2 Story Living Room. Balcony On The 2nd Floor To Bedrooms. Warm Honey Tone Wood Details, Mantel, And Trim Create A Very Inviting Atmosphere. Wonderful Home Backs Up To Th...

20 Pear Tree Point Rd, Chestertown, MD - $364,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,023 SQFT
  • 198 DOM
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Unique 2,208 Square Foot Home To Be Built In The Water Privileged Community Of Pear Tree Point. 3 Br, 2.5 Baths, Granite Counter Tops, Wood, Carpet And Tile Floors. This Home Provides A Very Functional Split-floor Plan, An Open Kitchen Layout With...

121 N Queen St, Chestertown, MD - $364,000

Residential, Semi-Detached
  • 3 Beds
  • 2 Baths
  • 1,849 SQFT
  • 167 DOM
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Lovely, Low-maintenance 3-bedroom, 2-bath Victorian Features A Charming Interior With Beautifully Restored Original Pine Floors And Updated Kitchen. The Home Also Offers A Third Floor Studio/loft Space And A Private, Fenced Rear Yard, Plus Off-st...

Photo of Listing #MDKE113992

9068 Point Ln, Chestertown, MD - $350,500

Residential, Detached
  • 2 Beds
  • 1 Baths
  • 800 SQFT
  • 199 DOM
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Location! Location! Location! Cozy 1940's Bay Front Cottage On .54 Acre Lot With Spacious Screened Porch & Detached 2 Bay Garage Offers Incomparable Panoramic Year Round Views Of The Chesapeake Bay. Distant Shores & Passing Ships. In Addition, Th...

101 S Mill St, Chestertown, MD - $348,000

Residential, Semi-Detached
  • 2 Beds
  • Baths
  • 1,476 SQFT
  • 62 DOM
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Quiet Mill St With Historic Charm. A Contemporary Open Floor Plan For This Classic Victorian. Original Wood Floors, East Lake Style Mantle, Bulls Eye Molding, Plantation Shutters, Wood Stove, Upgraded Kitchen. Large Rear Yard Has A Patio, Gardens,...

110 S Kent St, Chestertown, MD - $348,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,600 SQFT
  • 44 DOM
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A Charming Colonial On S Kent Street. This Tasteful Renovation Features 3 Bedrooms, 2 Full Updated Bathrooms, Pine And Slate Floors, Updated Hvac,a New Roof, And Modern Kitchen. Enjoy The Open Floor Plan Which Leads Out To A Brick Patio And Garden...

109 Adela Way, Chestertown, MD - $340,000

Residential, Detached
  • 4 Beds
  • Baths
  • 3,997 SQFT
  • 30 DOM
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Spectacular 4 Bedroom 3.5 Bath Home In Coventry Farms Ii For Sale. Located Just Outside Of Chestertown's Historic District. This Is The Beautiful Victoria Model From Ryan Homes. This Home Has All The Upgrades That Were Available At Time Of Purchas...

Photo of Listing #MDKE115148

7880 Chester Ct, Chestertown, MD - $335,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,464 SQFT
  • 110 DOM
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Opportunity Is Knocking!! This Beautiful Home Is Located In Heather Heights Conveniently Situated Between The Chester River Yacht And Country Club And Historic Chestertown. The Home Is Turn Key And Well Maintained With Spacious Rooms, Wood Floors,...

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.