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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 #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 ...

205 N Kent St, Chestertown, MD - $399,000

Residential, Detached
  • 2 Beds
  • Baths
  • 1,776 SQFT
  • 112 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...

9822 Fairlee Cove Dr, Chestertown, MD - $398,500

Residential, Detached
  • 3 Beds
  • Baths
  • 1,344 SQFT
  • 47 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...

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

Residential, Detached
  • 4 Beds
  • Baths
  • 2,660 SQFT
  • 185 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...

7698 Country Club Ln, Chestertown, MD - $395,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,358 SQFT
  • 38 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...

9797 Richards Rd, Chestertown, MD - $389,900

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 840 SQFT
  • 37 DOM
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This Property Is Private, Secluded And Beautiful Waterfront. It Also Includes Another Lot Which Will Be Transferred Which Is 1.15 Ac. Cute Cottage, In Good Condition, Featuring An Enclosed Porch With A Deck. Beautiful Water Front With A Private...

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

Residential, Condo, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,015 SQFT
  • 54 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
  • 126 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...

9068 Point Ln, Chestertown, MD - $369,500

Residential, Detached
  • 2 Beds
  • 1 Baths
  • 800 SQFT
  • 144 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 Panoramic Year Round Views Of The Chesapeake Bay. Distant Shores & Passing Ships. Fix Up Existing Cottage Or Bu...

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

Residential, Detached
  • 3 Beds
  • Baths
  • 1,524 SQFT
  • 16 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 ...

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

Residential, Detached
  • 3 Beds
  • Baths
  • 2,023 SQFT
  • 143 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
  • 112 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...

7880 Chester Ct, Chestertown, MD - $349,900

Residential, Detached
  • 4 Beds
  • Baths
  • 2,464 SQFT
  • 55 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 July 23rd, 2019 at 8:15am EDT.