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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 #MDKE115456

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

Residential, Semi-Detached
  • 2 Beds
  • Baths
  • 1,476 SQFT
  • 7 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,...

244 Devon Dr, Chestertown, MD - $332,000

Residential, Detached
  • 4 Beds
  • Baths
  • 3,708 SQFT
  • 47 DOM
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Simply Stunning!!! This 3700 Sq Ft Colonial Boasts Soaring Ceilings, Gleaming Hardwoods, Gourmet Kitchen, Spacious, Open Floor-plan, 4 Large Upper-level Bedrooms W/ A Master Suite To Rival Some Hotel Suites! His & Hers Walk-in- Closets, Large & Br...

21457 Belair Ave, Chestertown, MD - $329,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,694 SQFT
  • 20 DOM
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Looking For A Cottage In The Woods? This .60-acre Private Haven, Centrally Located 10 Minutes From Chestertown And Rock Hall, Is Quite The Secluded Spot. Bordered By Mature Landscape, The Property Welcomes Local Wildlife, Which Is Perfect For Nat...

Photo of Listing #MDQA140694

105 Sheaffer Road, Chestertown, MD - $329,000

Residential, Detached
  • 4 Beds
  • Baths
  • 1,784 SQFT
  • 14 DOM
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This Is It! $329,000 And 4 Years Young In The Grove. 4 Bedrooms, 2.5 Bathrooms, Kitchen With Soapstone Countertops, Porcelain Farm Kitchen Sink, Stainless Steel Appliances, 20x25 Rear Patio Off Of The Kitchen Ideal For Entertaining... While Thi...

Photo of Listing #1000083933

200 Mill St, Chestertown, MD - $327,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,198 SQFT
  • 850 DOM
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Lovely Victorian With Many Original Details.beautiful Wood Floors, Fireplace, Updated Kitchen And Baths, New Carpet In Master Bedroom And Fresh Paint Throughout.third Floor Bedroom Could Be Home Office.the Porches And Patio Provide Nice Outdoor Li...

207 N Queen St, Chestertown, MD - $325,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,244 SQFT
  • 61 DOM
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Welcome To This Prime Historic District Location In Charming Chestertown! This Home Features Victorian Style, Original Wide Plank Hardwood Floors, Many Of The Rooms Feature Chair Rail, And Cornices, With High Ceilings. Two Non-working Slate Fire ...

Photo of Listing #MDQA140560

114 Holly Ct, Chestertown, MD - $320,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,830 SQFT
  • 24 DOM
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3 Bedroom 2 Bath Rancher On 1.03 Acres In Qa County! Kitchen Offers Corian Counters, Stainless Appliances. New Flooring And Paint In Some Of The Rooms. Four Season Florida Room Overlooks Nicely Landscaped Yard With Mature Trees. Large Deck Off Of ...

Photo of Listing #1001408767

7 Cedar Chase Ct, Chestertown, MD - $299,900

Residential, Detached
  • 4 Beds
  • Baths
  • 2,397 SQFT
  • 631 DOM
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One Of A Kind Home In Mile Tree Village. With Views Of The Chester River And Your Own Private Pond! This Large Home Boasts 4 Bedrooms With 2.5 Baths! A Two Car Garage And Bonus Room At The Basement Level. The Elevator From The Basement/garage Area...

304 Princess Anne Dr, Chestertown, MD - $299,000

Residential, Detached
  • 3 Beds
  • Baths
  • 1,722 SQFT
  • 26 DOM
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Chestertown Life Is Waiting. This Beautifully Renovated Home Is Turn Key And Ready For You. Hgtv Inspired With Hardwood Floors Throughout. This Home Has All The Bells And Whistles. Spacious Entertaining Kitchen With Tile Floors, Tons Of Light, New...

23550 Canvasback Rd, Chestertown, MD - $298,000

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 2,284 SQFT
  • 22 DOM
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Located At The End Of A Culdesac, This Mill Creek Waterfront Home Offers Real Peace And Quiet. The Walk-out Basement Is Partially Finished With Potential For 1 Or 2 More Bedrooms. New Electric Panel, Water, Heater, Water Conditioner, Roof, Gutte...

114 Grant Ct, Chestertown, MD - $297,350

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 8 DOM
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Construction Underway. 3 Bedroom 2 Bath Rancher With Garage. One Of 9 Lots Two Pick From. House Going To Be Loaded With Upgrades. Sit Back And Enjoy The Views. Open Floor Plan Or Bring Us Your Plans As Well. You Can Pick Out Your Colors And Make T...

200 Richard Dr, Chestertown, MD - $295,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,653 SQFT
  • 41 DOM
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One Block Away From The Chester River And Two Blocks Away From Downtown Chestertown, This Home Offers An Updated Kitchen With Two Wall Ovens, Avanza Countertops, Ceramic Tile Floor With A Brick Fireplace And Skylight. The Large Addition On The Bac...

Photo of Listing #MDQA140848

121 Justin Buch Dr, Chestertown, MD - $295,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,680 SQFT
  • 5 DOM
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Immaculate!! Ready To Move In. 3 Bdr, 2 Full Bath, Den, Pantry, Custom Closet, All New Appliances, Attached 2 Car Garage, Full Attic, Deck, Out Building. Sitting On A Large Lot On A Quiet Cul-de-sac. Minutes From Charming Chestertown And Step...

530 Cannon St, Chestertown, MD - $294,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,012 SQFT
  • 54 DOM
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An Upgraded Colonial Home On Revitalized Cannon Street. This Home Features Hardwood Floors Throughout, Upgraded Kitchen And Baths, Vaulted Ceilings, Central Hvac, First Floor Powder Room, And A Tulikivi Pizza Oven! Outside Is A Custom Two Story Wo...

331 Devon Dr, Chestertown, MD - $289,000

Residential, Detached
  • 4 Beds
  • Baths
  • 3,834 SQFT
  • 82 DOM
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Located In The Desirable Coventry Farms Community. This Move In Ready Colonial Offers 4 Bedrooms, 2.5 Baths, Open Kitchen/breakfast Room/family Room With Surround Sound. Partially Finished Basement With Rough-ins For A Bathroom And A Wet Bar.

Photo of Listing #MDKE107880

21357 Bel Air Ave, Chestertown, MD - $287,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,008 SQFT
  • 173 DOM
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9 Year Old Cape With Wonderful Open Floor Plan. Nestled In The Woods For Privacy. Bay Water Privileges And Marina Nearby. This Property Is Part Of Tolchester Estates.

217 Richard Dr, Chestertown, MD - $285,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,231 SQFT
  • 13 DOM
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Charming Ranch Home Located A Stones Throw From Historic District Of Lovely Chestertown. This Home Boasts Three Bedrooms, 2.5 Baths, A Sunroom, Partially Finished Basement, One Car Garage And A Beautifully Landscaped Lot. The Basement Contains Ple...

Photo of Listing #MDQA140336

240 Duke Of Kent St, Chestertown, MD - $284,999

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 1,792 SQFT
  • 3 DOM
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This Won't Last Long! Well Maintained Rancher In A Great Neighborhood. Home Has Been Freshly Renovated Over The Last Year Which Includes New Roof, Beautiful Landscaping, Trex Multilevel Decking, Hardwood Floors, Interior/exterior Doors And Light F...

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.