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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 #1005560717

7689 Waterview Ln, Chestertown, MD - $625,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,138 SQFT
  • 541 DOM
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Beautiful Home Placed Along The 13th Fairway Of The Chester River Yacht & Country Club. Sit In The Pool, Porch, Hot Tub, Enjoy The Manicured Golf Course With Views Of The Chester River In The Distance.1st & 2nd Floor Masters Sitting Room, Washer/d...

Photo of Listing #1002400784

121 Lyons Ln, Chestertown, MD - $610,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,327 SQFT
  • 317 DOM
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Premium Materials And Finishes,including Yellow Pine Floors Reclaimed From Camden Yards,really Set This Waterfront Cape Apart.crown Moulding,wainscoting,panel Doors,fireplace,sun Room And Master On First Floor Are Among The Many Amenities.studio W...

Photo of Listing #MDQA136898

509 Fey Rd, Chestertown, MD - $599,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,906 SQFT
  • 149 DOM
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Just Reduced $50,000! Minutes From Chestertown, Shops, Washington College, Restaurants And Cultural Events. One Level Living On The Chester River On One And A Half Acres. Private Dock And A Nice Sandy Beach - You Will Feel Like You Are On Vacati...

7703 Waterview Ln, Chestertown, MD - $589,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 3,257 SQFT
  • 102 DOM
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This Magnificent Residence Is Situated Just Off The 13th Hole. If You Like To Golf, The Convenience Of Accessing The Course Doesn't Get Much Better! Expansive Views Over The Chester River Yacht & Country Club Golf Course To The Chester River Are...

0 Muirfield Dr, Chestertown, MD - $585,000

Residential, Detached
  • 3 Beds
  • Baths
  • 72 DOM
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Spec Home Located In Small 12 Home Development (to Be Built). Prestwick Offers The Best In Eastern Shore Living With The Small Town Charm Of Chestertown, Md, Yet Only 1 To 2 Hours From Wilmington, Philadelphia, Baltimore And Washington, Dc. Join...

10050 Forrest Ln, Chestertown, MD - $575,000

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 1,820 SQFT
  • 70 DOM
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Best Of All Worlds In This Waterfront Home With Easy Water Access And Natural Surroundings. Just Feel The Peace That Engulfs You As You Look Out From The Many Windows Of The Great Room. Boat, Walk, Bike, Or Drive To A Marina, Golf Course, Tennis, ...

Photo of Listing #MDKE114020

10191 Rileys Mill Rd, Chestertown, MD - $558,000

Residential, Detached
  • 3 Beds
  • Baths
  • 2,745 SQFT
  • 126 DOM
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Location, Location, Location The Best Of Both Worlds, A 3 Bedroom, 3.5 Bath Home In Park Like, Private Setting On Morgnec Creek Just Minutes From Historic Chestertown. This Home Offers Waterfront Views From Nearly Every Room, First Floor Bedroom, ...

Photo of Listing #1002276762

5830 Langford Bay Rd, Chestertown, MD - $538,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,437 SQFT
  • 331 DOM
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Cozy 3 Bdr Waterfront Home With All The Natural, Private Surroundings The Eastern Shore Has To Offer. Very Easy Access To More Than 300 Feet Of Bulkheaded Shoreline. 2 Large Detached Garages To Store All The Waterfront Toys You Will Need To Take...

Photo of Listing #MDKE115054

7842 Radcliffe Rd, Chestertown, MD - $535,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,928 SQFT
  • 74 DOM
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Water Views Of The Chester River Are A Visual Delight From This Outstanding Property On The Eastern Shore. Set On 1.3-acres In A Highly-desirable Residential Area, The Meticulously Cared For Home Is Just A Walk Away From Chester River Yacht & Coun...

Photo of Listing #1001973778

6100 Pine Acres Rd, Chestertown, MD - $525,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,138 SQFT
  • 376 DOM
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Nature's Paradise On Lovely Cove-enjoy A Short And Peaceful Boat/kayak Ride From Your Private Dock To The East Fork Of Langford Creek. This Comfortable Waterfront Home Celebrates 180 Degrees Water Views, Available From Virtually All Rooms. Outbuil...

0 Turnberry Ct, Chestertown, MD - $519,900

Residential, Detached
  • 3 Beds
  • Baths
  • 2,200 SQFT
  • 83 DOM
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Spec Home Located On Corner Lot Located In Small 12 Home Development (to Be Built). Prestwick Offers The Best In Eastern Shore Living With The Small Town Charm Of Chestertown Md, Yet Only 1 To 2 Hours From Wilmington, Philadelphia, Baltimore And ...

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...

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.