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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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8520 Airy Hill Rd, Chestertown, MD - $635,000

Residential, Detached
  • 4 Beds
  • Baths
  • 2,492 SQFT
  • 29 DOM
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Eastern Shore Vermont Style Farmhouse Built In 2006 Is Set On A Rural 10-acre Meadow Backing Up To Woods. The Farmland Across The Street Is In Conservation. This Beautiful, Thoughtfully Designed Home With Two Geo-thermal Wells, High Ceilings And L...

Photo of Listing #1002400784

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

Residential, Detached
  • 4 Beds
  • Baths
  • 2,327 SQFT
  • 372 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 #1005560717

7689 Waterview Ln, Chestertown, MD - $600,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,138 SQFT
  • 596 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 #MDQA136898

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

Residential, Detached
  • 4 Beds
  • Baths
  • 2,906 SQFT
  • 159 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...

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

Residential, Detached
  • 3 Beds
  • Baths
  • 127 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
  • 125 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 #MDKE115054

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

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,928 SQFT
  • 109 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
  • 431 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
  • 138 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
  • 358 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...

10191 Rileys Mill Rd, Chestertown, MD - $498,500

Residential, Detached
  • 3 Beds
  • Baths
  • 2,745 SQFT
  • 18 DOM
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This 3 Bedroom, 3-1/2 Bath Waterfront Home Is Located In A Beautiful Spot Overlooking Morgan Creek, Just Off Of The Chester River. Secluded And Private But Only 5 Miles From All The Charm And Events In Historic Chestertown. There Are Views Of The...

Photo of Listing #MDKE115430

9181 American Legion Rd, Chestertown, MD - $474,900

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,200 SQFT
  • 65 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...

5830 Langford Bay Rd, Chestertown, MD - $465,000

Residential, Detached
  • 3 Beds
  • Baths
  • 1,972 SQFT
  • 10 DOM
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Beautiful And Unique, 3 Bdr, 3 Level, Waterfront Home. Located In Langford Bay Estates And Nestled Back On The West Fork Of Langford Creek On Long Cove. This Property Offers 300ft Of Bulkheaded Shoreline, A Private Dock With Water And Electric Ac...

Photo of Listing #MDKE107934

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

Residential, Detached
  • 3 Beds
  • Baths
  • 229 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 ...

332 Queen St, Chestertown, MD - $449,900

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 2,060 SQFT
  • 18 DOM
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Circa 1870 Home With Chester River Views Situated On An Acre-plus Just Blocks From Downtown Chestertown And Washington College. Enjoy The Private, Park-like Setting Of This Hilltop Property Located In A Quiet Riverfront Neighborhood. The 3-story,...

Photo of Listing #1000479984

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

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,107 SQFT
  • 502 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 ...

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

Residential, Detached
  • 3 Beds
  • Baths
  • 2,202 SQFT
  • 129 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...

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.