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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 #MDQA140686

153 Longfellow Dr, Chestertown, MD - $159,900

Residential, Detached
  • 3 Beds
  • Baths
  • 1,376 SQFT
  • 7 DOM
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Offering This 3br Home That Backs To Open Farm Land In Water Oriented Community Situated On A Beautiful Shaded Lot.

134 Char Nor Manor Blvd, Chestertown, MD - $159,000

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,128 SQFT
  • 12 DOM
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House Is In Need Of Some Repairs And Work. No Central Heating Or Air Conditioning. A Few Upgrades Have Been Done With A New Bathroom. Rt. 213 To Rt. 544, To Past Duck Neck Camp Ground. Property On Right Down Char Nor Manor Blvd. Sign Posted.

807 High St, Chestertown, MD - $150,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 1,296 SQFT
  • 797 DOM
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Great Potential. This Fixer-upper Is Located Within Walking Distance Of The College, Downtown, And The Town Waterfront. It Also Has Great Investment Potential As A Rental Or Office Space. Currently Used As A Rental With A Month To Month Lease In P...

610 High St, Chestertown, MD - $149,950

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,536 SQFT
  • 149 DOM
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Home In The Historic District Has Been Recently Updated With New Cabinets, Counters And 25.5 Cu Ft Refrigerator, Laminate-wood Flooring, Wall-to-wall Carpet, Most Light Fixtures And Paint. Walk To Washington College, Shops, Restaurants And Waterf...

Photo of Listing #MDKE115460

118 Conley Dr, Chestertown, MD - $147,000

Residential, Semi-Detached
  • 3 Beds
  • Baths
  • 1,280 SQFT
  • 6 DOM
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Easy Living On A Quiet Street In Chestertown. Walk To The Grocery Store, Pharmacy And Other Shopping And Dining. 3 Bedrooms And One And A Half Bath. Enclosed Rear Porch. Fenced Back Yard And A Shed For Storage.

10141 Flatland Rd, Chestertown, MD - $139,000

Residential, Detached
  • 4 Beds
  • 1 Baths
  • 2,142 SQFT
  • 82 DOM
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Located On Spacious 2 Acres And Only Minutes From Down Town Chestertown. Room To Add Bathroom/s Or Extend Kitchen. Lots Of Charm With Wood Burning Stove And Fireplace. Cozy Side Porch, 3 Outbuildings/sheds, Gravel Drive, Updated Windows, Insulatio...

604 Cannon St, Chestertown, MD - $125,000

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,416 SQFT
  • 46 DOM
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A Must See Inside, Much Bigger Than It Looks From The Road. Covered Front Porch And Deep Rear Yard With Shed. Main Level Living Offers 3 Bedrooms And Fuill Bath. Fireplace In Living Room. Nice Size Kitchen & Dining Room. Full Basement With Walk Ou...

Photo of Listing #MDKE115458

8221 Tolchester Rd #7, Chestertown, MD - $123,000

Residential, Condo, End of Row/Townhouse
  • 3 Beds
  • 1 Baths
  • 1,269 SQFT
  • 6 DOM
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Buy For Less Than You Can Rent In Kent County's Newest Affordable Living Community! Six 3 Bedroom Townhouse-style Units Are Available In Tolchester Village Condominiums. The Complex Has Been Completely Renovated & Upgraded With Public Water & Sewe...

Photo of Listing #MDKE115466

8223 Tolchester Rd #1, Chestertown, MD - $109,000

Residential, Condo, Semi-Detached
  • 2 Beds
  • 1 Baths
  • 1,087 SQFT
  • 5 DOM
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Why Rent When You Can Buy One Of These Affordable Homes For Less Than $900 Per Month. There Are Three, 2 Bedroom Duplex-style Homes Available. Completely Renovated And Upgraded, These Single Level Units Have New Carpet, Stainless Steel Appliances,...

233 N Lynchburg St, Chestertown, MD - $99,000

Residential, Detached
  • 2 Beds
  • 1 Baths
  • 768 SQFT
  • 65 DOM
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Tired Of Renting? Looking For An Investment Property? This Might Be Your Solution. This Two Bedroom, One Bath Home Is Not Only Affordable But Convenient To Downtown Chestertown. Living, Dining And Kitchen Are Open And Inviting. Fixed Stairs Lead T...

7415 Wilkins Ln, Chestertown, MD - $86,000

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 1,000 SQFT
  • 30 DOM
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This Ranch Home Is Located About Five To Six Minutes Outside Of Chestertown. Home Has New Carpet, Some New Paint. Affordably Priced With Three Bedrooms, 1 Bath, And A Detached Storage Shed. Don't Be Mortgage Poor. With A Little Elbow Grease...

602 Cannon St, Chestertown, MD - $79,000

Residential, Detached
  • 2 Beds
  • Baths
  • 42 DOM
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Bring Your Plans & Start Building! The Footprint Is Solid, The Water & Sewer Lines Are Brand New, The Electric Supply And Breaker Box Are Brand New, And The Lot Is Huge With Tons Of Potential! All Within Walking Distance To Everything Downtown Che...

22974 Bay Shore Rd, Chestertown, MD - $79,000

Residential, Detached
  • 2 Beds
  • 1 Baths
  • 1,440 SQFT
  • 40 DOM
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Handyman Special, Needs Work, Lots Of Potential. Rt. 20, To Right In Fairlee To Bayshore Road, Property On The Right.

310 N College Ave, Chestertown, MD - $74,900

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 2,520 SQFT
  • 131 DOM
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Investor Alert! Two Buildings On One Property Near Downtown Chestertown And Washington College. Property Being Sold As-is.

102 Prospect St, Chestertown, MD - $74,900

Residential, Detached
  • 4 Beds
  • 2 Baths
  • 1,824 SQFT
  • 131 DOM
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Investor Opportunity Near Downtown Chestertown And Washington College. Previously Set Up As Four, 1 Bedroom Apartments. Property Sold As-is.

Photo of Listing #1001536056

21363 Indiana Ave, Chestertown, MD - $69,900

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 896 SQFT
  • 429 DOM
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Tolchester Beach Cottage - Cozy 3 Bedroom, 1 Bath Cottage With Public Sewer On Large Lot With Outbuilding And Mature Trees. Home Needs Some Cosmetic Tlc, But Would Be Perfect For Your Weekend Getaway. Community Access To Beach Area And Chesapeak...

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.