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Chestertown, MD Homes for Sale; Chestertown, MD MLS Listings

Comprehensive real estate search in the Chestertown area. We have over 365 listings to browse so you can find your perfect home. Whether you are looking through our 324 MLS properties, 5 for sale by owner, 30 foreclosures — you're sure to find your next property with Roost.com.


  • 103 Sutton Way Chestertown,MD 21620-3368
    $199,990
    3 Bd | 3 Ba
    103 Sutton Way Chestertown, MD 21620-3368
    Planned | New Homes
  • 103 Sutton Way Chestertown,MD 21620-3368
    $214,990
    4 Bd | 3 Ba
    103 Sutton Way Chestertown, MD 21620-3368
    Planned | New Homes
  • 103 Sutton Way Chestertown,MD 21620-3368
    $244,990
    4 Bd | 3 Ba
    103 Sutton Way Chestertown, MD 21620-3368
    Planned | New Homes
  • 103 Sutton Way Chestertown,MD 21620-3368
    $254,990
    4 Bd | 3 Ba
    103 Sutton Way Chestertown, MD 21620-3368
    Planned | New Homes

View our 6 New Homes Listings in Chestertown

See all homes by builder and community. View both planned and spec real estate properties including their floor plans. Here is a sample of our listings...

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  • 6340 Church Hill Rd Chestertown,MD 21620-2385
    $750,000
    6340 Church Hill Rd Chestertown, MD 21620-2385
    Commercial | For Sale By Owner
  • 234 N Kent St Chestertown,MD 21620-1341
    $274,900
    3 Bd | 1 Ba
    234 N Kent St Chestertown, MD 21620-1341
    Single Family | For Sale By Owner

View our 5 For Sale By Owner Listings in Chestertown

We've gathered For Sale By Owner listings for you. Filter them by price, bed bath, neighborhood, school district and more. Here are just a few of our FSBO listings...

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  • Camelot Dr Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $60,000
  • Church Hill Rd Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $300,000
  • Devon Dr Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $60,000
  • Garland Way Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $65,000
  • Harlan Loop Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $80,000
  • Pine St Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This 1 bath single family home is 1,054 ft.²
    The status of this foreclosure is listed as Bank Owned with a price of: $107,000
  • Pondtown Rd Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This 1 bath single family home is 864 ft.²
    The status of this foreclosure is listed as Bank Owned with a price of: $235,079
  • Church Hill Rd Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This commercial is 4,800 ft.²
    The status of this foreclosure is listed as Bank Owned with a price of: $300,000
  • Devon Dr Chestertown, MD 21620 See similar Chestertown homes in Bank Owned
    This miscellaneous
    The status of this foreclosure is listed as Bank Owned with a price of: $70,000

See the 30 Foreclosure Listings in Chestertown, MD

We have one of the best collections of foreclosure listings available! Filter them by status: Default, Auction or Bank Owned.

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About Chestertown, Maryland

Congratulations! You are about to set out on the exciting journey the road to home ownership. Our Chestertown homes for sale and MLS listings are the most comprehensive available. You can search Roost.com for all your real estate needs; including Multiple Listing Service ( MLS ) properties for sale; homes for sale by owner (FSBO); new construction listings and foreclosures / foreclosed properties.

There are approximately 207 residential MLS listings available having an average price of $565,300. If you have children, you may be interested in homes for sale in these school districts: Kent County Public Schools and Queen Annes County Public Schools. Streets with the most MLS listings include: Washington Ave.

Are you looking for tangible features or are you looking for a home in the Chestertown MLS that just feels right? Start with the basics like number of beds and baths then use our intuitive filters to zero in on homes for sale by neighborhood or school district. You can even search for amenities such as pool, remodeled kitchen, hardwood and more! Roost is the perfect search for your perfect home.

Residential Property Listing Facts
  Avg Price Price/Sq Ft 0-250k 251-500k 501-750k 751-1M 1M+
MLS Listings $566,757 $202 73 82 18 11 21
For Sale By Owner $412,450 $213 0 1 1 0 0
New Homes $231,657 $103 5 1 0 0 0
Foreclosure $209,274 $181 12 1 0 0 0
Homes that have recently sold in Chestertown

Search all of our recent sold information and compare them to homes on the MLS

Address City Price Beds Baths Sq.Ft Date Sold
26959 MORGNEC RD CHESTERTOWN $987,000 - 4 1,500 08/14/2009
7834 RADCLIFFE RD CHESTERTOWN $469,000 - 2 2,600 08/03/2009
203 CONCORD RD CHESTERTOWN $159,000 - 1 1,200 07/30/2009
107 TRAFFORD DR CHESTERTOWN $336,000 - - - 07/27/2009
10771 CARIMON RD CHESTERTOWN $187,000 - 2 1,700 07/24/2009
310 DEVON DR CHESTERTOWN $340,000 - - - 07/21/2009
403 CANNON ST CHESTERTOWN $580,000 - 3 1,000 07/20/2009
329 DEVON DR CHESTERTOWN $357,000 - - - 07/20/2009
Roost Blog
Real Estate Brokers in the area
  • Coldwell Banker Residential Brokerage
  • Champion Realty, Inc.
  • The Hogans Agency
  • The Hogans Agency Inc.
  • Davis Real Estate, Inc.
  • Chesapeake Real Estate Associates, LLC
  • W F Chesley Real Estate
  • Sam Martin Realty Assoc., LLC
Real Estate Inventory
MLS Listings324
New Construction6
For Sale by Owner5
Foreclosures30
Total Listings365

Featured Builder Communities

Search all of our recent sold information and compare them to homes on the MLS

Click to expand map view of listings
Featured Homes
  • 303 N Kent St Chestertown,MD 21620-1609
    303 N Kent St
    3 Bd | 2 Ba
    Single Family | For Sale By Owner
  • 103 Sutton Way Chestertown,MD 21620-3368
    103 Sutton Way
    3 Bd | 2 Ba
    Planned | New Homes
  • 23161 Daniel Black Rd Chestertown,MD 21620-4044
    23161 Daniel Black Rd
    3 Bd | 1 Ba
    Single Family | For Sale By Owner
  • 103 Sutton Way Chestertown,MD 21620-3368
    103 Sutton Way
    4 Bd | 3 Ba
    Planned | New Homes
  • 200 Mill  Street Chestertown,MD 21620
    200 Mill Street
    3 Bd | 3 Ba
    Single Family | For Sale By Owner
Average Chestertown Sales Price (12 Month Trend)
These MLS listings represent the most currently available real estate including single family homes, multiple family homes, condos, foreclosures and other property types for CITY NAME STATE. These residences are featured by BROKER NAME via Broker Reciprocity with the data updated nightly. Too many listings? Then refine your search by price, bedrooms, baths, square feet (lot size), or even local school district. Then work with our REALTOR(R) partners to find the perfect home for sale, and help you find the right mortgage financing, best mortgage rates & right insurance policies for your needs.
Why People Prefer Roost

Most real estate sites rely on individuals to upload their own listings. This usually results in a fragmented and partial view of what homes are truly available for sale. Even worse, it often means stale info. We partner with the local "Multiple Listing Services" ( MLS ) and local real estate brokers in Chestertown to ensure you have access to not only the most complete, but also the most up-to-date homes for sale available.

Zip Codes in Chestertown

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