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Chestertown, MD Homes for Sale; Chestertown Real Estate

Comprehensive real estate search in the Chestertown area. We have over 356 listings to browse so you can find your perfect home. Whether you are looking through our 342 MLS properties, 5 for sale by owner, — you're sure to find your next property with Roost.com.


  • 301 White's Heritage Lane Chestertown,MD 21620
    $429,900
    4 Bd | 3 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes
  • 301 White's Heritage Lane Chestertown,MD 21620
    $419,900
    2 Bd | 2 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes
  • 301 White's Heritage Lane Chestertown,MD 21620
    $379,900
    3 Bd | 3 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes
  • 301 White's Heritage Lane Chestertown,MD 21620
    $509,900
    4 Bd | 3 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes
  • 301 White's Heritage Lane Chestertown,MD 21620
    $469,900
    2 Bd | 3 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes
  • 108 Harlan Loop Chestertown,MD 21620-3367
    $259,990
    4 Bd | 3 Ba
    108 Harlan Loop Chestertown, MD 21620-3367
    Built (Spec Home) | New Homes
  • 301 White's Heritage Lane Chestertown,MD 21620
    $409,900
    3 Bd | 3 Ba
    301 White's Heritage Lane Chestertown, MD 21620
    Planned | New Homes

View our 9 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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  • 8978 Orchard Dr Chestertown,MD 21620-3406
    $544,900
    2 Bd | 4 Ba
    8978 Orchard Dr Chestertown, MD 21620-3406
    Single Family Home | For Sale By Owner
  • 200 Mill Street Chestertown,MD 21620
    $550,000
    3 Bd | 3 Ba
    200 Mill Street Chestertown, MD 21620
    Single Family Home | 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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About Chestertown, Maryland

The reality is that you're not looking for a house. You're looking for a home, and more-a space where you and your loved ones can feel secure, stimulated, and comfortable. Our Chestertown homes for sale and real estate 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 222 residential MLS listings available with an average price of $468,998. 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: Pearl Creek Ln.

Are you looking for tangible features or are you looking for a home in the Chestertown real estate market 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 $468,998 $223 88 84 25 9 16
For Sale By Owner $372,100 $176 2 0 2 0 0
New Homes $418,799 $149 0 8 1 0 0
Roost Blog
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.
Have you considered buying a home in one of these nearby locations?
Featured Builder Communities

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Featured Homes
  • 303 N Kent St Chestertown,MD 21620-1609
    303 N Kent St
    3 Bd | 2 Ba
    Single Family Home | For Sale By Owner
  • 301 White's Heritage Lane Chestertown,MD 21620
    301 White's Heritage Lane
    4 Bd | 3 Ba
    Planned | New Homes
  • 23161 Daniel Black Rd Chestertown,MD 21620-4044
    23161 Daniel Black Rd
    3 Bd | 1 Ba
    Single Family Home | For Sale By Owner
  • 301 White's Heritage Lane Chestertown,MD 21620
    301 White's Heritage Lane
    3 Bd | 3 Ba
    Planned | New Homes
  • 6340 Church Hill Rd Chestertown,MD 21620-2385
    6340 Church Hill Rd

    Commercial | For Sale By Owner
Real Estate Brokers in the area
  • Coldwell Banker Chesapeake Real Estate Co
  • Champion Realty, Inc.
  • The Hogans Agency
  • The Hogans Agency Inc.
  • Doug Ashley Realtors, LLC
  • Davis Real Estate, Inc.
  • W F Chesley Real Estate
  • Flaherty Group, Inc.
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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