7,017

Homes in ZIP Code 21620

Section Image
    • 204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      /12

      Est $907,023 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,945 Sq Ft

      204 Truslow Farm Ln, Chestertown, MD 21620

      204 Truslow Farm Ln, Chestertown, MD 21620
  • 201 Greenwood Ave, Chestertown, MD 21620
    201 Greenwood Ave, Chestertown, MD 21620
    201 Greenwood Ave, Chestertown, MD 21620
    /62

    $495,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 3,984 Sq Ft

    201 Greenwood Ave, Chestertown, MD 21620

    An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level

    Grace Crockett Doug Ashley Realtors, LLC

    201 Greenwood Ave, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /35

    $413,300 Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • 150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      /31

      Est $283,522 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      150 Longfellow Dr, Chestertown, MD 21620

      150 Longfellow Dr, Chestertown, MD 21620
  • 404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    /11

    $19,500 Under Contract

    • Land
    • 0.99 Acre
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Kent

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • 7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    /39

    $375,000 Sold Jan 08, 2026

    7653 Broad Neck Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft
    • Built 1987

    Last Sold Summary

    • $209/SF
    • 41 Days On Market

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • 200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      /26

      Est $390,631 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,477 Sq Ft

      200 Duke of Kent St, Chestertown, MD 21620

      200 Duke of Kent St, Chestertown, MD 21620
  • 0 Melitota Ln, Chestertown, MD 21620
    0 Melitota Ln, Chestertown, MD 21620
    /2

    $29,000 Under Contract

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, Chestertown, MD 21620
  • 249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    /28

    $343,600 Sold Mar 26, 2025

    249 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft
    • Built 2000

    Last Sold Summary

    • $221/SF
    • 14 Days On Market

    Current Estimated Value $351,089

    Last Listing Agent Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
    • 103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      /42

      Est $320,016 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft

      103 Creston Rd, Chestertown, MD 21620

      103 Creston Rd, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    /34

    $675,000 Coming Soon

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $75,000 Sold Dec 08, 2025

    109 2nd St, Chestertown, MD 21620

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 49 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
    • 218 Concord Rd, Chestertown, MD 21620
      218 Concord Rd, Chestertown, MD 21620
      218 Concord Rd, Chestertown, MD 21620
      /22

      Est $339,036 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      218 Concord Rd, Chestertown, MD 21620

      218 Concord Rd, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    /2

    $28,000 Pending

    • Land
    • 2 Acres
    • $14,000 per Acre

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    /66

    $868,000 Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Current Estimated Value $850,298

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • 411 Fairview Dr, Chestertown, MD 21620
      411 Fairview Dr, Chestertown, MD 21620
      411 Fairview Dr, Chestertown, MD 21620
      /30

      Est $660,382 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      411 Fairview Dr, Chestertown, MD 21620

      411 Fairview Dr, Chestertown, MD 21620
  • 8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    /47

    $364,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    8833 Georgetown Rd, Chestertown, MD 21620

    Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    /2

    $30,000 Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 0.83 Acre
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    • 240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      /34

      Est $445,715 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,067 Sq Ft

      240 Princess Anne Dr, Chestertown, MD 21620

      240 Princess Anne Dr, Chestertown, MD 21620
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    /38

    $575,000 Sold Jun 06, 2025

    129 N Queen St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 19 Days On Market

    Current Estimated Value $572,215

    Last Listing Agent William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
    • 209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      /26

      Est $420,325 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      209 Princess Anne Dr, Chestertown, MD 21620

      209 Princess Anne Dr, Chestertown, MD 21620
  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /40

    $598,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $392,500 Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
    • 112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      /21

      Est $339,583 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      112 Pine Chip Rd, Chestertown, MD 21620

      112 Pine Chip Rd, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 9048 Georgetown Rd, Chestertown, MD 21620
    9048 Georgetown Rd, Chestertown, MD 21620
    /2

    $45,000 Sold Mar 26, 2025

    9048 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 1.21 Acres
    • $37,190 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 713 Days On Market

    Current Estimated Value $46,693

    Last Listing Agent Beverly Sloane Benson & Mangold, LLC

    9048 Georgetown Rd, Chestertown, MD 21620
    • 1316 Ewingtown Rd, Chestertown, MD 21620
      1316 Ewingtown Rd, Chestertown, MD 21620
      1316 Ewingtown Rd, Chestertown, MD 21620
      /60

      Est $592,235 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,476 Sq Ft

      1316 Ewingtown Rd, Chestertown, MD 21620

      1316 Ewingtown Rd, Chestertown, MD 21620
  • 129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, MD 21620
    /41

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft

    129 Parma Rd, Chestertown, MD 21620

    Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

    Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma Rd, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $508,954 Sold Dec 04, 2025

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • $198/SF
    • 10 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
    • 201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      /5

      Est $401,552 Not Listed For Sale

      201 Duke of Kent St, Chestertown, MD 21620

      201 Duke of Kent St, Chestertown, MD 21620
  • 0 Elm Rd, Chestertown, MD 21620
    0 Elm Rd, Chestertown, MD 21620
    /2

    $40,000 Under Contract

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $312,000 Sold Jun 13, 2025

    306 Cedar St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1959

    Last Sold Summary

    • $222/SF
    • 55 Days On Market

    Current Estimated Value $323,057

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
    • 2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      /24

      Est $310,982 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft

      2607 Mcginnes Rd, Chestertown, MD 21620

      2607 Mcginnes Rd, Chestertown, MD 21620
  • Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • 7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    /24

    $299,900 Sold Jan 31, 2025

    7500 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2018

    Last Sold Summary

    • $233/SF
    • 30 Days On Market

    Current Estimated Value $321,017

    Last Listing Agent Lona Todd Taylor Properties

    7500 Shortall St, Chestertown, MD 21620
    • 208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      /23

      Est $284,284 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      208 Central Dr, Chestertown, MD 21620

      208 Central Dr, Chestertown, MD 21620
  • 108 Primrose Rd, Chestertown, MD 21620
    108 Primrose Rd, Chestertown, MD 21620
    108 Primrose Rd, Chestertown, MD 21620
    /49

    $375,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft

    108 Primrose Rd, Chestertown, MD 21620

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
  • 10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    /35

    $355,675 Sold Feb 28, 2025

    10724 Foreston Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1995

    Last Sold Summary

    • $190/SF
    • 3 Days On Market

    Current Estimated Value $376,198

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620
    • 112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      /48

      Est $513,958 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,864 Sq Ft

      112 Sheaffer Rd, Chestertown, MD 21620

      112 Sheaffer Rd, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 18

Maryland Kent County Chestertown 21620

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group