7,013

Homes in ZIP Code 21620

Section Image
    • 216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      /62

      Est $400,532 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      216 Princess Anne Dr, Chestertown, MD 21620

      216 Princess Anne Dr, Chestertown, MD 21620
  • 10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    /41

    $750,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    10230 John Carvill Rd, Chestertown, MD 21620

    Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock

    Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /5

    $160,000 Sold Sep 15, 2025

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $15,920 per Acre

    Last Sold Summary

    • 26 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    0 Hoffecker Rd, Chestertown, MD 21620
    • 306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      /25

      Est $436,592 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,871 Sq Ft

      306 Rosin Dr, Chestertown, MD 21620

      306 Rosin Dr, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000 Pending

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    /47

    $690,000 Sold Aug 25, 2025

    7071 Pomona Rd, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,544 Sq Ft
    • Built 1991

    Last Sold Summary

    • $271/SF
    • 3 Days On Market

    Current Estimated Value $682,263

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, Chestertown, MD 21620
    • 545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      /8

      Est $1,295,365 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft

      545 Fey Rd, Chestertown, MD 21620

      545 Fey Rd, Chestertown, MD 21620
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $470,000

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    /20

    $150,000 Sold Jun 06, 2025

    508 Cannon St, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1921

    Last Sold Summary

    • $67/SF
    • 0 Days On Market

    Current Estimated Value $255,648

    Last Listing Agent Deborah Dawkins Coldwell Banker Realty

    508 Cannon St, Chestertown, MD 21620
    • 120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      /18

      Est $323,500 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      120 Edmore Rd, Chestertown, MD 21620

      120 Edmore Rd, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /71

    $649,000

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    /5

    $11,000 Sold May 29, 2025

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    • Land
    • 0.34 Acre
    • $32,353 per Acre

    Last Sold Summary

    • 371 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    • 102 Concord Rd, Chestertown, MD 21620
      102 Concord Rd, Chestertown, MD 21620
      102 Concord Rd, Chestertown, MD 21620
      /16

      Est $343,062 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      102 Concord Rd, Chestertown, MD 21620

      102 Concord Rd, Chestertown, MD 21620
  • 411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    /32

    $419,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft

    411 Greenwood Ave, Chestertown, MD 21620

    Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
  • 111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    /38

    $349,000 Sold Oct 16, 2025

    111 Cee Jay Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $249/SF
    • 10 Days On Market

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
    • 118 Westwood Ln, Chestertown, MD 21620
      118 Westwood Ln, Chestertown, MD 21620
      118 Westwood Ln, Chestertown, MD 21620
      /80

      Est $617,043 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,248 Sq Ft

      118 Westwood Ln, Chestertown, MD 21620

      118 Westwood Ln, Chestertown, MD 21620
  • 234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    /3

    $164,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location!Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation

    Anastasia Zivkovic Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • 10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    /22

    $359,000 Sold Jul 31, 2025

    10575 Hyala Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 2003

    Last Sold Summary

    • $181/SF
    • 5 Days On Market

    Current Estimated Value $354,330

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
    • 119 Darden Rd, Chestertown, MD 21620
      119 Darden Rd, Chestertown, MD 21620
      119 Darden Rd, Chestertown, MD 21620
      /48

      Est $315,584 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,424 Sq Ft

      119 Darden Rd, Chestertown, MD 21620

      119 Darden Rd, Chestertown, MD 21620
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900

    • Land
    • 0.48 Acre
    • $185,208 per Acre

    0 East St, Chestertown, MD 21620

    This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience.The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those

    William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $215,000 Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
    • 209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      /28

      Est $426,675 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft

      209 Myers Rd, Chestertown, MD 21620

      209 Myers Rd, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /46

    $619,000

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • 9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    /38

    $285,000 Sold Sep 05, 2025

    9190 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1969

    Last Sold Summary

    • $246/SF
    • 12 Days On Market

    Current Estimated Value $298,697

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • 129 Char Nor Manor Blvd, Chestertown, MD 21620
      129 Char Nor Manor Blvd, Chestertown, MD 21620
      129 Char Nor Manor Blvd, Chestertown, MD 21620
      /43

      Est $421,057 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 810 Sq Ft

      129 Char Nor Manor Blvd, Chestertown, MD 21620

      129 Char Nor Manor Blvd, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land

    Lori Sample EXIT Preferred Realty

    0 Fairlee Rd, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /39

    $695,000 Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
    • 2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      /30

      Est $410,703 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,714 Sq Ft

      2771 Mcginnes Rd, Chestertown, MD 21620

      2771 Mcginnes Rd, Chestertown, MD 21620
  • 0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 0.11 Acre
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • 107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    /19

    $230,000 Sold May 01, 2025

    107 Chester Arms Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2022

    Last Sold Summary

    • $202/SF
    • 14 Days On Market

    Current Estimated Value $242,617

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
    • 305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      /6

      Est $665,286 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 2,627 Sq Ft

      305 Hickory Ln, Chestertown, MD 21620

      305 Hickory Ln, Chestertown, MD 21620
  • 112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    /43

    $369,900 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft

    112 Silver Heel Dr, Chestertown, MD 21620

    Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with

    Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
  • 0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    /12

    $162,000 Sold Nov 10, 2025

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620

    • Land
    • 5.34 Acres
    • $30,337 per Acre

    Last Sold Summary

    • 64 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    • 1521 Dudley Corners Rd, Millington, MD 21651
      1521 Dudley Corners Rd, Millington, MD 21651
      1521 Dudley Corners Rd, Millington, MD 21651
      /21

      Est $199,403 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,032 Sq Ft

      1521 Dudley Corners Rd, Millington, MD 21651

      1521 Dudley Corners Rd, Millington, MD 21651
  • 0 Sheldrake Dr, Chestertown, MD 21620
    0 Sheldrake Dr, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, Chestertown, MD 21620
  • 22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    /73

    $435,000 Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • 131 E Step Rd, Chestertown, MD 21620
      131 E Step Rd, Chestertown, MD 21620
      131 E Step Rd, Chestertown, MD 21620
      /19

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft

      131 E Step Rd, Chestertown, MD 21620

      131 E Step Rd, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /20

    $249,950

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed for

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • 10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    /31

    $305,000 Sold Apr 01, 2025

    10640 Watonga Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1995

    Last Sold Summary

    • $255/SF
    • 2 Days On Market

    Current Estimated Value $308,477

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620
    • 193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      /5

      Est $673,699 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,572 Sq Ft

      193 Westwood Ln, Chestertown, MD 21620

      193 Westwood Ln, Chestertown, MD 21620

Showing Results 201 - 240, Page 6 of 18

Maryland Kent County Chestertown 21620

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