7,017

Homes in ZIP Code 21620

Section Image
  • 107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    /23

    $379,989 Sold Jan 30, 2025

    107 Char Nor Manor Blvd, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,128 Sq Ft
    • Built 1999

    Last Sold Summary

    • $179/SF
    • 56 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    107 Char Nor Manor Blvd, Chestertown, MD 21620
    • 216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      /62

      Est $408,957 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
  • 303 Cedar St, Chestertown, MD 21620
    303 Cedar St, Chestertown, MD 21620
    303 Cedar St, Chestertown, MD 21620
    /26

    $333,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    303 Cedar St, Chestertown, MD 21620

    Great Chestertown location in College Heights. Large corner lot consisting of .51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and

    Hayley Norris Select Land & Homes, LLC

    303 Cedar St, 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

    $740,000 Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
    • 306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      /25

      Est $429,746 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 $681,823

    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 $1,163,738 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

    $455,000

    • 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 $248,305

    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 $316,684 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

    This property will be back on the market in the spring/2026. If you are interested please reach out for a private tour! The listing agreement is still in place. 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

    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 $345,456 Not Listed For Sale

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

      102 Concord Rd, Chestertown, MD 21620

      102 Concord Rd, 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 or

    Anastasia Zivkovic Cummings & Co. Realtors

    234 N College 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

    Current Estimated Value $351,997

    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 $588,236 Not Listed For Sale

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

      118 Westwood Ln, Chestertown, MD 21620

      118 Westwood Ln, Chestertown, MD 21620
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900 Under Contract

    • 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
  • 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 $356,641

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
    • 209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      /28

      Est $411,223 Not Listed For Sale

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

      209 Myers Rd, Chestertown, MD 21620

      209 Myers Rd, Chestertown, MD 21620
  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $445,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, 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

    Current Estimated Value $217,005

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, 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 $412,923 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
  • 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 $301,081

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • 2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      /30

      Est $413,038 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
  • 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
    • 305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      /6

      Est $669,765 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
  • 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
  • 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 $242,577

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, 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 $223,078 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
  • 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
  • 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
    • 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
  • 0 Towhee Rd 21620
    0 Towhee Rd 21620
    0 Towhee Rd 21620
    /4

    $10,000

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

    0 Towhee Rd 21620

    POST AUCTION - Make an offer, buy it now! 4 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road.

    Adam Shpritz Ashland Auction Group LLC

    0 Towhee Rd 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

    Current Estimated Value $439,051

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • 193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      /5

      Est $620,823 Not Listed For Sale

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

      193 Westwood Ln, Chestertown, MD 21620

      193 Westwood Ln, Chestertown, MD 21620
  • 105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    /73

    $449,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 1,961 Sq Ft

    105 Pearl Creek Ln, Chestertown, MD 21620

    (Open House January 31 from 10:00 - 12:00) Welcome to your private Eastern Shore retreat on 1.37 acres. Built in 2018, this beautiful custom one-level home is thoughtfully designed for relaxed, everyday living and effortless entertaining. Sun-filled and inviting, the open layout creates a warm, comfortable atmosphere—perfect for gathering with family and friends or enjoying quiet moments at home.

    Lona Todd Taylor Properties

    105 Pearl Creek Ln, 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 $310,459

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620

Showing Results 201 - 240, Page 6 of 18

Maryland Kent County Chestertown 21620

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