7,033

Homes in ZIP Code 21620

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  • /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
  • /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 $163,317

    Last Listing Agent Deborah Dawkins Coldwell Banker Realty

    508 Cannon St, Chestertown, MD 21620
    • /16

      Est $344,976 Not Listed For Sale

      102 Concord Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2023
      102 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $271/SF
      • 11 Days On Market

      Last Sold Price $334,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /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
  • /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
    • /80

      Est $639,689 Not Listed For Sale

      118 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,248 Sq Ft
      • Built 1985
      118 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $272/SF
      • 39 Days On Market

      Last Sold Price $612,500

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /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
  • /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 $359,201

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
    • /28

      Est $427,044 Not Listed For Sale

      209 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 1996
      209 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $207/SF
      • 67 Days On Market

      Last Sold Price $383,000

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /4

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Towhee Rd 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 3/16/2026 @ 10:00 AM. Bidding ends 3/18/2026 @ 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Towhee Rd 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 $362,213

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
    • /43

      Est $377,845 Not Listed For Sale

      129 Char Nor Manor Blvd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1961
      129 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Below List Price
      • $508/SF
      • 5 Days On Market

      Last Sold Price $411,500

      Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

  • /45

    $549,000 Under Contract

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

    206 S Water St, Chestertown, MD 21620

    Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, 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 $223,419

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
    • /30

      Est $420,636 Not Listed For Sale

      2771 Mcginnes Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,714 Sq Ft
      • Built 1999
      2771 Mcginnes Rd, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $216/SF
      • 5 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /39

    $295,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft

    107 Oak Leaf Dr, Chestertown, MD 21620

    Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience. Enjoy both sunrise and sunset views with an

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, 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 $305,336

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • /6

      Est $670,922 Not Listed For Sale

      305 Hickory Ln, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 2,627 Sq Ft
      • Built 1998
      305 Hickory Ln, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $234/SF

      Last Sold Price $615,000

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • /2

    $24,000

    • Land
    • 0.5 Acre
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23710 L Rd, 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

    Current Estimated Value $681,541

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
    • /21

      Est $194,989 Not Listed For Sale

      1521 Dudley Corners Rd, Millington, MD 21651

      • 3 Beds
      • 2 Baths
      • 1,032 Sq Ft
      • Built 1983
      1521 Dudley Corners Rd, Millington, MD 21651

      Last Sold Summary

      • 11% Above List Price
      • $170/SF
      • 101 Days On Market

      Last Sold Price $175,000

      Last Listing Agent John Smith HomeSmart

  • /46

    $369,000 Under Contract

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

    148 E Step Rd, Chestertown, MD 21620

    Price Improvement! This pristine rancher is barely three and a half years old and still looks brand new! Exceptionally well maintained and move-in ready! The home sits on nearly one-half acre (.457) and is one of the largest lots in the neighborhood. The lot is shaped in such a manner this it's like getting two for the price of one! There is plenty of space for play and entertaining immediately

    Norman Lee III Anne Arundel Properties, Inc.

    148 E Step Rd, 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 $249,118

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
    • /19

      Not Listed For Sale

      131 E Step Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1991
      131 E Step Rd, Chestertown, MD 21620

      Last Sold Summary

      • $121/SF
      • 3 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Lona Todd Taylor Properties

  • /33

    $395,000 Under Contract

    • 7 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    349 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 High St, 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
    • /5

      Est $592,212 Not Listed For Sale

      193 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,572 Sq Ft
      • Built 1974
      193 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $154/SF
      • 0 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /51

    $1,279,000

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, 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 $447,993

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • /23

      Not Listed For Sale

      107 Char Nor Manor Blvd, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,128 Sq Ft
      • Built 1999
      107 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • $179/SF
      • 56 Days On Market

      Last Sold Price $379,989

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /56

    $675,000 Open Sat 10AM - 12PM

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

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • /32

    $415,000 Sold Jan 07, 2026

    411 Greenwood Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft
    • Built 2003

    Last Sold Summary

    • $248/SF
    • 1 Day On Market

    Current Estimated Value $423,577

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
    • /24

      Est $232,990 Not Listed For Sale

      235 Burchard Sawmill Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1930
      235 Burchard Sawmill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Below List Price
      • $289/SF
      • 115 Days On Market

      Last Sold Price $250,000

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /2

    $10,000

    • Land
    • 0.55 Acre
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing 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 $316,395

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620
    • /49

      Est $427,555 Not Listed For Sale

      205 Deep Landing Rd, Chestertown, MD 21620

      • 4 Beds
      • 1 Bath
      • 1,456 Sq Ft
      • Built 1957
      205 Deep Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 50% Above List Price
      • $196/SF
      • 6 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Christopher Nolte Coldwell Banker Realty

  • /2

    $38,000

    • Land
    • 0.56 Acre
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, Chestertown, MD 21620
  • /34

    $265,000 Sold May 02, 2025

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1965

    Last Sold Summary

    • $238/SF
    • 120 Days On Market

    Current Estimated Value $275,210

    Last Listing Agent Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
    • /8

      Est $368,867 Not Listed For Sale

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft
      • Built 1965
      101 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $285/SF
      • 1 Day On Market

      Last Sold Price $330,000

      Last Listing Agent Samantha Powell Keller Williams Real Estate - Media

  • /4

    $10,000

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

    0 Bunting Rd, 6, Fairlee, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 4/24/2026 @ 10:00 AM. Bidding ends 4/28/2026, 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Bunting Rd, 6, Fairlee, MD 21620

Showing Results 241 - 280, Page 7 of 18

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