7,035

Homes in ZIP Code 21620

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    • /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

    $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
  • /2

    $325,000 Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $335,557

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, 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

  • /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
  • /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 $685,638

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, 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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /56

    $675,000 Open House 4/04

    • 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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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 3/16/2026 @ 10:00 AM. Bidding ends 3/18/2026 @ 12:30 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
  • /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
    • /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

  • /18

    $225,000 Under Contract

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

    513 Round Top Rd, Chestertown, MD 21620

    Ready for your next investment with built-in equity? 513 Round Top Rd presents a fantastic opportunity for homeowners and investors who love forced appreciation! With all major systems in place, this 4bd/1ba rancher ready for your vision without breaking the bank. Simple cosmetic improvements can make this home rent ready or produce a nice profit on a fix and flip. Being sold as is. Bring your

    Ben Garner Cummings & Co. Realtors

    513 Round Top 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
    • /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

  • /26

    $786,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, 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
    • /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

  • /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon 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
    • /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

  • /2

    $40,000 Under Contract

    • Land
    • 0.34 Acre
    • $117,647 per Acre

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620

    Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

    Jo Ann Edwards The Hogans Agency

    0 Tonopah Rd Unit MDKE2005564, 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
    • /17

      Est $226,420 Not Listed For Sale

      305 Pine Tree Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1961
      305 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13% Below List Price
      • $315/SF
      • 298 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /19

    $3,000,000

    • Land
    • 87.34 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community.

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, 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
    • /71

      Est $541,107 Not Listed For Sale

      139 Church Meadow Ct, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 2008
      139 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $183/SF
      • 3 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Scott Hogan Long & Foster

Showing Results 241 - 280, Page 7 of 18

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