6,952

Homes in ZIP Code 21620

Section Image
    • /33

      Est $326,155

      Not Listed For Sale

      10550 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2006
      10550 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /38

    $474,990

    Sold May 18, 2026

    728 Aldora Dr Unit 113, Chestertown, MD 21620

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

    Last Sold Summary

    • $185/SF
    • 286 Days On Market

    Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

    728 Aldora Dr Unit 113, Chestertown, MD 21620
    • /28

      Est $534,514

      Not Listed For Sale

      116 Harlan Loop, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 4,067 Sq Ft
      • Built 2009
      116 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Robert Kaetzel Real Estate Professionals, Inc.

  • /23

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • /42

    $360,000

    Sold Jun 12, 2026

    720 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $283/SF
    • 13 Days On Market

    Current Estimated Value $361,164

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    720 Deep Landing Rd, Chestertown, MD 21620
    • /7

      Est $326,301

      Not Listed For Sale

      23235 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23235 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /9

    $99,999

    • Land
    • 3,096 Sq Ft
    • $1,406,963 per Acre

    620 Cannon St, Chestertown, MD 21620

    Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available.

    Julie Santoboni Taylor Properties

    620 Cannon St, Chestertown, MD 21620
  • /74

    $459,000

    Sold Mar 27, 2026

    105 Pearl Creek Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,961 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Above List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $449,547

    Last Listing Agent Lona Todd Taylor Properties

    105 Pearl Creek Ln, Chestertown, MD 21620
    • /29

      Est $295,680

      Not Listed For Sale

      10670 Tintah Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      10670 Tintah Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Bronwyn Scott Samson Properties

  • /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
  • /2

    $318,000

    Sold Aug 14, 2026

    109 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,397 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Below List Price
    • $228/SF
    • 4 Days On Market

    Current Estimated Value $326,807

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    109 Cedar St, Chestertown, MD 21620
    • /13

      Est $330,322

      Not Listed For Sale

      23399 Cloquet Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2004
      23399 Cloquet Rd, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /60

    $1,495,000

    $155K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • /45

    $545,000

    Sold Apr 30, 2026

    206 S Water St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,008 Sq Ft
    • Built 1900

    Last Sold Summary

    • 7% Below List Price
    • $271/SF
    • 40 Days On Market

    Current Estimated Value $546,490

    Last Listing Agent Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
    • /28

      Est $573,144

      Not Listed For Sale

      305 Washington Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,476 Sq Ft
      • Built 1930
      305 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • /29

    $264,900

    Sold Oct 30, 2025

    24415 Chestertown Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft
    • Built 1962

    Last Sold Summary

    • $239/SF
    • 23 Days On Market

    Current Estimated Value $268,838

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • /12

      Est $343,440

      Not Listed For Sale

      203 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1963
      203 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Alex Modaressi RE/MAX Distinctive Real Estate, Inc.

  • /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
  • /70

    $550,000

    Sold Dec 05, 2025

    302 Rosin Dr, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 3,877 Sq Ft
    • Built 1996

    Last Sold Summary

    • $142/SF
    • 5 Days On Market

    Current Estimated Value $554,137

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    302 Rosin Dr, Chestertown, MD 21620
    • /27

      Est $276,684

      Not Listed For Sale

      316 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1966
      316 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • /48

    $535,000

    Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Current Estimated Value $533,048

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • /20

      Est $386,029

      Not Listed For Sale

      508 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1921
      508 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Deborah Dawkins Coldwell Banker Realty

  • /34

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

    A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • /14

    $329,000

    Sold May 27, 2026

    10594 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 2020

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $332,240

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    10594 Millbrook Dr, Chestertown, MD 21620
    • /13

      Est $239,988

      Not Listed For Sale

      21286 Maine Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 2001
      21286 Maine Ave, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Kristie Midash L. C. Parker Real Estate

  • /23

    $299,900

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

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis

    Beth Green Doug Ashley Realtors, LLC

    124 Wilton Rd, Chestertown, MD 21620
  • /42

    $260,000

    Sold Feb 18, 2026

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1954

    Last Sold Summary

    • $230/SF
    • 170 Days On Market

    Current Estimated Value $263,245

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
    • /9

      Est $195,633

      Not Listed For Sale

      619 Cannon St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 882 Sq Ft
      • Built 1983
      619 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • /2

    $38,000

    $23K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • /13

    $295,000

    Sold Mar 31, 2026

    107 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2004

    Last Sold Summary

    • $152/SF
    • 8 Days On Market

    Current Estimated Value $294,601

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
    • /28

      Est $295,100

      Not Listed For Sale

      545 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft
      • Built 1900
      545 High St, Chestertown, MD 21620

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • /20

    $314,000

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
  • /14

    $85,000

    Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Current Estimated Value $150,628

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • /47

      Est $325,580

      Not Listed For Sale

      9041 S Bayview Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 2009
      9041 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Gregory Osborn Long & Foster Real Estate, Inc.

  • /26

    $339,900

    Sold Jun 05, 2026

    21125 Iowa Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1962

    Last Sold Summary

    • $263/SF
    • 54 Days On Market

    Current Estimated Value $335,728

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21125 Iowa Ave, Chestertown, MD 21620
    • /31

      Est $302,872

      Not Listed For Sale

      10640 Watonga Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,196 Sq Ft
      • Built 1995
      10640 Watonga Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /67

    $2,100,000

    Sold Feb 02, 2026

    10121 Fairlee Rd, Chestertown, MD 21620

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft
    • Built 1858

    Last Sold Summary

    • $424/SF
    • 58 Days On Market

    Current Estimated Value $1,955,265

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620

Showing Results 361 - 400, Page 10 of 18

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