6,952

Homes in ZIP Code 21620

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  • /2

    $104,000

    Sold Aug 13, 2026

    116 N Cross St, Chestertown, MD 21620

    • Land
    • 7,840 Sq Ft
    • $577,778 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 74 Days On Market

    Current Estimated Value $107,426

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
    • /37

      Est $444,292

      Not Listed For Sale

      200 Ashley Ln, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft
      • Built 1980
      200 Ashley Ln, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • /2

    $37,000

    $22K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /60

    $1,165,000

    Sold Dec 01, 2025

    119 High St, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,409 Sq Ft
    • Built 1876

    Last Sold Summary

    • $264/SF
    • 5 Days On Market

    Current Estimated Value $1,153,904

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • /44

      Est $477,736

      Not Listed For Sale

      204 N Mill St, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft
      • Built 1920
      204 N Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /13

    $60,000

    • Land
    • 21,780 Sq Ft
    • $120,000 per Acre

    233 Merganser Dr, Chestertown, MD 21620

    Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

    Barbara Wallace Long & Foster Real Estate, Inc.

    233 Merganser Dr, Chestertown, MD 21620
  • /23

    $317,000

    Sold Mar 09, 2026

    213 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $257/SF
    • 67 Days On Market

    Current Estimated Value $315,898

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
    • /7

      Not Listed For Sale

      128 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft
      • Built 1900
      128 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /54

    $349,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    123 Heath Rd, Chestertown, MD 21620

    Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive

    Erin Anderson Chesapeake Real Estate Associates, LLC

    123 Heath Rd, Chestertown, MD 21620
  • /62

    $790,000

    Sold Sep 23, 2025

    209 Rivershore Rd, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft
    • Built 1978

    Last Sold Summary

    • $564/SF
    • 32 Days On Market

    Current Estimated Value $802,288

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • /23

      Est $402,566

      Not Listed For Sale

      101 S Kent St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 1880
      101 S Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Jennifer Gregorski Washington Fine Properties

  • /44

    $1,245,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /34

    $384,000

    Sold Jun 29, 2026

    23416 Cloquet Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2020

    Last Sold Summary

    • $254/SF
    • 6 Days On Market

    Current Estimated Value $385,938

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23416 Cloquet Rd, Chestertown, MD 21620
    • /61

      Est $537,820

      Not Listed For Sale

      325 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 4,086 Sq Ft
      • Built 2011
      325 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

  • /55

    $315,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    109 Parma Rd, Chestertown, MD 21620

    Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    109 Parma Rd, Chestertown, MD 21620
  • /16

    $240,000

    Sold Jan 16, 2026

    100 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $211/SF
    • 109 Days On Market

    Current Estimated Value $246,216

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
    • /38

      Est $595,786

      Not Listed For Sale

      129 N Queen St, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,296 Sq Ft
      • Built 1920
      129 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /11

    $19,500

    • Land
    • 43,124 Sq Ft
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Queen

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • /25

    $325,000

    Sold Jul 16, 2026

    10572 Watonga Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2007

    Last Sold Summary

    • $231/SF
    • 1 Day On Market

    Current Estimated Value $326,690

    Last Listing Agent Samantha Zarnes Serhant

    10572 Watonga Rd, Chestertown, MD 21620
    • /40

      Est $659,486

      Not Listed For Sale

      108 N Queen St, Chestertown, MD 21620

      • 5 Beds
      • 2.5 Baths
      • 2,536 Sq Ft
      • Built 1920
      108 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /2

    $135,000

    $15K PRICE DROP
    • Land
    • 1.8 Acres
    • $75,000 per Acre

    109 2nd St, Chestertown, MD 21620

    **STARTING 9/5 & ENDING 9/12: For one week only, list price is reduced to $125,000 with all closing costs covered by seller!** Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • /2

    $480,000

    Sold May 04, 2026

    101 Pine Tree Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1993

    Last Sold Summary

    • $260/SF
    • 0 Days On Market

    Current Estimated Value $480,030

    Last Listing Agent Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, Chestertown, MD 21620
    • /31

      Est $512,851

      Not Listed For Sale

      107 Adela Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft
      • Built 2010
      107 Adela Way, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Mike Herndon Engel & Völkers Annapolis

  • /25

    $315,000

    Coming Soon Sep 18
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space.The home

    Joseph A Zang III RE/MAX Chesapeake

    24775 Langford Rd, Chestertown, MD 21620
  • /16

    $120,000

    Sold Feb 27, 2026

    141 Prospect St, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 27% Below List Price
    • $104/SF
    • 33 Days On Market

    Current Estimated Value $139,248

    Last Listing Agent Jeff Guthrie Taylor Properties

    141 Prospect St, Chestertown, MD 21620
    • /43

      Est $433,341

      Not Listed For Sale

      105 Sutton Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2010
      105 Sutton Way, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:45 AM. 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 the Chester River. The area provides easy access to the

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
  • /15

    $155,000

    Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $206,734

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
    • /45

      Est $506,898

      Not Listed For Sale

      314 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,420 Sq Ft
      • Built 2010
      314 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Heather Branham The Parker Group

  • /4

    $110,000

    • Land
    • 1.93 Acres
    • $56,995 per Acre

    1906 Pondtown Rd, Chestertown, MD 21620

    Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes.

    Lonnie Gilmore Keller Williams Flagship

    1906 Pondtown Rd, Chestertown, MD 21620
  • /18

    $165,000

    Sold Jul 07, 2026

    144 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $152/SF
    • 24 Days On Market

    Current Estimated Value $156,981

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    144 Prospect St, Chestertown, MD 21620
    • /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      • Built 1982
      112 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Tammy Rosendale Rosendale Realty

  • /45

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    123 Trafford Dr, Chestertown, MD 21620

    Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    123 Trafford Dr, Chestertown, MD 21620
  • /17

    $335,000

    Sold Oct 03, 2025

    110 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 2023

    Last Sold Summary

    • $180/SF
    • 208 Days On Market

    Current Estimated Value $342,146

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
    • /8

      Est $415,162

      Not Listed For Sale

      200 Hoffman Ln, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,128 Sq Ft
      • Built 1957
      200 Hoffman Ln, Chestertown, MD 21620

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /35

    $359,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    101 S College Ave, Chestertown, MD 21620

    This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space.Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled

    Michele Palmer Doug Ashley Realtors, LLC

    101 S College Ave, Chestertown, MD 21620
  • /11

    $190,000

    Sold Mar 04, 2026

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $18,905 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 20 Days On Market

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
    • /28

      Est $369,558

      Not Listed For Sale

      249 Duke of Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,556 Sq Ft
      • Built 2000
      249 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Lee Wolff FSBO Broker

  • /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • /19

    $270,000

    Sold Mar 18, 2026

    119 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • Built 1997

    Last Sold Summary

    • 14% Below List Price
    • $190/SF
    • 14 Days On Market

    Current Estimated Value $272,083

    Last Listing Agent Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

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