7,041

Homes in ZIP Code 21620

Section Image
    • 332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      /29

      Est $307,910

      Not Listed For Sale

      332 Truslow Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft
      • Built 1900
      332 Truslow Rd, Chestertown, MD 21620

      Last Sold Summary

      • 22% Above List Price
      • $179/SF
      • 118 Days On Market
      • Last Sold Price $252,400
      • Aug 12, 2024

      Last Listing Agent James Blackwell Blackwell Real Estate, LLC

  • 0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 14,810 Sq Ft
    • $29,412 per Acre

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620

    Build Your Dream Home on Two Expansive Lots in Chesapeake Landing!15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks!Enjoy the charm of Chestertown living, just

    Rena Champaco Samson Properties

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, 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 $547,139

    Last Listing Agent Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
    • 707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      /31

      Est $343,595

      Not Listed For Sale

      707 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1976
      707 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1% Above List Price
      • $262/SF
      • 75 Days On Market
      • Last Sold Price $340,000
      • Jun 06, 2024

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • 24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    /29

    $229,990

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    24581 Willow Oak Ln, Chestertown, MD 21620

    If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

    Michele Palmer Doug Ashley Realtors, LLC

    24581 Willow Oak Ln, Chestertown, MD 21620
  • 24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, 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 $276,164

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • 324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      /25

      Est $348,510

      Not Listed For Sale

      324 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1988
      324 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $228/SF
      • 1 Day On Market
      • Last Sold Price $309,900
      • Dec 18, 2023

      Last Listing Agent Christopher Carr HomeZu

  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /30

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely

    Ashley Earle Compass

    423 Calvert St, Chestertown, MD 21620
  • 302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, 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 $568,486

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    302 Rosin Dr, Chestertown, MD 21620
    • 118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      /33

      Est $492,133

      Not Listed For Sale

      118 Harlan Loop, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,900 Sq Ft
      • Built 2009
      118 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $149/SF
      • 8 Days On Market
      • Last Sold Price $432,000
      • Aug 08, 2023

      Last Listing Agent Cindy Genther Rock Hall Properties

  • 101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    /56

    $524,900

    • 3 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    101 Coleman Dr, Chestertown, MD 21620

    Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life.Inside, the home is designed

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    101 Coleman Dr, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck 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 $520,751

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

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • 105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      /58

      Est $846,751

      Not Listed For Sale

      105 S Water St, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft
      • Built 1900
      105 S Water St, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $283/SF
      • 64 Days On Market
      • Last Sold Price $725,000
      • Jan 26, 2024

      Last Listing Agent Richard Keaveney Cross Street Realtors LLC

  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /92

    $865,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    /28

    $549,000

    Sold Jun 26, 2025

    305 Washington Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • Built 1930

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $590,842

    Last Listing Agent William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $278,213

      Not Listed For Sale

      114 School Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft
      • Built 1966
      114 School Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $227/SF
      • 71 Days On Market
      • Last Sold Price $249,900
      • Feb 27, 2024

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    /2

    $215,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft

    100 Prospect St, Chestertown, MD 21620

    Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything.Most homes in this price range make you choose: updated systems or a great location. This one delivers both.Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the

    David Moore Real Broker, LLC

    100 Prospect St, Chestertown, MD 21620
  • 26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    /49

    $840,000

    Sold Jun 27, 2025

    26865 Mallard Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft
    • Built 1963

    Last Sold Summary

    • $250/SF
    • 182 Days On Market

    Current Estimated Value $977,943

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $426,925

      Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $234/SF
      • 9 Days On Market
      • Last Sold Price $380,000
      • Oct 03, 2024

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • 9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    /48

    $535,000

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft

    9816 Fairlee Rd, Chestertown, MD 21620

    Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of

    Scott Hogan Long & Foster Real Estate, Inc.

    9816 Fairlee Rd, Chestertown, MD 21620
  • 811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    /45

    $459,000

    Sold Jun 23, 2025

    811 S Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $491,674

    Last Listing Agent Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $341,689

      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

      • 12% Above List Price
      • $217/SF
      • 2 Days On Market
      • Last Sold Price $305,000
      • Aug 02, 2024

      Last Listing Agent David Moore Real Broker, LLC

  • 0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    /7

    $5,000

    • Land
    • 16,117 Sq Ft
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/1/2026 @ 10:00 AM. Bidding ends 6/3/2026 @ 12:40 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 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /24

    $285,000

    Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $1,140,290

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $325,394

      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

      • 9% Above List Price
      • $214/SF
      • 12 Days On Market
      • Last Sold Price $299,900
      • Nov 27, 2023

      Last Listing Agent David Moore Real Broker, LLC

  • 21324 Persimmon Dr, Chestertown, MD 21620
    21324 Persimmon Dr, Chestertown, MD 21620
    21324 Persimmon Dr, Chestertown, MD 21620
    /17

    $124,900

    $27K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21324 Persimmon Dr, Chestertown, MD 21620

    2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with stainless steel appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Common areas include a playground. Affordable,

    JT Powell Coldwell Banker Realty - Washington

    21324 Persimmon Dr, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, 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 $262,507

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $331,819

      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

      • 11% Above List Price
      • $198/SF
      • 41 Days On Market
      • Last Sold Price $300,000
      • Oct 12, 2023

      Last Listing Agent David Moore Real Broker, LLC

  • 109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    /28

    $264,900

    New Construction Pending
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    109 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless-steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    109 Metcalfe Rd, Chestertown, MD 21620
  • 107 Oak Leaf Dr, Chestertown, MD 21620
    107 Oak Leaf Dr, Chestertown, MD 21620
    107 Oak Leaf Dr, 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 $293,113

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
    • 101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      /39

      Est $324,475

      Not Listed For Sale

      101 S College Ave, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft
      • Built 1920
      101 S College Ave, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $295/SF
      • 1 Day On Market
      • Last Sold Price $305,435
      • Aug 08, 2023

      Last Listing Agent Jimmy White Long & Foster

  • 154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    /27

    $299,000

    $16K PRICE DROP Under Contract
    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    154 Longfellow Dr, Chestertown, MD 21620

    Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy

    Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, Chestertown, MD 21620
  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, 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 $125,511

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $342,474

      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

      • 49% Above List Price
      • $131/SF
      • 12 Days On Market
      • Last Sold Price $230,111
      • Feb 09, 2024

      Last Listing Agent Alex Modaressi RE/MAX

  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $9,000

    $3K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • 10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    /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 $2,096,715

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
    • 316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      /27

      Est $272,931

      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

      • 3% Below List Price
      • $233/SF
      • 37 Days On Market
      • Last Sold Price $280,000
      • Feb 16, 2024

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • 110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    /2

    $525,000

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,785 Sq Ft

    110 S Queen St, Chestertown, MD 21620

    Prime Location in Downtown Chestertown. Approximately 1,785 square feet, zoned RB (live/work), has 4 off-street parking spaces, and much more. Coming Soon - Stay Tuned...

    J.P. Graham Cross Street Realtors LLC

    110 S Queen St, Chestertown, MD 21620
  • 212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    /21

    $309,500

    Sold Jul 31, 2025

    212 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1972

    Last Sold Summary

    • $280/SF
    • 2 Days On Market

    Current Estimated Value $315,969

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    212 Central Dr, Chestertown, MD 21620
    • 21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      /13

      Est $255,196

      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

      • 19% Above List Price
      • $215/SF
      • 83 Days On Market
      • Last Sold Price $215,000
      • Nov 27, 2023

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

Showing Results 321 - 360, Page 9 of 18

Maryland Kent County Chestertown 21620

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group