7,012

Homes in ZIP Code 21620

Section Image
    • 201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      /50

      Est $359,223 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft

      201 Tamarack Rd, Chestertown, MD 21620

      201 Tamarack Rd, Chestertown, MD 21620
  • 0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    /3

    $20,000

    • Land
    • 0.09 Acre
    • $222,222 per Acre

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
  • 202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    /37

    $290,000 Sold May 08, 2025

    202 Glen St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,252 Sq Ft
    • Built 1966

    Last Sold Summary

    • $232/SF
    • 104 Days On Market

    Current Estimated Value $296,819

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    202 Glen St, Chestertown, MD 21620
    • 319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      /16

      Est $244,447 Not Listed For Sale

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

      319 Round Top Rd, Chestertown, MD 21620

      319 Round Top Rd, Chestertown, MD 21620
  • 0 Cromwell Clark Rd, Chestertown, MD 21620
    0 Cromwell Clark Rd, Chestertown, MD 21620
    0 Cromwell Clark Rd, Chestertown, MD 21620
    /19

    $3,000,000 Pending

    • 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
  • 1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    /27

    $250,000 Sold May 22, 2025

    1106 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft
    • Built 1973

    Last Sold Summary

    • $200/SF
    • 16 Days On Market

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
    • 332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      /29

      Est $307,358 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft

      332 Truslow Rd, Chestertown, MD 21620

      332 Truslow Rd, Chestertown, MD 21620
  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /24

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Cross Street Realtors LLC

    109 S College Ave, Chestertown, MD 21620
  • 228 Concord Rd, Chestertown, MD 21620
    228 Concord Rd, Chestertown, MD 21620
    228 Concord Rd, Chestertown, MD 21620
    /26

    $325,000 Sold Dec 12, 2024

    228 Concord Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1974

    Last Sold Summary

    • $217/SF
    • 25 Days On Market

    Current Estimated Value $337,488

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    228 Concord Rd, Chestertown, MD 21620
    • 332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      /19

      Est $301,425 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,263 Sq Ft

      332 Longfellow Dr, Chestertown, MD 21620

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

    $10,000

    • Land
    • 0.34 Acre
    • $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
  • Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    /22

    $155,200 Sold Mar 31, 2025

    Lot 4 Muirfield Dr, Chestertown, MD 21620

    • Land
    • 1.9 Acres
    • $81,684 per Acre

    Last Sold Summary

    • 300 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    Lot 4 Muirfield Dr, Chestertown, MD 21620
    • 537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      /43

      Est $345,472 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,304 Sq Ft

      537 Truslow Rd, Chestertown, MD 21620

      537 Truslow Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /69

    $539,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 224 Spring Rd, Millington, MD 21651
    224 Spring Rd, Millington, MD 21651
    224 Spring Rd, Millington, MD 21651
    /26

    $375,000 Sold Feb 28, 2025

    224 Spring Rd, Millington, MD 21651

    • Land
    • 50 Acres
    • $7,500 per Acre

    Last Sold Summary

    • 171 Days On Market

    Current Estimated Value $377,514

    Last Listing Agent Rob Freyer Charis Realty Group

    224 Spring Rd, Millington, MD 21651
    • 707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      /31

      Est $345,431 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      707 Round Top Rd, Chestertown, MD 21620

      707 Round Top Rd, Chestertown, MD 21620
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $269,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    /71

    $745,000 Sold Jun 26, 2025

    9050 Point Ln, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,166 Sq Ft
    • Built 2000

    Last Sold Summary

    • $235/SF
    • 7 Days On Market

    Current Estimated Value $761,055

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
    • 324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      /25

      Est $337,853 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft

      324 Longfellow Dr, Chestertown, MD 21620

      324 Longfellow Dr, Chestertown, MD 21620
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /73

    $875,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 3,720 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • 110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    /29

    $600,000 Sold Feb 06, 2025

    110 Birch Run Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,672 Sq Ft
    • Built 2007

    Last Sold Summary

    • $225/SF
    • 155 Days On Market

    Current Estimated Value $647,272

    Last Listing Agent Paula Ruckelshaus Long & Foster Real Estate, Inc.

    110 Birch Run Rd, Chestertown, MD 21620
    • 121 Tuxedo Rd, Chestertown, MD 21620
      121 Tuxedo Rd, Chestertown, MD 21620
      121 Tuxedo Rd, Chestertown, MD 21620
      /35

      Est $293,181 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,144 Sq Ft

      121 Tuxedo Rd, Chestertown, MD 21620

      121 Tuxedo Rd, Chestertown, MD 21620
  • 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

    $10,000

    • Land
    • 0.37 Acre
    • $27,027 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    POST AUCTION/BUY NOW: MAKE AN OFFER! Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road.

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 833 Woods Rd, Chestertown, MD 21620
    833 Woods Rd, Chestertown, MD 21620
    /2

    $155,000 Sold Dec 17, 2024

    833 Woods Rd, Chestertown, MD 21620

    • Land
    • 3 Acres
    • $51,667 per Acre

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $149,333

    Last Listing Agent Tina Brown Benson & Mangold, LLC

    833 Woods Rd, Chestertown, MD 21620
    • 210 Creston Rd, Chestertown, MD 21620
      210 Creston Rd, Chestertown, MD 21620
      210 Creston Rd, Chestertown, MD 21620
      /6

      Est $281,268 Not Listed For Sale

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

      210 Creston Rd, Chestertown, MD 21620

      210 Creston Rd, Chestertown, MD 21620
  • 109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    /27

    $264,900 New Construction

    • 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
  • 149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    /25

    $385,000 Sold Apr 11, 2025

    149 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft
    • Built 1982

    Last Sold Summary

    • $213/SF
    • 19 Days On Market

    Current Estimated Value $387,840

    Last Listing Agent Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
    • 118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      /33

      Est $479,362 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,900 Sq Ft

      118 Harlan Loop, Chestertown, MD 21620

      118 Harlan Loop, Chestertown, MD 21620
  • 206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    /37

    $615,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft

    206 Valley Rd, Chestertown, MD 21620

    Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
  • 308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    /32

    $782,500 Sold May 09, 2025

    308 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2017

    Last Sold Summary

    • $355/SF
    • 10 Days On Market

    Current Estimated Value $784,569

    Last Listing Agent John Burke Gunther-McClary Real Estate

    308 Landing Ln, 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 $827,600 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft

      105 S Water St, Chestertown, MD 21620

      105 S Water St, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, 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

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $262,262 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft

      114 School Rd, Chestertown, MD 21620

      114 School Rd, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.61 Acre
    • $14,754 per Acre

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620

    Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
  • 204 Spring Rd, Millington, MD 21651
    204 Spring Rd, Millington, MD 21651
    /2

    $110,000 Sold Feb 28, 2025

    204 Spring Rd, Millington, MD 21651

    • 1 Bath
    • 759 Sq Ft
    • Built 1925

    Last Sold Summary

    • $145/SF
    • 59 Days On Market

    Current Estimated Value $163,000

    Last Listing Agent Karen Marshall Long & Foster Real Estate, Inc.

    204 Spring Rd, Millington, MD 21651
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $409,718 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft

      23118 Raleigh Rd, Chestertown, MD 21620

      23118 Raleigh Rd, Chestertown, MD 21620
  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • 201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    /22

    $319,000 Sold Mar 31, 2025

    201 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1985

    Last Sold Summary

    • $269/SF
    • 49 Days On Market

    Current Estimated Value $320,970

    Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $339,742 Not Listed For Sale

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

      10550 Klamath Rd, Chestertown, MD 21620

      10550 Klamath Rd, Chestertown, MD 21620

Showing Results 281 - 320, Page 8 of 18

Maryland Kent County Chestertown 21620

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