6,896

Chestertown, MD Homes

Section Image
  • 224 Valley Rd, Chestertown, MD 21620
    224 Valley Rd, Chestertown, MD 21620
    224 Valley Rd, Chestertown, MD 21620
    /24

    $455,000

    Sold Oct 21, 2025

    224 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1978

    Last Sold Summary

    • $241/SF
    • 13 Days On Market

    Current Estimated Value $462,081

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
    • 109 Coleman Dr, Chestertown, MD 21620
      109 Coleman Dr, Chestertown, MD 21620
      109 Coleman Dr, Chestertown, MD 21620
      /49

      Est $422,861

      Not Listed For Sale

      109 Coleman Dr, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 1,792 Sq Ft
      • Built 1988
      109 Coleman Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $228/SF
      • 1 Day On Market
      • Last Sold Price $409,000
      • May 31, 2024

      Last Listing Agent Ken Roderick Chesapeake Real Estate Associates, LLC

  • 208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    /16

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    208 Central Dr, Chestertown, MD 21620

    Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring

    Jennifer Pogoda Redfin Corp

    208 Central Dr, Chestertown, MD 21620
  • 124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    /31

    $250,000

    Sold Nov 11, 2025

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1967

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $252,267

    Last Listing Agent Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
    • 105 Coleman Dr, Chestertown, MD 21620
      105 Coleman Dr, Chestertown, MD 21620
      105 Coleman Dr, Chestertown, MD 21620
      /45

      Est $459,669

      Not Listed For Sale

      105 Coleman Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,128 Sq Ft
      • Built 1988
      105 Coleman Dr, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $207/SF
      • 2 Days On Market
      • Last Sold Price $440,000
      • Sep 16, 2024

      Last Listing Agent Jenn Klarman Long & Foster

  • 0 Spinnaker Rd, Chestertown, MD 21620
    0 Spinnaker Rd, Chestertown, MD 21620
    /2

    $38,000

    $17K PRICE INCREASE
    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • 24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    /45

    $310,000

    Sold Aug 15, 2025

    24095 Chestertown Rd, Chestertown, MD 21620

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

    Last Sold Summary

    • $281/SF
    • 87 Days On Market

    Current Estimated Value $302,895

    Last Listing Agent Lona Todd Taylor Properties

    24095 Chestertown Rd, Chestertown, MD 21620
    • 236 Duke of Kent St, Chestertown, MD 21620
      236 Duke of Kent St, Chestertown, MD 21620
      236 Duke of Kent St, Chestertown, MD 21620
      /29

      Est $411,899

      Not Listed For Sale

      236 Duke of Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1994
      236 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $202/SF
      • 1 Day On Market
      • Last Sold Price $359,000
      • Jun 08, 2023

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /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
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    /36

    $355,000

    Sold Aug 12, 2025

    114 Ryan Ct, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Built 1978

    Last Sold Summary

    • $237/SF
    • 83 Days On Market

    Current Estimated Value $374,169

    Last Listing Agent Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
    • 117 Primrose Rd, Chestertown, MD 21620
      117 Primrose Rd, Chestertown, MD 21620
      117 Primrose Rd, Chestertown, MD 21620
      /15

      Est $363,366

      Not Listed For Sale

      117 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,460 Sq Ft
      • Built 1972
      117 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $132/SF
      • 112 Days On Market
      • Last Sold Price $325,000
      • Feb 27, 2025

      Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

  • 115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    /40

    $296,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,864 Sq Ft

    115 Acorn Dr, Chestertown, MD 21620

    Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    115 Acorn Dr, Chestertown, MD 21620
  • 2010 Mcginnes Rd, Chestertown, MD 21620
    2010 Mcginnes Rd, Chestertown, MD 21620
    2010 Mcginnes Rd, Chestertown, MD 21620
    /19

    $354,900

    Sold Nov 10, 2025

    2010 Mcginnes Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,253 Sq Ft
    • Built 1962

    Last Sold Summary

    • $283/SF
    • 14 Days On Market

    Current Estimated Value $350,583

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
    • 205 Creston Rd, Chestertown, MD 21620
      205 Creston Rd, Chestertown, MD 21620
      205 Creston Rd, Chestertown, MD 21620
      /22

      Est $344,323

      Not Listed For Sale

      205 Creston Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,338 Sq Ft
      • Built 1975
      205 Creston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $252/SF
      • 16 Days On Market
      • Last Sold Price $337,000
      • Nov 08, 2024

      Last Listing Agent Jarnell Foster Benson & Mangold, LLC

  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /22

    $259,900

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

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in 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 walk-in

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    /29

    $359,900

    Sold Nov 24, 2025

    221 Old Bridge Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • Built 1924

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $368,532

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
    • 313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      /35

      Est $403,078

      Not Listed For Sale

      313 River Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft
      • Built 1964
      313 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $183/SF
      • 3 Days On Market
      • Last Sold Price $380,000
      • May 13, 2024

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /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
  • 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
    • 124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      /28

      Est $284,582

      Not Listed For Sale

      124 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1974
      124 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13% Above List Price
      • $239/SF
      • 2 Days On Market
      • Last Sold Price $252,000
      • May 22, 2024

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
    /2

    $40,000

    Under Contract
    • Land
    • 14,810 Sq Ft
    • $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
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,100,000

    Sold Jan 16, 2026

    300 Hickory Ln, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 1940

    Last Sold Summary

    • $302/SF
    • 163 Days On Market

    Current Estimated Value $1,121,345

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
    • 729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      /32

      Est $319,803

      Not Listed For Sale

      729 Rosin Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      729 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $275/SF
      • 5 Days On Market
      • Last Sold Price $289,900
      • Jul 30, 2024

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 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

    • 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
  • 206 Camelot Dr, Chestertown, MD 21620
    206 Camelot Dr, Chestertown, MD 21620
    206 Camelot Dr, Chestertown, MD 21620
    /65

    $455,000

    Sold Apr 13, 2026

    206 Camelot Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft
    • Built 2009

    Last Sold Summary

    • 13% Below List Price
    • $208/SF
    • 30 Days On Market

    Current Estimated Value $494,592

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
    • 201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      /50

      Est $324,410

      Not Listed For Sale

      201 Tamarack Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft
      • Built 1973
      201 Tamarack Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Below List Price
      • $279/SF
      • 1 Day On Market
      • Last Sold Price $342,000
      • Aug 14, 2024

      Last Listing Agent Petra Quinn Realty Navigator

  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /58

    $828,000

    Open House 5/30
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • 112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    /43

    $379,900

    Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $385,133

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, 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 $274,610

      Not Listed For Sale

      319 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1964
      319 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 96% Above List Price
      • $140/SF
      • 14 Days On Market
      • Last Sold Price $139,900
      • Aug 23, 2023

      Last Listing Agent Doug Ashley Doug Ashley Realtors, 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
  • 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 $789,505

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
    • 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

  • 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
  • 105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, 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 $452,473

    Last Listing Agent Lona Todd Taylor Properties

    105 Pearl Creek Ln, 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

  • 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
  • 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
    • 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

  • 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
  • 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

Showing Results 281 - 320, Page 8 of 18

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