6,890

Chestertown, MD Homes

Section Image
  • 23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    /31

    $310,000

    Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $314,902

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • 109 Edmore Rd, Chestertown, MD 21620
      109 Edmore Rd, Chestertown, MD 21620
      109 Edmore Rd, Chestertown, MD 21620
      /24

      Est $343,309

      Not Listed For Sale

      109 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1993
      109 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 24 Days On Market

  • 25750 Collins Ave, Chestertown, MD 21620
    25750 Collins Ave, Chestertown, MD 21620
    25750 Collins Ave, Chestertown, MD 21620
    /50

    $468,000

    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Charming Brick Rancher Near the Chester RiverThis custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home...Living Room: Walk

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /18

    $620,000

    Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Current Estimated Value $624,475

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • 130 Sheaffer Rd, Chestertown, MD 21620
      130 Sheaffer Rd, Chestertown, MD 21620
      130 Sheaffer Rd, Chestertown, MD 21620
      /25

      Est $451,072

      Not Listed For Sale

      130 Sheaffer Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,766 Sq Ft
      • Built 1999
      130 Sheaffer Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    /41

    $740,000

    Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Current Estimated Value $777,271

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
    • 228 Concord Rd, Chestertown, MD 21620
      228 Concord Rd, Chestertown, MD 21620
      228 Concord Rd, Chestertown, MD 21620
      /26

      Est $340,542

      Not Listed For Sale

      228 Concord Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1974
      228 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25 Days On Market

  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $10,000

    Pending
    • Land
    • 23,958 Sq Ft
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 303 Cedar St, Chestertown, MD 21620
    303 Cedar St, Chestertown, MD 21620
    /2

    $325,000

    Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $330,783

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
    • 415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      /24

      Est $612,784

      Not Listed For Sale

      415 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1973
      415 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

  • 121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 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

    121 Metcalf Rd, Chestertown, MD 21620
  • 301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    /40

    $293,000

    Sold Jun 08, 2026

    301 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 54 Days On Market

    Current Estimated Value $295,759

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
    • 319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      /37

      Est $684,733

      Not Listed For Sale

      319 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 2,128 Sq Ft
      • Built 1961
      319 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 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
  • 103 Flying Cloud Dr, Chestertown, MD 21620
    103 Flying Cloud Dr, Chestertown, MD 21620
    /2

    $339,900

    Sold Apr 21, 2026

    103 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2023

    Last Sold Summary

    • $197/SF
    • 0 Days On Market

    Current Estimated Value $339,854

    Last Listing Agent Laura Snyder American Premier Realty, LLC

    103 Flying Cloud Dr, Chestertown, MD 21620
    • 312 Princess Anne Dr, Chestertown, MD 21620
      312 Princess Anne Dr, Chestertown, MD 21620
      312 Princess Anne Dr, Chestertown, MD 21620
      /87

      Est $415,558

      Not Listed For Sale

      312 Princess Anne Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 1,848 Sq Ft
      • Built 1987
      312 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 31 Days On Market

  • 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
  • 7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    /47

    $690,000

    Sold Aug 25, 2025

    7071 Pomona Rd, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,544 Sq Ft
    • Built 1991

    Last Sold Summary

    • $271/SF
    • 3 Days On Market

    Current Estimated Value $717,128

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, Chestertown, MD 21620
    • 221 River Rd, Chestertown, MD 21620
      221 River Rd, Chestertown, MD 21620
      221 River Rd, Chestertown, MD 21620
      /80

      Est $413,815

      Not Listed For Sale

      221 River Rd, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1969
      221 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

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

    $259,900

    New Construction Pending
    • 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
  • 2032 Pondtown Rd, Chestertown, MD 21620
    2032 Pondtown Rd, Chestertown, MD 21620
    2032 Pondtown Rd, Chestertown, MD 21620
    /32

    $365,000

    Sold May 29, 2026

    2032 Pondtown Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2007

    Last Sold Summary

    • 12% Above List Price
    • $326/SF
    • 9 Days On Market

    Current Estimated Value $325,677

    Last Listing Agent Joie White Northrop Realty

    2032 Pondtown Rd, Chestertown, MD 21620
    • 125 Primrose Rd, Chestertown, MD 21620
      125 Primrose Rd, Chestertown, MD 21620
      125 Primrose Rd, Chestertown, MD 21620
      /48

      Est $382,953

      Not Listed For Sale

      125 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,102 Sq Ft
      • Built 1976
      125 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 50 Days On Market

  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $275,000

    Under Contract
    • 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
  • 111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    /38

    $349,000

    Sold Oct 16, 2025

    111 Cee Jay Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $249/SF
    • 10 Days On Market

    Current Estimated Value $353,440

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
    • 210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      /42

      Est $402,776

      Not Listed For Sale

      210 Rosin Dr, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,352 Sq Ft
      • Built 1987
      210 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 39 Days On Market

  • 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
  • 21363 Lynn Ln, Chestertown, MD 21620
    21363 Lynn Ln, Chestertown, MD 21620
    21363 Lynn Ln, Chestertown, MD 21620
    /28

    $205,000

    Sold Jul 02, 2026

    21363 Lynn Ln, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft
    • Built 1955

    Last Sold Summary

    • $156/SF
    • 5 Days On Market

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    21363 Lynn Ln, Chestertown, MD 21620
    • 126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      /57

      Est $511,105

      Not Listed For Sale

      126 Hilltop Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,733 Sq Ft
      • Built 2001
      126 Hilltop Dr, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

  • 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
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $215,000

    Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Current Estimated Value $220,647

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
    • 216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      /62

      Est $415,335

      Not Listed For Sale

      216 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1986
      216 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

  • 202 Pine St, Chestertown, MD 21620
    202 Pine St, Chestertown, MD 21620
    /2

    $205,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,341 Sq Ft

    202 Pine St, Chestertown, MD 21620

    Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights. A diamond in the rough and ready for new owners.

    Jay McCall Coldwell Banker Chesapeake Real Estate Company

    202 Pine St, Chestertown, MD 21620
  • 10584 Klamath Rd, Chestertown, MD 21620
    10584 Klamath Rd, Chestertown, MD 21620
    10584 Klamath Rd, Chestertown, MD 21620
    /20

    $320,000

    Sold Jul 08, 2026

    10584 Klamath Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    10584 Klamath Rd, Chestertown, MD 21620
    • 545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      /8

      Est $1,143,914

      Not Listed For Sale

      545 Fey Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft
      • Built 1948
      545 Fey Rd, Chestertown, MD 21620

      Last Sold Summary

  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /57

    $798,000

    $30K PRICE DROP Pending
    • 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
  • 9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    /38

    $285,000

    Sold Sep 05, 2025

    9190 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1969

    Last Sold Summary

    • $246/SF
    • 12 Days On Market

    Current Estimated Value $299,880

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • 120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      /18

      Est $338,956

      Not Listed For Sale

      120 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1986
      120 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 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 EXP Realty, LLC

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /39

    $695,000

    Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Current Estimated Value $675,787

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620

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