7,041

Homes in ZIP Code 21620

Section Image
  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000

    Sold Jun 20, 2025

    104 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1989

    Last Sold Summary

    • $263/SF
    • 21 Days On Market

    Current Estimated Value $326,005

    Last Listing Agent Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620
    • 101 Char Nor Manor Blvd, Chestertown, MD 21620
      101 Char Nor Manor Blvd, Chestertown, MD 21620
      101 Char Nor Manor Blvd, Chestertown, MD 21620
      /8

      Est $382,435

      Not Listed For Sale

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft
      • Built 1965
      101 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $285/SF
      • 1 Day On Market
      • Last Sold Price $330,000
      • Oct 13, 2023

      Last Listing Agent Samantha Powell Keller Williams Real Estate - Media

  • 214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    /26

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major systems like the roof, HVAC, and water heater are all just a few years old,

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,336,457

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • 305 Pine Tree Rd, Chestertown, MD 21620
      305 Pine Tree Rd, Chestertown, MD 21620
      305 Pine Tree Rd, Chestertown, MD 21620
      /17

      Est $246,523

      Not Listed For Sale

      305 Pine Tree Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1961
      305 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Below List Price
      • $315/SF
      • 298 Days On Market
      • Last Sold Price $260,000
      • Sep 13, 2024

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • 231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    /51

    $1,150,000

    $129K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • 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
    • 139 Church Meadow Ct, Chestertown, MD 21620
      139 Church Meadow Ct, Chestertown, MD 21620
      139 Church Meadow Ct, Chestertown, MD 21620
      /71

      Est $556,225

      Not Listed For Sale

      139 Church Meadow Ct, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 2008
      139 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $183/SF
      • 3 Days On Market
      • Last Sold Price $475,000
      • May 22, 2023

      Last Listing Agent Scott Hogan Long & Foster

  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /56

    $675,000

    $20K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, 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
    • 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

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

    $10,000

    • 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
  • 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
    • 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

  • 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
  • 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
    • 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

  • 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
  • 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
    • 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.

  • 0 Bunting Rd, 6, Fairlee, MD 21620
    0 Bunting Rd, 6, Fairlee, MD 21620
    0 Bunting Rd, 6, Fairlee, MD 21620
    /4

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Bunting Rd, 6, Fairlee, 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 @ 12:35 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 Bunting Rd, 6, Fairlee, 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
    • 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

  • 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
  • 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
    • 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

  • 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
  • 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
    • 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

  • 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
  • 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
    • 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

  • 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
  • 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
    • 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

  • 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
  • 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
    • 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 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
  • 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

Showing Results 281 - 320, Page 8 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