6,868

Chestertown, MD Homes

Section Image
  • 118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    /34

    $265,000 Sold May 02, 2025

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1965

    Last Sold Summary

    • $238/SF
    • 120 Days On Market

    Current Estimated Value $277,367

    Last Listing Agent Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
    • 235 Burchard Sawmill Rd, Chestertown, MD 21620
      235 Burchard Sawmill Rd, Chestertown, MD 21620
      235 Burchard Sawmill Rd, Chestertown, MD 21620
      /24

      Est $253,157 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft

      235 Burchard Sawmill Rd, Chestertown, MD 21620

      235 Burchard Sawmill Rd, Chestertown, MD 21620
  • 349 High St, Chestertown, MD 21620
    349 High St, Chestertown, MD 21620
    349 High St, Chestertown, MD 21620
    /33

    $395,000 Under Contract

    • 7 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    349 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 High St, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $750,000 Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • 205 Deep Landing Rd, Chestertown, MD 21620
      205 Deep Landing Rd, Chestertown, MD 21620
      205 Deep Landing Rd, Chestertown, MD 21620
      /49

      Est $420,797 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,456 Sq Ft

      205 Deep Landing Rd, Chestertown, MD 21620

      205 Deep Landing Rd, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $499,999 Pending

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 AcresDiscover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout.Step inside to find a

    Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
  • 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 $320,104

    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 $372,602 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      101 Char Nor Manor Blvd, Chestertown, MD 21620
  • 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
    /19

    $695,000 Coming Soon

    • 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 place that instantly feels like a breath of fresh air. Set inside the sought-after Chester River Landing community, this completely reimagined 3-bedroom, 2-bath waterfront condo offers the rare mix of modern comfort and true Eastern Shore charm. From the moment you walk in, the views of the Chester River pull you in. The entire condo was taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, 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

    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 $285,233 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft

      305 Pine Tree Rd, Chestertown, MD 21620

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

    $10,000

    • Land
    • 0.55 Acre
    • $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
  • 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

    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 $522,028 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft

      139 Church Meadow Ct, Chestertown, MD 21620

      139 Church Meadow Ct, Chestertown, MD 21620
  • 0 Spinnaker Rd, Chestertown, MD 21620
    0 Spinnaker Rd, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 0.56 Acre
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, Chestertown, MD 21620
  • 116 Island Lark Way, Chestertown, MD 21620
    116 Island Lark Way, Chestertown, MD 21620
    116 Island Lark Way, Chestertown, MD 21620
    /20

    $286,900 Sold Mar 17, 2025

    116 Island Lark Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,420 Sq Ft
    • Built 2023

    Last Sold Summary

    • $202/SF
    • 125 Days On Market

    Current Estimated Value $295,429

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    116 Island Lark Way, Chestertown, MD 21620
    • 329 Union Church Rd, Chestertown, MD 21620
      329 Union Church Rd, Chestertown, MD 21620
      329 Union Church Rd, Chestertown, MD 21620
      /28

      Est $539,711 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft

      329 Union Church Rd, Chestertown, MD 21620

      329 Union Church Rd, Chestertown, MD 21620
  • 204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    /31

    $370,000

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

    204 Rolling Rd, Chestertown, MD 21620

    Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling Rd, 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

    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 $446,741 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,792 Sq Ft

      109 Coleman Dr, Chestertown, MD 21620

      109 Coleman Dr, Chestertown, MD 21620
  • 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
  • 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 $298,699

    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 $455,593 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,128 Sq Ft

      105 Coleman Dr, Chestertown, MD 21620

      105 Coleman Dr, Chestertown, MD 21620
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $299,000

    • 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
  • 7675 Quaker Neck Rd, Chestertown, MD 21620
    7675 Quaker Neck Rd, Chestertown, MD 21620
    7675 Quaker Neck Rd, Chestertown, MD 21620
    /34

    $612,500 Sold Jan 02, 2025

    7675 Quaker Neck Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 2017

    Last Sold Summary

    • $340/SF
    • 13 Days On Market

    Current Estimated Value $624,830

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    7675 Quaker Neck 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 $404,629 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft

      236 Duke of Kent St, Chestertown, MD 21620

      236 Duke of Kent St, Chestertown, MD 21620
  • 0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 0.34 Acre
    • $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
  • 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 $364,448

    Last Listing Agent Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
    • 205 Creston Rd, Chestertown, MD 21620
      205 Creston Rd, Chestertown, MD 21620
      205 Creston Rd, Chestertown, MD 21620
      /22

      Est $341,306 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,338 Sq Ft

      205 Creston Rd, Chestertown, MD 21620

      205 Creston 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
  • 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

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
    • 313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      /35

      Est $397,706 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      313 River Rd, Chestertown, MD 21620

      313 River 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
  • 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

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
    • 124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      /28

      Est $295,534 Not Listed For Sale

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

      124 Edmore Rd, Chestertown, MD 21620

      124 Edmore 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
  • 3652 Gratitude Way, Chestertown, MD 21620
    3652 Gratitude Way, Chestertown, MD 21620
    3652 Gratitude Way, Chestertown, MD 21620
    /10

    $579,238 Sold Mar 20, 2025

    3652 Gratitude Way, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,642 Sq Ft
    • Built 2025

    Last Sold Summary

    • $219/SF
    • 1 Day On Market

    Last Listing Agent Tineshia Johnson NVR, INC.

    3652 Gratitude Way, Chestertown, MD 21620
    • 729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      /32

      Est $335,274 Not Listed For Sale

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

      729 Rosin Dr, Chestertown, MD 21620

      729 Rosin 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
  • 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

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