7,032

Homes in ZIP Code 21620

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  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $695,000

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • 517 High St Unit C, Chestertown, MD 21620
    517 High St Unit C, Chestertown, MD 21620
    517 High St Unit C, Chestertown, MD 21620
    /20

    $1,575 per month

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft
    • Condo for Rent

    517 High St Unit C, Chestertown, MD 21620

    Property Id: 2282226Welcome to this spacious 2-bedroom, 1-bath apartment located on the second floor of a classic Chestertown multi-family home. This well-laid-out unit offers comfortable living with attractive architectural details and plenty of natural light throughout. Residents also have access to a shared deck, fenced yard, and welcoming front porch, all just minutes from downtown

    517 High St Unit C, Chestertown, MD 21620
  • 108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    /21

    $364,900 Sold Feb 26, 2026

    108 Flying Cloud Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2023

    Last Sold Summary

    • $188/SF
    • 67 Days On Market

    Current Estimated Value $358,936

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • 3652 Gratitude Way, Chestertown, MD 21620
      3652 Gratitude Way, Chestertown, MD 21620
      3652 Gratitude Way, Chestertown, MD 21620
      /10

      Not Listed For Sale

      3652 Gratitude Way, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,642 Sq Ft
      • Built 2025
      3652 Gratitude Way, Chestertown, MD 21620

      Last Sold Summary

      • $219/SF
      • 1 Day On Market

      Last Sold Price $579,238

      Last Listing Agent Tineshia Johnson NVR, INC.

  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $509,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    /16

    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620

    If you’ve been searching for an open‐concept apartment with a stunning view, your search ends here. This fully renovated third‐floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming. Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or entertaining.

    Amanda Morgan Brenton Realty Group

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
  • 676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    /24

    $325,000 Sold Jan 23, 2026

    676 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft
    • Built 2014

    Last Sold Summary

    • $221/SF
    • 2 Days On Market

    Current Estimated Value $319,565

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
    • 409 Riverview Rd, Chestertown, MD 21620
      409 Riverview Rd, Chestertown, MD 21620
      409 Riverview Rd, Chestertown, MD 21620
      /29

      Est $397,665 Not Listed For Sale

      409 Riverview Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1998
      409 Riverview Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $211/SF
      • 118 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft

    21125 Iowa Ave, Chestertown, MD 21620

    Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 405-2192

    21125 Iowa Ave, Chestertown, MD 21620
  • 160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    /13

    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620

    This property features 1200 square feet of living space, including one bathroom and 2 designated bedrooms. The unit comes fully furnished and is smoke-free, providing a clean and comfortable environment. Key amenities include air conditioning for climate control, a dishwasher for convenient meal cleanup, and an in-unit washer and dryer for laundry needs. The living area is spacious, allowing for

    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
  • 220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    /46

    $474,000 Sold Apr 03, 2025

    220 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2024

    Last Sold Summary

    • $249/SF
    • 84 Days On Market

    Current Estimated Value $510,867

    Last Listing Agent Brenda Fornos Taylor Properties

    220 Blakefield 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 $429,347 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

      • 2% Below List Price
      • $238/SF
      • 31 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /26

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • 509 Cannon St, Chestertown, MD 21620
    509 Cannon St, Chestertown, MD 21620
    509 Cannon St, Chestertown, MD 21620
    /12

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft
    • House for Rent

    509 Cannon St, Chestertown, MD 21620

    Welcome to 509 Cannon Street! This cozy 2-bedroom, 1-bath home has been thoughtfully updated and is ready for you to move right in. Inside, you'll find a comfortable layout and a brand-new HVAC system to keep you comfortable year-round, plus the convenience of off-street parking. Tenants are responsible for electric, town water and sewer, and internet services. To qualify, applicants must have a

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    509 Cannon St, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $375,000 Sold Dec 01, 2025

    907 N Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft
    • Built 2002

    Last Sold Summary

    • $204/SF
    • 83 Days On Market

    Current Estimated Value $380,311

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      /63

      Est $631,461 Not Listed For Sale

      209 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,328 Sq Ft
      • Built 1885
      209 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $230/SF
      • 10 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Andrea Alderdice Long & Foster

  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 0.09 Acre
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Condo for Rent

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, Chestertown, MD 21620
  • 10175 John Carvill Rd, Chestertown, MD 21620
    10175 John Carvill Rd, Chestertown, MD 21620
    10175 John Carvill Rd, Chestertown, MD 21620
    /72

    $609,000 Sold Aug 27, 2025

    10175 John Carvill Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft
    • Built 1994

    Last Sold Summary

    • $193/SF
    • 11 Days On Market

    Current Estimated Value $636,295

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill 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

      Est $305,595 Not Listed For Sale

      116 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,420 Sq Ft
      • Built 2023
      116 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $202/SF
      • 125 Days On Market

      Last Sold Price $286,900

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /5

    $60,000

    • Land
    • 3 Acres
    • $20,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /2

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • House for Rent

    1010 Twin Ct, Chestertown, MD 21620

    4 Bedroom, 2 Bath Cape on beautiful lot in the Crestview neighborhood in Chestertown. Mature trees for privacy on all sides. Stainless steel appliances, soft closing cabinets and nice rear deck for BBQ's overlooking large back yard. Extra storage in knee wall attic space! Close to shopping, restaurants and historic Chestertown. $25 application fee per adult

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $350,000 Sold Mar 05, 2026

    21111 Texas Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $363,864

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 477 Pear Tree Point Rd, Chestertown, MD 21620
      477 Pear Tree Point Rd, Chestertown, MD 21620
      477 Pear Tree Point Rd, Chestertown, MD 21620
      /20

      Est $366,698 Not Listed For Sale

      477 Pear Tree Point Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2024
      477 Pear Tree Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $235/SF
      • 282 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Clint Evans Cross Street Realtors LLC

  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 8355 Broad Neck Rd, Chestertown, MD 21620
    8355 Broad Neck Rd, Chestertown, MD 21620
    8355 Broad Neck Rd, Chestertown, MD 21620
    /33

    $2,800 per month

    • 3 Beds
    • 2 Baths
    • 2,910 Sq Ft
    • House for Rent

    8355 Broad Neck Rd, Chestertown, MD 21620

    Historic charm with modern conveniences, this 3 bedroom home is just minutes from Chestertown. The 6+ acre property is surrounded by woods and farm land offering a lovely, peaceful setting. Grounds maintenance is included in the rent, so just relax and enjoy the beautiful country setting. The old Alms House is located adjacent to the home, but will be used for owner storage and not be available

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8355 Broad Neck Rd, Chestertown, MD 21620
  • 10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    /94

    $1,524,900 Sold Feb 17, 2026

    10800 Cliff Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 5,241 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Above List Price
    • $291/SF
    • 5 Days On Market

    Current Estimated Value $1,494,467

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
    • 225 S Water St Unit 6, Chestertown, MD 21620
      225 S Water St Unit 6, Chestertown, MD 21620
      225 S Water St Unit 6, Chestertown, MD 21620
      /56

      Est $1,026,145 Not Listed For Sale

      225 S Water St Unit 6, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,800 Sq Ft
      • Built 2006
      225 S Water St Unit 6, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $345/SF
      • 14 Days On Market

      Last Sold Price $965,500

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • 202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    /3

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo Dr, Chestertown, MD 21620
  • 6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    /41

    $320,000 Sold Mar 26, 2025

    6744 Church Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,298 Sq Ft
    • Built 1964

    Last Sold Summary

    • $247/SF
    • 199 Days On Market

    Current Estimated Value $329,690

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    6744 Church Hill Rd, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $462,355 Not Listed For Sale

      148 Grant Ct, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft
      • Built 2021
      148 Grant Ct, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $264/SF
      • 67 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /37

    $319,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent

    Agent Photo

    Ryan Fitzwater

    RE/MAX Advantage Realty

    (410) 835-4609

    24775 Langford Rd, Chestertown, MD 21620
  • 209 N Water St, Chestertown, MD 21620
    209 N Water St, Chestertown, MD 21620
    /2

    $1,100,000 Sold Jun 30, 2025

    209 N Water St, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft
    • Built 1900

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,147,734

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $255,564 Not Listed For Sale

      104 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2023
      104 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • 25 Days On Market

      Last Sold Price $234,900

      Last Listing Agent David Moore Real Broker, LLC

  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000 Under Contract

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    /35

    $479,495 Sold Apr 25, 2025

    720 Aldora Dr Unit 109, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $226/SF
    • 0 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    720 Aldora Dr Unit 109, Chestertown, MD 21620
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $419,824 Not Listed For Sale

      21357 Belair Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft
      • Built 2010
      21357 Belair Ave, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $179/SF
      • 1 Day On Market

      Last Sold Price $360,000

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    /26

    $287,500 Sold Dec 05, 2025

    7483 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 35 Days On Market

    Current Estimated Value $284,344

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • 204 Pine Cove Ln, Chestertown, MD 21620
      204 Pine Cove Ln, Chestertown, MD 21620
      204 Pine Cove Ln, Chestertown, MD 21620
      /30

      Est $412,608 Not Listed For Sale

      204 Pine Cove Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 2021
      204 Pine Cove Ln, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $185/SF
      • 19 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Kelly Harris Coldwell Banker (NRT-Southeast-MidAtlantic)

Showing Results 1 - 40, Page 1 of 18

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