7,017

Homes in ZIP Code 21620

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  • /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
  • /20

    $220,000 Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $222,902

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • /25

      Est $342,538 Not Listed For Sale

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

      121 Fairview Dr, Chestertown, MD 21620

      121 Fairview Dr, Chestertown, MD 21620
  • /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • /44

    $680,000 Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $680,593

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • /16

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 966 Sq Ft

      112 Snyder Ln, Chestertown, MD 21620

      112 Snyder Ln, Chestertown, MD 21620
  • /26

    $753,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • /52

    $795,000 Sold Jul 14, 2025

    211 David Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft
    • Built 1963

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $790,266

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • /27

      Est $261,772 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,260 Sq Ft

      117 Chester Arms Dr, Chestertown, MD 21620

      117 Chester Arms Dr, Chestertown, MD 21620
  • /38

    $474,990 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS QUICK MOVE-IN LUXURY VILLA! Settle by 1/31/26 and receive a FREE washer/dryer and Blinds. This stunning 4-bedroom villa offers a welcoming and functional layout with exceptional upgrades and finishes throughout. The main level features an oversized family room that opens to the kitchen and dining area—perfect for entertaining or everyday living. The upper level includes

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • /2

    $2,500 Sold Sep 12, 2025

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678

    • Land
    • 0.34 Acre
    • $7,353 per Acre

    Last Sold Summary

    • 252 Days On Market

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    • /25

      Est $419,836 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown Rd, Chestertown, MD 21620
  • /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 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 ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • /60

    $1,165,000 Sold Dec 01, 2025

    119 High St, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,409 Sq Ft
    • Built 1876

    Last Sold Summary

    • $264/SF
    • 5 Days On Market

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • /37

      Est $425,190 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft

      200 Ashley Ln, Chestertown, MD 21620

      200 Ashley Ln, Chestertown, MD 21620
  • /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • /41

    $385,000 Sold Apr 04, 2025

    109 Secor Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1977

    Last Sold Summary

    • $247/SF
    • 69 Days On Market

    Current Estimated Value $401,063

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
    • /33

      Est $694,293 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      209 Landing Ln, Chestertown, MD 21620

      209 Landing Ln, Chestertown, MD 21620
  • /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • /62

    $790,000 Sold Sep 23, 2025

    209 Rivershore Rd, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft
    • Built 1978

    Last Sold Summary

    • $564/SF
    • 32 Days On Market

    Current Estimated Value $778,069

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • /18

      Est $1,382,933 Not Listed For Sale

      • Studio

      141 Round Top Creek Ln, Chestertown, MD 21620

      141 Round Top Creek Ln, Chestertown, MD 21620
  • /90

    $2,500,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • /16

    $240,000 Sold Jan 16, 2026

    100 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $211/SF
    • 109 Days On Market

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
    • /44

      Est $440,639 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft

      204 N Mill St, Chestertown, MD 21620

      204 N Mill St, Chestertown, MD 21620
  • /20

    $135,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just steps from historic downtown Chestertown. LVP Flooring installed on 10/04/2025 on the main and upper levels. Carpet installed on the staircase. Materials, fixtures, applicances cabinetry, washer/dryer ready to install. Discover the potential of 423 Calvert Street — a two-story,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • /40

    $600,000 Sold May 16, 2025

    108 N Queen St, Chestertown, MD 21620

    • 5 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • Built 1920

    Last Sold Summary

    • $237/SF

    Current Estimated Value $629,898

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
    • /7

      Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft

      128 N Queen St, Chestertown, MD 21620

      128 N Queen St, Chestertown, MD 21620
  • /21

    $364,900

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

    108 Flying Cloud Dr, Chestertown, MD 21620

    New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living

    Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
  • /36

    $315,000 Sold Aug 29, 2025

    106 Wilton Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $298/SF
    • 18 Days On Market

    Current Estimated Value $310,595

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
    • /23

      Est $445,941 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft

      101 S Kent St, Chestertown, MD 21620

      101 S Kent St, Chestertown, MD 21620
  • /24

    $315,000 Under Contract

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

    676 Deep Landing Rd, Chestertown, MD 21620

    Situated on an open .59 acre lot in Queen Anne’s County, this charming 3 bedroom, 2.5 bath built home in 2014 offers buyers the perfect blend of modern comfort with spacious living. This property features a beautiful kitchen with granite countertops and a new range, a finished basement with a half bath that can be used for anything from an office to a playroom, and an attached front-loading

    Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
  • /27

    $280,000 Sold Jun 09, 2025

    100 Acorn Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft
    • Built 2004

    Last Sold Summary

    • $145/SF
    • 164 Days On Market

    Current Estimated Value $296,661

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
    • /54

      Est $617,519 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft

      116 N Queen St, Chestertown, MD 21620

      116 N Queen St, Chestertown, MD 21620
  • /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    Discover your own piece of paradise in Lenapah, Chestertown, MD! This expansive 14,500 square foot lot offers endless possibilities for your dream home or investment vision. Nestled in a serene setting, this raw land is ready for your creative touch. Embrace the tranquility of nature while being just a short drive from local amenities. Whether you’re looking to build your dream oasis or a savvy

    Solomon Zaldivar Compass

    0 Lenapah Rd, Chestertown, MD 21620
  • /15

    $155,000 Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $160,935

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
    • /31

      Est $511,634 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft

      107 Adela Way, Chestertown, MD 21620

      107 Adela Way, Chestertown, MD 21620
  • /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
  • /17

    $335,000 Sold Oct 03, 2025

    110 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 2023

    Last Sold Summary

    • $180/SF
    • 208 Days On Market

    Current Estimated Value $338,838

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
    • /43

      Est $437,139 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      105 Sutton Way, Chestertown, MD 21620

      105 Sutton Way, Chestertown, MD 21620
  • /16

    $370,000 Under Contract

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

    21111 Texas Ave, Chestertown, MD 21620

    Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage

    Glory Bee Costa Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

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