7,014

Homes in ZIP Code 21620

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  • 0 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    • Land
    • 13.46 Acres
    • $6,686 per Acre
    • 0 Days On Market

    0 None Unit MDKE2005014, Chestertown, MD 21620

    13.5 wooded acres with very limited access on north side of Chestertown. Should be excellent deer hunting. 16' paper right of way to access.

    William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $453,634 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $1,150,000 Pending

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    /44

    $680,000 Sold Sep 30, 2025

    • 3,820 Sq Ft
    • $178/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    8978 Orchard Dr, Chestertown, MD 21620

    Spacious, Stylish, and Designed for Real Life – Discover the perfect blend of comfort, flexibility, and convenience in this expansive 4-bedroom home, tucked into the sought-after Orchard Hill neighborhood in Chestertown. With thoughtful upgrades and versatile spaces, this residence is ideal for those looking to level up their lifestyle—whether you're a young professional seeking work-from-home

    Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $442,421 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      209 Blakefield Dr, Chestertown, MD 21620

      209 Blakefield Dr, Chestertown, MD 21620
  • 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 all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and 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. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    • 4,401 Sq Ft
    • $181/SF
    • 2 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1963

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • 121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      /25

      Est $353,535 Not Listed For Sale

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

      121 Fairview Dr, Chestertown, MD 21620

      121 Fairview Dr, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $492,464 Pending

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

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. Featuring a huge family room with gas fireplace, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 431-1757

    730 Aldora Dr Unit 114, Chestertown, MD 21620
  • 0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    /2

    $2,500 Sold Sep 12, 2025

    • Land
    • 0.34 Acre
    • $7,353 per Acre
    • 252 Days On Market

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

    The HO Assocation 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. Lot failed perc in 2005 and cannot be built on but a great place to use your boat!

    Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    • 112 Snyder Ln, Chestertown, MD 21620
      112 Snyder Ln, Chestertown, MD 21620
      112 Snyder Ln, 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
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, 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
  • 119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    /60

    $1,165,000 Sold Dec 01, 2025

    • 4,409 Sq Ft
    • $264/SF
    • 5 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1876

    119 High St, Chestertown, MD 21620

    From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of

    Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $422,355 Not Listed For Sale

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

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown Rd, Chestertown, MD 21620
  • 724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    /42

    $524,990 New Construction

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

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS STUNNING QUICK MOVE IN-Close by 12/31/25 and receive a FREE washer/dryer and blinds. Luxury end-of-group 4-bedroom villa with a fully finished walk-out lower level. The open and functional layout features an oversized family room that flows into the kitchen and dining area, perfect for entertaining. The upper level includes three spacious bedrooms, including a luxurious

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 883-7905

    724 Aldora Dr Unit 111, Chestertown, MD 21620
  • 109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    /41

    $385,000 Sold Apr 04, 2025

    • 1,560 Sq Ft
    • $247/SF
    • 69 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    109 Secor Rd, Chestertown, MD 21620

    Charming Home in Chester Harbor with Water Access!Welcome to 109 Secor Rd, Chestertown, MD 21620, nestled on a peaceful cul-de-sac in the desirable water-access community of Chester Harbor on the Queen Anne’s side of the Chester River. This home offers a perfect blend of comfort, charm, and recent updates, making it an exceptional choice for your next chapter.Key

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $435,186 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
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing 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
  • 209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    /62

    $790,000 Sold Sep 23, 2025

    • 1,401 Sq Ft
    • $564/SF
    • 32 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1978

    209 Rivershore Rd, Chestertown, MD 21620

    WELCOME TO 209 RIVERSHORE RD., CHESTERTOWN MD.,, Your natural waterfront retreat on the Chester River. Enjoy your time outside or inside of this tranquil property. As you step inside of this open flowy home with natural wood floors you will see the kitchen which has been partially remodeled with SS appliances, new counters and plenty of cabinet space. Overlooking the large spacious dining area

    Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • 218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      /44

      Est $527,612 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,932 Sq Ft

      218 Camelot Dr, Chestertown, MD 21620

      218 Camelot Dr, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $474,990 Open Sat 12PM - 4PM

    • 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 12/31/25 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
  • 23060 Old Fairlee Rd, Chestertown, MD 21620
    23060 Old Fairlee Rd, Chestertown, MD 21620
    23060 Old Fairlee Rd, Chestertown, MD 21620
    /7

    $45,000 Sold Dec 16, 2024

    • 1,040 Sq Ft
    • $43/SF
    • 210 Days On Market
    • Built 1900

    23060 Old Fairlee Rd, Chestertown, MD 21620

    Rare opportunity in a great residential location. Spacious garage/workshop, was most recently used for storage, situated on a half acre triangular lot. Check out the many possibilities! Great investor opportunity in a beautiful neighborhood. It is the buyer's responsibility to verify with Kent County Planning and Zoning any building use or renovation plans. Garage is hooked up to electric, but

    Julia Hilfiker Gunther-McClary Real Estate

    23060 Old Fairlee Rd, Chestertown, MD 21620
    • 209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      /33

      Est $676,459 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
  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, 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
  • 108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    /40

    $600,000 Sold May 16, 2025

    • 2,536 Sq Ft
    • $237/SF
    • 5 Beds
    • 2.5 Baths
    • Built 1920

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
    • 141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      /18

      Est $1,472,416 Not Listed For Sale

      • Studio

      141 Round Top Creek Ln, Chestertown, MD 21620

      141 Round Top Creek Ln, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing 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
  • 106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    /36

    $315,000 Sold Aug 29, 2025

    • 1,056 Sq Ft
    • $298/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    106 Wilton Rd, Chestertown, MD 21620

    Charming Updated and Well Maintained Rancher in the Chester Harbor Community of Queen Anne's County Chestertown! This house is the definition of "move-in ready" as the owner has taken tremendous pride in keeping the property updated. Over the years, they've installed new windows, new HVAC unit, new hot water heater, remodeled the kitchen, installed new appliances, painted the interior, added new

    Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
    • 204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      /44

      Est $459,635 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
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, 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
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    /27

    $280,000 Sold Jun 09, 2025

    • 1,930 Sq Ft
    • $145/SF
    • 164 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    100 Acorn Dr, Chestertown, MD 21620

    Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
    • 128 N Queen St, Chestertown, MD 21620
      128 N Queen St, Chestertown, MD 21620
      128 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
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, 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
  • 8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    /15

    $155,000 Sold Oct 17, 2025

    • 1,320 Sq Ft
    • $117/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1966

    8992 S Bayview Dr, Chestertown, MD 21620

    This property needs a complete rehab. Some work has been done previously. Property is sold AS IS- WHERE IS. Public sewer to house. Property is located in a water privileged community with access to the Chesapeake Bay. Just a short distance to a major bayfront marina with beach bar. Only several miles to Rock Hall restaurants, grocery store, and festivities.

    William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
    • 101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      /23

      Est $385,349 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
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /20

    $165,000

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

    423 Calvert St, Chestertown, MD 21620

    READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, Chestertown, MD 21620
    /17

    $335,000 Sold Oct 03, 2025

    • 1,856 Sq Ft
    • $180/SF
    • 208 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    110 Flying Cloud Dr, Chestertown, MD 21620

    SINGLE FAMILY HOME built just 2 years ago at this price! This beautiful home is ready for immediate occupancy. Clean lines and neutral tones make this an easy move-in with nothing to do! Just across the Vintage Chester River Bridge, you will enter a charming little town that surrounds Washington College that has all sorts of new centers and places to go and things to do! The home offers a

    Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
    • 116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      /54

      Est $630,826 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
  • 108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    /21

    $375,000

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

    108 Flying Cloud Dr, Chestertown, MD 21620

    Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, 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 spaces, while the laundry room offers added function

    Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
  • 117 Chester Arms Dr, Chestertown, MD 21620
    117 Chester Arms Dr, Chestertown, MD 21620
    117 Chester Arms Dr, Chestertown, MD 21620
    /27

    $247,500 Sold Dec 18, 2024

    • 1,260 Sq Ft
    • $196/SF
    • 30 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 2022

    117 Chester Arms Dr, Chestertown, MD 21620

    Discover this nearly new, beautifully maintained home in Chestertown. Featuring luxury vinyl flooring throughout, white cabinets, granite countertops, a spacious living room, an eat-in kitchen area, and a covered patio, this home offers a comfortable and stylish living space. The large primary bedroom suite and additional spacious bedrooms provide ample room for relaxation and

    David Moore Real Broker, LLC

    117 Chester Arms Dr, Chestertown, MD 21620

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