6,867

Chestertown, MD Homes

Section Image
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $535,000 Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $317,479 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      23235 Myers Rd, Chestertown, MD 21620

      23235 Myers Rd, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    /28

    $549,000 Sold Jun 26, 2025

    305 Washington Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • Built 1930

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $556,757

    Last Listing Agent William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $329,155 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      23399 Cloquet Rd, Chestertown, MD 21620

      23399 Cloquet Rd, Chestertown, MD 21620
  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $350,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft

    10751 Millbrook Dr, Chestertown, MD 21620

    Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another

    Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, Chestertown, MD 21620
  • 26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    /49

    $840,000 Sold Jun 27, 2025

    26865 Mallard Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft
    • Built 1963

    Last Sold Summary

    • $250/SF
    • 182 Days On Market

    Current Estimated Value $907,318

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • 101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      /39

      Est $322,921 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft

      101 S College Ave, Chestertown, MD 21620

      101 S College Ave, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $695,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • 811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    /45

    $459,000 Sold Jun 23, 2025

    811 S Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $466,200

    Last Listing Agent Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $359,025 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 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. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /24

    $285,000 Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $761,860

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • 316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      /27

      Est $269,588 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    /14

    $85,000 Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • 105 S Kent St, Chestertown, MD 21620
      105 S Kent St, Chestertown, MD 21620
      105 S Kent St, Chestertown, MD 21620
      /30

      Est $455,733 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,304 Sq Ft

      105 S Kent St, Chestertown, MD 21620

      105 S Kent St, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 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

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    /21

    $309,500 Sold Jul 31, 2025

    212 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1972

    Last Sold Summary

    • $280/SF
    • 2 Days On Market

    Current Estimated Value $307,091

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    212 Central Dr, Chestertown, MD 21620
    • 21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      /13

      Est $240,035 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft

      21286 Maine Ave, Chestertown, MD 21620

      21286 Maine Ave, Chestertown, MD 21620
  • 303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    /32

    $363,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    303 E Campus Ave, Chestertown, MD 21620

    Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and

    Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /2

    $539,000 Sold Jun 16, 2025

    107 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 3,050 Sq Ft
    • Built 1879

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Current Estimated Value $558,367

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
    • 208 W Campus Ave, Chestertown, MD 21620
      208 W Campus Ave, Chestertown, MD 21620
      208 W Campus Ave, Chestertown, MD 21620
      /30

      Est $408,620 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,390 Sq Ft

      208 W Campus Ave, Chestertown, MD 21620

      208 W Campus Ave, Chestertown, MD 21620
  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /24

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    7521 Pine Ave, Chestertown, MD 21620

    Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine 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

    $355,000 Sold Mar 21, 2025

    477 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $235/SF
    • 282 Days On Market

    Current Estimated Value $361,998

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    477 Pear Tree Point Rd, Chestertown, MD 21620
    • 545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      /28

      Est $279,337 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft

      545 High St, Chestertown, MD 21620

      545 High St, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /7

    $89,500

    • Land
    • 3.92 Acres
    • $22,832 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated palustrine forested shrub wetlands, though

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    /9

    $190,500 Sold Jul 22, 2025

    619 Cannon St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 882 Sq Ft
    • Built 1983

    Last Sold Summary

    • $216/SF
    • 50 Days On Market

    Current Estimated Value $201,070

    Last Listing Agent Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
    • 9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      /47

      Est $338,619 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      9041 S Bayview Dr, Chestertown, MD 21620

      9041 S Bayview Dr, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    /35

    $438,000 Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
    • 10069 John Carvill Rd, Chestertown, MD 21620
      10069 John Carvill Rd, Chestertown, MD 21620
      10069 John Carvill Rd, Chestertown, MD 21620
      /69

      Est $1,229,071 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft

      10069 John Carvill Rd, Chestertown, MD 21620

      10069 John Carvill Rd, Chestertown, MD 21620
  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 0.34 Acre
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • 111 Elm St, Chestertown, MD 21620
    111 Elm St, Chestertown, MD 21620
    111 Elm St, Chestertown, MD 21620
    /12

    $212,000 Sold Dec 30, 2024

    111 Elm St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,275 Sq Ft
    • Built 1959

    Last Sold Summary

    • $166/SF
    • 16 Days On Market

    Current Estimated Value $237,939

    Last Listing Agent Andy Batch Keller Williams Select Realtors of Annapolis

    111 Elm St, Chestertown, MD 21620
    • 217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      /37

      Est $513,731 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft

      217 Radcliffe Dr, Chestertown, MD 21620

      217 Radcliffe Dr, Chestertown, MD 21620
  • 121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    /22

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    121 Primrose Rd, Chestertown, MD 21620

    Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose Rd, Chestertown, MD 21620
  • 123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    /53

    $485,000 Sold May 01, 2025

    123 Burchard Sawmill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,648 Sq Ft
    • Built 1918

    Last Sold Summary

    • $294/SF
    • 4 Days On Market

    Current Estimated Value $483,735

    Last Listing Agent Crystal Pickett EXP Realty, LLC

    123 Burchard Sawmill Rd, Chestertown, MD 21620
    • 502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      /45

      Est $425,866 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • 105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    /28

    $322,000 Sold Nov 14, 2025

    105 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1992

    Last Sold Summary

    • $261/SF
    • 5 Days On Market

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    105 Parma Rd, Chestertown, MD 21620

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