6,890

Chestertown, MD Homes

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    • /30

      Est $481,319

      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

      • 67 Days On Market

  • /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

    102 Little Harbor Way, Chestertown, MD 21620
  • /24

    $410,000

    Sold Jun 26, 2026

    109 S College Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $337/SF
    • 71 Days On Market

    Current Estimated Value $410,711

    Last Listing Agent Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
    • /17

      Est $247,947

      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

      • 25 Days On Market

  • /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

    36 Landing Ln, Chestertown, MD 21620
  • /36

    $349,500

    Sold Jun 05, 2026

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1971

    Last Sold Summary

    • $268/SF
    • 9 Days On Market

    Current Estimated Value $347,341

    Last Listing Agent Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, Chestertown, MD 21620
    • /27

      Est $400,902

      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

      • 1 Day On Market

  • /38

    $474,990

    New Construction Pending
    • 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! $5000 towards closing. 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 three spacious bedrooms, including an

    Agent Photo

    Mrs. Terri E Hill

    Builder Solutions Realty

    728 Aldora Dr Unit 113, 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 $286,604

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • /30

      Est $414,911

      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

      • 19 Days On Market

  • /24

    $240,000

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    107 Conley Dr, Chestertown, MD 21620

    Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl

    Taylor Leaverton Benson & Mangold, LLC

    107 Conley Dr, Chestertown, MD 21620
  • /5

    $25,000

    Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $165,667

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /16

      Est $386,058

      Not Listed For Sale

      213 Pine Cove Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2023
      213 Pine Cove Ln, Chestertown, MD 21620

      Last Sold Summary

  • /21

    $189,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21324 Persimmon Dr, Chestertown, MD 21620

    Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining

    Taylor Leaverton Benson & Mangold, LLC

    21324 Persimmon Dr, Chestertown, MD 21620
  • /10

    $175,000

    Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $191,983

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • /34

      Est $281,039

      Not Listed For Sale

      7499 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2018
      7499 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

  • /41

    $525,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,824 Sq Ft

    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620

    Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from a small Chester River boat landing where you can easily launch a kayak, Sunfish or small power boat. This comfortable home offers same floor living for much of the house, but also has a partly finished full basement with tv room.

    Robert G. Shannahan Shoreline Realty

    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620
  • /2

    $9,500

    Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 21,780 Sq Ft
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Millbrook Dr, Chestertown, MD 21620
    • /27

      Est $420,851

      Not Listed For Sale

      142 Church Meadow Ct, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 2014
      142 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 39 Days On Market

  • /46

    $565,000

    $47K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, 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 $223,423

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • /27

      Est $468,022

      Not Listed For Sale

      106 Church Aly, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1880
      106 Church Aly, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:50 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major

    Adam Shpritz Ashland Auction Group LLC

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
  • /3

    $7,200

    Sold Jun 04, 2026

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $21,176 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 457 Days On Market

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    • /56

      Est $406,624

      Not Listed For Sale

      10570 Cogar Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft
      • Built 2010
      10570 Cogar Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

  • /15

    $350,000

    $100K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,518 Sq Ft

    522 High St, Chestertown, MD 21620

    Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3

    Taylor Leaverton Benson & Mangold, LLC

    522 High St, Chestertown, MD 21620
  • /51

    $640,000

    Sold Jul 29, 2026

    7844 Chester Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft
    • Built 2005

    Last Sold Summary

    • $197/SF
    • 222 Days On Market

    Current Estimated Value $687,003

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    7844 Chester Ct, Chestertown, MD 21620
    • /9

      Est $446,058

      Not Listed For Sale

      209 Blakefield Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • Built 2022
      209 Blakefield Dr, Chestertown, MD 21620

      Last Sold Summary

      • 130 Days On Market

  • /61

    $2,200,000

    Open Sat 11AM - 1PM Under Contract
    • 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
  • /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 $698,829

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • /34

      Est $606,459

      Not Listed For Sale

      7675 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 2017
      7675 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

  • /10

    $320,000

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

    8706 Elm Rd, Chestertown, MD 21620

    Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, 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

    Current Estimated Value $1,147,980

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • /25

      Est $353,656

      Not Listed For Sale

      121 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2024
      121 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

  • /13

    $59,999

    $39K PRICE DROP Pending
    • Land
    • 22,215 Sq Ft
    • $117,645 per Acre

    228 Merganser Dr, Chestertown, MD 21620

    Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown

    Mae Nordhoff Benson & Mangold, LLC

    228 Merganser Dr, Chestertown, MD 21620
  • /23

    $317,000

    Sold Mar 09, 2026

    213 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $257/SF
    • 67 Days On Market

    Current Estimated Value $312,316

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
    • /19

      Est $242,027

      Not Listed For Sale

      107 Chester Arms Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2022
      107 Chester Arms Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

  • /16

    $10,000

    • Land
    • 39,204 Sq Ft
    • $11,111 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    HUGE PRICE REDUCTION on a 0.9-acre Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, 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 $782,406

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • /35

      Est $375,157

      Not Listed For Sale

      117 Court St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 744 Sq Ft
      • Built 1885
      117 Court St, Chestertown, MD 21620

      Last Sold Summary

      • 23 Days On Market

Showing Results 41 - 80, Page 2 of 18

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