6,890

Chestertown, MD Homes

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  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /23

    Starting at $1,300 Per Month

    • 1 - 3 Beds

    101 Morgnec Rd, Chestertown, MD 21620

    Quiet community, beautifully landscaped. Close to Washington College, can walk to downtown historic Chestertown and shops. A must see.

    Kent Crossing Apartments

    101 Morgnec Rd, Chestertown, MD 21620
  • 521 N Kent St, Chestertown, MD 21620
    521 N Kent St, Chestertown, MD 21620
    /2

    $365,000

    Sold Jul 22, 2026

    521 N Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,934 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $189/SF

    Current Estimated Value $444,216

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    521 N Kent St, Chestertown, MD 21620
    • 314 Devon Dr, Chestertown, MD 21620
      314 Devon Dr, Chestertown, MD 21620
      314 Devon Dr, Chestertown, MD 21620
      /45

      Est $503,058

      Not Listed For Sale

      314 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,420 Sq Ft
      • Built 2010
      314 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 79 Days On Market

  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $898,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 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

    226 S Water St, Chestertown, MD 21620
  • 129a Manor Ave N, Chestertown, MD 21620
    129a Manor Ave N, Chestertown, MD 21620
    129a Manor Ave N, Chestertown, MD 21620
    /12

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • House for Rent

    129a Manor Ave N, Chestertown, MD 21620

    Property Id: 1589400 **PLEASE CONFIRM PROPERTY IS AVAILABLE BEFORE APPLYING** 129A Manor Ave, Chestertown, MD. This charming 3-bedroom, 2-bath home is move-in ready with a brand new HVAC system for year-round comfort. The spacious interior offers a welcoming living space, while the detached 1-bay garage provides the perfect spot for storage or a workshop. Located in a convenient area,

    129a Manor Ave N, 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 $357,696

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • 212 Central Dr, Chestertown, MD 21620
      212 Central Dr, Chestertown, MD 21620
      212 Central Dr, Chestertown, MD 21620
      /21

      Est $305,179

      Not Listed For Sale

      212 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1972
      212 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 305 Roosevelt Dr, Chestertown, MD 21620
    305 Roosevelt Dr, Chestertown, MD 21620
    /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • 128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    /10

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, seperate dining room, galley kitchen, full bathroom and bedroom. Unit is available immediately, utilities included: electric, water and sewer. Security

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, 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 $325,644

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
    • 110 Philosophers Terrace, Chestertown, MD 21620
      110 Philosophers Terrace, Chestertown, MD 21620
      110 Philosophers Terrace, Chestertown, MD 21620
      /22

      Est $195,846

      Not Listed For Sale

      110 Philosophers Terrace, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 896 Sq Ft
      • Built 1955
      110 Philosophers Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

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

    $59,000

    $5K PRICE DROP
    • 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. Unsuccessful land evaluation

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 109 Fairview Dr, Chestertown, MD 21620
    109 Fairview Dr, Chestertown, MD 21620
    109 Fairview Dr, Chestertown, MD 21620
    /9

    $1,900 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    109 Fairview Dr, Chestertown, MD 21620

    Property Id: 49100 Clean, updated 3 BR, 1 BA home in Chester Harbor. Nice yard, big screened porch, mud room/laundry room. QAC schools. No smoking, no pets, verifiable income required, good credit with no history of eviction, failure to pay rent, etc. First/last months' rent plus security deposit required for move in.

    109 Fairview Dr, Chestertown, MD 21620
  • 25475 Turnberry Ct, Chestertown, MD 21620
    25475 Turnberry Ct, Chestertown, MD 21620
    25475 Turnberry Ct, Chestertown, MD 21620
    /79

    $825,000

    Sold May 26, 2026

    25475 Turnberry Ct, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 4,145 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 9 Days On Market

    Current Estimated Value $843,438

    Last Listing Agent Lona Todd Taylor Properties

    25475 Turnberry Ct, Chestertown, MD 21620
    • 10670 Tintah Rd, Chestertown, MD 21620
      10670 Tintah Rd, Chestertown, MD 21620
      10670 Tintah Rd, Chestertown, MD 21620
      /29

      Est $295,680

      Not Listed For Sale

      10670 Tintah Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      10670 Tintah Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

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

    $185,000

    $27K PRICE DROP 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

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 104 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
    /27

    $1,920 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    104 Maple Ave Unit 6, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm. This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 6, 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 $384,391

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 619 Cannon St, Chestertown, MD 21620
      619 Cannon St, Chestertown, MD 21620
      619 Cannon St, Chestertown, MD 21620
      /9

      Est $195,633

      Not Listed For Sale

      619 Cannon St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 882 Sq Ft
      • Built 1983
      619 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 50 Days On Market

  • 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
    • 3,920 Sq Ft
    • $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

    108 Little Harbor Way, Chestertown, MD 21620
  • 104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    /12

    $1,820 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    104 Maple Ave Unit 4, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm. This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 4, 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 $628,960

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • 310 Hilltop Ln, Chestertown, MD 21620
      310 Hilltop Ln, Chestertown, MD 21620
      310 Hilltop Ln, Chestertown, MD 21620
      /18

      Est $212,343

      Not Listed For Sale

      310 Hilltop Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,216 Sq Ft
      • Built 2005
      310 Hilltop Ln, Chestertown, MD 21620

      Last Sold Summary

      • 24 Days On Market

  • 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

    Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    0 Georgetown Rd SE Unit MDKE2005218, 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
    /17

    $1,800 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
  • 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 $354,405

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 10575 Hyala Ct, Chestertown, MD 21620
      10575 Hyala Ct, Chestertown, MD 21620
      10575 Hyala Ct, Chestertown, MD 21620
      /22

      Est $357,843

      Not Listed For Sale

      10575 Hyala Ct, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,978 Sq Ft
      • Built 2003
      10575 Hyala Ct, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /25

    $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

    222 Dutchess Rd, Chestertown, MD 21620
  • 8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    /6

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    8890 Fairlee Rd, Chestertown, MD 21620

    Beautiful and clean ranch featuring open floor plan and separated primary bedroom. Adorable kitchen and dining area with slider to rear deck. laundry included

    Darlene Winegardner RE/MAX Executive

    8890 Fairlee Rd, Chestertown, MD 21620
  • 108 Pine St, Chestertown, MD 21620
    108 Pine St, Chestertown, MD 21620
    /2

    $85,000

    Sold Jun 30, 2026

    108 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1957

    Last Sold Summary

    • 40% Below List Price
    • $93/SF
    • 6 Days On Market

    Current Estimated Value $117,450

    Last Listing Agent David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
    • 420 Cannon St, Chestertown, MD 21620
      420 Cannon St, Chestertown, MD 21620
      420 Cannon St, Chestertown, MD 21620
      /39

      Est $343,338

      Not Listed For Sale

      420 Cannon St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1900
      420 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 29 Days On Market

  • 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

    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
  • 704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    /43

    $453,000

    Sold Jul 14, 2026

    704 Truslow Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Above List Price
    • $220/SF
    • 22 Days On Market

    Current Estimated Value $439,601

    Last Listing Agent Crystal Smith RE/MAX Executive

    704 Truslow Rd, Chestertown, MD 21620
    • 7682 Waterview Ln, Chestertown, MD 21620
      7682 Waterview Ln, Chestertown, MD 21620
      7682 Waterview Ln, Chestertown, MD 21620
      /32

      Est $661,817

      Not Listed For Sale

      7682 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1989
      7682 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 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

    0 Little Harbor Way Unit 1, 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 $1,475,404

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
    • 211 David Dr, Chestertown, MD 21620
      211 David Dr, Chestertown, MD 21620
      211 David Dr, Chestertown, MD 21620
      /52

      Est $806,147

      Not Listed For Sale

      211 David Dr, Chestertown, MD 21620

      • 4 Beds
      • 4 Baths
      • 4,401 Sq Ft
      • Built 1963
      211 David Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 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

    104 Landing Ln, Chestertown, MD 21620
  • 8629 Airy Hill Rd, Chestertown, MD 21620
    8629 Airy Hill Rd, Chestertown, MD 21620
    /2

    $395,000

    Sold Jun 25, 2026

    8629 Airy Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $274/SF
    • 7 Days On Market

    Current Estimated Value $426,030

    Last Listing Agent Lauren Smith Keller Williams Realty

    8629 Airy Hill Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County

Real Estate & Homes

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $361,950, down 5% year-over-year. Homes in Chestertown sell in 42 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$361,950
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$262,400
Median 2 Bedroom Sale Price
$323,250
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$214
Number of Homes for Sale
30
Last 12 months Home Sales
96
Months of Supply
3.80
Median List Price
$357,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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