6,886

Chestertown, MD Homes

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  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $509,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 9919 Augustine Herman Hwy, Chestertown, MD 21620
    9919 Augustine Herman Hwy, Chestertown, MD 21620
    9919 Augustine Herman Hwy, Chestertown, MD 21620
    /14

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    9919 Augustine Herman Hwy, Chestertown, MD 21620

    Property Id: 2151738This secluded home sits quietly on a family farm nestled on the bank of Morgnec creek. Built in 1990, it has 4 bedrooms and 2 baths with a full basement for storage. Although no pets are allowed, you can enjoy watching the wildlife walk through your yard while you sit outside on the deck. If interested, call or text Chris with Kendall Properties at . Credit checks and

    9919 Augustine Herman Hwy, 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 $358,936

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • 317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      /33

      Est $696,944 Not Listed For Sale

      317 Union Church Rd, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,512 Sq Ft
      • Built 2021
      317 Union Church Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $273/SF
      • 0 Days On Market

      Last Sold Price $685,000

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /26

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, 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
    /16

    $2,100 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
  • 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 $314,605

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
    • 116 Fairview Dr, Chestertown, MD 21620
      116 Fairview Dr, Chestertown, MD 21620
      116 Fairview Dr, Chestertown, MD 21620
      /21

      Est $304,837 Not Listed For Sale

      116 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,028 Sq Ft
      • Built 1976
      116 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • $297/SF
      • 13 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $745,000

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

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • 202 High St Unit E, Chestertown, MD 21620
    202 High St Unit E, Chestertown, MD 21620
    202 High St Unit E, Chestertown, MD 21620
    /13

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Condo for Rent

    202 High St Unit E, Chestertown, MD 21620

    Property Id: 1453253Bright, open, newly remodeled, two bedroom apartment in downtown Chestertown. Open kitchen/living/dining room, flooded with light. Kitchen has stainless appliances, including dishwasher, and granite counters. Two large bedrooms, plentiful storage space. In-unit washer and dryer. The building has recently undergone extensive renovations, with many energy improvements,

    202 High St Unit E, Chestertown, MD 21620
  • 220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    /46

    $474,000 Sold Apr 03, 2025

    220 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2024

    Last Sold Summary

    • $249/SF
    • 84 Days On Market

    Current Estimated Value $506,560

    Last Listing Agent Brenda Fornos Taylor Properties

    220 Blakefield Dr, Chestertown, MD 21620
    • 117 Primrose Rd, Chestertown, MD 21620
      117 Primrose Rd, Chestertown, MD 21620
      117 Primrose Rd, Chestertown, MD 21620
      /15

      Est $358,763 Not Listed For Sale

      117 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,460 Sq Ft
      • Built 1972
      117 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $132/SF
      • 112 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /36

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent

    Agent Photo

    Ryan Fitzwater

    RE/MAX Advantage Realty

    (410) 835-4609

    24775 Langford Rd, Chestertown, MD 21620
  • 509 Cannon St, Chestertown, MD 21620
    509 Cannon St, Chestertown, MD 21620
    509 Cannon St, Chestertown, MD 21620
    /12

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft
    • House for Rent

    509 Cannon St, Chestertown, MD 21620

    Welcome to 509 Cannon Street! This cozy 2-bedroom, 1-bath home has been thoughtfully updated and is ready for you to move right in. Inside, you'll find a comfortable layout and a brand-new HVAC system to keep you comfortable year-round, plus the convenience of off-street parking. Tenants are responsible for electric, town water and sewer, and internet services. To qualify, applicants must have a

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    509 Cannon St, 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 $380,311

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      /35

      Est $385,081 Not Listed For Sale

      10724 Foreston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1995
      10724 Foreston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $190/SF
      • 3 Days On Market

      Last Sold Price $355,675

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /2

    $339,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft

    21125 Iowa Ave, Chestertown, MD 21620

    Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 405-2192

    21125 Iowa Ave, Chestertown, MD 21620
  • 425 High St Unit 4, Chestertown, MD 21620
    425 High St Unit 4, Chestertown, MD 21620
    425 High St Unit 4, Chestertown, MD 21620
    /14

    $1,050 per month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    425 High St Unit 4, Chestertown, MD 21620

    Property Id: 1770574Studio apartment in walking distance to Washington College and downtown Chestertown. Second floor studio apartment in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants’ use. Available early June. Landlord requires a minimum 650 credit score and month

    425 High St 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 $635,772

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • 104 Oak Leaf Dr, Chestertown, MD 21620
      104 Oak Leaf Dr, Chestertown, MD 21620
      104 Oak Leaf Dr, Chestertown, MD 21620
      /17

      Est $316,634 Not Listed For Sale

      104 Oak Leaf Dr, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 1,840 Sq Ft
      • Built 2003
      104 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $154/SF
      • 38 Days On Market

      Last Sold Price $283,000

      Last Listing Agent Krystal Zellner Crown Homes Real Estate

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

    $185,000 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

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Condo for Rent

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, 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 $363,864

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      /21

      Est $342,867 Not Listed For Sale

      10061 Flatland Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 2,376 Sq Ft
      • Built 1969
      10061 Flatland Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $137/SF
      • 18 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • 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
    • 0.09 Acre
    • $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

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 425 High St Unit 5, Chestertown, MD 21620
    425 High St Unit 5, Chestertown, MD 21620
    425 High St Unit 5, Chestertown, MD 21620
    /9

    $1,450 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    425 High St Unit 5, Chestertown, MD 21620

    Property Id: 1426365A modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College, this third floor, 2 bedroom apartment is in a building that was recently renovated to the studs, with modern windows and HVAC and original features, such as wood floors and exposed beams. In-building laundry and shared yard for tenants' use. Available immediately. Landlord

    425 High St Unit 5, Chestertown, MD 21620
  • 225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    /56

    $965,500 Sold Mar 21, 2025

    225 S Water St Unit 6, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • Built 2006

    Last Sold Summary

    • $345/SF
    • 14 Days On Market

    Current Estimated Value $1,030,313

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    225 S Water St Unit 6, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $460,241 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

      • 5% Above List Price
      • $264/SF
      • 67 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 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

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 425 High St Unit 3, Chestertown, MD 21620
    425 High St Unit 3, Chestertown, MD 21620
    425 High St Unit 3, Chestertown, MD 21620
    /17

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    425 High St Unit 3, Chestertown, MD 21620

    Property Id: 1770537Modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College. Second floor 1 bedroom in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants’ use. Available April 1. Landlord requires a minimum 650 credit score and month

    425 High St Unit 3, 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 $1,301,499

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $253,190 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

      • 8% Above List Price
      • 25 Days On Market

      Last Sold Price $234,900

      Last Listing Agent David Moore Real Broker, LLC

  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $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

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
    /13

    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620

    This property features 1200 square feet of living space, including one bathroom and 2 designated bedrooms. The unit comes fully furnished and is smoke-free, providing a clean and comfortable environment. Key amenities include air conditioning for climate control, a dishwasher for convenient meal cleanup, and an in-unit washer and dryer for laundry needs. The living area is spacious, allowing for

    160 Twin Oaks Farm Ln Unit Main level unit, Chestertown, MD 21620
  • 6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    /41

    $320,000 Sold Mar 26, 2025

    6744 Church Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,298 Sq Ft
    • Built 1964

    Last Sold Summary

    • $247/SF
    • 199 Days On Market

    Current Estimated Value $329,690

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    6744 Church Hill Rd, Chestertown, MD 21620
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $410,637 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

      • 14% Above List Price
      • $179/SF
      • 1 Day On Market

      Last Sold Price $360,000

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 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
  • 7121 Quaker Neck Rd, Chestertown, MD 21620
    7121 Quaker Neck Rd, Chestertown, MD 21620
    7121 Quaker Neck Rd, Chestertown, MD 21620
    /13

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    7121 Quaker Neck Rd, Chestertown, MD 21620

    This is a perfect little house in the country on a 1 acre secluded lot 1 1/2 miles from Chestertown. It is brand new on the inside with high end finishes. New Anderson windows, new doors, tile and laminate floors, SS appliances, granite countertops, Rinnai hot water heater, mini split heat pump, Owner will cut grass and maintain exterior ( 2 tomato plants) for one year, high speed internet

    7121 Quaker Neck Rd, Chestertown, MD 21620
  • 209 N Water St, Chestertown, MD 21620
    209 N Water St, Chestertown, MD 21620
    /2

    $1,100,000 Sold Jun 30, 2025

    209 N Water St, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft
    • Built 1900

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,158,433

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $382,750 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

      • 11% Above List Price
      • $246/SF

      Last Sold Price $344,500

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County Chestertown

Real Estate & Homes

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 48 days on the market compared to the national average of 54 days. The median sale price for homes in Chestertown, MD over the last 12 months is $379,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$379,000
Median Single Family Sale Price
$392,500
Median Townhouse Sale Price
$284,750
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$222
Number of Homes for Sale
29
Last 12 months Home Sales
99
Months of Supply
3.50
Median List Price
$377,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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