6,896

Chestertown, MD Homes

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

    $670,000

    • 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
  • 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
    /9

    $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
  • 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 $364,881

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, 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

      Est $654,598

      Not Listed For Sale

      108 N Queen St, Chestertown, MD 21620

      • 5 Beds
      • 2.5 Baths
      • 2,536 Sq Ft
      • Built 1920
      108 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $237/SF
      • Last Sold Price $600,000
      • May 16, 2025

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 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
  • 104 Cedar St, Chestertown, MD 21620
    104 Cedar St, Chestertown, MD 21620
    104 Cedar St, Chestertown, MD 21620
    /15

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,612 Sq Ft
    • House for Rent

    104 Cedar St, Chestertown, MD 21620

    Great 3 Bedroom 2.5 Bath home located in Chestertown within close proximity of the college, downtown, and local shopping. The house will be available starting June 1st. There is a credit check, background check and rental application needed. No pets, no smoking. Excellent credit is required.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Cedar St, 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 $327,132

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
    • 0 Fairlee Rd, Chestertown, MD 21620
      0 Fairlee Rd, Chestertown, MD 21620
      0 Fairlee Rd, Chestertown, MD 21620
      /8

      Not Listed For Sale

      0 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • Built 1979
      0 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • $52/SF
      • 159 Days On Market
      • Last Sold Price $50,000
      • May 16, 2025

      Last Listing Agent William Norris Select Land & Homes, LLC

  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    Under Contract
    • 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
  • 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

    $2,050 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 $379,942

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $464,151

      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
      • Apr 11, 2024

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /22

    $450,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Coventry Farms—Reduced to Sell, Offers EncouragedLocated in the highly desirable Coventry Farms community, this home presents a wonderful opportunity for its next owner to bring fresh vision and personal touches. With the seller preparing for a move out of the area, the property has been reduced to reflect its current condition and to encourage a timely sale. Inside, you’ll find generous

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford 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
  • 107 Conley Dr, Chestertown, MD 21620
    107 Conley Dr, Chestertown, MD 21620
    107 Conley Dr, Chestertown, MD 21620
    /16

    $150,000

    Sold May 15, 2026

    107 Conley Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $132/SF
    • 32 Days On Market

    Current Estimated Value $169,790

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $251,353

      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

      • 7% Above List Price
      • 25 Days On Market
      • Last Sold Price $234,900
      • Dec 15, 2023

      Last Listing Agent David Moore Real Broker, LLC

  • 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

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    /26

    $1,520 Per Month

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

    104 Maple Ave Unit 3, 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 3, 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 $654,566

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $451,618

      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

      • 25% Above List Price
      • $179/SF
      • 1 Day On Market
      • Last Sold Price $360,000
      • May 07, 2024

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 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

    Pending
    • 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
  • 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 $352,700

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 204 Pine Cove Ln, Chestertown, MD 21620
      204 Pine Cove Ln, Chestertown, MD 21620
      204 Pine Cove Ln, Chestertown, MD 21620
      /30

      Est $429,263

      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

      • 7% Above List Price
      • $185/SF
      • 19 Days On Market
      • Last Sold Price $400,000
      • Mar 12, 2025

      Last Listing Agent Kelly Harris Coldwell Banker (NRT-Southeast-MidAtlantic)

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

    $320,000

    Under Contract
    • 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
  • 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 $1,484,391

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, 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 $381,921

      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
      • Sep 29, 2023

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    /28

    $340,000

    $49K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo Dr, 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 $1,168,482

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      /34

      Est $281,386

      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

      • 20% Above List Price
      • $191/SF
      • 14 Days On Market
      • Last Sold Price $235,000
      • Nov 30, 2023

      Last Listing Agent Petra Quinn Realty Navigator

  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /37

    $319,900

    Under Contract
    • 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
  • 7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, 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 $286,974

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • 142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      /27

      Est $428,869

      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

      • 6% Above List Price
      • $284/SF
      • 39 Days On Market
      • Last Sold Price $405,000
      • Nov 22, 2024

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 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 10AM - 2PM
    • 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

    (410) 936-3661

    226 S Water St, Chestertown, MD 21620
  • 23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, 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 $173,333

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • 106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      /27

      Est $521,890

      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

      • 5% Above List Price
      • $350/SF
      • 7 Days On Market
      • Last Sold Price $495,000
      • Dec 13, 2024

      Last Listing Agent Cindy Genther Rock Hall Properties

  • 113 Pear Tree Point Rd, Chestertown, MD 21620
    113 Pear Tree Point Rd, Chestertown, MD 21620
    /2

    $250,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    113 Pear Tree Point Rd, Chestertown, MD 21620

    OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here --

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 373-5178

    113 Pear Tree Point Rd, Chestertown, MD 21620
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, 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 $185,880

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $423,568

      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

      • 21% Above List Price
      • $122/SF
      • 118 Days On Market
      • Last Sold Price $349,000
      • Apr 26, 2024

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 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

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620

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 50 days on the market compared to the national average of 58 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$398,000
Median Townhouse Sale Price
$280,000
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$211
Number of Homes for Sale
37
Last 12 months Home Sales
100
Months of Supply
4.40
Median List Price
$379,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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