12,112

Kent County, MD Homes

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

    $339,900

    • 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
  • 112 Flying Cloud Dr, Chestertown, MD 21620
    112 Flying Cloud Dr, Chestertown, MD 21620
    112 Flying Cloud Dr, Chestertown, MD 21620
    /15

    $2,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,056 Sq Ft
    • House for Rent

    112 Flying Cloud Dr, Chestertown, MD 21620

    Property Id: 2458980Built in 2023, this beautifully designed 4-bedroom, 2.5-bath home offers 2,056 square feet of modern living in a well-maintained, desirable neighborhood. Thoughtfully laid out with both comfort and functionality in mind, the home features open-concept living spaces, generous natural light, and well-proportioned bedrooms ideal for everyday living or working from

    112 Flying Cloud Dr, Chestertown, MD 21620
  • 25070 E Kentfield Rd, Worton, MD 21678
    25070 E Kentfield Rd, Worton, MD 21678
    25070 E Kentfield Rd, Worton, MD 21678
    /57

    $740,000 Sold May 07, 2025

    25070 E Kentfield Rd, Worton, MD 21678

    • 5 Beds
    • 3.5 Baths
    • 3,222 Sq Ft
    • Built 1995

    Last Sold Summary

    • $230/SF
    • 10 Days On Market

    Current Estimated Value $766,954

    Last Listing Agent Crystal Smith RE/MAX Executive

    25070 E Kentfield Rd, Worton, MD 21678
    • 107 Chester Arms Dr, Chestertown, MD 21620
      107 Chester Arms Dr, Chestertown, MD 21620
      107 Chester Arms Dr, Chestertown, MD 21620
      /19

      Est $248,809 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

      • 8% Above List Price
      • $202/SF
      • 14 Days On Market
      • Last Sold Price $230,000
      • May 01, 2025

      Last Listing Agent Casey Scattergood Cross Street Realtors LLC

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

    $450,000

    • 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
  • 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
  • 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 $364,294

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • 303 Carville Dr, Millington, MD 21651
      303 Carville Dr, Millington, MD 21651
      303 Carville Dr, Millington, MD 21651
      /26

      Est $404,837 Not Listed For Sale

      303 Carville Dr, Millington, MD 21651

      • 4 Beds
      • 2.5 Baths
      • 2,460 Sq Ft
      • Built 2007
      303 Carville Dr, Millington, MD 21651

      Last Sold Summary

      • 7% Above List Price
      • $154/SF
      • 0 Days On Market
      • Last Sold Price $380,000
      • Apr 30, 2025

      Last Listing Agent David Landon Patterson Schwartz

  • 206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    /31

    $250,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    206 Virginia Ave, Galena, MD 21635

    Are you looking for a classic home with a ton of charm? Do you love original wood floors? Not afraid of updating? This could just be the home for you! Screened in porch welcomes you to a beautiful foyer, and a classic living room with a fireplace that has been closed up but still provides a nice focal point. Owner is not sure if it could become a working wood-burning fireplace or not, but a gas

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 843-7243

    206 Virginia Ave, Galena, MD 21635
  • 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
  • 5855 Crosby Rd, Rock Hall, MD 21661
    5855 Crosby Rd, Rock Hall, MD 21661
    5855 Crosby Rd, Rock Hall, MD 21661
    /14

    $214,000 Sold Jun 18, 2025

    5855 Crosby Rd, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2005

    Last Sold Summary

    • $159/SF
    • 82 Days On Market

    Current Estimated Value $230,099

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    5855 Crosby Rd, Rock Hall, MD 21661
    • 5535 Boundary Ave, Rock Hall, MD 21661
      5535 Boundary Ave, Rock Hall, MD 21661
      5535 Boundary Ave, Rock Hall, MD 21661
      /30

      Est $406,918 Not Listed For Sale

      5535 Boundary Ave, Rock Hall, MD 21661

      • 4 Beds
      • 2.5 Baths
      • 1,769 Sq Ft
      • Built 1923
      5535 Boundary Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 2% Above List Price
      • $226/SF
      • 11 Days On Market
      • Last Sold Price $400,000
      • May 02, 2025

      Last Listing Agent Jeff Guthrie Taylor Properties

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

    $695,000

    • 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
    /5

    $1,000 per month

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

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 1. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. First floor studio apartment. Unit is available immediately, utilities included: electric, water and sewer. Security Deposit plus one month rent (plus any proration) due at signing. Applications submitted via

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, 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 $378,947

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 5886 Williams St, Rock Hall, MD 21661
      5886 Williams St, Rock Hall, MD 21661
      5886 Williams St, Rock Hall, MD 21661
      /33

      Est $292,024 Not Listed For Sale

      5886 Williams St, Rock Hall, MD 21661

      • 3 Beds
      • 1 Bath
      • 1,256 Sq Ft
      • Built 1954
      5886 Williams St, Rock Hall, MD 21661

      Last Sold Summary

      • 8% Above List Price
      • $215/SF
      • 84 Days On Market
      • Last Sold Price $270,000
      • May 02, 2025

      Last Listing Agent Joseph A Zang III RE/MAX

  • 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
  • 13755 Shallcross Wharf Rd, Kennedyville, MD 21645
    13755 Shallcross Wharf Rd, Kennedyville, MD 21645
    13755 Shallcross Wharf Rd, Kennedyville, MD 21645
    /43

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    13755 Shallcross Wharf Rd, Kennedyville, MD 21645

    Wonderful 2 Bedroom / 2 Bath Cape Cod on a Bluff with Water View. This open concept home has great views and presents the opportunity to live off the beaten path. If living in and amongst nature interests you this home could be perfect. Hardwood floors, modern kitchen, full UN-finished basement, and the opportunity to watch and enjoy the seasons overlooking a tributary of the Sassafras River.

    Michael Davis Phoenix Real Estate

    13755 Shallcross Wharf Rd, Kennedyville, MD 21645
  • 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 $639,971

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • 11478 Lynch Rd, Worton, MD 21678
      11478 Lynch Rd, Worton, MD 21678
      11478 Lynch Rd, Worton, MD 21678
      /32

      Est $211,326 Not Listed For Sale

      11478 Lynch Rd, Worton, MD 21678

      • 3 Beds
      • 1 Bath
      • 1,178 Sq Ft
      • Built 1940
      11478 Lynch Rd, Worton, MD 21678

      Last Sold Summary

      • 11% Above List Price
      • $161/SF
      • 5 Days On Market
      • Last Sold Price $190,000
      • Apr 30, 2025

      Last Listing Agent Jamie Taraila Keller Williams Realty Central-Delaware

  • 21305 Haven Rd, Rock Hall, MD 21661
    21305 Haven Rd, Rock Hall, MD 21661
    21305 Haven Rd, Rock Hall, MD 21661
    /53

    $350,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,499 Sq Ft

    21305 Haven Rd, Rock Hall, MD 21661

    Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch,

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    (410) 213-3053

    21305 Haven Rd, Rock Hall, MD 21661
  • 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
  • 407 Jarman Ave, Galena, MD 21635
    407 Jarman Ave, Galena, MD 21635
    407 Jarman Ave, Galena, MD 21635
    /30

    $297,500 Sold May 16, 2025

    407 Jarman Ave, Galena, MD 21635

    • 3 Beds
    • 1.5 Baths
    • 2,135 Sq Ft
    • Built 1969

    Last Sold Summary

    • $139/SF
    • 23 Days On Market

    Current Estimated Value $311,706

    Last Listing Agent David Moore Real Broker, LLC

    407 Jarman Ave, Galena, MD 21635
    • 25161 Smithville Rd, Worton, MD 21678
      25161 Smithville Rd, Worton, MD 21678
      25161 Smithville Rd, Worton, MD 21678
      /30

      Est $301,315 Not Listed For Sale

      25161 Smithville Rd, Worton, MD 21678

      • 2 Beds
      • 1.5 Baths
      • 1,189 Sq Ft
      • Built 1970
      25161 Smithville Rd, Worton, MD 21678

      Last Sold Summary

      • 2% Above List Price
      • $248/SF
      • 26 Days On Market
      • Last Sold Price $295,000
      • May 02, 2025

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    /46

    $699,900 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    24204 Drayton Landing Dr, Worton, MD 21678

    Privacy meets modern updates on two private acres in the sought-after Kinnaird’s Point community. This thoughtfully renovated home offers a peaceful setting with convenient access to the water, located just minutes from both Chestertown and Rock Hall. The property includes two community waterfront access points, featuring a private swim beach and boat launch along Still Pond Creek and Churn

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • 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 $365,994

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 4511 Piney Neck Rd, Rock Hall, MD 21661
      4511 Piney Neck Rd, Rock Hall, MD 21661
      4511 Piney Neck Rd, Rock Hall, MD 21661
      /46

      Est $3,323,168 Not Listed For Sale

      4511 Piney Neck Rd, Rock Hall, MD 21661

      • 5 Beds
      • 3.5 Baths
      • 4,050 Sq Ft
      • Built 1939
      4511 Piney Neck Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 1% Below List Price
      • $827/SF
      • 11 Days On Market
      • Last Sold Price $3,350,000
      • Apr 29, 2025

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /32

    $898,000

    • 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
  • 12440 Woods Rd, Worton, MD 21678
    12440 Woods Rd, Worton, MD 21678
    12440 Woods Rd, Worton, MD 21678
    /37

    $1,080,000 Sold May 12, 2025

    12440 Woods Rd, Worton, MD 21678

    • 4 Beds
    • 2 Baths
    • 1,955 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 12 Days On Market

    Current Estimated Value $1,101,469

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12440 Woods Rd, Worton, MD 21678
    • 505 N Kent St, Chestertown, MD 21620
      505 N Kent St, Chestertown, MD 21620
      505 N Kent St, Chestertown, MD 21620
      /23

      Est $370,965 Not Listed For Sale

      505 N Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,402 Sq Ft
      • Built 1985
      505 N Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $251/SF
      • 9 Days On Market
      • Last Sold Price $352,500
      • Apr 30, 2025

      Last Listing Agent Sarah Ulrick Rock Hall Properties

  • 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
  • 13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    /57

    $1,075,000 Sold Aug 28, 2025

    13931 Eagles Nest Farm Ln, Still Pond, MD 21667

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1987

    Last Sold Summary

    • $582/SF
    • 22 Days On Market

    Current Estimated Value $1,100,641

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    • 25214 Wymont Park Rd, Worton, MD 21678
      25214 Wymont Park Rd, Worton, MD 21678
      25214 Wymont Park Rd, Worton, MD 21678
      /51

      Est $779,869 Not Listed For Sale

      25214 Wymont Park Rd, Worton, MD 21678

      • 3 Beds
      • 2.5 Baths
      • 3,225 Sq Ft
      • Built 2009
      25214 Wymont Park Rd, Worton, MD 21678

      Last Sold Summary

      • 5% Above List Price
      • $229/SF
      • 7 Days On Market
      • Last Sold Price $740,000
      • May 02, 2025

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • 10 Ericsson Ave Unit 37, Betterton, MD 21610
    10 Ericsson Ave Unit 37, Betterton, MD 21610
    10 Ericsson Ave Unit 37, Betterton, MD 21610
    /40

    $315,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft

    10 Ericsson Ave Unit 37, Betterton, MD 21610

    Beach day... or boat day.......maybe pool day? Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury.This condo is perfectly positioned with breathtaking views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the Sassafras River.Step inside this inviting 2-bedroom, 2 full bath

    Agent Photo

    Julie Strickler

    Remax Vision

    (410) 339-8749

    10 Ericsson Ave Unit 37, Betterton, MD 21610
  • 21133 Striper Run, Rock Hall, MD 21661
    21133 Striper Run, Rock Hall, MD 21661
    21133 Striper Run, Rock Hall, MD 21661
    /9

    $364,900 Sold Apr 30, 2026

    21133 Striper Run, Rock Hall, MD 21661

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Built 2025

    Last Sold Summary

    • $224/SF
    • 132 Days On Market

    Current Estimated Value $362,944

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661
    • 313 Race St, Millington, MD 21651
      313 Race St, Millington, MD 21651
      313 Race St, Millington, MD 21651
      /8

      Est $79,512 Not Listed For Sale

      313 Race St, Millington, MD 21651

      313 Race St, Millington, MD 21651

      Last Sold Summary

      • 170% Above List Price
      • 241 Days On Market
      • Last Sold Price $29,500
      • Feb 27, 2025

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • 14037 E Beechwood Rd, Galena, MD 21635
    14037 E Beechwood Rd, Galena, MD 21635
    /2

    $365,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    14037 E Beechwood Rd, Galena, MD 21635

    Welcome to 14037 E. Beechwood Road- set on a spacious, nearly one-acre lot, this property offers privacy, scenic views, and the kind of laid-back lifestyle the Eastern Shore is known for. Enjoy the beauty of rural surroundings with plenty of room for outdoor living, gardening or simply relaxing and taking in the natural landscape. Inside, the move-in ready home features three comfortable bedrooms

    Agent Photo

    Candice Santoro

    CR Realty

    (410) 881-8209

    14037 E Beechwood Rd, Galena, MD 21635
  • 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
    • 1 Bayview Rd Unit 3, Betterton, MD 21610
      1 Bayview Rd Unit 3, Betterton, MD 21610
      1 Bayview Rd Unit 3, Betterton, MD 21610
      /24

      Not Listed For Sale

      1 Bayview Rd Unit 3, Betterton, MD 21610

      • 2 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1989
      1 Bayview Rd Unit 3, Betterton, MD 21610

      Last Sold Summary

      • $169/SF
      • 1 Day On Market
      • Last Sold Price $270,000
      • Aug 02, 2024

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  • 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

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group