12,106

Kent County, MD Homes

Section Image Section Image
    • 147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      /70

      Est $719,008 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft

      147 Carriage Heath, Chester, MD 21619

      147 Carriage Heath, Chester, MD 21619
  • 14183 Roberts Dr, Galena, MD 21635
    14183 Roberts Dr, Galena, MD 21635
    14183 Roberts Dr, Galena, MD 21635
    /50

    $1,975,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 3,915 Sq Ft

    14183 Roberts Dr, Galena, MD 21635

    Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 784-4852

    14183 Roberts Dr, Galena, MD 21635
  • 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

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • 106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      /27

      Est $508,433 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft

      106 Church Aly, Chestertown, MD 21620

      106 Church Aly, Chestertown, MD 21620
  • 11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    /25

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    This classic home has been beautifully renovated and updated while maintaining the original charm. Enjoy cooking meals in the gourmet kitchen with stainless steel appliances, double wall oven and downdraft cooktop. The kitchen leads to the formal dining room and large open living space, perfect for entertaining. There are four bedrooms, two full bathrooms, and a third-floor bonus room, which

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 892-1081

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • 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
    • 0.34 Acre
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $473,416 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000

    • 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 0 Millbrook Dr, Chestertown, MD 21620
    0 Millbrook Dr, Chestertown, MD 21620
    /2

    $9,500 Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 0.5 Acre
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Millbrook Dr, Chestertown, MD 21620
    • 10 School House Rd, Millington, MD 21651
      10 School House Rd, Millington, MD 21651
      10 School House Rd, Millington, MD 21651
      /25

      Not Listed For Sale

      10 School House Rd, Millington, MD 21651

      10 School House Rd, Millington, MD 21651
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 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

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 0 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    0 None Unit MDKE2005014, Chestertown, MD 21620

    • Land
    • 13.46 Acres
    • $6,686 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • 7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      /34

      Est $619,701 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft

      7675 Quaker Neck Rd, Chestertown, MD 21620

      7675 Quaker Neck Rd, Chestertown, MD 21620
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • 21311 Lee St, Rock Hall, MD 21661
    21311 Lee St, Rock Hall, MD 21661
    21311 Lee St, Rock Hall, MD 21661
    /39

    $415,000 Sold Sep 17, 2025

    21311 Lee St, Rock Hall, MD 21661

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1979

    Last Sold Summary

    • $240/SF
    • 13 Days On Market

    Current Estimated Value $413,239

    Last Listing Agent Sarah King Cross Street Realtors LLC

    21311 Lee St, Rock Hall, MD 21661
    • 5837 Clam Cove, Rock Hall, MD 21661
      5837 Clam Cove, Rock Hall, MD 21661
      5837 Clam Cove, Rock Hall, MD 21661
      /27

      Est $401,027 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,707 Sq Ft

      5837 Clam Cove, Rock Hall, MD 21661

      5837 Clam Cove, Rock Hall, MD 21661
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /20

    $220,000 Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $222,902

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • 5246 Eastern Neck Rd, Rock Hall, MD 21661
      5246 Eastern Neck Rd, Rock Hall, MD 21661
      5246 Eastern Neck Rd, Rock Hall, MD 21661
      /7

      Est $77,381 Not Listed For Sale

      5246 Eastern Neck Rd, Rock Hall, MD 21661

      5246 Eastern Neck Rd, Rock Hall, MD 21661
  • 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
  • 8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    /44

    $680,000 Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $680,593

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • 10578 Chesterville Forest Rd, Millington, MD 21651
      10578 Chesterville Forest Rd, Millington, MD 21651
      10578 Chesterville Forest Rd, Millington, MD 21651
      /9

      Est $361,108 Not Listed For Sale

      10578 Chesterville Forest Rd, Millington, MD 21651

      10578 Chesterville Forest Rd, Millington, MD 21651
  • 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

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • 12083 Blacks Station Rd, Kennedyville, MD 21645
    12083 Blacks Station Rd, Kennedyville, MD 21645
    12083 Blacks Station Rd, Kennedyville, MD 21645
    /73

    $910,000 Sold Jul 31, 2025

    12083 Blacks Station Rd, Kennedyville, MD 21645

    • 5 Beds
    • 4.5 Baths
    • 2,542 Sq Ft
    • Built 1990

    Last Sold Summary

    • $358/SF
    • 11 Days On Market

    Current Estimated Value $883,289

    Last Listing Agent Joe Hickman Cross Street Realtors LLC

    12083 Blacks Station Rd, Kennedyville, MD 21645
    • 11430 Lynch Rd, Worton, MD 21678
      11430 Lynch Rd, Worton, MD 21678
      11430 Lynch Rd, Worton, MD 21678
      /35

      Not Listed For Sale

      • 2 Beds

      11430 Lynch Rd, Worton, MD 21678

      11430 Lynch Rd, Worton, MD 21678
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    211 David Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft
    • Built 1963

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $790,266

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • 5785 Liberty St, Rock Hall, MD 21661
      5785 Liberty St, Rock Hall, MD 21661
      5785 Liberty St, Rock Hall, MD 21661
      /52

      Est $391,475 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,520 Sq Ft

      5785 Liberty St, Rock Hall, MD 21661

      5785 Liberty St, Rock Hall, MD 21661
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,500,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 19 1st Ave, Betterton, MD 21610
    19 1st Ave, Betterton, MD 21610
    19 1st Ave, Betterton, MD 21610
    /35

    $210,000 Sold Oct 03, 2025

    19 1st Ave, Betterton, MD 21610

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft
    • Built 1951

    Last Sold Summary

    • $417/SF
    • 3 Days On Market

    Current Estimated Value $210,900

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    19 1st Ave, Betterton, MD 21610
    • 120 N Main St, Galena, MD 21635
      120 N Main St, Galena, MD 21635
      120 N Main St, Galena, MD 21635
      /35

      Est $285,574 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft

      120 N Main St, Galena, MD 21635

      120 N Main St, Galena, MD 21635
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /20

    $135,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just steps from historic downtown Chestertown. LVP Flooring installed on 10/04/2025 on the main and upper levels. Carpet installed on the staircase. Materials, fixtures, applicances cabinetry, washer/dryer ready to install. Discover the potential of 423 Calvert Street — a two-story,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    /2

    $2,500 Sold Sep 12, 2025

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678

    • Land
    • 0.34 Acre
    • $7,353 per Acre

    Last Sold Summary

    • 252 Days On Market

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    • 5788 Liberty St, Rock Hall, MD 21661
      5788 Liberty St, Rock Hall, MD 21661
      5788 Liberty St, Rock Hall, MD 21661
      /24

      Est $303,670 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,220 Sq Ft

      5788 Liberty St, Rock Hall, MD 21661

      5788 Liberty St, Rock Hall, MD 21661
  • 21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    /22

    $749,900

    • Land
    • 7.9 Acres
    • $94,924 per Acre

    21610 Hidden Creek Dr, Rock Hall, MD 21661

    Enjoy a long, secluded driveway to 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Greys Creek. The home features vaulted ceilings and has access to a private pier and dock; its perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this property

    Mike Arajakis Whitetail Properties Real Estate

    21610 Hidden Creek Dr, Rock Hall, MD 21661
  • 31703 Olivet Cir, Galena, MD 21635
    31703 Olivet Cir, Galena, MD 21635
    31703 Olivet Cir, Galena, MD 21635
    /4

    $31,000 Sold Apr 09, 2025

    31703 Olivet Cir, Galena, MD 21635

    • Land
    • 0.53 Acre
    • $58,491 per Acre

    Last Sold Summary

    • 69 Days On Market

    Current Estimated Value $38,000

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    31703 Olivet Cir, Galena, MD 21635
    • 117 Chester Arms Dr, Chestertown, MD 21620
      117 Chester Arms Dr, Chestertown, MD 21620
      117 Chester Arms Dr, Chestertown, MD 21620
      /27

      Est $261,772 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,260 Sq Ft

      117 Chester Arms Dr, Chestertown, MD 21620

      117 Chester Arms Dr, Chestertown, MD 21620
  • 12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    /29

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    12400 Woods Rd, Worton, MD 21678

    Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by

    Jack Boniface Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • 119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    /60

    $1,165,000 Sold Dec 01, 2025

    119 High St, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,409 Sq Ft
    • Built 1876

    Last Sold Summary

    • $264/SF
    • 5 Days On Market

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • 209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      /33

      Est $694,293 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      209 Landing Ln, Chestertown, MD 21620

      209 Landing Ln, Chestertown, MD 21620

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