12,132

Kent County, MD Homes

Section Image
  • /13

    $364,900

    Sold Feb 20, 2026

    21141 Striper Run, Rock Hall, MD 21661

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

    Last Sold Summary

    • $224/SF
    • 69 Days On Market

    Current Estimated Value $365,898

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21141 Striper Run, Rock Hall, MD 21661
    • /25

      Est $342,592

      Not Listed For Sale

      5924 Henry Ave, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft
      • Built 1953
      5924 Henry Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 97 Days On Market

  • /41

    $475,000

    • 4 Beds
    • 3 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /34

    $550,000

    Sold Jul 31, 2025

    21026 Rock Hall Ave, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,649 Sq Ft
    • Built 2014

    Last Sold Summary

    • $334/SF
    • 127 Days On Market

    Current Estimated Value $573,904

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21026 Rock Hall Ave, Rock Hall, MD 21661
    • /93

      Est $852,315

      Not Listed For Sale

      30741 Duck Puddle Rd, Kennedyville, MD 21645

      • 5 Beds
      • 3.5 Baths
      • 5,118 Sq Ft
      • Built 1999
      30741 Duck Puddle Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 109 Days On Market

  • /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /67

    $490,000

    Sold May 08, 2026

    100 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft
    • Built 2008

    Last Sold Summary

    • $129/SF
    • 182 Days On Market

    Current Estimated Value $494,407

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
    • /29

      Est $372,188

      Not Listed For Sale

      21053 Striper Run, Rock Hall, MD 21661

      • 4 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 2013
      21053 Striper Run, Rock Hall, MD 21661

      Last Sold Summary

      • 0 Days On Market

  • /26

    $284,900

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

    104 Acorn Dr, Chestertown, MD 21620

    Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car

    Sarah King Cross Street Realtors LLC

    104 Acorn Dr, Chestertown, MD 21620
  • /70

    $1,450,000

    Sold May 01, 2026

    24241 Drayton Landing Dr, Worton, MD 21678

    • 3 Beds
    • 3 Baths
    • 3,526 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Above List Price
    • $411/SF

    Current Estimated Value $982,902

    Last Listing Agent Brooke Penders Coldwell Banker Realty

    24241 Drayton Landing Dr, Worton, MD 21678
    • /27

      Est $280,097

      Not Listed For Sale

      316 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1966
      316 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

  • /33

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft

    5862 N Main St, Rock Hall, MD 21661

    Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main

    Jordan Larigan LPT Realty, LLC

    5862 N Main St, Rock Hall, MD 21661
  • /19

    $249,000

    Sold Jun 12, 2026

    112 Elm St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Below List Price
    • $184/SF
    • 14 Days On Market

    Current Estimated Value $269,331

    Last Listing Agent Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
    • /36

      Est $247,368

      Not Listed For Sale

      21010 Rock Hall Ave, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,304 Sq Ft
      • Built 1968
      21010 Rock Hall Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 7 Days On Market

  • /73

    $1,600,000

    • 7 Beds
    • 5 Baths
    • 5,400 Sq Ft

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

    **Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • /40

    $252,500

    Sold Jun 25, 2025

    100 N Main St, Galena, MD 21635

    • 2 Beds
    • 1 Bath
    • 2,230 Sq Ft
    • Built 1900

    Last Sold Summary

    • $113/SF
    • 465 Days On Market

    Last Listing Agent Jenyne Ward Patterson-Schwartz Real Estate

    100 N Main St, Galena, MD 21635
    • /33

      Est $380,048

      Not Listed For Sale

      13037 Augustine Herman Hwy, Kennedyville, MD 21645

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1961
      13037 Augustine Herman Hwy, Kennedyville, MD 21645

      Last Sold Summary

      • 81 Days On Market

  • /6

    $79,000

    • Land
    • 1.95 Acres
    • $40,513 per Acre

    0 Sandy Bottom Rd, 6, Fairlee, MD 21620

    Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of mature trees and a partially open entrance area, this property is ideal for camping, hunting, recreation, or simply enjoying nature in a tranquil setting. Bring your RV or pitch a tent and enjoy the great outdoors! Electric is

    John Carroll Village Real Estate Company LLC

    0 Sandy Bottom Rd, 6, Fairlee, MD 21620
  • /2

    $30,000

    Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 36,154 Sq Ft
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    • /20

      Est $171,381

      Not Listed For Sale

      508 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1921
      508 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • /33

    $445,000

    $65K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    32135 River Rd, Millington, MD 21651

    Experience waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining

    Christine Catalano Coldwell Banker Realty

    32135 River Rd, Millington, MD 21651
  • /3

    $64,000

    Sold Jan 26, 2026

    212 Crane St, Millington, MD 21651

    • 3 Beds
    • 1 Bath
    • 1,220 Sq Ft
    • Built 1920

    Last Sold Summary

    • $52/SF

    Current Estimated Value $118,333

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    212 Crane St, Millington, MD 21651
    • /27

      Est $350,462

      Not Listed For Sale

      27978 Redmill St, Kennedyville, MD 21645

      • 3 Beds
      • 2 Baths
      • 1,617 Sq Ft
      • Built 2009
      27978 Redmill St, Kennedyville, MD 21645

      Last Sold Summary

      • 4 Days On Market

  • /33

    $425,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    21007 Bayside Ave, Rock Hall, MD 21661

    Adorable updated cottage in the heart of town on popular Bayside Avenue offering approximately 1,400 sq. ft. of charming coastal living. This delightful Cape Cod features 3 bedrooms and 2 full baths, with seasonal water views of Rock Hall Harbor from the second floor. The main level offers an open floor plan with a cozy propane fireplace, 2 bedrooms, and 1 full bath, while the entire upper level

    Cindy Genther Rock Hall Properties Real Estate

    21007 Bayside Ave, Rock Hall, MD 21661
  • /57

    $475,000

    Sold Jul 08, 2025

    28743 Anglewood Rd, Kennedyville, MD 21645

    • 4 Beds
    • 3 Baths
    • 2,184 Sq Ft
    • Built 2003

    Last Sold Summary

    • $217/SF
    • 19 Days On Market

    Current Estimated Value $499,612

    Last Listing Agent Patricia Kern Gunther-McClary Real Estate

    28743 Anglewood Rd, Kennedyville, MD 21645
    • /13

      Est $241,760

      Not Listed For Sale

      21286 Maine Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 2001
      21286 Maine Ave, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

  • /6

    $8,000

    • Land
    • 14,810 Sq Ft
    • $23,529 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/30/2026, 10:00 AM. Bidding ends 7/2/2026, 12:45 PM. The list price is the suggested opening bid. Deposit: $5,000. Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, &

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /12

    $1,100,000

    Sold Jan 23, 2026

    24028 Cliff Drive Extension, Worton, MD 21678

    • 3 Beds
    • 2.5 Baths
    • 2,415 Sq Ft
    • Built 1992

    Last Sold Summary

    • 21% Below List Price
    • $455/SF
    • 0 Days On Market

    Current Estimated Value $1,160,325

    Last Listing Agent John Burke Gunther-McClary Real Estate

    24028 Cliff Drive Extension, Worton, MD 21678
    • /69

      Est $2,745,635

      Not Listed For Sale

      6299 Burris Rd, Rock Hall, MD 21661

      • 4 Beds
      • 3.5 Baths
      • 3,718 Sq Ft
      • Built 1989
      6299 Burris Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 141 Days On Market

  • /6

    $119,895

    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft

    110 Prospect St, Chestertown, MD 21620

    Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This

    Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
  • /50

    $370,000

    Sold Aug 11, 2025

    169 Millington Rd, Millington, MD 21651

    • 4 Beds
    • 2 Baths
    • 2,414 Sq Ft
    • Built 2007

    Last Sold Summary

    • $153/SF
    • 12 Days On Market

    Current Estimated Value $376,651

    Last Listing Agent Penny Hollis Keller Williams Select Realtors of Annapolis

    169 Millington Rd, Millington, MD 21651
    • /10

      Est $283,732

      Not Listed For Sale

      5543 Boundary Ave, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,374 Sq Ft
      • Built 1883
      5543 Boundary Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 5 Days On Market

  • /63

    $317,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft

    10 Ericsson Ave Unit 33, Betterton, MD 21610

    Welcome to 10 Ericsson Ave #33 in the waterfront community of Betterton, where everyday living feels like a permanent getaway. Nestled within the peaceful enclave of Rigbie Bluff, this inviting, updated, and move-in ready condo offers a rare blend of tranquility, charm, and scenic beauty. This well-appointed two-bedroom, two-bath residence is conveniently located on the ground level, making

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    10 Ericsson Ave Unit 33, Betterton, MD 21610
  • /28

    $350,000

    Sold Jun 23, 2025

    180 Birchwood Ln, Galena, MD 21635

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Built 1997

    Last Sold Summary

    • $271/SF
    • 13 Days On Market

    Current Estimated Value $369,787

    Last Listing Agent Kathleen Pigliacampi Patterson-Schwartz-Hockessin

    180 Birchwood Ln, Galena, MD 21635
    • /28

      Est $271,947

      Not Listed For Sale

      545 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft
      • Built 1900
      545 High St, Chestertown, MD 21620

      Last Sold Summary

      • 46 Days On Market

  • /89

    $2,500,000

    • 4 Beds
    • 3.5 Baths
    • 5,236 Sq Ft

    31436 Sassafras River Ave, Galena, MD 21635

    Sassafras Riverfront Retreat | Log cabin custom built home with Deep Water Pier, (seller had their 70 ft boat docked there for 10 years) with space for several boats to be docked as well. Indoor Pool looking to the outdoors with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So

    Tammy Studebaker EXP Realty, LLC

    31436 Sassafras River Ave, Galena, MD 21635
  • /27

    $290,000

    Sold Jan 16, 2026

    107 Malone Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1962

    Last Sold Summary

    • $242/SF
    • 69 Days On Market

    Current Estimated Value $289,023

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
    • /47

      Est $331,093

      Not Listed For Sale

      9041 S Bayview Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 2009
      9041 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

  • /82

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8276 Broad Neck Rd, Chestertown, MD 21620
  • /36

    $270,000

    Sold Feb 19, 2026

    24339 Chestertown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1964

    Last Sold Summary

    • $281/SF
    • 4 Days On Market

    Current Estimated Value $266,428

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    24339 Chestertown Rd, Chestertown, MD 21620

Showing Results 241 - 280, Page 7 of 18

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