11,962

Kent County, MD Homes

Section Image
  • /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • /39

    $500,000

    Sold Sep 01, 2026

    101 S Mill St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $339/SF
    • 36 Days On Market

    Current Estimated Value $506,699

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • /64

      Est $1,461,398

      Not Listed For Sale

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 1986
      9545 Chantilly Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /15

    $115,000

    $74K PRICE DROP
    • Land
    • 21,780 Sq Ft
    • $230,000 per Acre

    26765 Dutchtown Rd, Still Pond, MD 21667

    Situated at the end of a quiet dead-end street with only a handful of neighboring homes, this private 1/2 acre lot with a 1250 SF Rancher , 3 bedroom, 2 bath offers a serene setting backing to woods, with open farmland across the street. Enjoy the peace of rural living just minutes from the waterfront—only about 3 minutes to Betterton Beach. Location is the ultimate Pet safe environment as you're

    Michael Kelczewski DMV Prime Properties

    26765 Dutchtown Rd, Still Pond, MD 21667
  • /29

    $433,000

    Sold Sep 01, 2026

    222 Mount Vernon Ave, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft
    • Built 1916

    Last Sold Summary

    • $261/SF
    • 273 Days On Market

    Current Estimated Value $418,024

    Last Listing Agent Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
    • /28

      Est $521,596

      Not Listed For Sale

      21958 Harrington Park Rd, Rock Hall, MD 21661

      • 4 Beds
      • 2 Baths
      • 2,190 Sq Ft
      • Built 1973
      21958 Harrington Park Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:30 AM. The list price is the suggested opening bid. Deposit: $5,000.This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the

    Adam Shpritz Ashland Auction Group LLC

    0 Lenapah Rd, Chestertown, MD 21620
  • /31

    $215,000

    Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Current Estimated Value $222,520

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
    • /29

      Est $248,152

      Not Listed For Sale

      11778 Augustine Herman Hwy, Kennedyville, MD 21645

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1967
      11778 Augustine Herman Hwy, Kennedyville, MD 21645

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Sharon Clark Clark & Co Realty, LLC

  • /40

    $545,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    21090 W Sharp St Unit 133, Rock Hall, MD 21661

    Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern

    Lynn Hilfiker Gunther-McClary Real Estate

    21090 W Sharp St Unit 133, Rock Hall, MD 21661
  • /20

    $320,000

    Sold Jul 08, 2026

    10584 Klamath Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    10584 Klamath Rd, Chestertown, MD 21620
    • /44

      Est $594,078

      Not Listed For Sale

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1890
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Christopher McClary Gunther-McClary Real Estate

  • /68

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, Chestertown, MD 21620
  • /39

    $695,000

    Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Current Estimated Value $688,935

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
    • /52

      Est $1,145,233

      Not Listed For Sale

      12445 Coopers Ln, Worton, MD 21678

      • 4 Beds
      • 5.5 Baths
      • 3,243 Sq Ft
      • Built 1995
      12445 Coopers Ln, Worton, MD 21678

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • /36

    $389,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    21123 Striper Run, Rock Hall, MD 21661

    ROCK HALL — ON THE GRID, NOT OFF THE GRID! Discover Eastern Shore living in this beautifully maintained end-unit townhome offering 2,040+ sq ft, a flexible floor plan and a premium oversized lot—with NO HOA! The standout feature is the oversized rear sunroom/4th bedroom, larger than the primary suite, with its own private exterior entrance and direct kitchen access. Ideal as a guest room, home

    susan taylor Chaney Homes, LLC

    21123 Striper Run, Rock Hall, MD 21661
  • /70

    $620,000

    Sold Apr 20, 2026

    11040 Kylie Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft
    • Built 2000

    Last Sold Summary

    • $168/SF
    • 497 Days On Market

    Current Estimated Value $635,508

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
    • /25

      Est $496,097

      Not Listed For Sale

      8500 Broad Neck Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 2014
      8500 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Ginny Dauses Coldwell Banker Waterman Realty

  • /61

    $649,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    22400 Great Oak Landing Rd, Chestertown, MD 21620

    Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    22400 Great Oak Landing Rd, Chestertown, MD 21620
  • /73

    $435,000

    Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Current Estimated Value $450,145

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • /16

      Est $304,467

      Not Listed For Sale

      11811 Augustine Herman Hwy, Kennedyville, MD 21645

      • 3 Beds
      • 1.5 Baths
      • 2,217 Sq Ft
      • Built 1967
      11811 Augustine Herman Hwy, Kennedyville, MD 21645

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Gina Gargeu Century 21 Downtown

  • /53

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • /32

    $415,000

    Sold Jan 07, 2026

    411 Greenwood Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft
    • Built 2003

    Last Sold Summary

    • $248/SF
    • 1 Day On Market

    Current Estimated Value $422,072

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
    • /13

      Est $522,757

      Not Listed For Sale

      32155 River Rd, Millington, MD 21651

      • 4 Beds
      • 2.5 Baths
      • 2,234 Sq Ft
      • Built 2005
      32155 River Rd, Millington, MD 21651

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Adam Shpritz Ashland Auction Group LLC

  • /50

    $339,000

    $106K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • /36

    $750,000

    Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • /44

      Est $415,908

      Not Listed For Sale

      208 Byford Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,045 Sq Ft
      • Built 1976
      208 Byford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • /16

    $147,000

    • Land
    • 1 Acre
    • $147,000 per Acre

    Lot 30 Hagy Rd, Rock Hall, MD 21661

    Build your dream home in Little Neck Farm! Lot #30 is a spacious residential property on Hagy Road with a deeded deep-water boat slip. The future home site offers beautiful pastoral views and is nicely edged with crape myrtles and evergreens. The deeded boat slip, located in the Little Neck community waterfront, is just a short stroll or drive away. The community docks were recently updated and

    Julia Hilfiker Gunther-McClary Real Estate

    Lot 30 Hagy Rd, Rock Hall, MD 21661
  • /32

    $560,000

    Sold Mar 20, 2026

    5791 S Hawthorne Ave, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 2024

    Last Sold Summary

    • $365/SF
    • 127 Days On Market

    Current Estimated Value $548,801

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    5791 S Hawthorne Ave, Rock Hall, MD 21661
    • /28

      Est $318,120

      Not Listed For Sale

      30984 River Rd, Millington, MD 21651

      • 3 Beds
      • 2 Baths
      • 1,330 Sq Ft
      • Built 1971
      30984 River Rd, Millington, MD 21651

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

  • /3

    $175,000

    • Land
    • 32,670 Sq Ft
    • $233,333 per Acre

    9 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    9 Wilson Point Rd, Galena, MD 21635
  • /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,330,551

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • /3

      Est $656,338

      Not Listed For Sale

      213 N Queen St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,945 Sq Ft
      • Built 1904
      213 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • /2

    $40,000

    • Land
    • 4,791 Sq Ft
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • /24

    $455,000

    Sold Oct 21, 2025

    224 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1978

    Last Sold Summary

    • $241/SF
    • 13 Days On Market

    Current Estimated Value $466,142

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
    • /47

      Est $360,321

      Not Listed For Sale

      363 Cypress St, Millington, MD 21651

      • 3 Beds
      • 2.5 Baths
      • 2,052 Sq Ft
      • Built 1920
      363 Cypress St, Millington, MD 21651

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • /26

    $799,000

    $51K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,300 Sq Ft

    4020 Eastern Neck Rd, Rock Hall, MD 21661

    This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at

    Cindy Genther Rock Hall Properties Real Estate

    4020 Eastern Neck Rd, Rock Hall, MD 21661
  • /3

    $550,000

    Sold Mar 16, 2026

    25051 Smithville Rd, Worton, MD 21678

    • 1 Bed
    • 1 Bath
    • 1,328 Sq Ft
    • Built 1947

    Last Sold Summary

    • 29% Above List Price
    • $414/SF
    • 8 Days On Market

    Current Estimated Value $532,872

    Last Listing Agent Joe Hickman Cross Street Realtors LLC

    25051 Smithville Rd, Worton, MD 21678
    • /24

      Est $398,885

      Not Listed For Sale

      213 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft
      • Built 2005
      213 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Christopher Buss Weichert Realtors - Blue Ribbon

  • /2

    $10,000

    $5K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $29,412 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, Chestertown, MD 21620

Showing Results 401 - 440, Page 11 of 18

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