12,109

Kent County, MD Homes

Section Image
    • /27

      Est $267,791 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

      • 4% Below List Price
      • $233/SF
      • 37 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /3

    $150,000

    • Land
    • 0.75 Acre
    • $200,000 per Acre

    11 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

    11 Wilson Point Rd, Galena, MD 21635
  • /8

    $60,000 Sold Oct 03, 2025

    0 Adventist Church Ln Unit MDKE2004634, Rock Hall, MD 21661

    • Land
    • 0.8 Acre
    • $75,000 per Acre

    Last Sold Summary

    • 255 Days On Market

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    0 Adventist Church Ln Unit MDKE2004634, Rock Hall, MD 21661
    • /36

      Est $255,799 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

      • 28% Above List Price
      • $153/SF
      • 7 Days On Market

      Last Sold Price $200,000

      Last Listing Agent LaKeta Burgess NextHome Forward

  • /3

    $120,000

    • Land
    • 0.75 Acre
    • $160,000 per Acre

    3 Wilson Point Rd, Galena, MD 21635

    Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style

    Aaron Clark Patterson-Schwartz-Middletown

    3 Wilson Point Rd, Galena, MD 21635
  • /25

    $294,000 Sold Dec 24, 2025

    25135 Smithville Rd, Worton, MD 21678

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1968

    Last Sold Summary

    • $306/SF
    • 59 Days On Market

    Current Estimated Value $284,032

    Last Listing Agent Jane Duvall RE/MAX Advantage Realty

    25135 Smithville Rd, Worton, MD 21678
    • /33

      Est $391,385 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

      • 19% Above List Price
      • $300/SF
      • 81 Days On Market

      Last Sold Price $330,000

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /28

    $225,000 Open Sat 11AM - 1PM

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

    139 Prospect St, Chestertown, MD 21620

    Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

    Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
  • /46

    $3,350,000 Sold Apr 29, 2025

    4511 Piney Neck Rd, Rock Hall, MD 21661

    • 5 Beds
    • 3.5 Baths
    • 4,050 Sq Ft
    • Built 1939

    Last Sold Summary

    • $827/SF
    • 11 Days On Market

    Current Estimated Value $3,323,168

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    4511 Piney Neck Rd, Rock Hall, MD 21661
    • /27

      Est $346,258 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

      • 5% Above List Price
      • $203/SF
      • 4 Days On Market

      Last Sold Price $328,599

      Last Listing Agent Tara Trout Samson Properties

  • /3

    $3,000

    • Land
    • 0.34 Acre
    • $8,824 per Acre

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 4/15/2026 @ 10:00 AM. Bidding ends 4/17/2026 @ 11:35 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 major

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
  • /4

    $15,000 Sold Jun 02, 2025

    22671 Wood Yard Ln, Chestertown, MD 21620

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $152,508

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • /13

      Est $264,740 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

      • 23% Above List Price
      • $215/SF
      • 83 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Kristie Midash L. C. Parker Real Estate

  • /2

    $29,000

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, Chestertown, MD 21620
  • /13

    $229,000 Sold Mar 31, 2026

    11029 Brindley Dr, Worton, MD 21678

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $271/SF
    • 18 Days On Market

    Current Estimated Value $236,846

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    11029 Brindley Dr, Worton, MD 21678
    • /69

      Est $2,806,283 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

      • 12% Above List Price
      • $672/SF
      • 141 Days On Market

      Last Sold Price $2,500,000

      Last Listing Agent Richard Keaveney Cross Street Realtors LLC

  • /17

    $259,900 New Construction

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

    107 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxuryvinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granitecountertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment.Upstairs you'll find generously sized bedrooms including a large primary

    David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
  • /15

    $165,000 Sold Mar 05, 2026

    6179 Dorlon Dr, Rock Hall, MD 21661

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1994

    Last Sold Summary

    • 14% Above List Price
    • $165/SF
    • 6 Days On Market

    Current Estimated Value $146,255

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    6179 Dorlon Dr, Rock Hall, MD 21661
    • /10

      Est $274,053 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

      • 22% Above List Price
      • $164/SF
      • 5 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Vince Raimond Doug Ashley Realtors, LLC

  • /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /53

    $375,000 Sold Apr 16, 2025

    25740 Collins Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,389 Sq Ft
    • Built 1956

    Last Sold Summary

    • $111/SF
    • 29 Days On Market

    Current Estimated Value $422,556

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • /28

      Est $282,293 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

      • 13% Above List Price
      • $269/SF
      • 46 Days On Market

      Last Sold Price $249,900

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • /27

    $225,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,112 Sq Ft

    381 Hurtt Ave, Millington, MD 21651

    Charming and affordable 2-bedroom, 1-bath bungalow tucked away on a quiet street. This move-in ready home has been well maintained and features a newer metal roof for long-term durability and peace of mind. Ideal as a starter home or for anyone looking to downsize without sacrificing space. Enjoy a large lot plus a detached two-car garage complete with electricity and propane heat — perfect for

    Ray Davis Cross Street Realtors LLC

    381 Hurtt Ave, Millington, MD 21651
  • /47

    $700,000 Sold Dec 04, 2025

    8951 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2014

    Last Sold Summary

    • $187/SF
    • 2 Days On Market

    Current Estimated Value $705,488

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /47

      Est $334,587 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

      • 12% Above List Price
      • $221/SF
      • 45 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Gregory Osborn Long & Foster

  • /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
  • /15

    $357,000 Sold Jun 13, 2025

    5814 Clam Cove, Rock Hall, MD 21661

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Built 2024

    Last Sold Summary

    • $220/SF
    • 0 Days On Market

    Current Estimated Value $362,802

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    5814 Clam Cove, Rock Hall, MD 21661
    • /69

      Est $1,308,378 Not Listed For Sale

      10069 John Carvill Rd, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft
      • Built 1978
      10069 John Carvill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $436/SF
      • 5 Days On Market

      Last Sold Price $1,250,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /73

    $1,600,000

    • 7 Beds
    • 6 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
  • /19

    $309,000 Sold Apr 18, 2025

    11119 Old Worton Rd, Worton, MD 21678

    • 4 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 1985

    Last Sold Summary

    • $186/SF
    • 113 Days On Market

    Current Estimated Value $320,314

    Last Listing Agent Beth Green Doug Ashley Realtors, LLC

    11119 Old Worton Rd, Worton, MD 21678
    • /7

      Est $458,175 Not Listed For Sale

      12206 Galena Rd, Massey, MD 21650

      • 3 Beds
      • 2 Baths
      • 1,792 Sq Ft
      • Built 1900
      12206 Galena Rd, Massey, MD 21650

      Last Sold Summary

      • 87% Below List Price
      • $1,953/SF
      • 441 Days On Market

      Last Sold Price $3,500,000

      Last Listing Agent Cindy Genther Rock Hall Properties

  • /6

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 4/15/2026 @ 10:00 AM. Bidding ends 4/17/2026 @ 11:45 AM. This auction takes place on the Ashland Auction Group Website Bidding Platform. List Price is Suggested Opening Bid. Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /30

    $185,000 Sold Apr 17, 2025

    21015 Haven Rd, Rock Hall, MD 21661

    • 3 Beds
    • 1 Bath
    • 1,554 Sq Ft
    • Built 1920

    Last Sold Summary

    • $119/SF
    • 364 Days On Market

    Current Estimated Value $189,349

    Last Listing Agent Michelle Anderson Coldwell Banker Premier - Rehoboth

    21015 Haven Rd, Rock Hall, MD 21661
    • /37

      Est $547,847 Not Listed For Sale

      217 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft
      • Built 2003
      217 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3% Below List Price
      • $385/SF
      • 6 Days On Market

      Last Sold Price $564,500

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /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
  • /2

    $35,000 Sold Mar 20, 2026

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 0.33 Acre
    • $106,061 per Acre

    Last Sold Summary

    • 756 Days On Market

    Last Listing Agent Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
    • /45

      Est $466,248 Not Listed For Sale

      502 Cannon St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft
      • Built 1922
      502 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $275/SF
      • 7 Days On Market

      Last Sold Price $402,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /24

    $80,000

    • Land
    • 0.17 Acre
    • $470,588 per Acre

    0 1st Ave, Betterton, MD 21610

    PRICE REDUCTION!!Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the "Jewel of the Chesapeake". Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    0 1st Ave, Betterton, MD 21610
  • /2

    $180,000 Sold Mar 27, 2026

    9925 Flatland Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft
    • Built 1900

    Last Sold Summary

    • 26% Above List Price
    • $132/SF

    Current Estimated Value $144,210

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • /44

      Est $423,724 Not Listed For Sale

      111 Manor Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2007
      111 Manor Ave, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $229/SF
      • 3 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

Showing Results 201 - 240, Page 6 of 18

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