12,132

Kent County, MD Homes

Section Image
  • /21

    $215,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft

    100 Prospect St, Chestertown, MD 21620

    Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything.Most homes in this price range make you choose: updated systems or a great location. This one delivers both.Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the

    David Moore Real Broker, LLC

    100 Prospect St, Chestertown, MD 21620
  • /26

    $360,000

    Sold Jan 20, 2026

    186 Birchwood Ln, Galena, MD 21635

    • 3 Beds
    • 2.5 Baths
    • 1,780 Sq Ft
    • Built 1994

    Last Sold Summary

    • $202/SF
    • 27 Days On Market

    Current Estimated Value $364,420

    Last Listing Agent Heather Carrow Crown Homes Real Estate

    186 Birchwood Ln, Galena, MD 21635
    • /50

      Est $532,435

      Not Listed For Sale

      217 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,208 Sq Ft
      • Built 1984
      217 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

  • /47

    $918,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,668 Sq Ft

    31902 Swantown Dr, Galena, MD 21635

    Completely renovated four-bedroom home offering an ideal Upper Eastern Shore location where Swantown Creek meets the Sassafras River. This private retreat features convenient first-floor living, with water views from the living room, dining area, kitchen, and two primary bedrooms. The home is enhanced by a spacious deck overlooking the water, a finished basement, outdoor shower, hot tub, fire pit

    Christopher McClary Gunther-McClary Real Estate

    31902 Swantown Dr, Galena, MD 21635
  • /38

    $475,000

    Sold Dec 11, 2025

    101 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1979

    Last Sold Summary

    • $242/SF
    • 38 Days On Market

    Current Estimated Value $480,879

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
    • /28

      Est $290,171

      Not Listed For Sale

      20705 Wilkins Ave, Rock Hall, MD 21661

      • 4 Beds
      • 1 Bath
      • 922 Sq Ft
      • Built 1900
      20705 Wilkins Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 7 Days On Market

  • /48

    $535,000

    Pending
    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft

    9816 Fairlee Rd, Chestertown, MD 21620

    Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of

    Scott Hogan Long & Foster Real Estate, Inc.

    9816 Fairlee Rd, Chestertown, MD 21620
  • /21

    $39,000

    Sold May 28, 2026

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661

    • Land
    • 1 Acre
    • $39,000 per Acre

    Last Sold Summary

    • 218 Days On Market

    Last Listing Agent Micheal Vakas EXP Realty, LLC

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661
    • /15

      Est $237,874

      Not Listed For Sale

      7509 Sunburst Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1989
      7509 Sunburst Ave, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

  • /39

    $380,000

    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • /56

    $759,000

    Sold Jul 01, 2025

    7988 Aldan Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 2 Days On Market

    Current Estimated Value $794,516

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
    • /24

      Est $221,435

      Not Listed For Sale

      25032 Lambs Meadow Rd, Worton, MD 21678

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft
      • Built 1994
      25032 Lambs Meadow Rd, Worton, MD 21678

      Last Sold Summary

      • 117 Days On Market

  • /40

    $585,000

    $13K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,672 Sq Ft

    5807 Blue Claw Ct, Rock Hall, MD 21661

    Welcome to luxury living in Waterman’s Estates in the heart of Rock Hall! This beautifully updated 4-bedroom, 3-bath home offers over 2,600 square feet of light-filled living space with soaring vaulted ceilings and an open, inviting floor plan. Propane fireplaces in the living and family rooms create a warm and welcoming focal point, while plenty of storage throughout the home adds everyday

    Cindy Genther Rock Hall Properties Real Estate

    5807 Blue Claw Ct, Rock Hall, MD 21661
  • /56

    $649,000

    Sold Oct 17, 2025

    6134 Rock Hall Rd, Rock Hall, MD 21661

    • 4 Beds
    • 5 Baths
    • 3,549 Sq Ft
    • Built 1910

    Last Sold Summary

    • $183/SF
    • 5 Days On Market

    Current Estimated Value $660,900

    Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

    6134 Rock Hall Rd, Rock Hall, MD 21661
    • /19

      Est $1,044,553

      Not Listed For Sale

      10785 Big Stone Rd, Millington, MD 21651

      • 3 Beds
      • 1 Bath
      • 1,372 Sq Ft
      • Built 1968
      10785 Big Stone Rd, Millington, MD 21651

      Last Sold Summary

      • 4 Days On Market

  • /7

    $5,000

    • Land
    • 16,117 Sq Ft
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, 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 @ 12:35 PM. 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 all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /20

    $246,000

    Sold Aug 15, 2025

    10624 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $246/SF
    • 17 Days On Market

    Current Estimated Value $241,482

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
    • /39

      Est $344,230

      Not Listed For Sale

      100 Malone Ave, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft
      • Built 1967
      100 Malone Ave, Chestertown, MD 21620

      Last Sold Summary

      • 94 Days On Market

  • /16

    $2,800,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    33658 Golts Rd, Massey, MD 21650

    Investment Opportunity is here! Kent County, Md farm offered with 207+/- acres total. The property is unencumbered by any preservation or similar easements such as MALPF or other conservation groups. A quality 1344 square foot rancher home with attached 728 square foot garage with a 216 square foot deck overlooking the pond and fields. The home was built around 1988 and a very substantial

    BRIAN MORRIS The Land Group

    33658 Golts Rd, Massey, MD 21650
  • /56

    $660,000

    Sold Jun 05, 2026

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 5% Below List Price
    • $412/SF
    • 83 Days On Market

    Current Estimated Value $663,136

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    • /16

      Est $241,377

      Not Listed For Sale

      5804 Liberty St, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 884 Sq Ft
      • Built 1967
      5804 Liberty St, Rock Hall, MD 21661

      Last Sold Summary

      • 113 Days On Market

  • /27

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    11942 Flour Mill St, Kennedyville, MD 21645

    Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    11942 Flour Mill St, Kennedyville, MD 21645
  • /3

    $675,000

    Sold Jun 25, 2025

    213 N Queen St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,945 Sq Ft
    • Built 1904

    Last Sold Summary

    • $347/SF
    • 2 Days On Market

    Current Estimated Value $698,196

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
    • /36

      Est $471,189

      Not Listed For Sale

      32159 River Rd, Millington, MD 21651

      • 3 Beds
      • 2.5 Baths
      • 2,018 Sq Ft
      • Built 2006
      32159 River Rd, Millington, MD 21651

      Last Sold Summary

      • 145 Days On Market

  • /8

    $4,950,000

    Pending

    0 Worton Hopewell Rd Unit MDKE2006584, Worton, MD 21678

    360± acre farm located outside of Worton consisting of approximately 286 tillable acres along with multiple ponds covering roughly 25 acres. The tract is made up primarily of Matapeake soils with an average NCCPI rating of 59.The property offers a strong balance of productive farmland, wildlife habitat, and recreational appeal. The ponds and surrounding timber create ideal habitat for

    Jack Boniface Cross Street Realtors LLC

    0 Worton Hopewell Rd Unit MDKE2006584, Worton, MD 21678
  • /19

    $145,000

    Sold Oct 30, 2025

    5814 Locust St, Rock Hall, MD 21661

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1960

    Last Sold Summary

    • $173/SF
    • 5 Days On Market

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    5814 Locust St, Rock Hall, MD 21661
    • /53

      Est $390,610

      Not Listed For Sale

      14086 E Beechwood Rd, Galena, MD 21635

      • 2 Beds
      • 2 Baths
      • 1,951 Sq Ft
      • Built 1991
      14086 E Beechwood Rd, Galena, MD 21635

      Last Sold Summary

      • 19 Days On Market

  • /3

    $100,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • /25

    $262,000

    Sold Jun 04, 2026

    10971 Bottom Rd, Worton, MD 21678

    • 2 Beds
    • 2 Baths
    • 720 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $364/SF
    • 112 Days On Market

    Current Estimated Value $263,456

    Last Listing Agent Andy Batch Keller Williams Select Realtors of Annapolis

    10971 Bottom Rd, Worton, MD 21678
    • /53

      Est $1,030,971

      Not Listed For Sale

      24319 Waterview Dr, Worton, MD 21678

      • 5 Beds
      • 3.5 Baths
      • 3,795 Sq Ft
      • Built 2007
      24319 Waterview Dr, Worton, MD 21678

      Last Sold Summary

      • 28 Days On Market

  • /2

    $9,000

    $3K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • /45

    $705,000

    Sold Sep 26, 2025

    9194 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1939

    Last Sold Summary

    • $483/SF
    • 19 Days On Market

    Current Estimated Value $709,811

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
    • /43

      Est $544,097

      Not Listed For Sale

      5718 N Main St, Rock Hall, MD 21661

      • 4 Beds
      • 3.5 Baths
      • 2,418 Sq Ft
      • Built 1920
      5718 N Main St, Rock Hall, MD 21661

      Last Sold Summary

      • 50 Days On Market

  • /28

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    11976 Flour Mill St, Kennedyville, MD 21645

    Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11976 Flour Mill St, Kennedyville, MD 21645
  • /21

    $315,000

    Sold Jul 02, 2025

    21740 Lovers Ln, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 2025

    Last Sold Summary

    • $217/SF
    • 62 Days On Market

    Last Listing Agent Carlos Contreras Caprika Realty

    21740 Lovers Ln, Rock Hall, MD 21661
    • /31

      Est $328,529

      Not Listed For Sale

      11110 Old Worton Rd, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,461 Sq Ft
      • Built 1956
      11110 Old Worton Rd, Worton, MD 21678

      Last Sold Summary

      • 187 Days On Market

  • /3

    $7,500

    • Land
    • 37,461 Sq Ft
    • $8,721 per Acre

    0 Medders Rd, Still Pond, MD 21667

    Priced to sell! 0.86 acres of non-buildable, recreational land in the quaint town of Still Pond, MD. Located just down the road from Betterton beach and boat ramp. The neighboring lot is also for sale MDKE2004176 so you could buy two lots next door to each other. Campers are not permitted. Lots can be used to garden, make a nature trail, bird watch etc. Buyer responsible for due diligence.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Medders Rd, Still Pond, MD 21667
  • /31

    $340,000

    Sold Mar 19, 2026

    204 Rolling Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft
    • Built 1975

    Last Sold Summary

    • $148/SF
    • 56 Days On Market

    Current Estimated Value $344,833

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling Rd, Chestertown, MD 21620
    • /51

      Est $590,255

      Not Listed For Sale

      24386 Waterview Dr, Worton, MD 21678

      • 3 Beds
      • 2.5 Baths
      • 2,871 Sq Ft
      • Built 1987
      24386 Waterview Dr, Worton, MD 21678

      Last Sold Summary

      • 285 Days On Market

  • /20

    $244,500

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620

Showing Results 561 - 600, Page 15 of 18

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