11,962

Kent County, MD Homes

Section Image
    • /7

      Est $326,301

      Not Listed For Sale

      23235 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23235 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • /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 $285,099

    Last Listing Agent Jane Duvall RE/MAX Advantage Realty

    25135 Smithville Rd, Worton, MD 21678
    • /29

      Est $295,680

      Not Listed For Sale

      10670 Tintah Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      10670 Tintah Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Bronwyn Scott Samson Properties

  • /50

    $1,375,000

    $75K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm 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 $228,064

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    11029 Brindley Dr, Worton, MD 21678
    • /21

      Est $253,944

      Not Listed For Sale

      4827 Piney Neck Rd, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1954
      4827 Piney Neck Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

  • /29

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jun 17, 2026

    202 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,427 Sq Ft
    • Built 1956

    Last Sold Summary

    • $228/SF
    • 0 Days On Market

    Current Estimated Value $327,383

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620
    • /13

      Est $330,322

      Not Listed For Sale

      23399 Cloquet Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2004
      23399 Cloquet Rd, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • /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 $714,866

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /35

      Est $346,613

      Not Listed For Sale

      7071 Rock Hall Rd, Rock Hall, MD 21661

      • 3 Beds
      • 1.5 Baths
      • 1,340 Sq Ft
      • Built 1993
      7071 Rock Hall Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 123 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /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
  • /33

    $425,000

    Sold Aug 04, 2026

    21007 Bayside Ave, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1953

    Last Sold Summary

    • $304/SF
    • 45 Days On Market

    Current Estimated Value $419,700

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21007 Bayside Ave, Rock Hall, MD 21661
    • /28

      Est $573,144

      Not Listed For Sale

      305 Washington Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,476 Sq Ft
      • Built 1930
      305 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /26

    $275,000

    $10K PRICE DROP
    • 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
  • /2

    $35,000

    Sold Mar 20, 2026

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 14,374 Sq Ft
    • $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
    • /12

      Est $343,440

      Not Listed For Sale

      203 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1963
      203 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Alex Modaressi RE/MAX Distinctive Real Estate, Inc.

  • /73

    $1,500,000

    $100K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 5,400 Sq Ft

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

    **Listing price is for FOUR units for sale as an investment package!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 package, or as individuals. Each unit has been remodeled and

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • /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 $186,516

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • /25

      Est $343,791

      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

      Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

  • /6

    $49,000

    $30K PRICE DROP
    • Land
    • 1.95 Acres
    • $25,128 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
  • /6

    $55,000

    Sold Aug 21, 2026

    110 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft
    • Built 1900

    Last Sold Summary

    • 54% Below List Price
    • $25/SF
    • 65 Days On Market

    Current Estimated Value $109,211

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
    • /29

      Est $389,095

      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

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /30

    $389,000

    $121K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    32135 River Rd, Millington, MD 21651

    THE PRICE HAS CHANGED — THE WATERFRONT LIFESTYLE HASN'T.Newly reduced $10,000! Where else can you find Chester River waterfront with a private dock at this price?Welcome to 32135 River Road in Millington, where peaceful waterfront living, beautiful views, and convenience come together. Situated on 0.53 acres along the upper Chester River, this inviting carriage house offers panoramic

    Christine Catalano Coldwell Banker Realty

    32135 River Rd, Millington, MD 21651
  • /63

    $315,000

    Sold Jun 26, 2026

    10 Ericsson Ave Unit 33, Betterton, MD 21610

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • Built 1991

    Last Sold Summary

    • 1% Below List Price
    • $206/SF
    • 7 Days On Market

    Current Estimated Value $319,086

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    10 Ericsson Ave Unit 33, Betterton, MD 21610
    • /27

      Est $276,684

      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

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /6

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:20 AM. 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

    Adam Shpritz Ashland Auction Group LLC

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

    $150,000

    Sold Feb 12, 2026

    21250 Green Ln, Rock Hall, MD 21661

    • 2 Beds
    • 1 Bath
    • 1,226 Sq Ft
    • Built 1900

    Last Sold Summary

    • $122/SF
    • 1 Day On Market

    Current Estimated Value $158,668

    Last Listing Agent Missy Miller Aldave Northrop Realty

    21250 Green Ln, Rock Hall, MD 21661
    • /36

      Est $249,261

      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

      Last Listing Agent LaKeta Burgess NextHome Forward

  • /24

    $325,000

    • 4 Beds
    • 1 Bath
    • 926 Sq Ft

    20705 Wilkins Ave, Rock Hall, MD 21661

    This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides

    Courtney Chipouras TTR Sotheby's International Realty

    20705 Wilkins Ave, Rock Hall, MD 21661
  • /24

    $75,000

    Sold Jul 01, 2026

    0 1st Ave, Betterton, MD 21610

    • Land
    • 7,405 Sq Ft
    • $441,176 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 269 Days On Market

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    0 1st Ave, Betterton, MD 21610
    • /33

      Est $385,739

      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

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /2

    $25,000

    • Land
    • 1.72 Acres
    • $14,535 per Acre

    12374 NEXT DOOR Galena Rd, Massey, MD 21650

    Don’t miss this rare opportunity to own 1.72 acres on Galena Rd. Perfect for a commercial or business development, this property offers excellent visibility and accessibility, just off Route 313 and minutes from Massey and Galena. Nearby landmarks include the Massey Aerodrome & Air Museum, combining convenience with local charm.

    Rena Champaco EXP Realty, LLC

    12374 NEXT DOOR Galena Rd, Massey, MD 21650
  • /39

    $375,000

    Sold Jan 08, 2026

    7653 Broad Neck Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft
    • Built 1987

    Last Sold Summary

    • $209/SF
    • 41 Days On Market

    Current Estimated Value $402,578

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • /20

      Est $386,029

      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

      Last Listing Agent Deborah Dawkins Coldwell Banker Realty

  • /41

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,801 Sq Ft

    374 Hurtt Ave, Millington, MD 21651

    Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    374 Hurtt Ave, Millington, MD 21651
  • /47

    $800,000

    Sold Feb 20, 2026

    4671 Cliffs City Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,783 Sq Ft
    • Built 1967

    Last Sold Summary

    • $449/SF

    Current Estimated Value $801,589

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • /27

      Est $345,479

      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

      Last Listing Agent Tara Trout Samson Properties

Showing Results 241 - 280, Page 7 of 18

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