12,132

Kent County, MD Homes

Section Image
  • /28

    $225,000

    • 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
  • /27

    $310,000

    Sold Dec 16, 2025

    21119 Striper Run, Rock Hall, MD 21661

    • 3 Beds
    • 4 Baths
    • 1,628 Sq Ft
    • Built 1996

    Last Sold Summary

    • $190/SF
    • 408 Days On Market

    Current Estimated Value $312,024

    Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

    21119 Striper Run, Rock Hall, MD 21661
    • /42

      Est $322,824

      Not Listed For Sale

      5292 Skinners Neck Rd, Rock Hall, MD 21661

      • 3 Beds
      • 1 Bath
      • 1,698 Sq Ft
      • Built 1918
      5292 Skinners Neck Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 20 Days On Market

  • /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $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 6/30/2026, 10:00 AM. Bidding ends 7/2/2026, 1:00 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 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
  • /29

    $230,000

    Sold Jun 27, 2025

    192 Comegys St, Millington, MD 21651

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1949

    Last Sold Summary

    • $160/SF
    • 112 Days On Market

    Current Estimated Value $243,023

    Last Listing Agent Mary Julie Long & Foster Real Estate, Inc.

    192 Comegys St, Millington, MD 21651
    • /36

      Est $402,762

      Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

  • /18

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    5666 Walnut St, Rock Hall, MD 21661

    Great location for this older manufactured home near Rock Hall harbor. The house needs renovation and repairs, but the site offers a great location with nice views of North Point Marina and Rock Hall harbor. With three bedrooms and 2 baths on one-level living, this 1,200+ sq.ft. home would make a wonderful vacation or retirement home. The property is being sold as-is. Cleared, level lot.

    Cindy Genther Rock Hall Properties Real Estate

    5666 Walnut St, Rock Hall, MD 21661
  • /8

    $60,000

    Sold Oct 03, 2025

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

    • Land
    • 34,848 Sq Ft
    • $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
    • /33

      Est $327,113

      Not Listed For Sale

      10550 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2006
      10550 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • /4

    $6,000

    • Land
    • 30,056 Sq Ft
    • $8,696 per Acre

    23683 L Rd, Chestertown, MD 21620

    List Price is opening bid at online auction. Auction at or above $6,000. Bidding begins Saturday, June 20th, and ends Thursday, June 25, 2026 at 11:30am. 0.69± Acres of Unimproved Land in Chestertown, Kent County Zoning - Village (V) district. Is intended for:• Small, historic, or traditional rural villages• A mix of residential uses (mostly single-family homes, sometimes limited

    Larry Cooper Alex Cooper Auctioneers, Inc.

    23683 L 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 $283,932

    Last Listing Agent Jane Duvall RE/MAX Advantage Realty

    25135 Smithville Rd, Worton, MD 21678
    • /35

      Est $412,649

      Not Listed For Sale

      107 Dogwood Dr, Galena, MD 21635

      • 3 Beds
      • 2 Baths
      • 1,804 Sq Ft
      • Built 2000
      107 Dogwood Dr, Galena, MD 21635

      Last Sold Summary

      • 3 Days On Market

  • /41

    $1,300,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,987 Sq Ft

    13840 Mill Creek Ln, Galena, MD 21635

    Do you crave peace, privacy and waterfront? Escape to your own slice of paradise in this meticulously maintained 3-bedroom, 2-bathroom estate, where luxury meets sustainability. Nestled on a beautifully wooded and private 1.58 acre lot, this home is a true sanctuary for nature lovers and water enthusiasts alike. The interior features a thoughtful layout designed for comfort, but the true magic

    Mary Binns EXP Realty, LLC

    13840 Mill Creek Ln, Galena, MD 21635
  • /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 $229,133

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    11029 Brindley Dr, Worton, MD 21678
    • /42

      Est $273,834

      Not Listed For Sale

      11052 Austin Ct, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 2005
      11052 Austin Ct, Worton, MD 21678

      Last Sold Summary

      • 24 Days On Market

  • /4

    $111,000

    Under Contract
    • Land
    • 10.25 Acres
    • $10,829 per Acre

    0 Black Bottom Rd, Galena, MD 21635

    Need to get away from it all? 10 acres of privacy! Located in rural Kent County MD. but close to Rt. 301, Middletown Delaware and all that Maryland's Eastern Shore has to offer. Perfect place to build your dream home, hunting cabin, family compound. Heavily wooded and abutting vacant land owned by the state of Maryland Dept. of Natural Resources. Residential zoning. Boundary survey has been

    Ruth Clancy BHHS Fox & Roach - Hockessin

    0 Black Bottom Rd, Galena, MD 21635
  • /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 $166,026

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    6179 Dorlon Dr, Rock Hall, MD 21661
    • /28

      Est $543,097

      Not Listed For Sale

      116 Harlan Loop, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 4,067 Sq Ft
      • Built 2009
      116 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • /39

    $650,000

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

    20563 Rock Hall Ave Unit 16, Rock Hall, MD 21661

    Bayfront condo with exceptional views, located in the heart of Rock Hall! Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range. The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The

    Julia Hilfiker Gunther-McClary Real Estate

    20563 Rock Hall Ave Unit 16, Rock Hall, MD 21661
  • /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 $322,017

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620
    • /14

      Est $211,781

      Not Listed For Sale

      6121 Tolchester Rd, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,165 Sq Ft
      • Built 1920
      6121 Tolchester Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 84 Days On Market

  • /27

    $247,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    104 Conley Dr, Chestertown, MD 21620

    Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC

    Heather Kooser Cummings & Co. Realtors

    104 Conley 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 $707,166

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /7

      Est $322,131

      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

  • /51

    $385,000

    $10K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    NEW PRICE – Exceptional value for over 2,500 square feet of newer construction in the Village of Chestertown! A stunning 2023-built home with well-designed architectural elevations; two tone complimentary shades which beautifully compliment these unique features. The curb appeal captures your attention and the welcoming front porch invites you to slow down and relax.. your home! Step through the

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud 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
    • /21

      Est $251,433

      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

  • /2

    $9,500

    • Land
    • 14,810 Sq Ft
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Buck Neck Landing Rd, 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 $181,476

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • /13

      Est $327,907

      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

  • /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
  • /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 $154,841

    Last Listing Agent Missy Miller Aldave Northrop Realty

    21250 Green Ln, Rock Hall, MD 21661
    • /35

      Est $350,573

      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

  • /41

    $329,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    102 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large

    Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
  • /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 $385,215

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • /39

      Est $326,207

      Not Listed For Sale

      101 S College Ave, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft
      • Built 1920
      101 S College Ave, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /49

    $1,450,000

    • 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
  • /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 $802,178

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • /12

      Est $347,534

      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

  • /29

    $285,000

    • 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

Showing Results 201 - 240, Page 6 of 18

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