11,962

Kent County, MD Homes

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  • /31

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    226 S Water St, Chestertown, MD 21620
  • /9

    $364,900

    Sold Apr 30, 2026

    21133 Striper Run, Rock Hall, MD 21661

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Built 2025

    Last Sold Summary

    • $224/SF
    • 132 Days On Market

    Current Estimated Value $365,868

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661
    • /25

      Not Listed For Sale

      25126 Lambs Meadow Rd, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2007
      25126 Lambs Meadow Rd, Worton, MD 21678

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Julie Strickler Remax Vision

  • /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • /94

    $1,524,900

    Sold Feb 17, 2026

    10800 Cliff Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 5,241 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Above List Price
    • $291/SF
    • 5 Days On Market

    Current Estimated Value $1,491,124

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
    • /8

      Est $30,451

      Not Listed For Sale

      313 Race St, Millington, MD 21651

      313 Race St, Millington, MD 21651

      Last Sold Summary

      • 241 Days On Market

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • /4

    $245,000

    • Studio
    • 2,718 Sq Ft

    11989 Augustine Herman Hwy, Kennedyville, MD 21645

    Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    11989 Augustine Herman Hwy, Kennedyville, MD 21645
  • /21

    $315,000

    Sold Mar 13, 2026

    11047 Bottom Rd, Worton, MD 21678

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2023

    Last Sold Summary

    • $262/SF
    • 20 Days On Market

    Current Estimated Value $312,628

    Last Listing Agent Jeff Guthrie Taylor Properties

    11047 Bottom Rd, Worton, MD 21678
    • /24

      Not Listed For Sale

      1 Bayview Rd Unit 3, Betterton, MD 21610

      • 2 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1989
      1 Bayview Rd Unit 3, Betterton, MD 21610

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  • /7

    $86,000

    • Land
    • 18,730 Sq Ft
    • $200,000 per Acre

    0 River Bend Ln, Millington, MD 21651

    Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy commuting. Skip the hassle and expense of a perc test — the owners have already secured public water and sewer allocation, making the building process that much easier. Enjoy kayaking, fishing, and peaceful river views right from

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 River Bend Ln, Millington, MD 21651
  • /2

    $395,000

    Sold Jun 25, 2026

    8629 Airy Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $274/SF
    • 7 Days On Market

    Current Estimated Value $428,003

    Last Listing Agent Lauren Smith Keller Williams Realty

    8629 Airy Hill Rd, Chestertown, MD 21620
    • /4

      Est $91,500

      Not Listed For Sale

      20765 Bayside Ave, Rock Hall, MD 21661

      • Built 1900
      20765 Bayside Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 1,174 Days On Market

      Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

  • /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • /24

    $410,000

    Sold Jun 26, 2026

    109 S College Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $337/SF
    • 71 Days On Market

    Current Estimated Value $410,642

    Last Listing Agent Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
    • /17

      Est $247,059

      Not Listed For Sale

      104 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2023
      104 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /2

    $219,000

    Under Contract
    • Land
    • 2.88 Acres
    • $76,042 per Acre

    14075 Crataegus Ct, Galena, MD 21635

    Located in the community of Gentle Winds just minutes from the Eastern Shore and 10 minutes to Middletown, Delaware, this 2.88-acre private lot is shaped like a baseball field (and approximately the same size as a professional baseball field). Enclosed by mature trees for maximum privacy and complimented by 2 large beautiful trees (similar to large bonsai trees), this land is the ideal setting

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    14075 Crataegus Ct, Galena, MD 21635
  • /61

    $1,900,000

    Sold Aug 14, 2026

    7989 Quaker Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft
    • Built 1950

    Last Sold Summary

    • $441/SF
    • 311 Days On Market

    Current Estimated Value $1,971,604

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
    • /59

      Est $281,573

      Not Listed For Sale

      128 N Main St, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 1,560 Sq Ft
      • Built 1920
      128 N Main St, Galena, MD 21635

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Amber Stapleton Patterson-Schwartz-Newark

  • /135

    $487,000

    $62K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,948 Sq Ft

    16 Howell Point Rd, Betterton, MD 21610

    Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000.Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach!This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    16 Howell Point Rd, Betterton, MD 21610
  • /26

    $287,500

    Sold Dec 05, 2025

    7483 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 35 Days On Market

    Current Estimated Value $285,938

    Last Listing Agent Christine Johnson Dalton Wade, Inc.

    7483 Shortall St, Chestertown, MD 21620
    • /27

      Est $396,109

      Not Listed For Sale

      21357 Belair Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft
      • Built 2010
      21357 Belair Ave, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /3

    $699,900

    $50K PRICE DROP
    • Land
    • 41,817 Sq Ft
    • $729,062 per Acre

    5738 Beach Rd, Rock Hall, MD 21661

    Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breathtaking panoramic views stretching across the Chesapeake Bay to the iconic Bay Bridge and the distant Baltimore skyline, creating an ever-changing backdrop of stunning sunrises, sailboats, and shimmering waterfront

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    5738 Beach Rd, Rock Hall, MD 21661
  • /5

    $25,000

    Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $127,333

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /34

      Est $279,006

      Not Listed For Sale

      7499 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2018
      7499 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Petra Quinn Realty Navigator

  • /24

    $813,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    104 Landing Ln, Chestertown, MD 21620
  • /51

    $567,000

    Sold Aug 14, 2026

    13983 Turners Point Rd, Kennedyville, MD 21645

    • 2 Beds
    • 2.5 Baths
    • 4,054 Sq Ft
    • Built 1987

    Last Sold Summary

    • $140/SF
    • 206 Days On Market

    Current Estimated Value $593,750

    Last Listing Agent Patricia Kern Gunther-McClary Real Estate

    13983 Turners Point Rd, Kennedyville, MD 21645
    • /12

      Est $509,744

      Not Listed For Sale

      102 N Main St, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1900
      102 N Main St, Galena, MD 21635

      Last Sold Summary

      • 260 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /23

    $839,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    102 Little Harbor Way, Chestertown, MD 21620
  • /38

    $319,000

    Sold Apr 30, 2026

    11969 Augustine Herman Hwy, Kennedyville, MD 21645

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft
    • Built 1920

    Last Sold Summary

    • $127/SF
    • 145 Days On Market

    Current Estimated Value $316,281

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    11969 Augustine Herman Hwy, Kennedyville, MD 21645
    • /34

      Not Listed For Sale

      10967 Bottom Rd, Worton, MD 21678

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft
      • Built 1983
      10967 Bottom Rd, Worton, MD 21678

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

  • /26

    $753,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • /10

    $175,000

    Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $190,890

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • /26

      Est $323,172

      Not Listed For Sale

      24990 Heather Ln, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 2022
      24990 Heather Ln, Worton, MD 21678

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Jordan Larigan LPT Realty, LLC

  • /25

    $1,459,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • /38

    $370,000

    Sold Aug 11, 2026

    105 Dogwood Dr, Galena, MD 21635

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $210/SF
    • 33 Days On Market

    Current Estimated Value $481,157

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    105 Dogwood Dr, Galena, MD 21635
    • /29

      Est $240,067

      Not Listed For Sale

      192 Comegys St, Millington, MD 21651

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1949
      192 Comegys St, Millington, MD 21651

      Last Sold Summary

      • 112 Days On Market

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

  • /39

    $950,000

    $300K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,527 Sq Ft

    5979 Lawton Ave, Rock Hall, MD 21661

    This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, five bedrooms, an office and four and a half baths, there is abundant space for family, guests, and effortless entertaining.The ground level welcomes you with a spacious game room, sitting area, exercise space, and an oversized

    Cindy Genther Rock Hall Properties Real Estate

    5979 Lawton Ave, Rock Hall, MD 21661
  • /59

    $740,000

    Sold Aug 19, 2026

    20992 Rock Hall Ave, Rock Hall, MD 21661

    • 4 Beds
    • 3 Baths
    • 1,912 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $387/SF
    • 145 Days On Market

    Current Estimated Value $741,772

    Last Listing Agent Michael Roenigk Chaney Homes, LLC

    20992 Rock Hall Ave, Rock Hall, MD 21661
    • /18

      Est $274,412

      Not Listed For Sale

      11951 Kennedyville Rd, Kennedyville, MD 21645

      • 3 Beds
      • 1 Bath
      • 1,194 Sq Ft
      • Built 1920
      11951 Kennedyville Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /21

    $179,900

    $19K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21324 Persimmon Dr, Chestertown, MD 21620

    Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining

    Taylor Leaverton Benson & Mangold, LLC

    21324 Persimmon Dr, Chestertown, MD 21620

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