12,134

Kent County, MD Homes

Section Image
  • /51

    $1,150,000

    $129K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • /45

    $545,000

    Sold Apr 30, 2026

    206 S Water St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,008 Sq Ft
    • Built 1900

    Last Sold Summary

    • 7% Below List Price
    • $271/SF
    • 40 Days On Market

    Current Estimated Value $545,295

    Last Listing Agent Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
    • /39

      Est $1,165,993

      Not Listed For Sale

      14234 Gregg Neck Rd, Galena, MD 21635

      • 2 Beds
      • 3.5 Baths
      • 2,530 Sq Ft
      • Built 2020
      14234 Gregg Neck Rd, Galena, MD 21635

      Last Sold Summary

      • 7 Days On Market

  • /21

    $319,999

    $30K PRICE DROP
    • 6 Beds
    • 1.5 Baths
    • 3,270 Sq Ft

    12733 Still Pond Rd, Still Pond, MD 21667

    Step back in time with this spacious 1920 Colonial offering over 3,200+ sq ft and room for everyone. With 6 bedrooms, 1.5 Bath, two large living rooms, and a formal dining room, this home provides incredible flexibility for large households, multi-generational living, or anyone needing extra space to spread out. The home features generously sized rooms, classic character, and plenty of natural

    Jeff Guthrie Taylor Properties

    12733 Still Pond Rd, Still Pond, MD 21667
  • /40

    $1,100,000

    Sold Jul 14, 2025

    24196 Still Pond Neck Rd, Worton, MD 21678

    • 4 Beds
    • 3.5 Baths
    • 4,148 Sq Ft
    • Built 2005

    Last Sold Summary

    • $265/SF
    • 2 Days On Market

    Current Estimated Value $1,135,960

    Last Listing Agent William Norris Select Land & Homes, LLC

    24196 Still Pond Neck Rd, Worton, MD 21678
    • /9

      Est $519,053

      Not Listed For Sale

      31795 Griffith Dr, Galena, MD 21635

      • 4 Beds
      • 2.5 Baths
      • 2,510 Sq Ft
      • Built 2005
      31795 Griffith Dr, Galena, MD 21635

      Last Sold Summary

      • 14 Days On Market

  • /3

    $40,000

    Pending
    • Land
    • 17,859 Sq Ft
    • $97,561 per Acre

    0 Chesterville Forest Rd Unit PARCEL 60, 1, Massey, MD 21651

    Wooded, 0.4+ acre buildable lot on Chesterville Forest Rd with sewer allocation already paid—a $11,800 value! Buyer just needs to install a grinder pump and connect. Survey and setbacks included in documents for easy due diligence. Conveniently located near Rt. 301 for quick access north to Middletown, DE, or south to the Bay Bridge.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Chesterville Forest Rd Unit PARCEL 60, 1, Massey, MD 21651
  • /4

    $60,000

    Sold Oct 31, 2025

    0 Station Rd, 2, Kennedyville, MD 21678

    • Land
    • 1 Acre
    • $60,000 per Acre

    Last Sold Summary

    • 96 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    0 Station Rd, 2, Kennedyville, MD 21678
    • /31

      Est $502,103

      Not Listed For Sale

      31821 Griffith Dr, Galena, MD 21635

      • 3 Beds
      • 2.5 Baths
      • 2,003 Sq Ft
      • Built 2005
      31821 Griffith Dr, Galena, MD 21635

      Last Sold Summary

      • 6 Days On Market

  • /50

    $468,000

    Open Sat 11AM - 1PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Charming Brick Rancher Near the Chester RiverThis custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home...Living Room: Walk

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • /29

    $264,900

    Sold Oct 30, 2025

    24415 Chestertown Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft
    • Built 1962

    Last Sold Summary

    • $239/SF
    • 23 Days On Market

    Current Estimated Value $270,867

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • /57

      Est $318,720

      Not Listed For Sale

      14112 Oxford Rd, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 1,176 Sq Ft
      • Built 1981
      14112 Oxford Rd, Galena, MD 21635

      Last Sold Summary

      • 9 Days On Market

  • /2

    $10,000

    • Land
    • 23,958 Sq Ft
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /28

    $362,500

    Sold Jul 22, 2025

    1 A Bayview Rd Unit 7A, Betterton, MD 21610

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1989

    Last Sold Summary

    • $227/SF
    • 41 Days On Market

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    1 A Bayview Rd Unit 7A, Betterton, MD 21610
    • /30

      Est $319,882

      Not Listed For Sale

      407 Jarman Ave, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 2,135 Sq Ft
      • Built 1969
      407 Jarman Ave, Galena, MD 21635

      Last Sold Summary

      • 23 Days On Market

  • /5

    $48,000

    • Land
    • 20,037 Sq Ft
    • $104,348 per Acre

    0 Sharp St Unit MDKE2005760, Rock Hall, MD 21661

    Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today. Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sharp St Unit MDKE2005760, Rock Hall, MD 21661
  • /28

    $549,000

    Sold Jun 26, 2025

    305 Washington Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • Built 1930

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $582,744

    Last Listing Agent William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • /44

      Est $558,647

      Not Listed For Sale

      31802 Griffith Dr, Galena, MD 21635

      • 5 Beds
      • 2.5 Baths
      • 2,784 Sq Ft
      • Built 2005
      31802 Griffith Dr, Galena, MD 21635

      Last Sold Summary

      • 89 Days On Market

  • /9

    $364,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    21131 Striper Run, Rock Hall, MD 21661

    New construction duplex in desirable Waterman’s Estates! Move-in ready 3BR, 2.5BA home with quality finishes throughout including luxury vinyl plank flooring on both levels, quartz countertops, and stainless steel appliances. Open-concept first floor offers spacious living, dining, and kitchen areas, plus powder room and separate laundry room. Upstairs features a primary suite with walk-in closet

    Cindy Genther Rock Hall Properties Real Estate

    21131 Striper Run, Rock Hall, MD 21661
  • /48

    $535,000

    Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Current Estimated Value $527,454

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • /45

      Est $547,490

      Not Listed For Sale

      14100 Turners Point Rd, Kennedyville, MD 21645

      • 4 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1930
      14100 Turners Point Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 29 Days On Market

  • /2

    $38,000

    $17K PRICE INCREASE
    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • /18

    $182,000

    Sold May 22, 2026

    31695 Olivet Cir, Galena, MD 21635

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • Built 1920

    Last Sold Summary

    • $107/SF
    • 182 Days On Market

    Current Estimated Value $194,521

    Last Listing Agent Donnie Horton RE/MAX Chesapeake

    31695 Olivet Cir, Galena, MD 21635
    • /46

      Est $180,227

      Not Listed For Sale

      7 Horning Dr, Betterton, MD 21610

      • 2 Beds
      • 1 Bath
      • 628 Sq Ft
      • Built 1951
      7 Horning Dr, Betterton, MD 21610

      Last Sold Summary

      • 10 Days On Market

  • /4

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Bunting Rd, 6, Fairlee, 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 @ 12:25 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 Bunting Rd, 6, Fairlee, MD 21620
  • /49

    $840,000

    Sold Jun 27, 2025

    26865 Mallard Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft
    • Built 1963

    Last Sold Summary

    • $250/SF
    • 182 Days On Market

    Current Estimated Value $979,218

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • /76

      Est $512,987

      Not Listed For Sale

      11948 Augustine Herman Hwy, Kennedyville, MD 21645

      • 5 Beds
      • 3.5 Baths
      • 2,964 Sq Ft
      • Built 1914
      11948 Augustine Herman Hwy, Kennedyville, MD 21645

      Last Sold Summary

      • 5 Days On Market

  • /26

    $786,900

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

    35 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

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • /56

    $1,270,000

    Sold Dec 22, 2025

    10434 Big Stone Rd, Millington, MD 21651

    • 1,720 Sq Ft
    • Built 1920

    Last Sold Summary

    • $738/SF
    • 28 Days On Market

    Current Estimated Value $973,439

    Last Listing Agent Zachary Shelley Streett Hopkins Real Estate, LLC

    10434 Big Stone Rd, Millington, MD 21651
    • /28

      Est $293,894

      Not Listed For Sale

      403 E Campus Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1947
      403 E Campus Ave, Chestertown, MD 21620

      Last Sold Summary

      • 62 Days On Market

  • /22

    $259,900

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

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, 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 suite with walk-in

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • /45

    $459,000

    Sold Jun 23, 2025

    811 S Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $485,474

    Last Listing Agent Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
    • /27

      Est $303,952

      Not Listed For Sale

      10572 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1996
      10572 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 70 Days On Market

  • /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • /24

    $285,000

    Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $1,140,265

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • /30

      Est $311,945

      Not Listed For Sale

      5966 Boyce Ln, Rock Hall, MD 21661

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1990
      5966 Boyce Ln, Rock Hall, MD 21661

      Last Sold Summary

      • 33 Days On Market

  • /2

    $40,000

    Under Contract
    • Land
    • 14,810 Sq Ft
    • $117,647 per Acre

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620

    Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

    Jo Ann Edwards The Hogans Agency

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
  • /17

    $307,000

    Sold Jan 30, 2026

    6345 Rock Hall Rd, Rock Hall, MD 21661

    • 3 Beds
    • 1.5 Baths
    • 1,622 Sq Ft
    • Built 1969

    Last Sold Summary

    • $189/SF
    • 91 Days On Market

    Current Estimated Value $320,532

    Last Listing Agent Robin Fithian Rock Hall Properties Real Estate

    6345 Rock Hall Rd, Rock Hall, MD 21661
    • /8

      Est $443,964

      Not Listed For Sale

      219 Philosophers Terrace, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1932
      219 Philosophers Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • /73

    $430,000

    $15K PRICE DROP Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,857 Sq Ft

    24295 Langford Rd, Chestertown, MD 21620

    Welcome to 24295 Langford Road in Chestertown, Maryland—a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you’ve been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    24295 Langford Rd, Chestertown, MD 21620

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