12,132

Kent County, MD Homes

Section Image
  • /2

    $15,000

    • Land
    • 22,651 Sq Ft
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • /4

    $40,000

    Sold Jan 16, 2026

    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651

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

    Last Sold Summary

    • 146 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
    • /25

      Est $243,880

      Not Listed For Sale

      5951 Rock Hall Rd, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1952
      5951 Rock Hall Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 14 Days On Market

  • /62

    $549,000

    • 6 Beds
    • 6 Baths
    • 4,305 Sq Ft

    12714 Still Pond Rd, Still Pond, MD 21667

    Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12714 Still Pond Rd, Still Pond, MD 21667
  • /31

    $310,000

    Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $320,289

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • /13

      Est $785,743

      Not Listed For Sale

      7694 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,322 Sq Ft
      • Built 1966
      7694 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

  • /40

    $395,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    31673 W Edge Rd, Millington, MD 21651

    Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor

    Doug Ashley Doug Ashley Realtors, LLC

    31673 W Edge Rd, Millington, MD 21651
  • /18

    $620,000

    Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Current Estimated Value $642,503

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • /43

      Est $373,091

      Not Listed For Sale

      12198 Coopers Ln, Worton, MD 21678

      • 4 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1982
      12198 Coopers Ln, Worton, MD 21678

      Last Sold Summary

      • 2 Days On Market

  • /2

    $9,000

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

    0 Kinglet Rd, 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 Kinglet Rd, Chestertown, MD 21620
  • /61

    $655,000

    Sold Jun 24, 2025

    24383 Waterview Dr, Worton, MD 21678

    • 3 Beds
    • 2.5 Baths
    • 3,114 Sq Ft
    • Built 2003

    Last Sold Summary

    • $210/SF
    • 2 Days On Market

    Current Estimated Value $708,744

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24383 Waterview Dr, Worton, MD 21678
    • /53

      Est $822,109

      Not Listed For Sale

      32483 Galena Sassafras Rd, Galena, MD 21635

      • 3 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 2002
      32483 Galena Sassafras Rd, Galena, MD 21635

      Last Sold Summary

      • 11 Days On Market

  • /38

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 1,893 Sq Ft

    13235 Knotts Ln, Galena, MD 21635

    A Very Special Property, Hunting Fishing, Horses, 26 ac grain farm with acres of ponds and impoundments with deep woods. Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Enjoy natures ever changing natural wonders. Deer, turkey, ducks, wood ducks and bass. All the while as the snow geese just fly over as the desire large open fields, we have narrow

    Phil Riordan Meredith Fine Properties

    13235 Knotts Ln, Galena, MD 21635
  • /39

    $550,000

    Sold Jul 01, 2025

    25285 Foxchase Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 1992

    Last Sold Summary

    • $274/SF
    • 3 Days On Market

    Current Estimated Value $572,820

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
    • /50

      Est $1,337,265

      Not Listed For Sale

      10705 Tilden Ln, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,345 Sq Ft
      • Built 1943
      10705 Tilden Ln, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

  • /24

    $765,900

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

    37 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 bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • /41

    $740,000

    Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Current Estimated Value $779,665

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
    • /30

      Est $368,100

      Not Listed For Sale

      215 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1992
      215 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /22

    $299,900

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    21103 Striper Run, Rock Hall, MD 21661

    Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint

    Courtney Chipouras TTR Sotheby's International Realty

    21103 Striper Run, Rock Hall, MD 21661
  • /78

    $186,000

    Sold Sep 30, 2025

    1 Kent Dr, Betterton, MD 21610

    • 2 Beds
    • 1 Bath
    • 658 Sq Ft
    • Built 1976

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

    Current Estimated Value $192,294

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    1 Kent Dr, Betterton, MD 21610
    • /69

      Est $527,552

      Not Listed For Sale

      110 Camelot Dr, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft
      • Built 2007
      110 Camelot Dr, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • /12

    $164,000

    • Land
    • 2.15 Acres
    • $76,279 per Acre

    7224 Rock Hall Rd, Rock Hall, MD 21661

    Discover the charm of Kent County’s rural lifestyle on this fenced, 2.15-acre cleared lot. Perfectly situated along Rock Hall Road, the property features an existing two-car garage, a 6’x8’ storage shed, and mature trees framing vast pastoral views. With electric service and an existing well already in place, it’s ready for your vision—whether that’s building your dream home, creating a weekend

    Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
  • /43

    $449,000

    Sold May 29, 2026

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

    • 3 Beds
    • 2.5 Baths
    • Built 2000

    Last Sold Summary

    • 25 Days On Market

    Current Estimated Value $446,952

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    1 Idlewhile Ave Unit 4, Betterton, MD 21610
    • /37

      Est $308,758

      Not Listed For Sale

      23315 Sandpiper Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,272 Sq Ft
      • Built 1973
      23315 Sandpiper Rd, Chestertown, MD 21620

      Last Sold Summary

      • 120 Days On Market

  • /62

    $549,000

    • Studio
    • 4,305 Sq Ft

    12714 Still Pond Rd, Still Pond, MD 21667

    Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12714 Still Pond Rd, Still Pond, MD 21667
  • /2

    $325,000

    Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $331,975

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
    • /14

      Est $126,050

      Not Listed For Sale

      21903 Yerkey Rd, Rock Hall, MD 21661

      • 1 Bed
      • 1 Bath
      • 572 Sq Ft
      • Built 1910
      21903 Yerkey Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 368 Days On Market

  • /60

    $475,000

    $59K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,821 Sq Ft

    31729 W Edge Rd, Millington, MD 21651

    Spacious waterfront rancher with pole barn—priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for instant equity on the upper Chester River. Conveniently located with easy access to Rt. 301, making commuting to Philadelphia, Middletown, or the Chesapeake Bay Bridge surprisingly convenient while still enjoying the perks of

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    31729 W Edge Rd, Millington, MD 21651
  • /2

    $58,000

    Sold Mar 24, 2026

    0 Bottom Rd, 3, Worton (Betterton), MD 21678

    • Land
    • 30,927 Sq Ft
    • $81,690 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 7 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Bottom Rd, 3, Worton (Betterton), MD 21678
    • /26

      Est $444,160

      Not Listed For Sale

      21089 Haven Rd, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 1,797 Sq Ft
      • Built 2009
      21089 Haven Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 46 Days On Market

  • /23

    $350,000

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft

    117 N Water St Unit 2B, Chestertown, MD 21620

    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 upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2B, Chestertown, MD 21620
  • /65

    $505,000

    Sold Jul 21, 2025

    207 Lee Ave, Galena, MD 21635

    • 3 Beds
    • 2.5 Baths
    • 2,696 Sq Ft
    • Built 1993

    Last Sold Summary

    • $187/SF
    • 5 Days On Market

    Current Estimated Value $516,298

    Last Listing Agent Kim Simpson Thyme Real Estate Co LLC

    207 Lee Ave, Galena, MD 21635
    • /67

      Est $586,911

      Not Listed For Sale

      32960 Galena Sassafras Rd, Galena, MD 21635

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1980
      32960 Galena Sassafras Rd, Galena, MD 21635

      Last Sold Summary

      • 1 Day On Market

  • /3

    $110,000

    • Land
    • 32,670 Sq Ft
    • $146,667 per Acre

    14 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    14 Wilson Point Rd, Galena, MD 21635
  • /40

    $293,000

    Sold Jun 08, 2026

    301 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 54 Days On Market

    Current Estimated Value $295,756

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
    • /26

      Est $369,778

      Not Listed For Sale

      503 N Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 1974
      503 N Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 79 Days On Market

  • /30

    $394,900

    $5K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,535 Sq Ft

    104 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,500 square feet of thoughtfully designed living space. With five bedrooms and three and a half bathrooms, this home provides the perfect balance of comfort, functionality, and flexibility for modern living.Step inside to an inviting foyer that leads to the bright and open main living area, where the family room

    David Moore Real Broker, LLC

    104 Flying Cloud Dr, Chestertown, MD 21620
  • /2

    $339,900

    Sold Apr 21, 2026

    103 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2023

    Last Sold Summary

    • $197/SF
    • 0 Days On Market

    Current Estimated Value $337,088

    Last Listing Agent Laura Snyder American Premier Realty, LLC

    103 Flying Cloud Dr, Chestertown, MD 21620
    • /14

      Est $249,808

      Not Listed For Sale

      6053 N Main St, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft
      • Built 1920
      6053 N Main St, Rock Hall, MD 21661

      Last Sold Summary

      • 473 Days On Market

  • /28

    $205,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft

    21363 Lynn Ln, Chestertown, MD 21620

    Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    21363 Lynn Ln, Chestertown, MD 21620

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