12,134

Kent County, MD Homes

Section Image
  • /14

    $329,000

    Sold May 27, 2026

    10594 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 2020

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $327,991

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    10594 Millbrook Dr, Chestertown, MD 21620
    • /51

      Est $383,992

      Not Listed For Sale

      8605 Camp Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1968
      8605 Camp Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • /19

    $3,000,000

    Pending
    • Land
    • 87.34 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community.

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, Chestertown, MD 21620
  • /13

    $295,000

    Sold Mar 31, 2026

    107 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2004

    Last Sold Summary

    • $152/SF
    • 8 Days On Market

    Current Estimated Value $294,369

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
    • /35

      Est $370,457

      Not Listed For Sale

      10724 Foreston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1995
      10724 Foreston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • /57

    $798,000

    $30K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • /26

    $339,900

    Sold Jun 05, 2026

    21125 Iowa Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1962

    Last Sold Summary

    • $263/SF
    • 54 Days On Market

    Current Estimated Value $333,902

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21125 Iowa Ave, Chestertown, MD 21620
    • /71

      Est $601,529

      Not Listed For Sale

      11310 Urieville Ln, Worton, MD 21678

      • 3 Beds
      • 4 Baths
      • 1,896 Sq Ft
      • Built 1991
      11310 Urieville Ln, Worton, MD 21678

      Last Sold Summary

      • 28 Days On Market

  • /2

    $10,000

    • Land
    • 14,810 Sq Ft
    • $29,412 per Acre

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620

    Build Your Dream Home on Two Expansive Lots in Chesapeake Landing!15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks!Enjoy the charm of Chestertown living, just

    Rena Champaco Samson Properties

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
  • /67

    $2,100,000

    Sold Feb 02, 2026

    10121 Fairlee Rd, Chestertown, MD 21620

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft
    • Built 1858

    Last Sold Summary

    • $424/SF
    • 58 Days On Market

    Current Estimated Value $2,107,305

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
    • /21

      Est $355,313

      Not Listed For Sale

      106 Boxwood Ln, Galena, MD 21635

      • 3 Beds
      • 2 Baths
      • 1,276 Sq Ft
      • Built 2001
      106 Boxwood Ln, Galena, MD 21635

      Last Sold Summary

      • 20 Days On Market

  • /29

    $229,990

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    24581 Willow Oak Ln, Chestertown, MD 21620

    If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

    Michele Palmer Doug Ashley Realtors, LLC

    24581 Willow Oak Ln, Chestertown, MD 21620
  • /25

    $205,000

    Sold Aug 29, 2025

    25126 Lambs Meadow Rd, Worton, MD 21678

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 2007

    Last Sold Summary

    • $194/SF
    • 8 Days On Market

    Last Listing Agent Julie Strickler Remax Vision

    25126 Lambs Meadow Rd, Worton, MD 21678
    • /27

      Est $197,440

      Not Listed For Sale

      28020 Creamery St, Kennedyville, MD 21645

      • 2 Beds
      • 1 Bath
      • 704 Sq Ft
      • Built 1920
      28020 Creamery St, Kennedyville, MD 21645

      Last Sold Summary

      • 6 Days On Market

  • /30

    $185,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely

    Ashley Earle Compass

    423 Calvert St, Chestertown, MD 21620
  • /24

    $435,000

    Sold Sep 26, 2025

    21055 Bayside Ave, Rock Hall, MD 21661

    • 4 Beds
    • 2 Baths
    • 1,514 Sq Ft
    • Built 1934

    Last Sold Summary

    • $287/SF
    • 21 Days On Market

    Current Estimated Value $449,881

    Last Listing Agent Robin Fithian Rock Hall Properties Real Estate

    21055 Bayside Ave, Rock Hall, MD 21661
    • /34

      Est $748,656

      Not Listed For Sale

      112 S Mill St, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft
      • Built 1840
      112 S Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 49 Days On Market

  • /32

    $339,000

    Under Contract
    • Studio
    • 2,236 Sq Ft

    11955 Augustine Herman Hwy, Kennedyville, MD 21645

    Welcome to this spacious 2,236 square foot, 4-bedroom, 3-bath property located in the heart of Kennedyville, currently configured as a two-unit, multi-use home offering exceptional flexibility. The property can easily be converted back to a single-family 4-bedroom, 3-full-bath residence or utilized as a live/work opportunity with potential storefront space in the front unit while generating

    Sarah Ulrick Rock Hall Properties Real Estate

    11955 Augustine Herman Hwy, Kennedyville, MD 21645
  • /2

    $64,000

    Sold Oct 13, 2025

    210 Crane St, Millington, MD 21651

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1920

    Last Sold Summary

    • $53/SF

    Current Estimated Value $106,415

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    210 Crane St, Millington, MD 21651
    • /54

      Est $566,251

      Not Listed For Sale

      14182 N 1st Ave, Kennedyville, MD 21645

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 1950
      14182 N 1st Ave, Kennedyville, MD 21645

      Last Sold Summary

      • 110 Days On Market

  • /19

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,247 Sq Ft

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open

    Julia Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • /2

    $562,000

    Sold May 11, 2026

    31667 W Edge Rd, Millington, MD 21651

    • 3 Beds
    • 2.5 Baths
    • 2,892 Sq Ft
    • Built 2006

    Last Sold Summary

    • $194/SF
    • 7 Days On Market

    Current Estimated Value $564,387

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    31667 W Edge Rd, Millington, MD 21651
    • /76

      Est $650,757

      Not Listed For Sale

      31621 W Edge Rd, Millington, MD 21651

      • 4 Beds
      • 3.5 Baths
      • 2,848 Sq Ft
      • Built 2008
      31621 W Edge Rd, Millington, MD 21651

      Last Sold Summary

      • 5 Days On Market

  • /3

    $55,000

    • Land
    • 12,632 Sq Ft
    • $189,655 per Acre

    0 Judefind Ave Unit MDKE2001688, Rock Hall, MD 21661

    Wooded building lot on Judefind Ave in Rock Hall town limits. No flood plain, no critical area, no wetlands. Water & sewer hook ups will be required. Lot is 75 ft wide by 165 ft deep. Nice walkable in-town location on a quiet, private street. Just minutes to the Main Street shopping district and the Mainstay.

    Robin Fithian Rock Hall Properties Real Estate

    0 Judefind Ave Unit MDKE2001688, Rock Hall, MD 21661
  • /16

    $270,000

    Sold Aug 15, 2025

    21114 Striper Run, Rock Hall, MD 21661

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

    Last Sold Summary

    • $166/SF
    • 28 Days On Market

    Current Estimated Value $281,439

    Last Listing Agent Alyson Anderson Allfirst Realty, Inc.

    21114 Striper Run, Rock Hall, MD 21661
    • /25

      Est $586,906

      Not Listed For Sale

      209 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,488 Sq Ft
      • Built 1980
      209 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • /6

    $12,000

    • Land
    • 1.49 Acres
    • $8,054 per Acre

    23737 Smithville Rd, Worton, MD 21678

    This 1.49-acre wooded lot offers a strong opportunity for buyers seeking flexibility and value. The property provides space for recreational use and the potential for a long-term investment.Ideal for hunting and camping, the land offers a range of outdoor activities. With a location just 5 miles from Worton Creek Marina, this brings you convenient access for boating the Chesapeake Bay and its

    Jack Boniface Cross Street Realtors LLC

    23737 Smithville Rd, Worton, MD 21678
  • /9

    $190,500

    Sold Jul 22, 2025

    619 Cannon St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 882 Sq Ft
    • Built 1983

    Last Sold Summary

    • $216/SF
    • 50 Days On Market

    Current Estimated Value $198,201

    Last Listing Agent Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
    • /25

      Est $223,714

      Not Listed For Sale

      11059 Brindley Dr, Worton, MD 21678

      • 3 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1991
      11059 Brindley Dr, Worton, MD 21678

      Last Sold Summary

      • 0 Days On Market

  • /70

    $499,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /2

    $749,500

    Sold Apr 13, 2026

    6 Byford Ct, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1978

    Last Sold Summary

    • $239/SF
    • 0 Days On Market

    Current Estimated Value $750,670

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6 Byford Ct, Chestertown, MD 21620
    • /57

      Est $307,596

      Not Listed For Sale

      12 3rd Ave, Betterton, MD 21610

      • 4 Beds
      • 2 Baths
      • 2,500 Sq Ft
      • Built 2005
      12 3rd Ave, Betterton, MD 21610

      Last Sold Summary

      • 10 Days On Market

  • /3

    $135,000

    • Land
    • 32,670 Sq Ft
    • $180,000 per Acre

    5 Wilson Point Rd, Galena, MD 21635

    Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style

    Aaron Clark Patterson-Schwartz-Middletown

    5 Wilson Point Rd, Galena, MD 21635
  • /2

    $12,500

    Sold Apr 27, 2026

    23665 Smithville Rd, Worton, MD 21678

    • Land
    • 2.08 Acres
    • $6,010 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 5 Days On Market

    Current Estimated Value $139,020

    Last Listing Agent Jack Boniface Cross Street Realtors LLC

    23665 Smithville Rd, Worton, MD 21678
    • /41

      Est $460,803

      Not Listed For Sale

      203 Leeds Ct, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft
      • Built 2005
      203 Leeds Ct, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • /54

    $525,000

    Open Sat 12PM - 2PM $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,132 Sq Ft

    14136 Kentmore Park Rd, Kennedyville, MD 21645

    Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and

    Patricia Kern Gunther-McClary Real Estate

    14136 Kentmore Park Rd, Kennedyville, MD 21645
  • /2

    $40,000

    Sold Apr 29, 2026

    0 Olivet Hill Cir, Galena, MD 21635

    • Land
    • 1.4 Acres
    • $28,571 per Acre

    Last Sold Summary

    • 25% Above List Price
    • 265 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Olivet Hill Cir, Galena, MD 21635
    • /50

      Est $532,435

      Not Listed For Sale

      217 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,208 Sq Ft
      • Built 1984
      217 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

  • /92

    $865,000

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • /35

    $438,000

    Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $455,158

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620

Showing Results 521 - 560, Page 14 of 18

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