6,868

Chestertown, MD Homes

Section Image
    • 201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      /5

      Est $391,991 Not Listed For Sale

      201 Duke of Kent St, Chestertown, MD 21620

      201 Duke of Kent St, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 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

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    /35

    $355,675 Sold Feb 28, 2025

    10724 Foreston Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1995

    Last Sold Summary

    • $190/SF
    • 3 Days On Market

    Current Estimated Value $374,241

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620
    • 2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      /24

      Est $309,736 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft

      2607 Mcginnes Rd, Chestertown, MD 21620

      2607 Mcginnes Rd, Chestertown, MD 21620
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $325,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    /21

    $325,000 Sold Mar 06, 2025

    10061 Flatland Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 2,376 Sq Ft
    • Built 1969

    Last Sold Summary

    • $137/SF
    • 18 Days On Market

    Current Estimated Value $335,032

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    10061 Flatland Rd, Chestertown, MD 21620
    • 208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      /23

      Est $306,573 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      208 Central Dr, Chestertown, MD 21620

      208 Central Dr, Chestertown, MD 21620
  • 0 Rd, Chestertown, MD 21620
    0 Rd, Chestertown, MD 21620
    /2

    $120,000

    • Land
    • 1.8 Acres
    • $66,667 per Acre

    0 Rd, Chestertown, MD 21620

    Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Rd, Chestertown, MD 21620
  • 226 Blakefield Dr, Chestertown, MD 21620
    226 Blakefield Dr, Chestertown, MD 21620
    /2

    $539,000 Sold Mar 31, 2025

    226 Blakefield Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $225/SF

    Current Estimated Value $548,267

    Last Listing Agent datacorrect BrightMLS Non Subscribing Office

    226 Blakefield Dr, Chestertown, MD 21620
    • 112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      /48

      Est $546,994 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,864 Sq Ft

      112 Sheaffer Rd, Chestertown, MD 21620

      112 Sheaffer Rd, Chestertown, MD 21620
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /29

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace

    Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • 317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    /33

    $685,000 Sold Mar 07, 2025

    317 Union Church Rd, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,512 Sq Ft
    • Built 2021

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Current Estimated Value $687,806

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    317 Union Church Rd, Chestertown, MD 21620
    • 224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      /25

      Est $383,285 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft

      224 Fey Rd, Chestertown, MD 21620

      224 Fey Rd, Chestertown, MD 21620
  • 0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    /6

    $8,000 Under Contract

    • Land
    • 0.42 Acre
    • $19,048 per Acre

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    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. Lot failed percolation Test in March of 1989.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
  • 473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    /24

    $359,900 Sold Apr 11, 2025

    473 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $238/SF
    • 67 Days On Market

    Current Estimated Value $371,529

    Last Listing Agent David Moore Real Broker, LLC

    473 Pear Tree Point Rd, Chestertown, MD 21620
    • 327 Pine Tree Rd, Chestertown, MD 21620
      327 Pine Tree Rd, Chestertown, MD 21620
      327 Pine Tree Rd, Chestertown, MD 21620
      /5

      Est $220,349 Not Listed For Sale

      • Studio
      • 1,008 Sq Ft

      327 Pine Tree Rd, Chestertown, MD 21620

      327 Pine Tree Rd, Chestertown, MD 21620
  • 349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    /47

    $395,000 Under Contract

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • 8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    /51

    $370,000 Sold May 08, 2025

    8605 Camp Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1968

    Last Sold Summary

    • $285/SF
    • 10 Days On Market

    Current Estimated Value $378,524

    Last Listing Agent Crystal Smith RE/MAX Executive

    8605 Camp Rd, Chestertown, MD 21620
    • 340 Pine Tree Rd, Chestertown, MD 21620
      340 Pine Tree Rd, Chestertown, MD 21620
      340 Pine Tree Rd, Chestertown, MD 21620
      /22

      Est $205,610 Not Listed For Sale

      • Studio
      • 1,080 Sq Ft

      340 Pine Tree Rd, Chestertown, MD 21620

      340 Pine Tree Rd, Chestertown, MD 21620
  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    /30

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    8750 Georgetown Rd, Chestertown, MD 21620

    Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bed, 2-bathroom home situated on 1 acre with public water/sewer, no HOA, and a detached garage with electric. Whether you're dreaming of a workshop, a hobby space, extra storage, or room for your equipment, this property delivers flexibility that’s hard to find at this price point. Inside, you’ll love the

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • 1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    /8

    $86,000 Sold Jun 09, 2025

    1814 Pondtown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 973 Sq Ft
    • Built 1974

    Last Sold Summary

    • $88/SF
    • 18 Days On Market

    Current Estimated Value $175,538

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    1814 Pondtown Rd, Chestertown, MD 21620
    • 206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      /16

      Est $377,721 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft

      206 Tamarack Rd, Chestertown, MD 21620

      206 Tamarack Rd, Chestertown, MD 21620
  • 0 Kinglet Rd, Chestertown, MD 21620
    0 Kinglet Rd, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • 221 River Rd, Chestertown, MD 21620
    221 River Rd, Chestertown, MD 21620
    221 River Rd, Chestertown, MD 21620
    /80

    $385,000 Sold Dec 20, 2024

    221 River Rd, Chestertown, MD 21620

    • 5 Beds
    • 2 Baths
    • 2,240 Sq Ft
    • Built 1969

    Last Sold Summary

    • $172/SF
    • 35 Days On Market

    Current Estimated Value $398,320

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    221 River Rd, Chestertown, MD 21620
    • 118 Hilltop Dr, Chestertown, MD 21620
      118 Hilltop Dr, Chestertown, MD 21620
      118 Hilltop Dr, Chestertown, MD 21620
      /28

      Est $484,997 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,188 Sq Ft

      118 Hilltop Dr, Chestertown, MD 21620

      118 Hilltop Dr, Chestertown, MD 21620
  • 216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    /2

    $579,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    216 Blakefield Dr, Chestertown, MD 21620

    Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
  • 23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    /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

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • 240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      /33

      Est $420,653 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft

      240 Duke of Kent St, Chestertown, MD 21620

      240 Duke of Kent St, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /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
  • 325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    /61

    $525,000 Sold Jun 13, 2025

    325 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 4,086 Sq Ft
    • Built 2011

    Last Sold Summary

    • $128/SF
    • 7 Days On Market

    Current Estimated Value $525,082

    Last Listing Agent Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

    325 Devon Dr, Chestertown, MD 21620
    • 415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      /24

      Est $639,550 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft

      415 Fairview Dr, Chestertown, MD 21620

      415 Fairview Dr, Chestertown, MD 21620
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    /15

    $625,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    26933 Mallard Rd, Chestertown, MD 21620

    Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /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

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • 319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      /37

      Est $633,404 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,128 Sq Ft

      319 Fairview Dr, Chestertown, MD 21620

      319 Fairview Dr, Chestertown, MD 21620
  • 10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    /41

    $750,000 Under Contract

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

    10230 John Carvill Rd, Chestertown, MD 21620

    Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock

    Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
  • 25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    /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 $555,568

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
    • 210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      /42

      Est $401,768 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,352 Sq Ft

      210 Rosin Dr, Chestertown, MD 21620

      210 Rosin Dr, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000 Pending

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    /23

    $379,989 Sold Jan 30, 2025

    107 Char Nor Manor Blvd, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,128 Sq Ft
    • Built 1999

    Last Sold Summary

    • $179/SF
    • 56 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    107 Char Nor Manor Blvd, Chestertown, MD 21620
    • 126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      /57

      Est $492,481 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,733 Sq Ft

      126 Hilltop Dr, Chestertown, MD 21620

      126 Hilltop Dr, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 18

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