6,817

Chestertown, MD Homes

Section Image
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $750,000

    Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • 201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      /50

      Est $345,256

      Not Listed For Sale

      201 Tamarack Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft
      • Built 1973
      201 Tamarack Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Petra Quinn Realty Navigator

  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,330,551

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • 332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      /29

      Est $317,640

      Not Listed For Sale

      332 Truslow Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft
      • Built 1900
      332 Truslow Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent James Blackwell Blackwell Real Estate, LLC

  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    117 N Water St Unit 1A, 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 1A, Chestertown, MD 21620
  • 224 Valley Rd, Chestertown, MD 21620
    224 Valley Rd, Chestertown, MD 21620
    224 Valley Rd, Chestertown, MD 21620
    /24

    $455,000

    Sold Oct 21, 2025

    224 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1978

    Last Sold Summary

    • $241/SF
    • 13 Days On Market

    Current Estimated Value $466,142

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
    • 707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      /31

      Est $339,467

      Not Listed For Sale

      707 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1976
      707 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • 105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    /49

    $475,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, Chestertown, MD 21620
  • 517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    /28

    $289,000

    Sold Aug 21, 2026

    517 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 17% Below List Price
    • $232/SF
    • 41 Days On Market

    Current Estimated Value $307,743

    Last Listing Agent Barry Hess Keller Williams Flagship

    517 Round Top Rd, Chestertown, MD 21620
    • 212 Central Dr, Chestertown, MD 21620
      212 Central Dr, Chestertown, MD 21620
      212 Central Dr, Chestertown, MD 21620
      /21

      Est $301,386

      Not Listed For Sale

      212 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1972
      212 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
  • 124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    /31

    $250,000

    Sold Nov 11, 2025

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1967

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $259,514

    Last Listing Agent Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
    • 324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      /25

      Est $341,545

      Not Listed For Sale

      324 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1988
      324 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Christopher Carr HomeZu

  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $75,000

    Sold Aug 13, 2026

    0 East St, Chestertown, MD 21620

    • Land
    • 20,908 Sq Ft
    • $156,250 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620
    • 118 Tuxedo Rd, Chestertown, MD 21620
      118 Tuxedo Rd, Chestertown, MD 21620
      118 Tuxedo Rd, Chestertown, MD 21620
      /26

      Est $246,988

      Not Listed For Sale

      118 Tuxedo Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      118 Tuxedo Rd, Chestertown, MD 21620

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • 200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • 2010 Mcginnes Rd, Chestertown, MD 21620
    2010 Mcginnes Rd, Chestertown, MD 21620
    2010 Mcginnes Rd, Chestertown, MD 21620
    /19

    $354,900

    Sold Nov 10, 2025

    2010 Mcginnes Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,253 Sq Ft
    • Built 1962

    Last Sold Summary

    • $283/SF
    • 14 Days On Market

    Current Estimated Value $360,363

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
    • 110 Philosophers Terrace, Chestertown, MD 21620
      110 Philosophers Terrace, Chestertown, MD 21620
      110 Philosophers Terrace, Chestertown, MD 21620
      /22

      Est $195,846

      Not Listed For Sale

      110 Philosophers Terrace, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 896 Sq Ft
      • Built 1955
      110 Philosophers Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 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. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    /29

    $359,900

    Sold Nov 24, 2025

    221 Old Bridge Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • Built 1924

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $364,289

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
    • 105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      /58

      Est $850,804

      Not Listed For Sale

      105 S Water St, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft
      • Built 1900
      105 S Water St, Chestertown, MD 21620

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Richard Keaveney Cross Street Realtors LLC

  • 7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,100,000

    Sold Jan 16, 2026

    300 Hickory Ln, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 1940

    Last Sold Summary

    • $302/SF
    • 163 Days On Market

    Current Estimated Value $1,129,907

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $263,794

      Not Listed For Sale

      114 School Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft
      • Built 1966
      114 School Rd, Chestertown, MD 21620

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 114 Chester View, Chestertown, MD 21620
    114 Chester View, Chestertown, MD 21620
    /2

    $1,650,000

    Sold Jun 30, 2026

    114 Chester View, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $799/SF
    • 0 Days On Market

    Current Estimated Value $1,177,591

    Last Listing Agent Jack Boniface Cross Street Realtors LLC

    114 Chester View, Chestertown, MD 21620
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $400,308

      Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 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

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 206 Camelot Dr, Chestertown, MD 21620
    206 Camelot Dr, Chestertown, MD 21620
    206 Camelot Dr, Chestertown, MD 21620
    /65

    $455,000

    Sold Apr 13, 2026

    206 Camelot Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft
    • Built 2009

    Last Sold Summary

    • 13% Below List Price
    • $208/SF
    • 30 Days On Market

    Current Estimated Value $464,468

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $326,155

      Not Listed For Sale

      10550 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2006
      10550 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • 620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    /9

    $99,999

    • Land
    • 3,096 Sq Ft
    • $1,406,963 per Acre

    620 Cannon St, Chestertown, MD 21620

    Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available.

    Julie Santoboni Taylor Properties

    620 Cannon St, Chestertown, MD 21620
  • 112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    /43

    $379,900

    Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $391,610

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
    • 116 Harlan Loop, Chestertown, MD 21620
      116 Harlan Loop, Chestertown, MD 21620
      116 Harlan Loop, Chestertown, MD 21620
      /28

      Est $534,514

      Not Listed For Sale

      116 Harlan Loop, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 4,067 Sq Ft
      • Built 2009
      116 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Robert Kaetzel Real Estate Professionals, Inc.

  • 0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $474,990

    Sold May 18, 2026

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • $185/SF
    • 286 Days On Market

    Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

    728 Aldora Dr Unit 113, Chestertown, MD 21620
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $326,301

      Not Listed For Sale

      23235 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23235 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,495,000

    $155K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • 720 Deep Landing Rd, Chestertown, MD 21620
    720 Deep Landing Rd, Chestertown, MD 21620
    720 Deep Landing Rd, Chestertown, MD 21620
    /42

    $360,000

    Sold Jun 12, 2026

    720 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $283/SF
    • 13 Days On Market

    Current Estimated Value $361,164

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    720 Deep Landing Rd, Chestertown, MD 21620

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