6,817

Chestertown, MD Homes

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  • /26

    $753,500

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

    36 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • /2

    $395,000

    Sold Jun 25, 2026

    8629 Airy Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $274/SF
    • 7 Days On Market

    Current Estimated Value $428,003

    Last Listing Agent Lauren Smith Keller Williams Realty

    8629 Airy Hill Rd, Chestertown, MD 21620
    • /56

      Est $403,317

      Not Listed For Sale

      10570 Cogar Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft
      • Built 2010
      10570 Cogar Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /21

    $179,900

    $19K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21324 Persimmon Dr, Chestertown, MD 21620

    Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining

    Taylor Leaverton Benson & Mangold, LLC

    21324 Persimmon Dr, Chestertown, MD 21620
  • /24

    $410,000

    Sold Jun 26, 2026

    109 S College Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $337/SF
    • 71 Days On Market

    Current Estimated Value $410,642

    Last Listing Agent Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
    • /9

      Est $441,237

      Not Listed For Sale

      209 Blakefield Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • Built 2022
      209 Blakefield Dr, Chestertown, MD 21620

      Last Sold Summary

      • 130 Days On Market

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • /38

    $38,200,000

    • 4 Beds
    • 2 Baths
    • 2,330 Sq Ft

    8184 Rock Hall Rd, Chestertown, MD 21620

    Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a

    Joe Hickman Cross Street Realtors LLC

    8184 Rock Hall Rd, Chestertown, MD 21620
  • /61

    $1,900,000

    Sold Aug 14, 2026

    7989 Quaker Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft
    • Built 1950

    Last Sold Summary

    • $441/SF
    • 311 Days On Market

    Current Estimated Value $1,971,604

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
    • /34

      Est $604,531

      Not Listed For Sale

      7675 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 2017
      7675 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • /18

    $295,000

    • 1 Bed
    • 1 Bath

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

    Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    117 N Water St Unit 3B, Chestertown, MD 21620
  • /36

    $349,500

    Sold Jun 05, 2026

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1971

    Last Sold Summary

    • $268/SF
    • 9 Days On Market

    Current Estimated Value $346,340

    Last Listing Agent Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, Chestertown, MD 21620
    • /25

      Est $344,505

      Not Listed For Sale

      121 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2024
      121 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /38

    $545,000

    $67K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance.The first floor features an open and functional layout designed for everyday

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, Chestertown, MD 21620
  • /26

    $287,500

    Sold Dec 05, 2025

    7483 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 35 Days On Market

    Current Estimated Value $285,938

    Last Listing Agent Christine Johnson Dalton Wade, Inc.

    7483 Shortall St, Chestertown, MD 21620
    • /36

      Not Listed For Sale

      206 Silver Heel Dr, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft
      • Built 2022
      206 Silver Heel Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent TJ Bennett Samson Properties

  • /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:25 AM. 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 the Chester River. The area provides easy access to the

    Adam Shpritz Ashland Auction Group LLC

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
  • /5

    $25,000

    Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $127,333

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /19

      Est $242,869

      Not Listed For Sale

      107 Chester Arms Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2022
      107 Chester Arms Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Casey Scattergood Cross Street Realtors LLC

  • /15

    $289,900

    $160K PRICE DROP Under Contract
    • 2 Beds
    • 3 Baths
    • 1,518 Sq Ft

    522 High St, Chestertown, MD 21620

    Historic Charm in the Heart of Downtown ChestertownStep back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about.Featuring 2 spacious bedrooms with the potential

    Taylor Leaverton Benson & Mangold, LLC

    522 High St, Chestertown, MD 21620
  • /10

    $175,000

    Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $190,890

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • /19

      Est $330,843

      Not Listed For Sale

      10578 Tonopah Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 2025
      10578 Tonopah Rd, Chestertown, MD 21620

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /10

    $315,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    * SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • /20

    $220,000

    Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $225,524

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • /18

      Not Listed For Sale

      3650 Gratitude Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 3,599 Sq Ft
      • Built 2025
      3650 Gratitude Way, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /17

    $225,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    533 Round Top Rd, Chestertown, MD 21620

    Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your

    Chris Craddock EXP Realty, LLC

    533 Round Top Rd, Chestertown, MD 21620
  • /3

    $7,200

    Sold Jun 04, 2026

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $21,176 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 457 Days On Market

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    • /35

      Not Listed For Sale

      716 Aldora Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,120 Sq Ft
      • Built 2025
      716 Aldora Dr, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

  • /16

    $10,000

    • Land
    • 39,204 Sq Ft
    • $11,111 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    HUGE PRICE REDUCTION on a 0.9-acre Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • /51

    $640,000

    Sold Jul 29, 2026

    7844 Chester Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft
    • Built 2005

    Last Sold Summary

    • $197/SF
    • 222 Days On Market

    Current Estimated Value $687,003

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    7844 Chester Ct, Chestertown, MD 21620
    • /10

      Not Listed For Sale

      3652 Gratitude Way, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,642 Sq Ft
      • Built 2025
      3652 Gratitude Way, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /4

    $89,000

    • Land
    • 5.17 Acres
    • $17,215 per Acre

    27942 Old Morgnec Rd, Chestertown, MD 21620

    Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

    Brett Davis Gunther-McClary Real Estate

    27942 Old Morgnec Rd, Chestertown, MD 21620
  • /13

    $42,000

    Sold Aug 14, 2026

    228 Merganser Dr, Chestertown, MD 21620

    • Land
    • 22,215 Sq Ft
    • $82,353 per Acre

    Last Sold Summary

    • 58% Below List Price
    • 67 Days On Market

    Last Listing Agent Mae Nordhoff Benson & Mangold, LLC

    228 Merganser Dr, Chestertown, MD 21620
    • /35

      Not Listed For Sale

      720 Aldora Dr Unit 109, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,120 Sq Ft
      • Built 2025
      720 Aldora Dr Unit 109, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

  • /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • /44

    $680,000

    Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $702,071

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • /16

      Not Listed For Sale

      112 Snyder Ln, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 966 Sq Ft
      • Built 1988
      112 Snyder Ln, Chestertown, MD 21620

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /54

    $429,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10781 Fermoy Rd, Chestertown, MD 21620

    Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country

    David Moore Real Broker, LLC

    10781 Fermoy Rd, Chestertown, MD 21620
  • /2

    $104,000

    Sold Aug 13, 2026

    116 N Cross St, Chestertown, MD 21620

    • Land
    • 7,840 Sq Ft
    • $577,778 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 74 Days On Market

    Current Estimated Value $107,426

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
    • /5

      Not Listed For Sale

      0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

      0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

      Last Sold Summary

      • 371 Days On Market

      Last Listing Agent Adam Shpritz Ashland Auction Group LLC

  • /2

    $675,000

    Open House 10/03 Coming Soon Oct 3
    • 5 Beds
    • 3 Baths
    • 2,838 Sq Ft

    212 Washington Ave, Chestertown, MD 21620

    Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    212 Washington Ave, Chestertown, MD 21620

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