6,890

Chestertown, MD Homes

Section Image
  • /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
  • /34

    $384,000

    Sold Jun 29, 2026

    23416 Cloquet Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2020

    Last Sold Summary

    • $254/SF
    • 6 Days On Market

    Current Estimated Value $384,117

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23416 Cloquet Rd, 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

  • /9

    $109,999

    Pending
    • Land
    • 7,840 Sq Ft
    • $611,106 per Acre

    116 N Cross St, Chestertown, MD 21620

    Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing

    Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
  • /16

    $240,000

    Sold Jan 16, 2026

    100 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $211/SF
    • 109 Days On Market

    Current Estimated Value $245,124

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf 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

  • /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
  • /25

    $325,000

    Sold Jul 16, 2026

    10572 Watonga Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2007

    Last Sold Summary

    • $231/SF
    • 1 Day On Market

    Current Estimated Value $334,458

    Last Listing Agent Samantha Zarnes Serhant

    10572 Watonga Rd, 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

  • /2

    $37,000

    $22K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /2

    $480,000

    Sold May 04, 2026

    101 Pine Tree Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1993

    Last Sold Summary

    • $260/SF
    • 0 Days On Market

    Current Estimated Value $481,149

    Last Listing Agent Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, 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

  • /13

    $60,000

    • Land
    • 21,780 Sq Ft
    • $120,000 per Acre

    233 Merganser Dr, Chestertown, MD 21620

    Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

    Barbara Wallace Long & Foster Real Estate, Inc.

    233 Merganser Dr, Chestertown, MD 21620
  • /16

    $120,000

    Sold Feb 27, 2026

    141 Prospect St, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 27% Below List Price
    • $104/SF
    • 33 Days On Market

    Current Estimated Value $137,042

    Last Listing Agent Jeff Guthrie Taylor Properties

    141 Prospect St, 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

  • /54

    $349,000

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

    123 Heath Rd, Chestertown, MD 21620

    Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive

    Erin Anderson Chesapeake Real Estate Associates, LLC

    123 Heath Rd, Chestertown, MD 21620
  • /36

    $315,000

    Sold Aug 29, 2025

    106 Wilton Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $298/SF
    • 18 Days On Market

    Current Estimated Value $313,578

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, 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

  • /44

    $1,245,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /15

    $155,000

    Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $169,808

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
    • /27

      Est $251,195

      Not Listed For Sale

      117 Chester Arms Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,260 Sq Ft
      • Built 2022
      117 Chester Arms Dr, Chestertown, MD 21620

      Last Sold Summary

      • 30 Days On Market

  • /11

    $19,500

    • Land
    • 43,124 Sq Ft
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Queen

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • /18

    $165,000

    Sold Jul 07, 2026

    144 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $152/SF
    • 24 Days On Market

    Current Estimated Value $175,512

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    144 Prospect St, Chestertown, MD 21620
    • /37

      Est $474,074

      Not Listed For Sale

      200 Ashley Ln, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft
      • Built 1980
      200 Ashley Ln, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

  • /13

    $615,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 4,536 Sq Ft

    103 Maple Ave, Chestertown, MD 21620

    The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    103 Maple Ave, Chestertown, MD 21620
  • /17

    $335,000

    Sold Oct 03, 2025

    110 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 2023

    Last Sold Summary

    • $180/SF
    • 208 Days On Market

    Current Estimated Value $342,352

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
    • /33

      Est $658,805

      Not Listed For Sale

      209 Landing Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft
      • Built 2009
      209 Landing Ln, Chestertown, MD 21620

      Last Sold Summary

      • 209 Days On Market

  • /2

    $135,000

    $15K PRICE DROP
    • Land
    • 1.8 Acres
    • $75,000 per Acre

    109 2nd St, Chestertown, MD 21620

    Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton,

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • /11

    $190,000

    Sold Mar 04, 2026

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $18,905 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 20 Days On Market

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
    • /44

      Est $481,163

      Not Listed For Sale

      204 N Mill St, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft
      • Built 1920
      204 N Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 49 Days On Market

  • /3

    $3,000

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

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 1:00 PM. 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 major

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
  • /19

    $270,000

    Sold Mar 18, 2026

    119 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • Built 1997

    Last Sold Summary

    • 14% Below List Price
    • $190/SF
    • 14 Days On Market

    Current Estimated Value $272,083

    Last Listing Agent Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
    • /7

      Not Listed For Sale

      128 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft
      • Built 1900
      128 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

  • /4

    $110,000

    • Land
    • 1.93 Acres
    • $56,995 per Acre

    1906 Pondtown Rd, Chestertown, MD 21620

    Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes.

    Lonnie Gilmore Keller Williams Flagship

    1906 Pondtown Rd, Chestertown, MD 21620
  • /62

    $495,000

    Sold Apr 17, 2026

    201 Greenwood Ave, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,984 Sq Ft
    • Built 1960

    Last Sold Summary

    • $124/SF
    • 36 Days On Market

    Current Estimated Value $496,014

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    201 Greenwood Ave, Chestertown, MD 21620
    • /23

      Est $391,944

      Not Listed For Sale

      101 S Kent St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 1880
      101 S Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 58 Days On Market

  • /27

    $239,900

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    104 Conley Dr, Chestertown, MD 21620

    Price Improvement! Now offered at $239,900Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a

    Heather Kooser Cummings & Co. Realtors

    104 Conley Dr, Chestertown, MD 21620
  • /65

    $525,000

    Sold May 29, 2026

    22360 Great Oak Landing Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft
    • Built 1989

    Last Sold Summary

    • $195/SF
    • 0 Days On Market

    Current Estimated Value $574,718

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, Chestertown, MD 21620
    • /61

      Est $543,467

      Not Listed For Sale

      325 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 4,086 Sq Ft
      • Built 2011
      325 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • /51

    $375,000

    $20K PRICE DROP Under Contract
    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

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