6,886

Chestertown, MD Homes

Section Image
    • /33

      Est $733,084 Not Listed For Sale

      121 Lyons Ln, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,327 Sq Ft
      • Built 1990
      121 Lyons Ln, Chestertown, MD 21620

      Last Sold Summary

      • 2% Below List Price
      • $322/SF
      • 22 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Jennifer Gregorski Washington Fine Properties

  • /11

    $19,500 Under Contract

    • Land
    • 0.99 Acre
    • $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 Kent

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • /3

    $124,000 Sold Aug 25, 2025

    209 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $122,772 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $128,694

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • /12

      Est $756,954 Not Listed For Sale

      204 Truslow Farm Ln, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,945 Sq Ft
      • Built 1917
      204 Truslow Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 24% Below List Price
      • $340/SF
      • 9 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

  • /2

    $29,000 Under Contract

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, Chestertown, MD 21620
  • /47

    $359,000 Sold Feb 03, 2026

    8833 Georgetown Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 1900

    Last Sold Summary

    • $221/SF
    • 76 Days On Market

    Current Estimated Value $354,000

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
    • /31

      Est $285,520 Not Listed For Sale

      150 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      150 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $251/SF
      • 5 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Kerry D'Azevedo Integrity Real Estate

  • /34

    $675,000 Pending

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

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • /32

    $700,000 Sold Oct 22, 2025

    26889 Morgnec Rd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft
    • Built 1966

    Last Sold Summary

    • $356/SF
    • 156 Days On Market

    Current Estimated Value $735,193

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • /26

      Est $400,340 Not Listed For Sale

      200 Duke of Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,477 Sq Ft
      • Built 1995
      200 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $251/SF
      • 4 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /13

    $259,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    107 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxuryvinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granitecountertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment.Upstairs you'll find generously sized bedrooms including a large primary

    David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
  • /7

    $80,000 Sold Dec 22, 2025

    5700 Johnsontown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1900

    Last Sold Summary

    • $70/SF
    • 107 Days On Market

    Current Estimated Value $138,560

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • /42

      Est $319,572 Not Listed For Sale

      103 Creston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1973
      103 Creston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Below List Price
      • $304/SF
      • 6 Days On Market

      Last Sold Price $332,100

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /20

    $125,000 Sold Mar 02, 2026

    423 Calvert St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1992

    Last Sold Summary

    • $110/SF
    • 112 Days On Market

    Current Estimated Value $136,189

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
    • /21

      Est $304,837 Not Listed For Sale

      116 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,028 Sq Ft
      • Built 1976
      116 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • $297/SF
      • 13 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /8

    $150,000

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

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /2

    $57,500 Sold Apr 30, 2025

    113 Pine Cove Ln, Chestertown, MD 21620

    • Land
    • 0.45 Acre
    • $127,778 per Acre

    Last Sold Summary

    • 185 Days On Market

    Current Estimated Value $134,000

    Last Listing Agent William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • /22

      Est $335,301 Not Listed For Sale

      218 Concord Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1997
      218 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Below List Price
      • $285/SF
      • 3 Days On Market

      Last Sold Price $342,000

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /41

    $330,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft

    129 Parma Rd, Chestertown, MD 21620

    Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

    Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma Rd, Chestertown, MD 21620
  • /19

    $300,000 Sold Sep 26, 2025

    925 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $284/SF
    • 50 Days On Market

    Current Estimated Value $304,904

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
    • /30

      Est $552,282 Not Listed For Sale

      411 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1977
      411 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 15% Below List Price
      • $386/SF
      • 27 Days On Market

      Last Sold Price $649,000

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /73

    $1,600,000

    • 7 Beds
    • 6 Baths
    • 5,400 Sq Ft

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

    **Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 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

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • /4

    $15,000 Sold Jun 02, 2025

    22671 Wood Yard Ln, Chestertown, MD 21620

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $157,484

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • /34

      Est $455,901 Not Listed For Sale

      240 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,067 Sq Ft
      • Built 2003
      240 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 6% Below List Price
      • $235/SF
      • 23 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Denis Gasper Benson & Mangold, LLC

  • /2

    $40,000 Pending

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • /53

    $375,000 Sold Apr 16, 2025

    25740 Collins Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,389 Sq Ft
    • Built 1956

    Last Sold Summary

    • $111/SF
    • 29 Days On Market

    Current Estimated Value $444,963

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • /26

      Est $405,568 Not Listed For Sale

      209 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 2001
      209 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $224/SF
      • 45 Days On Market

      Last Sold Price $398,000

      Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

  • /2

    $143,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft

    9925 Flatland Rd, Chestertown, MD 21620

    As - Is

    Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
  • /47

    $700,000 Sold Dec 04, 2025

    8951 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2014

    Last Sold Summary

    • $187/SF
    • 2 Days On Market

    Current Estimated Value $701,290

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /21

      Est $352,339 Not Listed For Sale

      112 Pine Chip Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1978
      112 Pine Chip Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $260/SF
      • 68 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /35

    $413,300 Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Current Estimated Value $407,136

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • /60

      Est $634,020 Not Listed For Sale

      1316 Ewingtown Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,476 Sq Ft
      • Built 2002
      1316 Ewingtown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1% Above List Price
      • $252/SF
      • 33 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Travis Gray Engel & Völkers Annapolis

  • /3

    $269,900 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft

    112 Elm St, Chestertown, MD 21620

    Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
  • /49

    $392,500 Sold Jan 28, 2026

    108 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Above List Price
    • $228/SF
    • 76 Days On Market

    Current Estimated Value $500,323

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
    • /24

      Est $311,826 Not Listed For Sale

      2607 Mcginnes Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft
      • Built 1978
      2607 Mcginnes Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $239/SF
      • 5 Days On Market

      Last Sold Price $290,267

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /6

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 3/16/2026 @ 10:00 AM. Bidding ends 3/18/2026 @ 12:25 PM. The list price is the suggested opening bid. Deposit: $5,000. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /8

    $50,000 Sold May 16, 2025

    0 Fairlee Rd, Chestertown, MD 21620

    • Land
    • 2.2 Acres
    • $22,727 per Acre

    Last Sold Summary

    • 159 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 Fairlee Rd, Chestertown, MD 21620
    • /23

      Est $282,226 Not Listed For Sale

      208 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1978
      208 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 21% Above List Price
      • $209/SF
      • 4 Days On Market

      Last Sold Price $234,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home