6,896

Chestertown, MD Homes

Section Image
  • /27

    $376,000

    Sold May 19, 2026

    136 Hilltop Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1995

    Last Sold Summary

    • 3% Above List Price
    • $263/SF
    • 5 Days On Market

    Current Estimated Value $399,127

    Last Listing Agent Joie White Northrop Realty

    136 Hilltop Dr, Chestertown, MD 21620
    • /42

      Est $319,275

      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
      • Jul 21, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /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
  • /67

    $490,000

    Sold May 08, 2026

    100 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft
    • Built 2008

    Last Sold Summary

    • $129/SF
    • 182 Days On Market

    Current Estimated Value $502,749

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
    • /21

      Est $298,899

      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

      • 2% Below List Price
      • $297/SF
      • 13 Days On Market
      • Last Sold Price $305,000
      • Feb 27, 2025

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /28

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    139 Prospect St, Chestertown, MD 21620

    Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

    Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
  • /66

    $868,000

    Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Current Estimated Value $873,396

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • /22

      Est $339,739

      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

      • 1% Below List Price
      • $285/SF
      • 3 Days On Market
      • Last Sold Price $342,000
      • Dec 09, 2024

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /2

    $150,000

    • Land
    • 1.8 Acres
    • $83,333 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
  • /2

    $30,000

    Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 36,154 Sq Ft
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    • /30

      Est $601,104

      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

      • 7% Below List Price
      • $386/SF
      • 27 Days On Market
      • Last Sold Price $649,000
      • Dec 20, 2024

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /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 5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:50 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
  • /38

    $575,000

    Sold Jun 06, 2025

    129 N Queen St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 19 Days On Market

    Current Estimated Value $607,993

    Last Listing Agent William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
    • /41

      Est $321,953

      Not Listed For Sale

      6744 Church Hill Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,298 Sq Ft
      • Built 1964
      6744 Church Hill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1% Above List Price
      • $247/SF
      • 199 Days On Market
      • Last Sold Price $320,000
      • Mar 26, 2025

      Last Listing Agent Sarah Ulrick Rock Hall Properties

  • /3

    $6,000

    • Land
    • 30,056 Sq Ft
    • $8,696 per Acre

    23683 L Rd, Chestertown, MD 21620

    List Price is opening bid at online auction. Absolute at or above $6,000. Bidding begins Wednesday, June 3rd, and ends Monday, June 8, 2026 at 1:30PM. 0.69± Acres of Unimproved Land in Chestertown, Kent County Zoning - Village (V) district. Is intended for:• Small, historic, or traditional rural villages• A mix of residential uses (mostly single-family homes, sometimes limited

    Larry Cooper Alex Cooper Auctioneers, Inc.

    23683 L Rd, Chestertown, MD 21620
  • /59

    $392,500

    Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Current Estimated Value $386,952

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
    • /34

      Est $460,910

      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

      • 5% Below List Price
      • $235/SF
      • 23 Days On Market
      • Last Sold Price $485,000
      • Aug 02, 2023

      Last Listing Agent Denis Gasper Benson & Mangold, LLC

  • /23

    $138,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Well priced 3 bedroom, 2 bath double wide in Duck Neck, Queen Annes County situated on a half an acre and shed , man cave and car ports included. House has a metal roof. Close to the Chester River and minutes from Deep Landing and Chestertown.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    127 Wood Duck Ln, Chestertown, MD 21620
  • /34

    $508,954

    Sold Dec 04, 2025

    730 Aldora Dr Unit 114, Chestertown, MD 21620

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

    Last Sold Summary

    • $198/SF
    • 10 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
    • /26

      Est $412,922

      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

      • 4% Above List Price
      • $224/SF
      • 45 Days On Market
      • Last Sold Price $398,000
      • Sep 27, 2024

      Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

  • /2

    $9,500

    • Land
    • 14,810 Sq Ft
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /36

    $379,000

    Sold Jan 30, 2026

    104 Iris Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 2006

    Last Sold Summary

    • $223/SF
    • 11 Days On Market

    Current Estimated Value $382,935

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    104 Iris Rd, Chestertown, MD 21620
    • /21

      Est $357,656

      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

      • 10% Above List Price
      • $260/SF
      • 68 Days On Market
      • Last Sold Price $325,000
      • May 31, 2024

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • /41

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    102 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large

    Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
  • /42

    $312,000

    Sold Jun 13, 2025

    306 Cedar St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1959

    Last Sold Summary

    • $222/SF
    • 55 Days On Market

    Current Estimated Value $330,688

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
    • /60

      Est $634,939

      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

      • 2% Above List Price
      • $252/SF
      • 33 Days On Market
      • Last Sold Price $625,000
      • Dec 10, 2024

      Last Listing Agent Travis Gray Engel & Völkers Annapolis

  • /3

    $1,450,000

    Coming Soon
    • 4 Beds
    • 4 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Coming Soon! Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with a deeded boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deeded deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • /27

    $290,000

    Sold Jan 16, 2026

    107 Malone Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1962

    Last Sold Summary

    • $242/SF
    • 69 Days On Market

    Current Estimated Value $289,600

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
    • /24

      Est $304,052

      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

      • 5% Above List Price
      • $239/SF
      • 5 Days On Market
      • Last Sold Price $290,267
      • Oct 10, 2023

      Last Listing Agent Doug Ashley Doug Ashley 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
  • /36

    $270,000

    Sold Feb 19, 2026

    24339 Chestertown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1964

    Last Sold Summary

    • $281/SF
    • 4 Days On Market

    Current Estimated Value $267,802

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    24339 Chestertown Rd, Chestertown, MD 21620
    • /48

      Est $522,180

      Not Listed For Sale

      112 Sheaffer Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,864 Sq Ft
      • Built 1989
      112 Sheaffer Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $170/SF
      • 52 Days On Market
      • Last Sold Price $486,000
      • Sep 13, 2024

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /2

    $325,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,427 Sq Ft

    202 Valley Rd, Chestertown, MD 21620

    Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620
  • /2

    $332,000

    Sold Apr 10, 2026

    23055 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 1948

    Last Sold Summary

    • 1% Above List Price
    • $204/SF
    • 5 Days On Market

    Current Estimated Value $322,233

    Last Listing Agent Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
    • /25

      Est $395,156

      Not Listed For Sale

      224 Fey Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft
      • Built 1988
      224 Fey Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $256/SF
      • 1 Day On Market
      • Last Sold Price $385,000
      • Jun 20, 2023

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • /73

    $1,600,000

    • 7 Beds
    • 5 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
  • /29

    $330,000

    Sold Apr 03, 2026

    23110 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft
    • Built 1938

    Last Sold Summary

    • $183/SF
    • 174 Days On Market

    Current Estimated Value $296,629

    Last Listing Agent Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • /22

      Est $184,272

      Not Listed For Sale

      340 Pine Tree Rd, Chestertown, MD 21620

      • Studio
      • 1,080 Sq Ft
      • Built 1920
      340 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $162/SF
      • 14 Days On Market
      • Last Sold Price $175,000
      • Sep 06, 2023

      Last Listing Agent Leigh Lawson Metro Bay Realty

  • /6

    $8,000

    • Land
    • 14,810 Sq Ft
    • $23,529 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:55 PM. This auction takes place on the Ashland Auction Group Website Bidding Platform. List Price is Suggested Opening Bid. 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

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /6

    $5,000

    Sold Jan 08, 2026

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

    • Land
    • 18,295 Sq Ft
    • $11,905 per Acre

    Last Sold Summary

    • 230 Days On Market

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

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

Showing Results 161 - 200, Page 5 of 18

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