6,890

Chestertown, MD Homes

Section Image
  • /28

    $195,000

    Sold Jul 31, 2026

    139 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1991

    Last Sold Summary

    • 13% Below List Price
    • $162/SF
    • 94 Days On Market

    Current Estimated Value $199,052

    Last Listing Agent Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
    • /38

      Est $596,049

      Not Listed For Sale

      129 N Queen St, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,296 Sq Ft
      • Built 1920
      129 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

  • /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
  • /34

    $665,000

    Sold Mar 30, 2026

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 8 Days On Market

    Current Estimated Value $650,350

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    • /40

      Est $640,499

      Not Listed For Sale

      108 N Queen St, Chestertown, MD 21620

      • 5 Beds
      • 2.5 Baths
      • 2,536 Sq Ft
      • Built 1920
      108 N Queen St, Chestertown, MD 21620

      Last Sold Summary

  • /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • /59

    $775,000

    Sold Nov 08, 2025

    8293 Brices Mill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,836 Sq Ft
    • Built 1900

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Current Estimated Value $773,164

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • /31

      Est $512,539

      Not Listed For Sale

      107 Adela Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft
      • Built 2010
      107 Adela Way, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

  • /41

    $329,900

    $10K PRICE DROP Under Contract
    • 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
  • /2

    $11,000

    Sold Feb 19, 2026

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    • Land
    • 2 Acres
    • $5,500 per Acre

    Last Sold Summary

    • 806 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    • /43

      Est $440,613

      Not Listed For Sale

      105 Sutton Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2010
      105 Sutton Way, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /50

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned 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 deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, 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 $130,377

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      • Built 1982
      112 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

  • /29

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • /19

    $259,900

    Sold May 18, 2026

    107 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • $217/SF
    • 41 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
    • /8

      Est $392,343

      Not Listed For Sale

      200 Hoffman Ln, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,128 Sq Ft
      • Built 1957
      200 Hoffman Ln, Chestertown, MD 21620

      Last Sold Summary

      • 15 Days On Market

  • /41

    $475,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /23

    $135,000

    Sold Jun 12, 2026

    127 Wood Duck Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $81/SF
    • 7 Days On Market

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    127 Wood Duck Ln, Chestertown, MD 21620
    • /28

      Est $368,178

      Not Listed For Sale

      249 Duke of Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,556 Sq Ft
      • Built 2000
      249 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

  • /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
  • /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 $345,881

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
    • /33

      Est $950,647

      Not Listed For Sale

      331 Park Ln, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1988
      331 Park Ln, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

  • /26

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    104 Acorn Dr, Chestertown, MD 21620

    Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car

    Sarah King Cross Street Realtors LLC

    104 Acorn Dr, 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 $744,680

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • /23

      Est $334,031

      Not Listed For Sale

      228 Dutchess Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,796 Sq Ft
      • Built 1978
      228 Dutchess Rd, Chestertown, MD 21620

      Last Sold Summary

      • 105 Days On Market

  • /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
  • /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 $110,666

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • /39

      Est $359,765

      Not Listed For Sale

      105 Justin Buch Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1991
      105 Justin Buch Dr, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

  • /6

    $8,000

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

    Parcel Buck Neck Ldg Rd, 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, 12:45 PM. The list price is the suggested opening bid. Deposit: $5,000. Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, &

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg 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 $176,236

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
    • /29

      Est $399,905

      Not Listed For Sale

      409 Riverview Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1998
      409 Riverview Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

  • /6

    $59,900

    $60K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft

    110 Prospect St, Chestertown, MD 21620

    Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This

    Matthew Altizer ANR Realty, LLC

    110 Prospect St, 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 $299,539

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
    • /11

      Est $304,265

      Not Listed For Sale

      102 Darden Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1986
      102 Darden Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • /54

    $1,395,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8276 Broad Neck Rd, Chestertown, MD 21620
  • /41

    $330,000

    Sold Mar 31, 2026

    129 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1985

    Last Sold Summary

    • $282/SF
    • 41 Days On Market

    Current Estimated Value $324,692

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma Rd, Chestertown, MD 21620
    • /27

      Est $352,763

      Not Listed For Sale

      310 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 2002
      310 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 20 Days On Market

  • /45

    $499,999

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jun 17, 2026

    202 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,427 Sq Ft
    • Built 1956

    Last Sold Summary

    • $228/SF
    • 0 Days On Market

    Current Estimated Value $326,431

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 18

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