6,817

Chestertown, MD Homes

Section Image
    • 200 Hoffman Ln, Chestertown, MD 21620
      200 Hoffman Ln, Chestertown, MD 21620
      200 Hoffman Ln, Chestertown, MD 21620
      /8

      Est $415,162

      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

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • 104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    /26

    $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
  • 22360 Great Oak Landing Rd, Chestertown, MD 21620
    22360 Great Oak Landing Rd, Chestertown, MD 21620
    22360 Great Oak Landing Rd, 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 $575,137

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, Chestertown, MD 21620
    • 249 Duke of Kent St, Chestertown, MD 21620
      249 Duke of Kent St, Chestertown, MD 21620
      249 Duke of Kent St, Chestertown, MD 21620
      /28

      Est $369,558

      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

      Last Listing Agent Lee Wolff FSBO Broker

  • 0 Sandpiper Rd Unit MDKE2006902, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2006902, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2006902, Chestertown, MD 21620
    /8

    $4,500

    Under Contract
    • Land
    • 22,651 Sq Ft
    • $8,654 per Acre

    0 Sandpiper Rd Unit MDKE2006902, Chestertown, MD 21620

    Recreational lot- access community amenities, bird watch, garden, make a trail, firewood, etc. Not buildable unless the county adds public sewer in the future. RVs are not permitted. Chespeake Landing has walking trails, community boat ramp, and a new restaurant at the marina to enjoy!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Sandpiper Rd Unit MDKE2006902, Chestertown, MD 21620
  • 103 Maple Ave, Chestertown, MD 21620
    103 Maple Ave, Chestertown, MD 21620
    103 Maple Ave, Chestertown, MD 21620
    /13

    $615,000

    Sold Aug 27, 2026

    103 Maple Ave, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 4,536 Sq Ft
    • Built 1890

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Current Estimated Value $628,355

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    103 Maple Ave, Chestertown, MD 21620
    • 331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      /33

      Est $1,017,244

      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

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /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
  • 139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    /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
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $342,905

      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

      Last Listing Agent Stephanie Lehane RE/MAX Eagle Realty

  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /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
  • 118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, 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 $639,167

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    • 105 Justin Buch Dr, Chestertown, MD 21620
      105 Justin Buch Dr, Chestertown, MD 21620
      105 Justin Buch Dr, Chestertown, MD 21620
      /39

      Est $345,820

      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

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • 22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    /50

    $1,375,000

    $75K PRICE DROP
    • 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
  • 8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill 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 $778,951

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • 409 Riverview Rd, Chestertown, MD 21620
      409 Riverview Rd, Chestertown, MD 21620
      409 Riverview Rd, Chestertown, MD 21620
      /29

      Est $388,257

      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

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • 956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    /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
  • 0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2002846, 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
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      /11

      Est $304,813

      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

      Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 107 Metcalfe Rd, Chestertown, MD 21620
    107 Metcalfe Rd, Chestertown, MD 21620
    107 Metcalfe Rd, 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
    • 310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      /27

      Est $348,118

      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

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /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
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, 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
    • 122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      /8

      Est $180,539

      Not Listed For Sale

      122 1st St, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1955
      122 1st St, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • 104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    /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
  • 107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    /51

    $380,000

    Sold Aug 18, 2026

    107 Flying Cloud Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft
    • Built 2023

    Last Sold Summary

    • 4% Below List Price
    • $150/SF
    • 64 Days On Market

    Current Estimated Value $389,447

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
    • 204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      /35

      Est $377,878

      Not Listed For Sale

      204 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1984
      204 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Jamil Wright EXP Realty, LLC

  • 117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    /73

    $1,500,000

    $100K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 5,400 Sq Ft

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

    **Listing price is for FOUR units for sale as an investment package!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 package, or as individuals. Each unit has been remodeled and

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • 8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, 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 $347,894

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
    • 109 Secor Rd, Chestertown, MD 21620
      109 Secor Rd, Chestertown, MD 21620
      109 Secor Rd, Chestertown, MD 21620
      /41

      Est $394,894

      Not Listed For Sale

      109 Secor Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1977
      109 Secor Rd, Chestertown, MD 21620

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

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

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:20 AM. 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

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • 102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    /41

    $324,000

    Sold Aug 14, 2026

    102 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $171/SF
    • 62 Days On Market

    Current Estimated Value $334,973

    Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
    • 104 Dutchess Rd, Chestertown, MD 21620
      104 Dutchess Rd, Chestertown, MD 21620
      104 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $316,803

      Not Listed For Sale

      104 Dutchess Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 1989
      104 Dutchess Rd, Chestertown, MD 21620

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Helen J Butler Taylor Properties

  • 218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    /45

    $499,999

    $25K PRICE DROP Under Contract
    • 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
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, 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 $715,932

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • 201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      /36

      Est $432,646

      Not Listed For Sale

      201 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 1998
      201 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 120 Days On Market

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

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

    $295,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,132 Sq Ft

    240 Round Top Rd, Chestertown, MD 21620

    Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced

    Karen Clark Clark & Co Realty, LLC

    240 Round Top Rd, Chestertown, MD 21620
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown 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 $110,666

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • 1106 Round Top Rd, Chestertown, MD 21620
      1106 Round Top Rd, Chestertown, MD 21620
      1106 Round Top Rd, Chestertown, MD 21620
      /27

      Not Listed For Sale

      1106 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1973
      1106 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Clint Evans Cross Street Realtors LLC

Showing Results 121 - 160, Page 4 of 18

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