7,032

Homes in ZIP Code 21620

Section Image Section Image
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $474,990 Open Sat 1PM - 3PM

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

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS QUICK MOVE-IN LUXURY VILLA! $5000 towards closing. This stunning 4-bedroom villa offers a welcoming and functional layout with exceptional upgrades and finishes throughout. The main level features an oversized family room that opens to the kitchen and dining area—perfect for entertaining or everyday living. The upper level includes three spacious bedrooms, including an

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    /5

    $25,000 Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 0.34 Acre
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $180,333

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $381,279 Not Listed For Sale

      213 Pine Cove Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2023
      213 Pine Cove Ln, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $246/SF

      Last Sold Price $344,500

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000 Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $174,750

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      /34

      Est $279,386 Not Listed For Sale

      7499 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2018
      7499 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 19% Above List Price
      • $191/SF
      • 14 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Petra Quinn Realty Navigator

  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • 0 Millbrook Dr, Chestertown, MD 21620
    0 Millbrook Dr, Chestertown, MD 21620
    /2

    $9,500 Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 0.5 Acre
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Millbrook Dr, Chestertown, MD 21620
    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $363,450 Not Listed For Sale

      724 Deep Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft
      • Built 2018
      724 Deep Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $240/SF
      • 45 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 0 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    0 None Unit MDKE2005014, Chestertown, MD 21620

    • Land
    • 13.46 Acres
    • $6,686 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • 142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      /27

      Est $420,030 Not Listed For Sale

      142 Church Meadow Ct, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 2014
      142 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $284/SF
      • 39 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /20

    $220,000 Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $225,318

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • 106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      /27

      Est $516,322 Not Listed For Sale

      106 Church Aly, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1880
      106 Church Aly, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $350/SF
      • 7 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Cindy Genther Rock Hall Properties

  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • 8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    /44

    $680,000 Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $689,815

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $443,517 Not Listed For Sale

      10570 Cogar Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft
      • Built 2010
      10570 Cogar Rd, Chestertown, MD 21620

      Last Sold Summary

      • 27% Above List Price
      • $122/SF
      • 118 Days On Market

      Last Sold Price $349,000

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    211 David Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft
    • Built 1963

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $816,124

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $448,588 Not Listed For Sale

      209 Blakefield Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • Built 2022
      209 Blakefield Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • 130 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • 204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    /46

    $612,000

    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, Chestertown, MD 21620
  • 0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    /2

    $2,500 Sold Sep 12, 2025

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678

    • Land
    • 0.34 Acre
    • $7,353 per Acre

    Last Sold Summary

    • 252 Days On Market

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    • 7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      /34

      Est $641,893 Not Listed For Sale

      7675 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 2017
      7675 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $340/SF
      • 13 Days On Market

      Last Sold Price $612,500

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • 108 Springbrook Ln, Millington, MD 21651
    108 Springbrook Ln, Millington, MD 21651
    108 Springbrook Ln, Millington, MD 21651
    /48

    $474,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    108 Springbrook Ln, Millington, MD 21651

    108 Springbrook Lane New Construction A must see Forget everything you know about "builder grade." This home boost a tasteful design throughout, nestled on 1.76 semi-secluded wooded acres, offering a level of custom detail and material quality not often found in todays new construction.Unmatched Curb Appeal, The exterior is a masterclass in texture and design. A massive 52-foot front porch

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    108 Springbrook Ln, Millington, MD 21651
  • 119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    /60

    $1,165,000 Sold Dec 01, 2025

    119 High St, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,409 Sq Ft
    • Built 1876

    Last Sold Summary

    • $264/SF
    • 5 Days On Market

    Current Estimated Value $1,175,016

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • 121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      /25

      Est $346,795 Not Listed For Sale

      121 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2024
      121 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1% Below List Price
      • $283/SF
      • 6 Days On Market

      Last Sold Price $349,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 101 Pine Tree Rd, Chestertown, MD 21620
    101 Pine Tree Rd, Chestertown, MD 21620
    /2

    $480,000 Under Contract

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

    101 Pine Tree Rd, Chestertown, MD 21620

    Classic Country Cape Cod on an acre in the country with a large Detached Garage. What more could you ask for ? This home is in a quiet country setting in the trees overlooking farmland. Offering an open floor plan, a Country Kitchen and Four Bedrooms and Two baths. A large mud/laundry room, a large deck and a newer roof and well. Don't delay, this one will be here today, and GONE tomorrow

    Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, Chestertown, MD 21620
  • 109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    /41

    $385,000 Sold Apr 04, 2025

    109 Secor Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1977

    Last Sold Summary

    • $247/SF
    • 69 Days On Market

    Current Estimated Value $402,953

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
    • 112 Snyder Ln, Chestertown, MD 21620
      112 Snyder Ln, Chestertown, MD 21620
      112 Snyder Ln, 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

      • $223/SF
      • 22 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • 201 Greenwood Ave, Chestertown, MD 21620
    201 Greenwood Ave, Chestertown, MD 21620
    201 Greenwood Ave, Chestertown, MD 21620
    /62

    $495,000 Under Contract

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

    201 Greenwood Ave, Chestertown, MD 21620

    An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level

    Grace Crockett Doug Ashley Realtors, LLC

    201 Greenwood Ave, Chestertown, MD 21620
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $317,000 Sold Mar 09, 2026

    213 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $257/SF
    • 67 Days On Market

    Current Estimated Value $315,313

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
    • 117 Chester Arms Dr, Chestertown, MD 21620
      117 Chester Arms Dr, Chestertown, MD 21620
      117 Chester Arms Dr, Chestertown, MD 21620
      /27

      Est $269,827 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

      • 9% Above List Price
      • $196/SF
      • 30 Days On Market

      Last Sold Price $247,500

      Last Listing Agent David Moore Real Broker, LLC

  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /40

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    REDUCED! 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

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • 209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    /62

    $790,000 Sold Sep 23, 2025

    209 Rivershore Rd, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft
    • Built 1978

    Last Sold Summary

    • $564/SF
    • 32 Days On Market

    Current Estimated Value $793,047

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $428,878 Not Listed For Sale

      1213 Ewingtown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft
      • Built 2022
      1213 Ewingtown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $242/SF
      • 132 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 206 Flyway Ln, Chestertown, MD 21620
    206 Flyway Ln, Chestertown, MD 21620
    206 Flyway Ln, Chestertown, MD 21620
    /25

    $499,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    206 Flyway Ln, Chestertown, MD 21620

    There’s no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a

    Kristin Lewis Integrity Real Estate

    206 Flyway Ln, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, 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 $241,031

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $447,983 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

      • 7% Above List Price
      • $254/SF
      • 19 Days On Market

      Last Sold Price $420,000

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

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

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Picture Perfect Colonial in Coventry Farms – Chestertown, MarylandWelcome 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

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

Maryland Kent County Chestertown 21620

Real Estate & Homes

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

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group