6,896

Chestertown, MD Homes

Section Image Section Image
  • 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
    • 21,780 Sq Ft
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Millbrook Dr, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $466,282

      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

      • 17% Above List Price
      • 130 Days On Market
      • Last Sold Price $400,000
      • Oct 20, 2023

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • 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
  • 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
    • 7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      7675 Quaker Neck Rd, Chestertown, MD 21620
      /34

      Est $648,541

      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

      • 6% Above List Price
      • $340/SF
      • 13 Days On Market
      • Last Sold Price $612,500
      • Jan 02, 2025

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500

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

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 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, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, 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 $226,194

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • 121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      121 Fairview Dr, Chestertown, MD 21620
      /25

      Est $349,218

      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

      • $283/SF
      • 6 Days On Market
      • Last Sold Price $349,000
      • Nov 08, 2024

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 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

    New Construction Open Sat 1PM - 3PM Pending
    • 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
  • 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 $705,544

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • 107 Chester Arms Dr, Chestertown, MD 21620
      107 Chester Arms Dr, Chestertown, MD 21620
      107 Chester Arms Dr, Chestertown, MD 21620
      /19

      Est $248,809

      Not Listed For Sale

      107 Chester Arms Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2022
      107 Chester Arms Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $202/SF
      • 14 Days On Market
      • Last Sold Price $230,000
      • May 01, 2025

      Last Listing Agent Casey Scattergood Cross Street Realtors 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
  • 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 $820,842

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • 117 Court St, Chestertown, MD 21620
      117 Court St, Chestertown, MD 21620
      117 Court St, Chestertown, MD 21620
      /35

      Est $387,688

      Not Listed For Sale

      117 Court St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 744 Sq Ft
      • Built 1885
      117 Court St, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $491/SF
      • 23 Days On Market
      • Last Sold Price $365,000
      • Mar 28, 2025

      Last Listing Agent Nancy McGuire Maryland Heritage Properties

  • 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
  • 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 $1,161,421

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • 3650 Gratitude Way, Chestertown, MD 21620
      3650 Gratitude Way, Chestertown, MD 21620
      3650 Gratitude Way, Chestertown, MD 21620
      /18

      Not Listed For Sale

      3650 Gratitude Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 3,599 Sq Ft
      • Built 2025
      3650 Gratitude Way, Chestertown, MD 21620

      Last Sold Summary

      • $177/SF
      • 1 Day On Market
      • Last Sold Price $636,383
      • Apr 24, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • 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
  • 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 $318,146

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
    • 3652 Gratitude Way, Chestertown, MD 21620
      3652 Gratitude Way, Chestertown, MD 21620
      3652 Gratitude Way, Chestertown, MD 21620
      /10

      Not Listed For Sale

      3652 Gratitude Way, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,642 Sq Ft
      • Built 2025
      3652 Gratitude Way, Chestertown, MD 21620

      Last Sold Summary

      • $219/SF
      • 1 Day On Market
      • Last Sold Price $579,238
      • Mar 20, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /38

    $329,900

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas

    Dawn Kane Redfin Corporation

    304 Hadaway 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 $805,858

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
    • 720 Aldora Dr Unit 109, Chestertown, MD 21620
      720 Aldora Dr Unit 109, Chestertown, MD 21620
      720 Aldora Dr Unit 109, Chestertown, MD 21620
      /35

      Not Listed For Sale

      720 Aldora Dr Unit 109, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,120 Sq Ft
      • Built 2025
      720 Aldora Dr Unit 109, Chestertown, MD 21620

      Last Sold Summary

      • $226/SF
      • 0 Days On Market
      • Last Sold Price $479,495
      • Apr 25, 2025

      Last Listing Agent Terri Hill Builder Solutions Realty

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

    $598,000

    $14K PRICE DROP
    • 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
  • 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 $243,695

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf 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
      • Nov 04, 2024

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • 704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    /43

    $440,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    704 Truslow Rd, Chestertown, MD 21620

    HOME IS STILL AVAILABLE TO SEE AND MAKE OFFERS!!! 72 Hour Kick Out Clause in Effect. Tucked away in the peaceful countryside on the Queen Anne’s County side of Chestertown, this charming one-level rancher offers the space, comfort, and tranquility you’ve been waiting for. Situated on a full acre and boasting over 2,000 sq. ft. of living space, this home is designed for easy, one-level living with

    Crystal Smith RE/MAX Executive

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

    $480,000

    Sold May 04, 2026

    101 Pine Tree Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1993

    Last Sold Summary

    • $260/SF
    • 0 Days On Market

    Current Estimated Value $476,168

    Last Listing Agent Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, 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 $270,131

      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
      • Dec 18, 2024

      Last Listing Agent David Moore Real Broker, LLC

  • 8629 Airy Hill Rd, Chestertown, MD 21620
    8629 Airy Hill Rd, Chestertown, MD 21620
    8629 Airy Hill Rd, Chestertown, MD 21620
    /45

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    8629 Airy Hill Rd, Chestertown, MD 21620

    Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring and 2 Full Baths. The Primary Bath has been completely renovated with a Walk-In Tiled Shower. Living Room offering a cozy Brick Fireplace with Hardwood Flooring. Family/Kitchen Combo with Slider leading to the tranquil back yard.

    Lauren Smith Keller Williams Realty

    8629 Airy Hill Rd, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $120,000

    Sold Feb 27, 2026

    141 Prospect St, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 27% Below List Price
    • $104/SF
    • 33 Days On Market

    Current Estimated Value $135,028

    Last Listing Agent Jeff Guthrie Taylor Properties

    141 Prospect St, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $419,513

      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

      • $254/SF
      • 19 Days On Market
      • Last Sold Price $420,000
      • Apr 15, 2024

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /24

    $419,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
  • 106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    /36

    $315,000

    Sold Aug 29, 2025

    106 Wilton Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $298/SF
    • 18 Days On Market

    Current Estimated Value $320,908

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
    • 209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      /33

      Est $711,059

      Not Listed For Sale

      209 Landing Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft
      • Built 2009
      209 Landing Ln, Chestertown, MD 21620

      Last Sold Summary

      • 35% Above List Price
      • $219/SF
      • 209 Days On Market
      • Last Sold Price $525,000
      • Aug 31, 2023

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

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

    $395,000

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

    107 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to this stunning 2023-built home with well-designed architectural elevations! The curb appeal captures your attention and the moment you arrive, the welcoming front porch invites you to slow down, relax, and imagine enjoying a glass of iced tea from your favorite wicker chair. Step through the handsome front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    /27

    $280,000

    Sold Jun 09, 2025

    100 Acorn Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft
    • Built 2004

    Last Sold Summary

    • $145/SF
    • 164 Days On Market

    Current Estimated Value $303,266

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
    • 204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      /44

      Est $532,255

      Not Listed For Sale

      204 N Mill St, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft
      • Built 1920
      204 N Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 44% Above List Price
      • $128/SF
      • 49 Days On Market
      • Last Sold Price $370,000
      • Apr 26, 2024

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /41

    $499,000

    • 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
  • 8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    /15

    $155,000

    Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $173,232

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

Maryland Kent County Chestertown

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