6,896

Chestertown, MD Homes

Section Image
  • 10584 Klamath Rd, Chestertown, MD 21620
    10584 Klamath Rd, Chestertown, MD 21620
    10584 Klamath Rd, Chestertown, MD 21620
    /20

    $319,900

    New Construction Pending
    • 3 Beds
    • 1.5 Baths

    10584 Klamath Rd, Chestertown, MD 21620

    Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance

    David Moore Real Broker, LLC

    10584 Klamath Rd, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    /5

    $11,000

    Sold May 29, 2025

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $32,353 per Acre

    Last Sold Summary

    • 371 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    • 118 Westwood Ln, Chestertown, MD 21620
      118 Westwood Ln, Chestertown, MD 21620
      118 Westwood Ln, Chestertown, MD 21620
      /80

      Est $589,485

      Not Listed For Sale

      118 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,248 Sq Ft
      • Built 1985
      118 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 4% Below List Price
      • $272/SF
      • 39 Days On Market
      • Last Sold Price $612,500
      • May 22, 2024

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    /38

    $349,000

    Sold Oct 16, 2025

    111 Cee Jay Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $249/SF
    • 10 Days On Market

    Current Estimated Value $361,099

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
    • 209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      209 Myers Rd, Chestertown, MD 21620
      /28

      Est $437,578

      Not Listed For Sale

      209 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 1996
      209 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $207/SF
      • 67 Days On Market
      • Last Sold Price $383,000
      • May 22, 2024

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • 0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Lenapah Rd, 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 @ 12:45 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 Lenapah Rd, Chestertown, MD 21620
  • 10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    /22

    $359,000

    Sold Jul 31, 2025

    10575 Hyala Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 2003

    Last Sold Summary

    • $181/SF
    • 5 Days On Market

    Current Estimated Value $364,788

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
    • 129 Char Nor Manor Blvd, Chestertown, MD 21620
      129 Char Nor Manor Blvd, Chestertown, MD 21620
      129 Char Nor Manor Blvd, Chestertown, MD 21620
      /43

      Est $396,799

      Not Listed For Sale

      129 Char Nor Manor Blvd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1961
      129 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Below List Price
      • $508/SF
      • 5 Days On Market
      • Last Sold Price $411,500
      • Nov 07, 2024

      Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900

    Pending
    • Land
    • 20,908 Sq Ft
    • $185,208 per Acre

    0 East St, Chestertown, MD 21620

    This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience.The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those

    William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $215,000

    Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Current Estimated Value $224,685

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
    • 2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      2771 Mcginnes Rd, Chestertown, MD 21620
      /30

      Est $432,474

      Not Listed For Sale

      2771 Mcginnes Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,714 Sq Ft
      • Built 1999
      2771 Mcginnes Rd, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $216/SF
      • 5 Days On Market
      • Last Sold Price $370,000
      • Jul 31, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $384,000

    $61K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • 9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    /38

    $285,000

    Sold Sep 05, 2025

    9190 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1969

    Last Sold Summary

    • $246/SF
    • 12 Days On Market

    Current Estimated Value $305,817

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • 305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      305 Hickory Ln, Chestertown, MD 21620
      /6

      Est $701,149

      Not Listed For Sale

      305 Hickory Ln, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 2,627 Sq Ft
      • Built 1998
      305 Hickory Ln, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $234/SF
      • Last Sold Price $615,000
      • Oct 25, 2024

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • 0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 4,791 Sq Ft
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /39

    $695,000

    Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Current Estimated Value $695,460

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
    • 131 E Step Rd, Chestertown, MD 21620
      131 E Step Rd, Chestertown, MD 21620
      131 E Step Rd, Chestertown, MD 21620
      /19

      Not Listed For Sale

      131 E Step Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1991
      131 E Step Rd, Chestertown, MD 21620

      Last Sold Summary

      • $121/SF
      • 3 Days On Market
      • Last Sold Price $230,000
      • Sep 15, 2023

      Last Listing Agent Lona Todd Taylor Properties

  • 0 Sheldrake Dr, Chestertown, MD 21620
    0 Sheldrake Dr, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 14,810 Sq Ft
    • $44,118 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /70

    $620,000

    Sold Apr 20, 2026

    11040 Kylie Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft
    • Built 2000

    Last Sold Summary

    • $168/SF
    • 497 Days On Market

    Current Estimated Value $729,671

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
    • 193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      193 Westwood Ln, Chestertown, MD 21620
      /5

      Est $632,763

      Not Listed For Sale

      193 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,572 Sq Ft
      • Built 1974
      193 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $154/SF
      • 0 Days On Market
      • Last Sold Price $550,000
      • May 22, 2024

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 720 Deep Landing Rd, Chestertown, MD 21620
    720 Deep Landing Rd, Chestertown, MD 21620
    720 Deep Landing Rd, Chestertown, MD 21620
    /42

    $369,999

    Pending
    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft

    720 Deep Landing Rd, Chestertown, MD 21620

    Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River and the Deep Landing Boat Launch. Surrounded by working farms and pastoral views this beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters, stainless-steel appliances, and

    Cornelia Fallon Coldwell Banker Waterman Realty

    720 Deep Landing Rd, Chestertown, MD 21620
  • 0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    /12

    $162,000

    Sold Nov 10, 2025

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620

    • Land
    • 5.34 Acres
    • $30,337 per Acre

    Last Sold Summary

    • 64 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    • 107 Char Nor Manor Blvd, Chestertown, MD 21620
      107 Char Nor Manor Blvd, Chestertown, MD 21620
      107 Char Nor Manor Blvd, Chestertown, MD 21620
      /23

      Not Listed For Sale

      107 Char Nor Manor Blvd, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,128 Sq Ft
      • Built 1999
      107 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • $179/SF
      • 56 Days On Market
      • Last Sold Price $379,989
      • Jan 30, 2025

      Last Listing Agent William Norris Select Land & Homes, LLC

  • 10594 Millbrook Dr, Chestertown, MD 21620
    10594 Millbrook Dr, Chestertown, MD 21620
    10594 Millbrook Dr, Chestertown, MD 21620
    /14

    $329,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft

    10594 Millbrook Dr, Chestertown, MD 21620

    Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    10594 Millbrook Dr, Chestertown, MD 21620
  • 22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    /73

    $435,000

    Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Current Estimated Value $451,652

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • 118 Char Nor Manor Blvd, Chestertown, MD 21620
      118 Char Nor Manor Blvd, Chestertown, MD 21620
      118 Char Nor Manor Blvd, Chestertown, MD 21620
      /34

      Est $285,476

      Not Listed For Sale

      118 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,114 Sq Ft
      • Built 1965
      118 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $238/SF
      • 120 Days On Market
      • Last Sold Price $265,000
      • May 02, 2025

      Last Listing Agent Rylie Patrick Chesapeake Real Estate Associates, LLC

  • 23710 L Rd, Chestertown, MD 21620
    23710 L Rd, Chestertown, MD 21620
    /2

    $24,000

    $4K PRICE INCREASE
    • Land
    • 21,780 Sq Ft
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    23710 L Rd, Chestertown, MD 21620
  • 411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    /32

    $415,000

    Sold Jan 07, 2026

    411 Greenwood Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft
    • Built 2003

    Last Sold Summary

    • $248/SF
    • 1 Day On Market

    Current Estimated Value $418,985

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
    • 235 Burchard Sawmill Rd, Chestertown, MD 21620
      235 Burchard Sawmill Rd, Chestertown, MD 21620
      235 Burchard Sawmill Rd, Chestertown, MD 21620
      /24

      Est $235,155

      Not Listed For Sale

      235 Burchard Sawmill Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1930
      235 Burchard Sawmill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6% Below List Price
      • $289/SF
      • 115 Days On Market
      • Last Sold Price $250,000
      • Sep 23, 2024

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • 214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    /26

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major systems like the roof, HVAC, and water heater are all just a few years old,

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $750,000

    Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • 101 Char Nor Manor Blvd, Chestertown, MD 21620
      101 Char Nor Manor Blvd, Chestertown, MD 21620
      101 Char Nor Manor Blvd, Chestertown, MD 21620
      /8

      Est $382,435

      Not Listed For Sale

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft
      • Built 1965
      101 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $285/SF
      • 1 Day On Market
      • Last Sold Price $330,000
      • Oct 13, 2023

      Last Listing Agent Samantha Powell Keller Williams Real Estate - Media

  • 231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    /51

    $1,150,000

    $129K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000

    Sold Jun 20, 2025

    104 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1989

    Last Sold Summary

    • $263/SF
    • 21 Days On Market

    Current Estimated Value $326,005

    Last Listing Agent Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620
    • 305 Pine Tree Rd, Chestertown, MD 21620
      305 Pine Tree Rd, Chestertown, MD 21620
      305 Pine Tree Rd, Chestertown, MD 21620
      /17

      Est $246,523

      Not Listed For Sale

      305 Pine Tree Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1961
      305 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5% Below List Price
      • $315/SF
      • 298 Days On Market
      • Last Sold Price $260,000
      • Sep 13, 2024

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /56

    $675,000

    $20K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,336,457

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • 139 Church Meadow Ct, Chestertown, MD 21620
      139 Church Meadow Ct, Chestertown, MD 21620
      139 Church Meadow Ct, Chestertown, MD 21620
      /71

      Est $556,225

      Not Listed For Sale

      139 Church Meadow Ct, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 2008
      139 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $183/SF
      • 3 Days On Market
      • Last Sold Price $475,000
      • May 22, 2023

      Last Listing Agent Scott Hogan Long & Foster

  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 23,958 Sq Ft
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing Rd, Chestertown, MD 21620

Showing Results 241 - 280, Page 7 of 18

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