7,041

Homes in ZIP Code 21620

Section Image
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $244,500

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /2

    $539,000

    Sold Jun 16, 2025

    107 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 3,050 Sq Ft
    • Built 1879

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Current Estimated Value $602,138

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
    • 545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      /28

      Est $273,900

      Not Listed For Sale

      545 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft
      • Built 1900
      545 High St, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $269/SF
      • 46 Days On Market
      • Last Sold Price $249,900
      • Mar 07, 2024

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $750,000

    $45K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $7,500,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    /46

    $365,000

    Sold Apr 17, 2026

    148 E Step Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $261/SF
    • 16 Days On Market

    Current Estimated Value $366,814

    Last Listing Agent Norman Lee III Anne Arundel Properties, Inc.

    148 E Step Rd, Chestertown, MD 21620
    • 9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      /47

      Est $354,985

      Not Listed For Sale

      9041 S Bayview Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 2009
      9041 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $221/SF
      • 45 Days On Market
      • Last Sold Price $300,000
      • Oct 31, 2023

      Last Listing Agent Gregory Osborn Long & Foster

  • 0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
  • 619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    /9

    $190,500

    Sold Jul 22, 2025

    619 Cannon St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 882 Sq Ft
    • Built 1983

    Last Sold Summary

    • $216/SF
    • 50 Days On Market

    Current Estimated Value $204,287

    Last Listing Agent Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
    • 10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      /31

      Est $316,136

      Not Listed For Sale

      10640 Watonga Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,196 Sq Ft
      • Built 1995
      10640 Watonga Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $255/SF
      • 2 Days On Market
      • Last Sold Price $305,000
      • Apr 01, 2025

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    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 upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 6 Byford Ct, Chestertown, MD 21620
    6 Byford Ct, Chestertown, MD 21620
    /2

    $749,500

    Sold Apr 13, 2026

    6 Byford Ct, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1978

    Last Sold Summary

    • $239/SF
    • 0 Days On Market

    Current Estimated Value $724,709

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6 Byford Ct, Chestertown, MD 21620
    • 217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      /37

      Est $592,795

      Not Listed For Sale

      217 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft
      • Built 2003
      217 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $385/SF
      • 6 Days On Market
      • Last Sold Price $564,500
      • Aug 19, 2024

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    /35

    $438,000

    Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $447,816

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
    • 502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      /45

      Est $484,213

      Not Listed For Sale

      502 Cannon St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft
      • Built 1922
      502 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 20% Above List Price
      • $275/SF
      • 7 Days On Market
      • Last Sold Price $402,000
      • Jul 14, 2023

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

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

    117 N Water St Unit 1A, Chestertown, MD 21620

    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 upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /21

    $160,000

    Sold Feb 13, 2026

    21316 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1955

    Last Sold Summary

    • $130/SF
    • 137 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21316 Persimmon Dr, Chestertown, MD 21620
    • 111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      /44

      Est $431,372

      Not Listed For Sale

      111 Manor Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2007
      111 Manor Ave, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $229/SF
      • 3 Days On Market
      • Last Sold Price $390,000
      • Sep 28, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /72

    $899,500

    New Construction Open Sat 11AM - 1PM $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft

    205 River Rd, Chestertown, MD 21620

    New price, same stunning home!!! Stop scrolling — this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly

    Karen Clark Clark & Co Realty, LLC

    205 River Rd, Chestertown, MD 21620
  • 105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    /28

    $322,000

    Sold Nov 14, 2025

    105 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1992

    Last Sold Summary

    • $261/SF
    • 5 Days On Market

    Current Estimated Value $331,082

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    105 Parma Rd, Chestertown, MD 21620
    • 631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      /9

      Est $249,080

      Not Listed For Sale

      631 High St, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,234 Sq Ft
      • Built 1917
      631 High St, Chestertown, MD 21620

      Last Sold Summary

      • $203/SF
      • 36 Days On Market
      • Last Sold Price $250,000
      • Sep 27, 2024

      Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $475,000

    Sold Dec 11, 2025

    101 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1979

    Last Sold Summary

    • $242/SF
    • 38 Days On Market

    Current Estimated Value $485,295

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
    • 207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      /44

      Est $668,167

      Not Listed For Sale

      207 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1900
      207 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $287/SF
      • 372 Days On Market
      • Last Sold Price $645,000
      • Apr 19, 2024

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    /39

    $299,500

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,867 Sq Ft

    108 Oak Leaf Dr, Chestertown, MD 21620

    This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in

    Grace Crockett Doug Ashley Realtors, LLC

    108 Oak Leaf Dr, Chestertown, MD 21620
  • 7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    /56

    $759,000

    Sold Jul 01, 2025

    7988 Aldan Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 2 Days On Market

    Current Estimated Value $800,093

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
    • 7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      /13

      Est $839,357

      Not Listed For Sale

      7694 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,322 Sq Ft
      • Built 1966
      7694 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $225/SF
      • Last Sold Price $749,000
      • Oct 01, 2024

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 1014 Twin Ct, Chestertown, MD 21620
    1014 Twin Ct, Chestertown, MD 21620
    1014 Twin Ct, Chestertown, MD 21620
    /29

    $499,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,817 Sq Ft

    1014 Twin Ct, Chestertown, MD 21620

    Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant

    Jody Baker Cross Street Realtors LLC

    1014 Twin Ct, Chestertown, MD 21620
  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $485,960

    Sold Oct 31, 2025

    726 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $229/SF
    • 14 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    726 Aldora Dr, Chestertown, MD 21620
    • 10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      /50

      Est $1,412,996

      Not Listed For Sale

      10705 Tilden Ln, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,345 Sq Ft
      • Built 1943
      10705 Tilden Ln, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $389/SF
      • 18 Days On Market
      • Last Sold Price $1,300,000
      • Sep 24, 2024

      Last Listing Agent Glenn Sutton TTR Sotheby's International Realty

  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    $5K PRICE DROP Under Contract
    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    /20

    $246,000

    Sold Aug 15, 2025

    10624 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $246/SF
    • 17 Days On Market

    Current Estimated Value $243,164

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
    • 215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      /30

      Est $376,221

      Not Listed For Sale

      215 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1992
      215 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $208/SF
      • 1 Day On Market
      • Last Sold Price $350,000
      • Feb 26, 2024

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 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. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    /3

    $675,000

    Sold Jun 25, 2025

    213 N Queen St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,945 Sq Ft
    • Built 1904

    Last Sold Summary

    • $347/SF
    • 2 Days On Market

    Current Estimated Value $708,021

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
    • 110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      /69

      Est $531,027

      Not Listed For Sale

      110 Camelot Dr, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft
      • Built 2007
      110 Camelot Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $148/SF
      • 10 Days On Market
      • Last Sold Price $475,000
      • Dec 29, 2023

      Last Listing Agent Chase Broadhurst RE/MAX Advantage Realty

  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 513 Round Top Rd, Chestertown, MD 21620
    513 Round Top Rd, Chestertown, MD 21620
    513 Round Top Rd, Chestertown, MD 21620
    /18

    $220,000

    Sold Apr 14, 2026

    513 Round Top Rd, Chestertown, MD 21620

    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $176/SF
    • 3 Days On Market

    Current Estimated Value $227,156

    Last Listing Agent Ben Garner Cummings & Co. Realtors

    513 Round Top Rd, Chestertown, MD 21620
    • 208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      /41

      Est $402,387

      Not Listed For Sale

      208 N Mill St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,537 Sq Ft
      • Built 1920
      208 N Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $243/SF
      • 15 Days On Market
      • Last Sold Price $373,500
      • May 22, 2023

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

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

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 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

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620

Showing Results 361 - 400, Page 10 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