6,890

Chestertown, MD Homes

Section Image
  • /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
  • /2

    $1,650,000

    Sold Jun 30, 2026

    114 Chester View, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $799/SF
    • 0 Days On Market

    Current Estimated Value $732,979

    Last Listing Agent Jack Boniface Cross Street Realtors LLC

    114 Chester View, Chestertown, MD 21620
    • /49

      Est $443,233

      Not Listed For Sale

      109 Coleman Dr, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 1,792 Sq Ft
      • Built 1988
      109 Coleman Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /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
  • /65

    $455,000

    Sold Apr 13, 2026

    206 Camelot Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft
    • Built 2009

    Last Sold Summary

    • 13% Below List Price
    • $208/SF
    • 30 Days On Market

    Current Estimated Value $466,547

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
    • /45

      Est $470,728

      Not Listed For Sale

      105 Coleman Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,128 Sq Ft
      • Built 1988
      105 Coleman Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • /49

    $475,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, Chestertown, MD 21620
  • /43

    $379,900

    Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $387,134

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
    • /15

      Est $379,690

      Not Listed For Sale

      117 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,460 Sq Ft
      • Built 1972
      117 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 112 Days On Market

  • /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
  • /42

    $360,000

    Sold Jun 12, 2026

    720 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $283/SF
    • 13 Days On Market

    Current Estimated Value $368,796

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    720 Deep Landing Rd, Chestertown, MD 21620
    • /22

      Est $349,388

      Not Listed For Sale

      205 Creston Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,338 Sq Ft
      • Built 1975
      205 Creston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

  • /88

    $279,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    22481 Goose Hollow Dr, Chestertown, MD 21620

    AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of

    Tom Atwood Keller Williams Legacy

    22481 Goose Hollow Dr, Chestertown, MD 21620
  • /74

    $459,000

    Sold Mar 27, 2026

    105 Pearl Creek Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,961 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Above List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $446,316

    Last Listing Agent Lona Todd Taylor Properties

    105 Pearl Creek Ln, Chestertown, MD 21620
    • /35

      Est $421,475

      Not Listed For Sale

      313 River Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft
      • Built 1964
      313 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • /45

    $545,000

    Sold Apr 30, 2026

    206 S Water St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,008 Sq Ft
    • Built 1900

    Last Sold Summary

    • 7% Below List Price
    • $271/SF
    • 40 Days On Market

    Current Estimated Value $550,515

    Last Listing Agent Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
    • /28

      Est $285,017

      Not Listed For Sale

      124 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1974
      124 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • /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
  • /29

    $264,900

    Sold Oct 30, 2025

    24415 Chestertown Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft
    • Built 1962

    Last Sold Summary

    • $239/SF
    • 23 Days On Market

    Current Estimated Value $267,841

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • /32

      Est $322,573

      Not Listed For Sale

      729 Rosin Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      729 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • /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
  • /70

    $550,000

    Sold Dec 05, 2025

    302 Rosin Dr, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 3,877 Sq Ft
    • Built 1996

    Last Sold Summary

    • $142/SF
    • 5 Days On Market

    Current Estimated Value $555,403

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    302 Rosin Dr, Chestertown, MD 21620
    • /50

      Est $355,945

      Not Listed For Sale

      201 Tamarack Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft
      • Built 1973
      201 Tamarack Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /5

    $625,000

    Coming Soon
    • 3 Beds
    • 4 Baths
    • 4,037 Sq Ft

    7903 Radcliffe Rd, Chestertown, MD 21620

    This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to

    Erin Anderson Chesapeake Real Estate Associates, LLC

    7903 Radcliffe Rd, Chestertown, MD 21620
  • /48

    $535,000

    Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Current Estimated Value $520,914

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • /16

      Est $256,335

      Not Listed For Sale

      319 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1964
      319 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

  • /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
  • /24

    $285,000

    Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $1,125,595

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • /29

      Est $301,344

      Not Listed For Sale

      332 Truslow Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft
      • Built 1900
      332 Truslow Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

  • /60

    $1,650,000

    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • /14

    $329,000

    Sold May 27, 2026

    10594 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 2020

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $329,059

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    10594 Millbrook Dr, Chestertown, MD 21620
    • /31

      Est $350,246

      Not Listed For Sale

      707 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1976
      707 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 75 Days On Market

  • /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • /42

    $260,000

    Sold Feb 18, 2026

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1954

    Last Sold Summary

    • $230/SF
    • 170 Days On Market

    Current Estimated Value $262,445

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
    • /25

      Est $344,639

      Not Listed For Sale

      324 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1988
      324 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /56

    $289,900

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    21146 Montana Ave, Chestertown, MD 21620

    Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom,

    Jody Baker Cross Street Realtors LLC

    21146 Montana Ave, Chestertown, MD 21620
  • /13

    $295,000

    Sold Mar 31, 2026

    107 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2004

    Last Sold Summary

    • $152/SF
    • 8 Days On Market

    Current Estimated Value $297,321

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
    • /33

      Est $481,208

      Not Listed For Sale

      118 Harlan Loop, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,900 Sq Ft
      • Built 2009
      118 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 8 Days On Market

  • /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

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

Showing Results 321 - 360, Page 9 of 18

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