Homes for Sale in 21620

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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /60

  $1,495,000

  $155K PRICE DROP

  • 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
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  /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
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  /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
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  /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
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  /2

  $15,000

  • Land
  • 1 Acre
  • $15,000 per Acre

  23741 L Rd, Chestertown, MD 21620

  Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

  Taylor Leaverton Benson & Mangold, LLC

  23741 L Rd, Chestertown, MD 21620
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  /34

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  896 Washington Ave, Chestertown, MD 21620

  A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

  Peter Heller Coldwell Banker Chesapeake Real Estate Company

  896 Washington Ave, Chestertown, MD 21620
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  /2

  $38,000

  $23K PRICE INCREASE

  • Land
  • 14,810 Sq Ft
  • $111,765 per Acre

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

  Dee Dee Miller Paul Wesley Real Estate

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
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  /20

  $344,000

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

  9126 Fairlee Rd, Chestertown, MD 21620

  Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

  Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

  9126 Fairlee Rd, Chestertown, MD 21620

Showing Results 81 - 98, Page 3 of 3