6,867

Chestertown, MD Homes

Section Image
    • 201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      201 Tamarack Rd, Chestertown, MD 21620
      /50

      Est $359,223 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft

      201 Tamarack Rd, Chestertown, MD 21620

      201 Tamarack Rd, Chestertown, MD 21620
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $269,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    /27

    $250,000 Sold May 22, 2025

    1106 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft
    • Built 1973

    Last Sold Summary

    • $200/SF
    • 16 Days On Market

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
    • 319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      /16

      Est $244,447 Not Listed For Sale

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

      319 Round Top Rd, Chestertown, MD 21620

      319 Round Top Rd, Chestertown, MD 21620
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /73

    $875,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 3,720 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    /22

    $155,200 Sold Mar 31, 2025

    Lot 4 Muirfield Dr, Chestertown, MD 21620

    • Land
    • 1.9 Acres
    • $81,684 per Acre

    Last Sold Summary

    • 300 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    Lot 4 Muirfield Dr, Chestertown, MD 21620
    • 332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      332 Truslow Rd, Chestertown, MD 21620
      /29

      Est $307,358 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft

      332 Truslow Rd, Chestertown, MD 21620

      332 Truslow Rd, Chestertown, MD 21620
  • 0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    /7

    $10,000

    • Land
    • 0.37 Acre
    • $27,027 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    POST AUCTION/BUY NOW: MAKE AN OFFER! Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road.

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    /71

    $745,000 Sold Jun 26, 2025

    9050 Point Ln, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,166 Sq Ft
    • Built 2000

    Last Sold Summary

    • $235/SF
    • 7 Days On Market

    Current Estimated Value $761,055

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
    • 332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      /19

      Est $301,425 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,263 Sq Ft

      332 Longfellow Dr, Chestertown, MD 21620

      332 Longfellow Dr, Chestertown, MD 21620
  • 109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    /27

    $264,900 New Construction

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    109 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    109 Metcalfe Rd, Chestertown, MD 21620
  • 110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    /29

    $600,000 Sold Feb 06, 2025

    110 Birch Run Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,672 Sq Ft
    • Built 2007

    Last Sold Summary

    • $225/SF
    • 155 Days On Market

    Current Estimated Value $647,272

    Last Listing Agent Paula Ruckelshaus Long & Foster Real Estate, Inc.

    110 Birch Run Rd, Chestertown, MD 21620
    • 537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      /43

      Est $345,472 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,304 Sq Ft

      537 Truslow Rd, Chestertown, MD 21620

      537 Truslow Rd, Chestertown, MD 21620
  • 206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    /37

    $615,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft

    206 Valley Rd, Chestertown, MD 21620

    Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
  • 833 Woods Rd, Chestertown, MD 21620
    833 Woods Rd, Chestertown, MD 21620
    /2

    $155,000 Sold Dec 17, 2024

    833 Woods Rd, Chestertown, MD 21620

    • Land
    • 3 Acres
    • $51,667 per Acre

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $149,333

    Last Listing Agent Tina Brown Benson & Mangold, LLC

    833 Woods Rd, Chestertown, MD 21620
    • 707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      707 Round Top Rd, Chestertown, MD 21620
      /31

      Est $345,431 Not Listed For Sale

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

      707 Round Top Rd, Chestertown, MD 21620

      707 Round Top Rd, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • 149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    /25

    $385,000 Sold Apr 11, 2025

    149 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft
    • Built 1982

    Last Sold Summary

    • $213/SF
    • 19 Days On Market

    Current Estimated Value $387,840

    Last Listing Agent Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
    • 324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      324 Longfellow Dr, Chestertown, MD 21620
      /25

      Est $337,853 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft

      324 Longfellow Dr, Chestertown, MD 21620

      324 Longfellow Dr, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.61 Acre
    • $14,754 per Acre

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620

    Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
  • 308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    /32

    $782,500 Sold May 09, 2025

    308 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2017

    Last Sold Summary

    • $355/SF
    • 10 Days On Market

    Current Estimated Value $784,569

    Last Listing Agent John Burke Gunther-McClary Real Estate

    308 Landing Ln, Chestertown, MD 21620
    • 121 Tuxedo Rd, Chestertown, MD 21620
      121 Tuxedo Rd, Chestertown, MD 21620
      121 Tuxedo Rd, Chestertown, MD 21620
      /35

      Est $293,181 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,144 Sq Ft

      121 Tuxedo Rd, Chestertown, MD 21620

      121 Tuxedo Rd, Chestertown, MD 21620
  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • 24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, 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

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • 210 Creston Rd, Chestertown, MD 21620
      210 Creston Rd, Chestertown, MD 21620
      210 Creston Rd, Chestertown, MD 21620
      /6

      Est $281,268 Not Listed For Sale

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

      210 Creston Rd, Chestertown, MD 21620

      210 Creston Rd, Chestertown, MD 21620
  • 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
  • 201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    /22

    $319,000 Sold Mar 31, 2025

    201 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1985

    Last Sold Summary

    • $269/SF
    • 49 Days On Market

    Current Estimated Value $320,970

    Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
    • 118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      /33

      Est $479,362 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,900 Sq Ft

      118 Harlan Loop, Chestertown, MD 21620

      118 Harlan Loop, Chestertown, MD 21620
  • 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

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    /30

    $400,000 Sold Mar 12, 2025

    204 Pine Cove Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft
    • Built 2021

    Last Sold Summary

    • $185/SF
    • 19 Days On Market

    Current Estimated Value $406,089

    Last Listing Agent Kelly Harris Coldwell Banker Realty

    204 Pine Cove Ln, Chestertown, MD 21620
    • 105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      /58

      Est $827,600 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft

      105 S Water St, Chestertown, MD 21620

      105 S Water St, Chestertown, MD 21620
  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $389,900 Pending

    • Studio
    • 1,728 Sq Ft

    517 High St, Chestertown, MD 21620

    Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit- super efficient space.The main

    Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
  • 105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    /39

    $355,000 Sold Mar 31, 2025

    105 Justin Buch Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1991

    Last Sold Summary

    • $296/SF
    • 19 Days On Market

    Current Estimated Value $349,493

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $262,262 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft

      114 School Rd, Chestertown, MD 21620

      114 School Rd, Chestertown, MD 21620
  • 24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    /55

    $425,000 Pending

    • 3 Beds
    • 2 Baths
    • 3,280 Sq Ft

    24543 Chestertown Rd, Chestertown, MD 21620

    Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or

    Terri Murray RE/MAX Executive

    24543 Chestertown Rd, Chestertown, MD 21620
  • 302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, 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

    Last Listing Agent Lori Willis Cross Street Realtors LLC

    302 Rosin Dr, Chestertown, MD 21620
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $409,718 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft

      23118 Raleigh Rd, Chestertown, MD 21620

      23118 Raleigh Rd, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /67

    $409,900

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living. This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy entertaining

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • 104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    /17

    $283,000 Sold Feb 19, 2025

    104 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 1,840 Sq Ft
    • Built 2003

    Last Sold Summary

    • $154/SF
    • 38 Days On Market

    Current Estimated Value $301,923

    Last Listing Agent Krystal Zellner Crown Homes Real Estate

    104 Oak Leaf Dr, Chestertown, MD 21620
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $339,742 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      10550 Klamath Rd, Chestertown, MD 21620

      10550 Klamath Rd, Chestertown, MD 21620

Showing Results 281 - 320, Page 8 of 18

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