Recently Sold Homes in 21620

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  /29

  $315,000 Sold Aug 29, 2025

  • 1,341 Sq Ft
  • $235/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  7425 Wilkins Ln, Chestertown, MD 21620

  Welcome to 7425 Wilkins Lane, Chestertown, MDJust two miles from the charming town of Chestertown, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of modern comfort and peaceful country living.Completely renovated down to the studs, this home features a new roof, new plywood, home addition including the kitchen, full bath and laundry room, siding,

  LAURIE KREIDER Realty ONE Group Unlimited

  7425 Wilkins Ln, Chestertown, MD 21620
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  /49

  $960,000 Sold Aug 27, 2025

  • 3,401 Sq Ft
  • $282/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  10715 Kasota Rd, Chestertown, MD 21620

  Private waterfront retreat on Mill Creek offering beautiful views, spacious living, and all the peace and quiet you have been looking for. This custom-built Cape-style home is nestled on a serene, protected stretch of water and offers the ideal blend of comfort and tranquility. With 4 bedrooms and 3 full baths, the home features a flexible floor plan designed for both everyday living and

  Sarah King Cross Street Realtors LLC

  10715 Kasota Rd, Chestertown, MD 21620
• 

  

  

  /72

  $609,000 Sold Aug 27, 2025

  • 3,155 Sq Ft
  • $193/SF
  • 11 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1994

  10175 John Carvill Rd, Chestertown, MD 21620

  Welcome to 10175 John Carvill Road, nestled in the desirable water-oriented community of Great Oak Estates. This spacious home offers an open floor plan with 5 bedrooms and 3.5 baths, hardwood floors throughout the first floor, a cathedral ceiling, gas fireplace in the family room, and two primary suites. Enjoy the private fenced backyard and the sense of space that comes with it. The

  Hayley Norris Select Land & Homes, LLC

  10175 John Carvill Rd, Chestertown, MD 21620
• 

  

  

  /47

  $690,000 Sold Aug 25, 2025

  • 2,544 Sq Ft
  • $271/SF
  • 3 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1991

  7071 Pomona Rd, Chestertown, MD 21620

  Welcome to your Eastern Shore escape—where timeless charm meets modern convenience on over four beautifully private acres in the heart of Quaker Neck. Just a short drive from historic Chestertown, this double-lot property invites you to embrace a slower pace, with all the major updates already completed: new septic, HVAC, and roof in 2021, plus thoughtful improvements through 2025 including a

  Liddy Campbell TTR Sotheby's International Realty

  7071 Pomona Rd, Chestertown, MD 21620
• 

  

  

  /3

  $124,000 Sold Aug 25, 2025

  • Land
  • 1.01 Acres
  • $122,772 per Acre

  • 8 Days On Market

  209 River Rd, Chestertown, MD 21620

  A perc approved one acre open lot in a an established neighborhood ready for your dream home. No trees to clear and no restrictions except Critical Area guidelines. Perfectly located within a couple of minutes to downtown Historic Chestertown.

  Hayley Norris Select Land & Homes, LLC

  209 River Rd, Chestertown, MD 21620
• 

  

  /20

  $246,000 Sold Aug 15, 2025

  • 1,000 Sq Ft
  • $246/SF
  • 17 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1988

  10624 Millbrook Dr, Chestertown, MD 21620

  Charming One-Level Living Near the Chesapeake Bay!This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind.Enjoy your mornings on

  Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  10624 Millbrook Dr, Chestertown, MD 21620
• 

  

  /36

  $375,000 Sold Aug 13, 2025

  • 2,302 Sq Ft
  • $163/SF
  • 1 Day On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2022

  206 Silver Heel Dr, Chestertown, MD 21620

  Welcome to The Verona in The Village at Chestertown—a beautifully designed, move-in ready home offering 2,302 square feet of flexible living space across three levels. With 5 bedrooms and 3.5 bathrooms, this home perfectly balances comfort, function, and style. Step inside to a welcoming foyer that leads into a spacious family room, ideal for relaxing or entertaining. The open-concept layout

  TJ Bennett Samson Properties

  206 Silver Heel Dr, Chestertown, MD 21620
• 

  

  /23

  $290,000 Sold Aug 13, 2025

  • 1,380 Sq Ft
  • $210/SF
  • 234 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  107 Dutchess Rd, Chestertown, MD 21620

  Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

  Jo Ann Edwards The Hogans Agency

  107 Dutchess Rd, Chestertown, MD 21620
• 

  

  /36

  $355,000 Sold Aug 12, 2025

  • 1,496 Sq Ft
  • $237/SF
  • 83 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  114 Ryan Ct, Chestertown, MD 21620

  Priced over $70,000 below recent appraised value! Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stone’s throw from historic

  Julie Santoboni Taylor Properties

  114 Ryan Ct, Chestertown, MD 21620
• 

  

  /10

  $65,000 Sold Aug 11, 2025

  • Land
  • 2.36 Acres
  • $27,542 per Acre

  • 54 Days On Market

  9020 Georgetown Rd, Chestertown, MD 21620

  Price improvement!!! Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any

  Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  9020 Georgetown Rd, Chestertown, MD 21620
• 

  

  /19

  $335,000 Sold Aug 08, 2025

  • 1,500 Sq Ft
  • $223/SF
  • 17 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  10578 Tonopah Rd, Chestertown, MD 21620

  Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living—featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite

  David Moore RE/MAX Executive

  10578 Tonopah Rd, Chestertown, MD 21620
• 

  

  /24

  $285,000 Sold Aug 08, 2025

  • 652 Sq Ft
  • $437/SF
  • 457 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1886

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

  A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

  John Burke Gunther-McClary Real Estate

  117 N Water St Unit 3B, Chestertown, MD 21620
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  /24

  $280,000 Sold Aug 07, 2025

  • 896 Sq Ft
  • $312/SF
  • 10 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1955

  21363 Indiana Ave, Chestertown, MD 21620

  Welcome to this low-maintenance coastal cottage in Tolchester, just two blocks from the community beach on the Chesapeake Bay. Set on nearly a half-acre, this home has been completely renovated inside and out. Inside, you'll find three bedrooms and one and a half baths. Recent upgrades include a new well, new water filtration and softener system, and an encapsulated crawlspace with

  Courtney Chipouras TTR Sotheby's International Realty

  21363 Indiana Ave, Chestertown, MD 21620
• 

  

  /26

  $235,000 Sold Aug 07, 2025

  • 1,056 Sq Ft
  • $223/SF
  • 121 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1975

  118 Tuxedo Rd, Chestertown, MD 21620

  Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

  Debbie Meikle Doug Ashley Realtors, LLC

  118 Tuxedo Rd, Chestertown, MD 21620
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  /60

  $725,000 Sold Aug 05, 2025

  • 4,023 Sq Ft
  • $180/SF
  • 134 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  24576 Langford Rd, Chestertown, MD 21620

  Designed by noted architectural historian and restoration consultant, Michael Bourne, Highfield exemplifies a deep appreciation and intimate knowledge of historic architectural composition and its elements. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, in form and style, Highfield is reminiscent of the vernacular farmhouses of southeastern

  Nancy McGuire Maryland Heritage Properties

  24576 Langford Rd, Chestertown, MD 21620
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  /36

  $250,000 Sold Jul 31, 2025

  • 1,325 Sq Ft
  • $189/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  304 Hadaway Dr, Chestertown, MD 21620

  It doesn’t get any more hometown than this new offering right smack in the heart of hometown Chestertown! It’s peaceful, it’s rural and it looks like a Norman Rockwell this town. This is the Eastern Shore at its finest with plenty amenities close to town and countless activities for those sportsman who like to hunt fish and crab. That’s what we do out here and you have the Chester River right in

  Joseph Craig Cummings & Co. Realtors

  304 Hadaway Dr, Chestertown, MD 21620
• 

  

  /32

  $645,000 Sold Jul 31, 2025

  • 2,240 Sq Ft
  • $288/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1989

  7682 Waterview Ln, Chestertown, MD 21620

  Lovely colonial in Country Club Estates. The property goes back to Country Club Lane. 3 bedrooms and 3 full baths. One of the full baths is on the first floor so there is potential for a main floor bedroom. Screened-in porch overlooking the landscaped yard. 2 gas fireplaces. Open kitchen to family room. Mature landscaping. Nicely set back from the road. Well water, public sewer. Side

  Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  7682 Waterview Ln, Chestertown, MD 21620
• 

  

  /22

  $359,000 Sold Jul 31, 2025

  • 1,978 Sq Ft
  • $181/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  10575 Hyala Ct, Chestertown, MD 21620

  Nestled in the tranquil Chesapeake Landing community. This large three bedroom, two bathroom contemporary rancher offers 1978 square feet of comfortable one-level living. This home is situated on a 0.33 acre corner lot with direct access to Worton Creek, minutes from downtown Chestertown. It has an open -concept floor plan with cathedral ceilings. Many upgrades have been done to this house

  Laura Anthony Benson & Mangold, LLC

  10575 Hyala Ct, Chestertown, MD 21620
• 

  

  /21

  $309,500 Sold Jul 31, 2025

  • 1,104 Sq Ft
  • $280/SF
  • 2 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  212 Central Dr, Chestertown, MD 21620

  Great house with good bones. Lots of the big ticket items have already been done. Situated on an oversized lot with a fully fenced yard. Large driveway for plenty of parking. 3 bedrooms and 1 bath. Central air and heat. Newer roof. BAT septic system. The house is older and needs updating. but wait until you see the basement! Huge unfinished basement that the seller uses for storage and

  Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  212 Central Dr, Chestertown, MD 21620
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  /73

  $380,000 Sold Jul 30, 2025

  • 2,106 Sq Ft
  • $180/SF
  • 11 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  10705 Millbrook Dr, Chestertown, MD 21620

  Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, you’ll find a freshly painted bright and open layout with beautiful

  Adam Murphy RE/MAX Realty Centre, Inc.

  10705 Millbrook Dr, Chestertown, MD 21620
• 

  

  /22

  $175,000 Sold Jul 25, 2025

  • 896 Sq Ft
  • $195/SF
  • 85 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  110 Philosophers Terrace, Chestertown, MD 21620

  Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

  Debbie Meikle Doug Ashley Realtors, LLC

  110 Philosophers Terrace, Chestertown, MD 21620
• 

  

  /9

  $190,500 Sold Jul 22, 2025

  • 882 Sq Ft
  • $216/SF
  • 50 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1983

  619 Cannon St, Chestertown, MD 21620

  Buyer Financing fell through, so their loss is your gain! Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect

  Sarah King Cross Street Realtors LLC

  619 Cannon St, Chestertown, MD 21620
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  /18

  $205,000 Sold Jul 18, 2025

  • 1,216 Sq Ft
  • $169/SF
  • 24 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  310 Hilltop Ln, Chestertown, MD 21620

  Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn

  Clint Evans Cross Street Realtors LLC

  310 Hilltop Ln, Chestertown, MD 21620
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  /39

  $350,000 Sold Jul 18, 2025

  • 1,080 Sq Ft
  • $324/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1900

  420 Cannon St, Chestertown, MD 21620

  Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fronts on historic Cannon Street and is surrounded by the new Cannon Square development. Enjoy it in comfort now with plenty of room for new equity over time: Maybe double the house? Add a first floor bedroom suite? A garage? (As

  Beth Ostrander Doug Ashley Realtors, LLC

  420 Cannon St, Chestertown, MD 21620
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  /45

  $485,000 Sold Jul 18, 2025

  • 3,420 Sq Ft
  • $142/SF
  • 79 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2010

  314 Devon Dr, Chestertown, MD 21620

  Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in every room. From the moment you step into the grand foyer, you’ll feel the openness and care that’s gone into every detail.The heart of the home is the spacious kitchen, featuring a large island that’s perfect for prepping meals, gathering with friends, or simply enjoying

  Heather Branham The Parker Group

  314 Devon Dr, Chestertown, MD 21620
• 

  

  /52

  $795,000 Sold Jul 14, 2025

  • 4,401 Sq Ft
  • $181/SF
  • 2 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1963

  211 David Dr, Chestertown, MD 21620

  Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

  Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  211 David Dr, Chestertown, MD 21620
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  /29

  $410,000 Sold Jul 08, 2025

  • 1,656 Sq Ft
  • $248/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1916

  222 Mount Vernon Ave, Chestertown, MD 21620

  Lovingly maintained, this charming home in Chestertown’s Historic District seamlessly blends classic character with modern comfort. Restored windows, original yellow heart pine floors, and cypress siding reflect its rich history, while newer appliances, a high-efficiency boiler, tankless on-demand hot water, 3-zone heating, and leaf filter system provide everyday ease. The third floor offers

  Casey Scattergood Cross Street Realtors LLC

  222 Mount Vernon Ave, Chestertown, MD 21620
• 

  

  /5

  $285,000 Sold Jul 08, 2025

  • 2,142 Sq Ft
  • $133/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  10141 Flatland Rd, Chestertown, MD 21620

  Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with electric and three garage doors. There is a shed that improvements have started on, but not complete. Property has two bedrooms and one bath, with a traditional floor plan typical for a farmhouse style home. The kitchen is in

  Retha Arrabal Doug Ashley Realtors, LLC

  10141 Flatland Rd, Chestertown, MD 21620
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  /39

  $550,000 Sold Jul 01, 2025

  • 2,010 Sq Ft
  • $274/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  25285 Foxchase Dr, Chestertown, MD 21620

  Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

  Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  25285 Foxchase Dr, Chestertown, MD 21620
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  /56

  $759,000 Sold Jul 01, 2025

  • 3,394 Sq Ft
  • $224/SF
  • 2 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2000

  7988 Aldan Dr, Chestertown, MD 21620

  This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

  Doug Ashley Doug Ashley Realtors, LLC

  7988 Aldan Dr, Chestertown, MD 21620
• 

  

  /34

  $237,000 Sold Jun 30, 2025

  • 1,384 Sq Ft
  • $171/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  898 Washington Ave, Chestertown, MD 21620

  This ranch property most recently was used as an accountants office and at one time a residential rental. The Village zoning allows for many uses. This could easily be turned back into a primary residence or an investment rental property. There are wood floors throughout most of the of the house with laminate flooring in the kitchen area. The HVAC heat pump is relatively new. There is a full

  Doug Ashley Doug Ashley Realtors, LLC

  898 Washington Ave, Chestertown, MD 21620
• 

  

  /37

  $525,000 Sold Jun 30, 2025

  • 3,016 Sq Ft
  • $174/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  201 Pondview Ct, Chestertown, MD 21620

  Impeccably maintained and thoughtfully upgraded, this custom-designed home is a true standout! Situated on over a half-acre just outside of town limits, this property offers the perfect blend of peace and convenience—within walking and biking distance to shopping, dining, and all the charm the town has to offer.Step inside to discover a warm, welcoming interior featuring gorgeous hardwood

  Jody Baker Cross Street Realtors LLC

  201 Pondview Ct, Chestertown, MD 21620
• 

  

  /8

  $360,000 Sold Jun 27, 2025

  • 1,128 Sq Ft
  • $319/SF
  • 15 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1957

  200 Hoffman Ln, Chestertown, MD 21620

  Investor’s Dream on the Chester River – 1.75 Acres with Endless Potential!Welcome to a rare opportunity along the stunning Chester River! This unique property combines two parcels totaling 1.75 acres and includes an 1100+ square foot home, with an additional 750+sq ft of unfinished space with a garage door, that’s ready for your vision. Whether you're a seasoned investor, a savvy flipper, or

  Joelle Dolch Cross Street Realtors LLC

  200 Hoffman Ln, Chestertown, MD 21620
• 

  

  /87

  $1,062,800 Sold Jun 27, 2025

  • 3,078 Sq Ft
  • $345/SF
  • 37 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1975

  22153 1st Point Rd, Chestertown, MD 21620

  Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and

  Liddy Campbell TTR Sotheby's International Realty

  22153 1st Point Rd, Chestertown, MD 21620
• 

  

  /49

  $840,000 Sold Jun 27, 2025

  • 3,355 Sq Ft
  • $250/SF
  • 182 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1963

  26865 Mallard Rd, Chestertown, MD 21620

  A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles,

  Liddy Campbell TTR Sotheby's International Realty

  26865 Mallard Rd, Chestertown, MD 21620
• 

  

  /28

  $549,000 Sold Jun 26, 2025

  • 2,476 Sq Ft
  • $222/SF
  • 0 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1930

  305 Washington Ave, Chestertown, MD 21620

  Wonderful Chestertown home with many endearing features including spacious rooms, hardwood floors, full basement, off street parking and more. Located across from the Washington College lawn and a block from the local hospital, this home is also ideally situated within walking distance to Historic downtown Chestertown, the Chester River, Kent Plaza, Starbucks and the Chestertown Middle and

  William Norris Select Land & Homes, LLC

  305 Washington Ave, Chestertown, MD 21620
• 

  /2

  $119,500 Sold Jun 26, 2025

  • Land
  • 1.01 Acres
  • $118,317 per Acre

  • 2 Days On Market

  205 River Rd, Chestertown, MD 21620

  A perc approved one acre open lot in a an established neighborhood ready for your dream home. No trees to clear and no restrictions except Critical Area guidelines. Perfectly located within a couple of minutes to downtown Historic Chestertown.

  Hayley Norris Select Land & Homes, LLC

  205 River Rd, Chestertown, MD 21620
• 

  

  /71

  $745,000 Sold Jun 26, 2025

  • 3,166 Sq Ft
  • $235/SF
  • 7 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2000

  9050 Point Ln, Chestertown, MD 21620

  Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet and friendly community of Tolchester Estates. This wonderful home is nestled just 10–15 minutes from the cities of Chestertown and Rock Hall. This close proximity provides access to shopping, restaurants, a farmers market, theater and local arts. The area abounds with

  Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  9050 Point Ln, Chestertown, MD 21620
• 

  

  /3

  $675,000 Sold Jun 25, 2025

  • 1,945 Sq Ft
  • $347/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1904

  213 N Queen St, Chestertown, MD 21620

  A 3 car garage in the Historic District! With a rare combination of desirable features including comfortable modern amenities, this historic home will likely find its new owner quickly! Highlights of the interior include a roomy Family Room between the open concept Kitchen and the Courtyard, a formal Dining Room with a bay window, a front Living Room with gas fireplace, a formal Entry Hall, two

  Beth Ostrander Doug Ashley Realtors, LLC

  213 N Queen St, Chestertown, MD 21620
• 

  

  /24

  $344,900 Sold Jun 25, 2025

  • 1,344 Sq Ft
  • $257/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  109 Edmore Rd, Chestertown, MD 21620

  Welcome to 109 Edmore Rd, a beautifully renovated 3-bedroom, 2-bath ranch-style home offering 1,344 sq. ft. of comfortable living space on a 0.34-acre lot. This move in ready home blends modern upgrades with cozy charm. Renovated in 2021 upgrades include HVAC, Roof, Encapsulated crawl space, appliances, reverse osmosis and water conditioner. Features a 16 x 12 screen porch for relaxing outdoors.

  Norma Coursey Benson & Mangold, LLC

  109 Edmore Rd, Chestertown, MD 21620

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