6,852

Chestertown, MD Homes

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  • 23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    /10

    $149,000

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft

    23065 Old Fairlee Rd, Chestertown, MD 21620

    This home is priced to SELL! Bring your vision and bring this sweet property back to life. Nice lot - with a storage shed, mature trees ring part of the property lines in the back yard. There are three bedrooms and one bath, kitchen, utility room, a fireplace in the living room. Located in tranquil Fairlee - with easy access to public landings, Chestertown, Rock Hall and the beautiful

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 888-0767

    23065 Old Fairlee Rd, Chestertown, MD 21620
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, 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
    • 141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      /18

      Est $1,236,558 Not Listed For Sale

      • Studio

      141 Round Top Creek Ln, Chestertown, MD 21620

      141 Round Top Creek Ln, Chestertown, MD 21620
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /25

    $179,000

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

    21316 Persimmon Dr, Chestertown, MD 21620

    Two bedroom & one bath townhome with a nice view from the living room/patio area. Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 708-2172

    21316 Persimmon Dr, Chestertown, MD 21620
  • 9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, 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
    • 204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      /44

      Est $456,688 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft

      204 N Mill St, Chestertown, MD 21620

      204 N Mill St, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $325,000

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

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 10578 Tonopah Rd, Chestertown, MD 21620
    10578 Tonopah Rd, Chestertown, MD 21620
    10578 Tonopah 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 Real Broker, LLC

    10578 Tonopah Rd, Chestertown, MD 21620
    • 128 N Queen St, Chestertown, MD 21620
      128 N Queen St, Chestertown, MD 21620
      128 N Queen St, Chestertown, MD 21620
      /7

      Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft

      128 N Queen St, Chestertown, MD 21620

      128 N Queen St, Chestertown, MD 21620
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,198,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory Ln, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, 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
    • 101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      /23

      Est $401,656 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft

      101 S Kent St, Chestertown, MD 21620

      101 S Kent St, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $509,990 Open Sat 12PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS QUICK MOVE IN. Luxury 4 Bedroom Villa. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    /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
    • 116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      /54

      Est $639,073 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft

      116 N Queen St, Chestertown, MD 21620

      116 N Queen St, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, 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
    • 107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      /31

      Est $487,401 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft

      107 Adela Way, Chestertown, MD 21620

      107 Adela Way, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /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
    • 105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      /43

      Est $429,623 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      105 Sutton Way, Chestertown, MD 21620

      105 Sutton Way, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 New Construction

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /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
    • 335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      /44

      Est $506,196 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,874 Sq Ft

      335 Devon Dr, Chestertown, MD 21620

      335 Devon Dr, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $492,464 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. Featuring a huge family room with gas fireplace, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 431-1757

    730 Aldora Dr Unit 114, Chestertown, MD 21620
  • 7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, 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
    • 112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      112 Pine Tree Rd, Chestertown, MD 21620
  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $484,990 Pending

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

    726 Aldora Dr, Chestertown, MD 21620

    2 DECORATED MODEL OPEN The Sophie is a luxury 3 Bedroom Villa with a layout that is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower and an additional

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (443) 429-1073

    726 Aldora Dr, Chestertown, MD 21620
  • 10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, 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
    • 118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      /8

      Est $646,910 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,512 Sq Ft

      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      118 Little Harbor Way Unit 102, Chestertown, MD 21620
  • 724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    /38

    $559,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THE HOME OF THE MONTHLuxury, End of Group, 4 Bedroom Villa with a walk-out lower level. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 883-7905

    724 Aldora Dr Unit 111, Chestertown, MD 21620
  • 212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    212 Central Dr, 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
    • 331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      /33

      Est $1,170,391 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft

      331 Park Ln, Chestertown, MD 21620

      331 Park Ln, Chestertown, MD 21620
  • 7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    /33

    $797,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    7514 Muirfield Dr, Chestertown, MD 21620

    Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 206-3727

    7514 Muirfield Dr, Chestertown, MD 21620
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    /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
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $335,106 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,796 Sq Ft

      228 Dutchess Rd, Chestertown, MD 21620

      228 Dutchess Rd, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,750,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, 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
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      /11

      Est $314,436 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      102 Darden Rd, Chestertown, MD 21620

      102 Darden Rd, Chestertown, MD 21620
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    /66

    $868,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    Welcome to a rare opportunity for luxury waterfront living on the Chester River. This beautifully maintained 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space, thoughtfully designed to embrace both comfort and elegance. Set on 1.08 acres of lush, well-landscaped grounds, this exceptional 2001-built two-story residence offers a park-like, deep, well-landscaped and level

    Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620

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