6,895

Chestertown, MD Homes

Section Image
  • /6

    $782,200 Sold Sep 03, 2024

    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    308 Landing Ln Unit 17, Chestertown, MD 21620

    Carefree waterfront living within a short stroll or bike ride to Charming Historic Downtown Chestertown, Washington College and the Chester River Yacht and Country Club. This home offers some of the finest waterfront views in the entire Chester River Landing Community. Just imagine a front row seat to the annual Chestertown Fourth of July fireworks, broad views of the Schooner Sultana sailing to

    William Norris Select Land & Homes, LLC

    308 Landing Ln Unit 17, Chestertown, MD 21620
    • /14

      Est $388,907 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,722 Sq Ft

      203 Pine St, Chestertown, MD 21620

      203 Pine St, Chestertown, MD 21620
  • /29

    $865,000 Sold Aug 30, 2024

    • 1,855 Sq Ft
    • $466/SF
    • 25 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1870

    123 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory. No expense has been spared in selecting the finest finishes and materials for this renovation and it extends beyond the interior, with the creation of an outdoor oasis. This meticulously landscaped gardens and charming patio provide a private

    John Burke Gunther-McClary Real Estate

    123 High St, Chestertown, MD 21620
    • /21

      Est $207,909 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      612 High St, Chestertown, MD 21620

      612 High St, Chestertown, MD 21620
  • /27

    $75,000 Sold Aug 29, 2024

    • 3,090 Sq Ft
    • $24/SF
    • 5 Days On Market
    • 2 Baths
    • Built 1851

    6595 Quaker Neck Rd, Chestertown, MD 21620

    Historic Bond Chapel Church built in 1851. Located in rural location. Would be a good candidate for residential conversion. Large addition of 1652 sq. ft. frame construction,, formerly housed the Sunday School rooms, kitchen and fellowship hall, has two half baths. The sanctuary, built in 1851 is of brick construction. The chapel is simple in design and contains 1656 sq. ft. These two

    Cynthia Stevens Wilson Realty

    6595 Quaker Neck Rd, Chestertown, MD 21620
    • /72

      Est $839,477 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft

      7996 Aldan Dr, Chestertown, MD 21620

      7996 Aldan Dr, Chestertown, MD 21620
  • /49

    $460,000 Sold Aug 29, 2024

    • 2,210 Sq Ft
    • $208/SF
    • 128 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1992

    8757 Orchard Dr, Chestertown, MD 21620

    Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds and located just minutes from Historic downtown Chestertown. Community living without any HOA restrictions. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. Property provides ample space to expand

    Ken Roderick Chesapeake Real Estate Associates, LLC

    8757 Orchard Dr, Chestertown, MD 21620
    • /22

      Est $288,399 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft

      211 Manor Ave, Chestertown, MD 21620

      211 Manor Ave, Chestertown, MD 21620
  • /28

    $848,000 Sold Aug 28, 2024

    • 1,660 Sq Ft
    • $511/SF
    • 98 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1945

    8049 Quaker Neck Rd, Chestertown, MD 21620

    Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops,

    John Burke Gunther-McClary Real Estate

    8049 Quaker Neck Rd, Chestertown, MD 21620
    • /56

      Est $824,681 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,414 Sq Ft

      10258 Mill Hollow Ln, Chestertown, MD 21620

      10258 Mill Hollow Ln, Chestertown, MD 21620
  • /37

    $564,500 Sold Aug 19, 2024

    • 1,467 Sq Ft
    • $385/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    217 Radcliffe Dr, Chestertown, MD 21620

    Beautifully maintained home tucked away on a quiet cul-de-sac but still within walking distance to downtown shops, restaurants, and riverfront. Open floor plan with 9ft ceilings in the living room. 3 bedrooms and 2 full bath with a 2 car attached garage. Covered front porch, secluded screened-in rear porch. Nicely landscaped. Schedule your personal tour!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    217 Radcliffe Dr, Chestertown, MD 21620
    • /12

      Est $720,292 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft

      8042 Brices Mill Rd, Chestertown, MD 21620

      8042 Brices Mill Rd, Chestertown, MD 21620
  • /13

    $221,000 Sold Aug 15, 2024

    • Land
    • 5 Acres
    • $41,231 per Acre
    • 7 Days On Market

    8842 Fairlee Rd, Chestertown, MD 21620

    Here's a chance to build your dream home just minutes from historic Chestertown or Rock Hall. There was a house fire on this property and the remains have been taken away leaving only a pole barn on over 5 acres that was once used as an orchard and is now mainly cleared. Public Water and Sewer are huge benefits to the design and construction process. The oversized pole barn was recently put up

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    8842 Fairlee Rd, Chestertown, MD 21620
    • /20

      Est $331,512 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      5772 Johnsontown Rd, Chestertown, MD 21620

      5772 Johnsontown Rd, Chestertown, MD 21620
  • /50

    $342,000 Sold Aug 14, 2024

    • 1,225 Sq Ft
    • $279/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 1973

    201 Tamarack Rd, Chestertown, MD 21620

    Discover the charm and tranquility of this inviting ranch-style home, perfectly situated on the Queen Anne's County side of Chestertown, Maryland. Just steps from Rosin Creek, this property offers not only spacious living but also exciting opportunities for canoeing, boating, fishing, and crabbing on the beautiful Chester River.Step inside to find large, airy bedrooms, a generously sized

    Petra Quinn Realty Navigator

    201 Tamarack Rd, Chestertown, MD 21620
    • /17

      Est $264,527 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,237 Sq Ft

      10755 Glenola Rd, Chestertown, MD 21620

      10755 Glenola Rd, Chestertown, MD 21620
  • /41

    $365,000 Sold Aug 13, 2024

    • 1,789 Sq Ft
    • $204/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    23120 Club Terrace, Chestertown, MD 21620

    Discover your dream home nestled in a serene water-privileged community with exclusive access to a boat ramp, a small marina, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and outdoor living, all situated on a generous 1-acre property composed of two separate parcels.Enjoy the spacious primary suite with new carpet, a

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    23120 Club Terrace, Chestertown, MD 21620
    • /25

      Est $335,992 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      8550 Caulks Field Rd, Chestertown, MD 21620

      8550 Caulks Field Rd, Chestertown, MD 21620
  • /29

    $252,400 Sold Aug 12, 2024

    • 1,408 Sq Ft
    • $179/SF
    • 118 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    332 Truslow Rd, Chestertown, MD 21620

    Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a

    James Blackwell Blackwell Real Estate, LLC

    332 Truslow Rd, Chestertown, MD 21620
    • /42

      Est $326,590 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,855 Sq Ft

      626 High St, Chestertown, MD 21620

      626 High St, Chestertown, MD 21620
  • /24

    $718,000 Sold Aug 09, 2024

    • 1,376 Sq Ft
    • $522/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    415 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the

    Richard Budden Coldwell Banker Chesapeake Real Estate Company

    415 Fairview Dr, Chestertown, MD 21620
    • /28

      Est $253,895 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      403 E Campus Ave, Chestertown, MD 21620

      403 E Campus Ave, Chestertown, MD 21620
  • /2

    $40,000 Sold Aug 05, 2024

    • Land
    • 4.03 Acres
    • $9,926 per Acre
    • 26 Days On Market

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620

    Wow 4 acres of privacy and public utilities available! Located just outside of Chestertown in Fairlee. Accessible through a 50' right of way shown in survey. Buyer to verify right of way and utilities. Call today!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    • /8

      Est $448,610 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      219 Philosophers Terrace, Chestertown, MD 21620

      219 Philosophers Terrace, Chestertown, MD 21620
  • /33

    $305,000 Sold Aug 02, 2024

    • 1,404 Sq Ft
    • $217/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2006

    10550 Klamath Rd, Chestertown, MD 21620

    Immerse yourself in waterfront living at this captivating Cape Cod in the sought-after Chesapeake Landing community! Embrace serenity with 3 bedrooms and 2 full baths, including a luxurious main-floor primary suite. Brand new luxury vinyl plank flooring flows throughout, creating a cohesive and modern feel. Unwind in the light-filled living area or prepare culinary delights in the updated kitchen

    David Moore RE/MAX Executive

    10550 Klamath Rd, Chestertown, MD 21620
    • /4

      Est $497,544 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,693 Sq Ft

      928 Gateway Dr, Chestertown, MD 21620

      928 Gateway Dr, Chestertown, MD 21620
  • /32

    $289,900 Sold Jul 30, 2024

    • 1,056 Sq Ft
    • $275/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    729 Rosin Dr, Chestertown, MD 21620

    Wonderful home with kitchen, dining and living room in an open floor plan. Laminate flooring through most of the house. Granite counters and island in the kitchen area with some recessed lighting and stainless appliances. Bathroom has been updated. A side deck with handicap ramp and a rear deck that overlooks the privacy fenced backyard. A new roof will be installed in the next several

    Doug Ashley Doug Ashley Realtors, LLC

    729 Rosin Dr, Chestertown, MD 21620
    • /34

      Est $737,399 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft

      112 S Mill St, Chestertown, MD 21620

      112 S Mill St, Chestertown, MD 21620
  • /23

    $370,000 Sold Jul 25, 2024

    • 729 Sq Ft
    • $508/SF
    • 77 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1886

    117 N Water St Unit 3A, 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 3A, Chestertown, MD 21620
    • /40

      Est $417,322 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,790 Sq Ft

      7653 Broad Neck Rd, Chestertown, MD 21620

      7653 Broad Neck Rd, Chestertown, MD 21620
  • /2

    $12,500 Sold Jul 24, 2024

    • Land
    • 1.00 Acre
    • $12,500 per Acre
    • 85 Days On Market

    0 Buck Neck Rd Unit MDKE2003864, Chestertown, MD 21620

    1-acre vacant lot in Chesapeake Landing off of Buck Neck Rd. Not perc approved. You have access to the public boat ramp in Chesapeake Landing and possible deer hunting opportunities.

    Hayley Norris Select Land & Homes, LLC

    0 Buck Neck Rd Unit MDKE2003864, Chestertown, MD 21620
    • /41

      Est $470,847 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft

      203 Leeds Ct, Chestertown, MD 21620

      203 Leeds Ct, Chestertown, MD 21620
  • /8

    $1,275,000 Sold Jul 18, 2024

    • 2,420 Sq Ft
    • $527/SF
    • 3 Beds
    • 2.5 Baths
    • Built 1948

    545 Fey Rd, Chestertown, MD 21620

    Waterfront property on the Chester River on Queen Anne's side of Chestertown.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    545 Fey Rd, Chestertown, MD 21620
    • /15

      Est $224,525 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft

      7509 Sunburst Ave, Chestertown, MD 21620

      7509 Sunburst Ave, Chestertown, MD 21620
  • /20

    $780,000 Sold Jul 15, 2024

    • 31 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    7514 Muirfield Dr, Chestertown, MD 21620

    Live in Luxury in this brand new home that seamlessly blends indoor-outdoor living with its prime location on nestled just off of the 10th tee box of the Chester River Yacht and Country club. Enjoy the convenience of this 3 bedroom, plus extra room for office, gym or playroom, 2.5 bath home full of light with a modern open floor plan with one floor living. Harwood Oak floors throughout whole

    John Burke Gunther-McClary Real Estate

    7514 Muirfield Dr, Chestertown, MD 21620
    • /39

      Est $319,046 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft

      100 Malone Ave, Chestertown, MD 21620

      100 Malone Ave, Chestertown, MD 21620
  • /15

    $333,000 Sold Jul 10, 2024

    • 1,300 Sq Ft
    • $256/SF
    • 3 Beds
    • 2 Baths
    • Built 2024

    8858 Georgetown Rd, Chestertown, MD 21620

    Welcome to your new home. Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and a color palette. Every appliance and amenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen offering granite counters, built-in

    Andy Batch Keller Williams Select Realtors of Annapolis

    8858 Georgetown Rd, Chestertown, MD 21620
    • /57

      Est $576,342 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,693 Sq Ft

      206 Leeds Ct, Chestertown, MD 21620

      206 Leeds Ct, Chestertown, MD 21620
  • /32

    $245,000 Sold Jul 09, 2024

    • 960 Sq Ft
    • $255/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    129 Manor Ave, Chestertown, MD 21620

    Cute rancher located in Foxley Manor. Laminate flooring through most of the house. There is an oversized 1 car detached garage that has room for a small handyman space. Nice backyard with a hot tub. Close to everything Chestertown has to offer.

    Doug Ashley Doug Ashley Realtors, LLC

    129 Manor Ave, Chestertown, MD 21620
    • /42

      Est $309,800 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,879 Sq Ft

      114 Oak Leaf Dr, Chestertown, MD 21620

      114 Oak Leaf Dr, Chestertown, MD 21620

Showing Results 401 - 440, Page 11 of 18

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