91

Homes for Sale in 21620

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  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, 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

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    /45

    $334,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $579,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    /15

    $150,000

    • Land
    • 1.18 Acres
    • $127,119 per Acre

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool,

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 331-9489

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /24

    $950,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • 230 S Water St Unit 1, Chestertown, MD 21620
    230 S Water St Unit 1, Chestertown, MD 21620
    230 S Water St Unit 1, Chestertown, MD 21620
    /31

    $995,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,490 Sq Ft

    230 S Water St Unit 1, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. Available Jan 2025

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 849-6629

    230 S Water St Unit 1, 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
    /19

    $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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /21

    $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
  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $484,990 New Construction

    • 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
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $779,000 Open Sat 11AM - 2PM

    • 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 maximize

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    /8

    $790,000 New Construction

    • 3 Beds
    • 2.5 Baths

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 966-6341

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /22

    $549,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a new roof with 50-year shingles and a transferable warranty, new water and sewer lines to the street (2022), EV

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    /36

    $459,000

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft

    114 Ryan Ct, Chestertown, MD 21620

    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 Chestertown, the property combines seclusion with

    Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
  • 100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    /57

    $725,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    100 Little Harbor Way, Chestertown, MD 21620

    Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom, 2 bath home offers the perfect blend of comfort and modern living and is ideal for quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find yourself within easy reach of local amenities, including parks and trails, the Chester

    Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
  • 129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    /38

    $649,000

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

    129 N Queen St, Chestertown, MD 21620

    Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

    William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $579,900

    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /57

    $440,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    /47

    $515,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    314 Devon Dr, Chestertown, MD 21620

    **Seller is motivated and ready to make a deal – bring your offer today!**Welcome to 314 Devon Dr, Chestertown, MD 21620—an elegant 4-bedroom, 3.5-bath home offering spacious living areas and thoughtful upgrades. The grand foyer leads to a beautifully designed kitchen with a large island, perfect for cooking and entertaining. The expansive master suite features a spa-like bath with a soaking tub,

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $515,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove,

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000

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

    104 Dutchess Rd, Chestertown, MD 21620

    This home is a must see! Join the Chester Harbor Community.A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the

    Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /2

    $150,000

    • Land
    • 2.00 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 the

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    /10

    $99,900

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    132 Prospect St, Chestertown, MD 21620

    Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

    Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $865,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • 23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    /3

    $15,000

    • Land
    • 0.69 Acre
    • $21,739 per Acre

    23683 L Rd, Chestertown, MD 21620

    This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront attractions just minutes from the town of Chestertown, Worton Creek Marina, and Great Oak Landing.

    Alyson Anderson Allfirst Realty, Inc.

    23683 L Rd, Chestertown, MD 21620
  • 22153 1st Point Rd, Chestertown, MD 21620
    22153 1st Point Rd, Chestertown, MD 21620
    22153 1st Point Rd, Chestertown, MD 21620
    /87

    $1,200,000

    • 5 Beds
    • 6 Baths
    • 3,078 Sq Ft

    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
  • 216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    /32

    $364,900

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft

    216 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by.Inside, the well-designed layout begins with a foyer and

    Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
  • 114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    /33

    $289,900

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

    114 Darden Rd, Chestertown, MD 21620

    All one floor living on quiet street with large fenced yard and mature trees close to the bay! Lovely renovations and brand new kitchen with solid white shaker cabinetry including soft close dovetailed drawers and new stainless steel appliances PLUS BRAND NEW ROOF! Brand New septic system to be installed by settlement! ABSOLUTE MUST SEE HOME!

    Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /20

    $235,000 Open House 5/03

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • 0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
    /2

    $35,000

    • Land
    • 0.34 Acre
    • $102,941 per Acre

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
  • 0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
    /2

    $35,000

    • Land
    • 0.34 Acre
    • $102,941 per Acre

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /60

    $1,395,000 Open Sat 9AM - 11AM

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    /22

    $225,000

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    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
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $319,000

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

    306 Cedar St, Chestertown, MD 21620

    Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside

    Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
  • 0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620
    /11

    $49,900

    • Land
    • 1.51 Acres
    • $33,046 per Acre

    0 Cloquet Rd Unit MDKE2004960, 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 MDKE2004960, Chestertown, MD 21620
  • 118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    /26

    $274,000

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

    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
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /16

    $267,500

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /91

    $885,000

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft

    24576 Langford Rd, Chestertown, MD 21620

    HIGHFIELD, has been home to the renown architectural historian MichaelBourne and his family for almost forty-years. Mr. Bourne who authored theimportant Historic Houses of Kent County and guided the restorations of over400 historic structures in the mid-Atlantic, together with his wife, Ann,created a home that reflects their deep appreciation for the refined beauty ofhistoric

    Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620

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