6,883

Chestertown, MD Homes

Section Image
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $865,000

    • 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
  • 409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    /29

    $380,000 Sold Mar 14, 2025

    • 1,800 Sq Ft
    • $211/SF
    • 118 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    409 Riverview Rd, Chestertown, MD 21620

    EXCEPTIONAL VALUE-This charming Cape Cod home offers exceptional value with a recent $10,000 price reduction and new carpet throughout. Located on a desirable corner lot in Kingstown, this property is just a short walk or bike ride from historic Chestertown. The home features a modernized kitchen, updated bathrooms, and custom tile floors. Enjoy the convenience of a first-floor bedroom, a

    Norma Coursey Benson & Mangold, LLC

    409 Riverview Rd, 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
  • 100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    /57

    $725,000

    • 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
  • 209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    /63

    $535,000 Sold Mar 13, 2025

    • 2,328 Sq Ft
    • $230/SF
    • 10 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1885

    209 N Queen St, Chestertown, MD 21620

    Welcome to the historic Fannie Stuart home, c 1885 - a delightful Victorian home, with the perfect blend of classic elegance and modern comfort, blocks to downtown historic Chestertown and all it has to offer. This special residence boasts four spacious bedrooms, and two beautifully renovated bathrooms, offering ample space for relaxation and entertaining. Step inside to discover a warm and

    Andrea Alderdice Long & Foster Real Estate, Inc.

    209 N Queen St, 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 $642,197 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
  • 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
  • 312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    /87

    $440,000 Sold Mar 13, 2025

    • 1,848 Sq Ft
    • $238/SF
    • 31 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    312 Princess Anne Dr, Chestertown, MD 21620

    ?? Just Renovated Creekside Beauty – Move-In Ready! ??Discover your dream home with this beautifully renovated 4-bedroom, 2.5-bath gem that overlooks a serene creek. Perfectly blending modern upgrades with cozy charm, this property has everything you need and more!? Key Features:Spacious 2-Car GarageBonus Room: Use as a 4th bedroom, home office, or entertainment

    Jim Davidson Coldwell Banker Waterman Realty

    312 Princess Anne Dr, Chestertown, MD 21620
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $292,570 Not Listed For Sale

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

      228 Dutchess Rd, Chestertown, MD 21620

      228 Dutchess 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

    • 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
  • 204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    /30

    $400,000 Sold Mar 12, 2025

    • 2,167 Sq Ft
    • $185/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2021

    204 Pine Cove Ln, Chestertown, MD 21620

    Discover the perfect blend of modern design and rustic charm at 204 Pine Cove Lane, a stunning 3-bedroom, 2.5-bathroom home built in 2021. Tucked away on a secluded lot and surrounded by picturesque farmland, this property offers unparalleled privacy and tranquility—a true sanctuary for those seeking a peaceful retreat.Step inside to be greeted by a thoughtfully designed interior,

    Kelly Harris Coldwell Banker Realty

    204 Pine Cove Ln, Chestertown, MD 21620
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      /11

      Est $319,421 Not Listed For Sale

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

      102 Darden Rd, Chestertown, MD 21620

      102 Darden Rd, 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
  • 317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    /33

    $685,000 Sold Mar 07, 2025

    • 2,512 Sq Ft
    • $273/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    317 Union Church Rd, Chestertown, MD 21620

    Welcome to 317 Union Church Rd, Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre. Open concept yet defined spaces allow this home to function wonderfully for entertaining and everyday living...The home exudes style and hospitality from its covered wraparound plantation porch through to the welcoming extra wide entry, seamlessly flowing to the

    Karen Clark Clark & Co Realty, LLC

    317 Union Church Rd, Chestertown, MD 21620
    • 414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      /42

      Est $362,978 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft

      414 Pine Tree Rd, Chestertown, MD 21620

      414 Pine Tree Rd, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /4

    $529,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 3,050 Sq Ft

    107 N Queen St, Chestertown, MD 21620

    The Vannort House stands proudly on historic Queen Street with a colonial-era smokehouse in the yard! Light & breezy: The 31' long screened-in side-porch has doors from the eat-in Kitchen, formal Dining Room, and the grand high-ceilinged Living Room! Keep all the doors open into the screened porch for an amazing indoor-outdoor way of living! A truly versatile layout for entertaining and

    Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
  • 10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    /21

    $325,000 Sold Mar 06, 2025

    • 2,376 Sq Ft
    • $137/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1969

    10061 Flatland Rd, Chestertown, MD 21620

    Charming, very well-maintained home located just outside historic Chestertown. The side entrance has a spacious deck and ramp that leads to a full blacktop driveway. Unique split level back entrance. 1.3 grassy acres. Large unfinished basement for extra living space. Hardwood flooring beneath the carpet. Updates include recent paint in interior rooms, (except Kitchen), new paint basement,

    Jo Ann Edwards The Hogans Agency

    10061 Flatland Rd, Chestertown, MD 21620
    • 326 Rolphs Wharf Rd, Chestertown, MD 21620
      326 Rolphs Wharf Rd, Chestertown, MD 21620
      326 Rolphs Wharf Rd, Chestertown, MD 21620
      /4

      Not Listed For Sale

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

      326 Rolphs Wharf Rd, Chestertown, MD 21620

      326 Rolphs Wharf Rd, Chestertown, MD 21620
  • 24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    /55

    $475,000 Pending

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

    24543 Chestertown Rd, Chestertown, MD 21620

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

    Terri Murray RE/MAX Executive

    24543 Chestertown Rd, Chestertown, MD 21620
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /21

    $165,300 Sold Mar 05, 2025

    • 1,545 Sq Ft
    • $107/SF
    • 129 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1938

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is

    Gina Gargeu Century 21 Downtown

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • 104 Woodstock Rd, Chestertown, MD 21620
      104 Woodstock Rd, Chestertown, MD 21620
      104 Woodstock Rd, Chestertown, MD 21620
      /33

      Est $283,796 Not Listed For Sale

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

      104 Woodstock Rd, Chestertown, MD 21620

      104 Woodstock Rd, Chestertown, MD 21620
  • 22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    /4

    $15,000

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    22671 Wood Yard Ln, Chestertown, MD 21620

    Almost half acre of recreational property available between Chestertown and Rock Hall! Best use would be hunting since it is surrounded by woods and farms. There is an existing structure that is a tear down of no value. There appears to be electric run to the property but condition is unknown. The county does not have records of the septic and would need to be perc tested to build on. The back of

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
  • 10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    /35

    $355,675 Sold Feb 28, 2025

    • 1,872 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    10724 Foreston Rd, Chestertown, MD 21620

    Your dream home is waiting! This remodeled home is waiting for you in the serene water-privileged community of Chesapeake Landing, just minutes from downtown Chestertown. The community offers exclusive access to a boat ramp, a small marina with boat slips, picnic area, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620
    • 318 River Rd, Chestertown, MD 21620
      318 River Rd, Chestertown, MD 21620
      318 River Rd, Chestertown, MD 21620
      /23

      Est $758,463 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,636 Sq Ft

      318 River Rd, Chestertown, MD 21620

      318 River 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
  • 116 Fairview Dr, Chestertown, MD 21620
    116 Fairview Dr, Chestertown, MD 21620
    116 Fairview Dr, Chestertown, MD 21620
    /21

    $305,000 Sold Feb 27, 2025

    • 1,028 Sq Ft
    • $297/SF
    • 13 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1976

    116 Fairview Dr, Chestertown, MD 21620

    Move-in ready and waiting for you! Start the new year in this charming 3-bedroom, 1-bath rancher. The brand-new kitchen is a showstopper, featuring sleek granite countertops, stylish new cabinets, and stainless steel appliances. Durable and attractive LVP flooring flows seamlessly throughout the home, creating a low-maintenance living space. Freshly painted from top to bottom, this home feels

    Jody Baker Cross Street Realtors LLC

    116 Fairview Dr, Chestertown, MD 21620
    • 101 Pine Tree Rd, Chestertown, MD 21620
      101 Pine Tree Rd, Chestertown, MD 21620
      101 Pine Tree Rd, Chestertown, MD 21620
      /36

      Est $471,700 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,848 Sq Ft

      101 Pine Tree Rd, Chestertown, MD 21620

      101 Pine Tree 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
  • 117 Primrose Rd, Chestertown, MD 21620
    117 Primrose Rd, Chestertown, MD 21620
    117 Primrose Rd, Chestertown, MD 21620
    /15

    $325,000 Sold Feb 27, 2025

    • 2,460 Sq Ft
    • $132/SF
    • 112 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    117 Primrose Rd, Chestertown, MD 21620

    Ranch home located in Primrose Point neighborhood( Queen Anne's County with Chestertown address), only ten minutes from downtown Chestertown. This home offers large rooms that could be modified to create a formal dining room and seperate family room if desired. The swimming pool has not been used for two years. This property is being sold "AS-IS". Sign posted.

    Herschell Claggett Davis Real Estate, Inc.

    117 Primrose Rd, Chestertown, MD 21620
    • 106 Darden Rd, Chestertown, MD 21620
      106 Darden Rd, Chestertown, MD 21620
      106 Darden Rd, Chestertown, MD 21620
      /11

      Est $306,363 Not Listed For Sale

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

      106 Darden Rd, Chestertown, MD 21620

      106 Darden Rd, 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
  • 104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    /17

    $283,000 Sold Feb 19, 2025

    • 1,840 Sq Ft
    • $154/SF
    • 38 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2003

    104 Oak Leaf Dr, Chestertown, MD 21620

    Welcome to your new home in the vibrant community of Chestertown! This beautiful 3-bedroom, 3.5-bath townhome features an open layout perfect for modern living. The heart of the home is the stylish kitchen, equipped with contemporary finishes and ample storage.Enjoy relaxing in the spacious living area or step outside to your private deck—ideal for entertaining or soaking up the sun. The

    Krystal Zellner Crown Homes Real Estate

    104 Oak Leaf Dr, Chestertown, MD 21620
    • 109 Lyons Ln, Chestertown, MD 21620
      109 Lyons Ln, Chestertown, MD 21620
      109 Lyons Ln, Chestertown, MD 21620
      /32

      Est $583,165 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft

      109 Lyons Ln, Chestertown, MD 21620

      109 Lyons Ln, 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
  • 109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    /38

    $389,900 Sold Feb 06, 2025

    • 1,344 Sq Ft
    • $290/SF
    • 40 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    109 Grant Ct, Chestertown, MD 21620

    This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect blend of comfort and modern features. Located in a tranquil setting that backs to farmland, it boasts an open floor plan with cathedral ceilings, creating a spacious and airy atmosphere throughout. The upgraded kitchen with stainless steel appliances that make it ideal for both cooking and entertaining. The

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    109 Grant Ct, Chestertown, MD 21620
    • 2010 Mcginnes Rd, Chestertown, MD 21620
      2010 Mcginnes Rd, Chestertown, MD 21620
      2010 Mcginnes Rd, Chestertown, MD 21620
      /27

      Est $360,100 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,253 Sq Ft

      2010 Mcginnes Rd, Chestertown, MD 21620

      2010 Mcginnes 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
  • 110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    110 Birch Run Rd, Chestertown, MD 21620
    /29

    $600,000 Sold Feb 06, 2025

    • 2,672 Sq Ft
    • $225/SF
    • 155 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2007

    110 Birch Run Rd, Chestertown, MD 21620

    CUSTOM - BUILT 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome maple flooring throughout the central living

    Paula Ruckelshaus Long & Foster Real Estate, Inc.

    110 Birch Run Rd, Chestertown, MD 21620
    • 106 Goose Roost Ln, Chestertown, MD 21620
      106 Goose Roost Ln, Chestertown, MD 21620
      106 Goose Roost Ln, Chestertown, MD 21620
      /53

      Est $681,106 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 5,366 Sq Ft

      106 Goose Roost Ln, Chestertown, MD 21620

      106 Goose Roost Ln, 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

Showing Results 81 - 120, Page 3 of 18

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