6,882

Chestertown, MD Homes

Section Image
    • 502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      /45

      Est $405,063 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • 1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    /27

    $289,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    1106 Round Top Rd, Chestertown, MD 21620

    Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start

    Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
  • 10572 Klamath Rd, Chestertown, MD 21620
    10572 Klamath Rd, Chestertown, MD 21620
    10572 Klamath Rd, Chestertown, MD 21620
    /27

    $269,900 Sold Sep 20, 2024

    • 1,232 Sq Ft
    • $219/SF
    • 70 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    10572 Klamath Rd, Chestertown, MD 21620

    Sellers offering $10,000 credit toward cosmetic repairs or settlement!!!! Cute rancher in Chesapeake Landing. Nice front porch. Large living room with a woodstove with brick hearth and mantle. Laminate flooring throughout most of the house. 3 bedrooms and 2 full baths. Guest bathroom is a great size and also contains the washer dryer. Stainless appliances. Kitchen Island. Nice sized lot

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    10572 Klamath Rd, Chestertown, MD 21620
    • 111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      /44

      Est $400,236 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      111 Manor Ave, Chestertown, MD 21620

      111 Manor Ave, Chestertown, MD 21620
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /22

    $485,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    101 S Mill St, Chestertown, MD 21620

    Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • 109 Birch Run Rd, Chestertown, MD 21620
    109 Birch Run Rd, Chestertown, MD 21620
    109 Birch Run Rd, Chestertown, MD 21620
    /54

    $450,000 Sold Sep 16, 2024

    • 1,428 Sq Ft
    • $315/SF
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    109 Birch Run Rd, Chestertown, MD 21620

    This 3 bedroom 2.5 bathroom Cape Cod has been recently updated and is located on one of Chestertown’s most desired streets. The sunroom provides a wonderful connection with nature. The newly added en suite bathroom with double vanity for the primary bedroom adds convenience and luxury. Dual zoned A/C ensures a refreshing summer and the wood burning fireplace provides a great extra boost of heat

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    109 Birch Run Rd, Chestertown, MD 21620
    • 8610 Camp Rd, Chestertown, MD 21620
      8610 Camp Rd, Chestertown, MD 21620
      8610 Camp Rd, Chestertown, MD 21620
      /40

      Est $425,915 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      8610 Camp Rd, Chestertown, MD 21620

      8610 Camp Rd, Chestertown, MD 21620
  • 116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    /38

    $289,500 Under Contract

    • 2 Beds
    • 4 Baths
    • 1,867 Sq Ft

    116 Oak Leaf Dr, Chestertown, MD 21620

    Charming & Move-In ReadyDiscover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come.The spacious master suite features vaulted ceilings,

    Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
  • 105 Coleman Dr, Chestertown, MD 21620
    105 Coleman Dr, Chestertown, MD 21620
    105 Coleman Dr, Chestertown, MD 21620
    /45

    $440,000 Sold Sep 16, 2024

    • 2,128 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    105 Coleman Dr, Chestertown, MD 21620

    KINGS COURT! This Colonial, sited on an acre of land, is move-in ready and boasts so many wonderful features! Here are just some that are sure to pique your interest! Freshly painted; gleaming floors; stainless steel appliances; lots of counter and cabinet space; breakfast room; separate pantry space; family room with large picture window; fireplace with stainless steel liner; newer LG washer and

    Jenn Klarman Long & Foster Real Estate, Inc.

    105 Coleman Dr, Chestertown, MD 21620
    • 207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      /44

      Est $628,442 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft

      207 N Queen St, Chestertown, MD 21620

      207 N Queen St, Chestertown, MD 21620
  • 109 Tamarack Rd, Chestertown, MD 21620
    109 Tamarack Rd, Chestertown, MD 21620
    109 Tamarack Rd, Chestertown, MD 21620
    /53

    $324,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    109 Tamarack Rd, Chestertown, MD 21620

    Welcome to this beautiful 3-level Colonial in the sought-after Chester Harbor community on the Queen Anne’s County side! Nestled on a private lot, this home offers timeless charm, modern updates, and access to the water. Inside, you'll find three spacious bedrooms with newer carpeten upstairs with a full bathroom, while the main level features a large kitchen, dining room, and a cozy sitting area

    Crystal Smith RE/MAX Executive

    109 Tamarack Rd, Chestertown, MD 21620
  • 112 Sheaffer Rd, Chestertown, MD 21620
    112 Sheaffer Rd, Chestertown, MD 21620
    112 Sheaffer Rd, Chestertown, MD 21620
    /48

    $486,000 Sold Sep 13, 2024

    • 2,864 Sq Ft
    • $170/SF
    • 52 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1989

    112 Sheaffer Rd, Chestertown, MD 21620

    Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort.Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the

    Retha Arrabal Doug Ashley Realtors, LLC

    112 Sheaffer Rd, Chestertown, MD 21620
    • 201 Radcliffe Dr, Chestertown, MD 21620
      201 Radcliffe Dr, Chestertown, MD 21620
      201 Radcliffe Dr, Chestertown, MD 21620
      /50

      Est $750,648 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,736 Sq Ft

      201 Radcliffe Dr, Chestertown, MD 21620

      201 Radcliffe Dr, Chestertown, MD 21620
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /66

    $5,500,000 Under Contract

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Lands End Rd, Chestertown, MD 21620

    Beautifully situated on the east fork of Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. Sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • 305 Pine Tree Rd, Chestertown, MD 21620
    305 Pine Tree Rd, Chestertown, MD 21620
    305 Pine Tree Rd, Chestertown, MD 21620
    /17

    $260,000 Sold Sep 13, 2024

    • 826 Sq Ft
    • $315/SF
    • 298 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    305 Pine Tree Rd, Chestertown, MD 21620

    BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main

    Kaitlyn Collins Benson & Mangold, LLC

    305 Pine Tree Rd, Chestertown, MD 21620
    • 21715 Tolchester Beach Rd, Chestertown, MD 21620
      21715 Tolchester Beach Rd, Chestertown, MD 21620
      21715 Tolchester Beach Rd, Chestertown, MD 21620
      /29

      Est $167,507 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft

      21715 Tolchester Beach Rd, Chestertown, MD 21620

      21715 Tolchester Beach Rd, Chestertown, MD 21620
  • 23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    /37

    $309,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,272 Sq Ft

    23315 Sandpiper Rd, Chestertown, MD 21620

    Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax

    Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, Chestertown, MD 21620
  • 8500 Broad Neck Rd, Chestertown, MD 21620
    8500 Broad Neck Rd, Chestertown, MD 21620
    8500 Broad Neck Rd, Chestertown, MD 21620
    /25

    $430,000 Sold Sep 11, 2024

    • 2,240 Sq Ft
    • $192/SF
    • 42 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2014

    8500 Broad Neck Rd, Chestertown, MD 21620

    This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2 pantry's. This home has a Large living and Dining room too! The 'Florida Sunroom' allows could be an office or a place to read a book in the sunshine and the

    Ginny Dauses Coldwell Banker Waterman Realty

    8500 Broad Neck Rd, Chestertown, MD 21620
    • 215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      /30

      Est $353,426 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft

      215 Devon Dr, Chestertown, MD 21620

      215 Devon Dr, Chestertown, MD 21620
  • 202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    /37

    $290,000 Pre-Foreclosure

    • 3 Beds
    • 1 Bath
    • 1,252 Sq Ft

    202 Glen St, Chestertown, MD 21620

    Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

    Debbie Meikle Doug Ashley Realtors, LLC

    202 Glen St, Chestertown, MD 21620
  • 21199 Iowa Ave, Chestertown, MD 21620
    21199 Iowa Ave, Chestertown, MD 21620
    21199 Iowa Ave, Chestertown, MD 21620
    /29

    $345,000 Sold Sep 10, 2024

    • 1,566 Sq Ft
    • $220/SF
    • 28 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    21199 Iowa Ave, Chestertown, MD 21620

    Charming Renovated Ranch Home in Tolchester EstatesWelcome to this beautifully renovated ranch home nestled in Tolchester Estates. Recently updated, this home offers a perfect blend of modern amenities and tranquil surroundings.As you step inside, you'll notice the new flooring throughout and fresh paint that creates a bright and inviting atmosphere. The remodeled kitchen is a chef's

    Thomas Huston Real Broker LLC

    21199 Iowa Ave, Chestertown, MD 21620
    • 110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      /69

      Est $504,889 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft

      110 Camelot Dr, Chestertown, MD 21620

      110 Camelot Dr, Chestertown, MD 21620
  • 118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    /34

    $269,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your

    Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
  • 10719 Mallard Point Rd, Chestertown, MD 21620
    10719 Mallard Point Rd, Chestertown, MD 21620
    10719 Mallard Point Rd, Chestertown, MD 21620
    /26

    $355,000 Sold Sep 06, 2024

    • 1,344 Sq Ft
    • $264/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2015

    10719 Mallard Point Rd, Chestertown, MD 21620

    Welcome to this charming raised rancher, built in 2015and located in the water-privileged community of Chesapeake Landing. This beautiful home features 3 spacious bedrooms and a desirable split bedroom floor plan, offering privacy and comfort for all. The open floor plan creates a seamless flow from room to room, enhancing both functionality and style, and offers a large kitchen with stainless

    Sarah King Cross Street Realtors LLC

    10719 Mallard Point Rd, Chestertown, MD 21620
    • 103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      /31

      Est $322,317 Not Listed For Sale

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

      103 Trafford Dr, Chestertown, MD 21620

      103 Trafford Dr, Chestertown, MD 21620
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    /27

    $285,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft

    100 Acorn Dr, Chestertown, MD 21620

    Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
  • 308 Landing Ln Unit 17, Chestertown, MD 21620
    308 Landing Ln Unit 17, Chestertown, MD 21620
    308 Landing Ln Unit 17, Chestertown, MD 21620
    /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
    • 208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      /41

      Est $379,949 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,537 Sq Ft

      208 N Mill St, Chestertown, MD 21620

      208 N Mill St, Chestertown, MD 21620
  • LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
  • 123 High St, Chestertown, MD 21620
    123 High St, Chestertown, MD 21620
    123 High 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
    • 123 N Queen St, Chestertown, MD 21620
      123 N Queen St, Chestertown, MD 21620
      123 N Queen St, Chestertown, MD 21620
      /54

      Est $576,659 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,659 Sq Ft

      123 N Queen St, Chestertown, MD 21620

      123 N Queen St, Chestertown, MD 21620
  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    /10

    $213,000

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    236 Merganser Dr, Chestertown, MD 21620

    Looking for that off the beaten path property, here it is! Property located in a water privileged community on the Chester River, access at end of road. Home offers a 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Subject is sold in as is condition, seller nor buyer can make any repairs. Property is owned by the US Dept. of HUD, HUD Case #241-770004. Insurability Code:

    Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
  • 6595 Quaker Neck Rd, Chestertown, MD 21620
    6595 Quaker Neck Rd, Chestertown, MD 21620
    6595 Quaker Neck Rd, 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
    • 10656 Millbrook Dr, Chestertown, MD 21620
      10656 Millbrook Dr, Chestertown, MD 21620
      10656 Millbrook Dr, Chestertown, MD 21620
      /36

      Est $358,209 Not Listed For Sale

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

      10656 Millbrook Dr, Chestertown, MD 21620

      10656 Millbrook Dr, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    /5

    $10,000 Pending

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Deposit: $5,000. Lot of land located in the Chestertown area of Kent County, MD.JUST MINUTES to the many attractions of the downtown Chestertown area. Easy access to major traffic artery Fairlee Rd. +/- 15,000 SF. Vacant lot of land.

    Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
  • 8757 Orchard Dr, Chestertown, MD 21620
    8757 Orchard Dr, Chestertown, MD 21620
    8757 Orchard 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
    • 202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      /34

      Est $396,436 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      202 Byford Dr, Chestertown, MD 21620

      202 Byford Dr, Chestertown, MD 21620
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    /43

    $327,750

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft

    10705 Millbrook Dr, Chestertown, MD 21620

    Welcome to 10705 Millbrook Drive, a charming Cape Cod-style home located in the desirable Chesapeake Landing community. This 3-bedroom, 2-bathroom residence offers comfortable living with modern updates, including bamboo flooring and a high-efficiency water heater. The open floor plan is perfect for entertaining, with a spacious living area and well-appointed kitchen featuring Meganite

    Edward Kowalski EXP Realty, LLC

    10705 Millbrook Dr, Chestertown, MD 21620
  • 8049 Quaker Neck Rd, Chestertown, MD 21620
    8049 Quaker Neck Rd, Chestertown, MD 21620
    8049 Quaker Neck Rd, 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
    • 9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      /69

      Est $1,141,748 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      9088 Point Ln, Chestertown, MD 21620

      9088 Point Ln, Chestertown, MD 21620

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