188

Recently Sold Chestertown, MD Homes

Section Image
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    /22

    $175,000 Sold Jul 25, 2025

    • 896 Sq Ft
    • $195/SF
    • 85 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    110 Philosophers Terrace, Chestertown, MD 21620

    Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

    Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • 619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    /9

    $190,500 Sold Jul 22, 2025

    • 882 Sq Ft
    • $216/SF
    • 50 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    619 Cannon St, Chestertown, MD 21620

    Buyer Financing fell through, so their loss is your gain! Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect

    Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    /18

    $205,000 Sold Jul 18, 2025

    • 1,216 Sq Ft
    • $169/SF
    • 24 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    310 Hilltop Ln, Chestertown, MD 21620

    Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn

    Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
  • 420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    /39

    $350,000 Sold Jul 18, 2025

    • 1,080 Sq Ft
    • $324/SF
    • 29 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    420 Cannon St, Chestertown, MD 21620

    Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fronts on historic Cannon Street and is surrounded by the new Cannon Square development. Enjoy it in comfort now with plenty of room for new equity over time: Maybe double the house? Add a first floor bedroom suite? A garage? (As

    Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
  • 314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    /45

    $485,000 Sold Jul 18, 2025

    • 3,420 Sq Ft
    • $142/SF
    • 79 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2010

    314 Devon Dr, Chestertown, MD 21620

    Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in every room. From the moment you step into the grand foyer, you’ll feel the openness and care that’s gone into every detail.The heart of the home is the spacious kitchen, featuring a large island that’s perfect for prepping meals, gathering with friends, or simply enjoying

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    • 4,401 Sq Ft
    • $181/SF
    • 2 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1963

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $410,000 Sold Jul 08, 2025

    • 1,656 Sq Ft
    • $248/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1916

    222 Mount Vernon Ave, Chestertown, MD 21620

    Lovingly maintained, this charming home in Chestertown’s Historic District seamlessly blends classic character with modern comfort. Restored windows, original yellow heart pine floors, and cypress siding reflect its rich history, while newer appliances, a high-efficiency boiler, tankless on-demand hot water, 3-zone heating, and leaf filter system provide everyday ease. The third floor offers

    Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    /5

    $285,000 Sold Jul 08, 2025

    • 2,142 Sq Ft
    • $133/SF
    • 8 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    10141 Flatland Rd, Chestertown, MD 21620

    Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with electric and three garage doors. There is a shed that improvements have started on, but not complete. Property has two bedrooms and one bath, with a traditional floor plan typical for a farmhouse style home. The kitchen is in

    Retha Arrabal Doug Ashley Realtors, LLC

    10141 Flatland Rd, Chestertown, MD 21620
  • 25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    /39

    $550,000 Sold Jul 01, 2025

    • 2,010 Sq Ft
    • $274/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1992

    25285 Foxchase Dr, Chestertown, MD 21620

    Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
  • 7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    /56

    $759,000 Sold Jul 01, 2025

    • 3,394 Sq Ft
    • $224/SF
    • 2 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2000

    7988 Aldan Dr, Chestertown, MD 21620

    This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

    Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    /34

    $237,000 Sold Jun 30, 2025

    • 1,384 Sq Ft
    • $171/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1967

    898 Washington Ave, Chestertown, MD 21620

    This ranch property most recently was used as an accountants office and at one time a residential rental. The Village zoning allows for many uses. This could easily be turned back into a primary residence or an investment rental property. There are wood floors throughout most of the of the house with laminate flooring in the kitchen area. The HVAC heat pump is relatively new. There is a full

    Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
  • 201 Pondview Ct, Chestertown, MD 21620
    201 Pondview Ct, Chestertown, MD 21620
    201 Pondview Ct, Chestertown, MD 21620
    /37

    $525,000 Sold Jun 30, 2025

    • 3,016 Sq Ft
    • $174/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    201 Pondview Ct, Chestertown, MD 21620

    Impeccably maintained and thoughtfully upgraded, this custom-designed home is a true standout! Situated on over a half-acre just outside of town limits, this property offers the perfect blend of peace and convenience—within walking and biking distance to shopping, dining, and all the charm the town has to offer.Step inside to discover a warm, welcoming interior featuring gorgeous hardwood

    Jody Baker Cross Street Realtors LLC

    201 Pondview Ct, Chestertown, MD 21620
  • 200 Hoffman Ln, Chestertown, MD 21620
    200 Hoffman Ln, Chestertown, MD 21620
    200 Hoffman Ln, Chestertown, MD 21620
    /8

    $360,000 Sold Jun 27, 2025

    • 1,128 Sq Ft
    • $319/SF
    • 15 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1957

    200 Hoffman Ln, Chestertown, MD 21620

    Investor’s Dream on the Chester River – 1.75 Acres with Endless Potential!Welcome to a rare opportunity along the stunning Chester River! This unique property combines two parcels totaling 1.75 acres and includes an 1100+ square foot home, with an additional 750+sq ft of unfinished space with a garage door, that’s ready for your vision. Whether you're a seasoned investor, a savvy flipper, or

    Joelle Dolch Cross Street Realtors LLC

    200 Hoffman Ln, 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

    $1,062,800 Sold Jun 27, 2025

    • 3,078 Sq Ft
    • $345/SF
    • 37 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1975

    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
  • 26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    /49

    $840,000 Sold Jun 27, 2025

    • 3,355 Sq Ft
    • $250/SF
    • 182 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1963

    26865 Mallard Rd, Chestertown, MD 21620

    A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles,

    Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
  • 305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    /28

    $549,000 Sold Jun 26, 2025

    • 2,476 Sq Ft
    • $222/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1930

    305 Washington Ave, Chestertown, MD 21620

    Wonderful Chestertown home with many endearing features including spacious rooms, hardwood floors, full basement, off street parking and more. Located across from the Washington College lawn and a block from the local hospital, this home is also ideally situated within walking distance to Historic downtown Chestertown, the Chester River, Kent Plaza, Starbucks and the Chestertown Middle and

    William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /2

    $119,500 Sold Jun 26, 2025

    • Land
    • 1.01 Acres
    • $118,317 per Acre
    • 2 Days On Market

    205 River Rd, Chestertown, MD 21620

    A perc approved one acre open lot in a an established neighborhood ready for your dream home. No trees to clear and no restrictions except Critical Area guidelines. Perfectly located within a couple of minutes to downtown Historic Chestertown.

    Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
  • 9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    9050 Point Ln, Chestertown, MD 21620
    /71

    $745,000 Sold Jun 26, 2025

    • 3,166 Sq Ft
    • $235/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2000

    9050 Point Ln, Chestertown, MD 21620

    Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet and friendly community of Tolchester Estates. This wonderful home is nestled just 10–15 minutes from the cities of Chestertown and Rock Hall. This close proximity provides access to shopping, restaurants, a farmers market, theater and local arts. The area abounds with

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
  • 213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    /3

    $675,000 Sold Jun 25, 2025

    • 1,945 Sq Ft
    • $347/SF
    • 2 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1904

    213 N Queen St, Chestertown, MD 21620

    A 3 car garage in the Historic District! With a rare combination of desirable features including comfortable modern amenities, this historic home will likely find its new owner quickly! Highlights of the interior include a roomy Family Room between the open concept Kitchen and the Courtyard, a formal Dining Room with a bay window, a front Living Room with gas fireplace, a formal Entry Hall, two

    Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
  • 109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    /24

    $344,900 Sold Jun 25, 2025

    • 1,344 Sq Ft
    • $257/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    109 Edmore Rd, Chestertown, MD 21620

    Welcome to 109 Edmore Rd, a beautifully renovated 3-bedroom, 2-bath ranch-style home offering 1,344 sq. ft. of comfortable living space on a 0.34-acre lot. This move in ready home blends modern upgrades with cozy charm. Renovated in 2021 upgrades include HVAC, Roof, Encapsulated crawl space, appliances, reverse osmosis and water conditioner. Features a 16 x 12 screen porch for relaxing outdoors.

    Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
  • 811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    /45

    $459,000 Sold Jun 23, 2025

    • 2,064 Sq Ft
    • $222/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    811 S Meadowview Dr, Chestertown, MD 21620

    Charming and Immaculately Maintained One-Level HomeStep onto the inviting front porch of this meticulously cared-for home, where every detail shines both inside and out. Featuring a thoughtful and spacious floor plan, this home offers a primary suite at one end and two additional bedrooms with a full bath at the opposite end for added privacy. In the heart of the home, you'll find a cozy

    Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000 Sold Jun 20, 2025

    • 1,188 Sq Ft
    • $263/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    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
  • 325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    /61

    $525,000 Sold Jun 13, 2025

    • 4,086 Sq Ft
    • $128/SF
    • 7 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    325 Devon Dr, Chestertown, MD 21620

    Welcome to this expansive, move-in-ready colonial in the sought-after Coventry Farms II community. Built in 2011 with all available square footage upgrades, this home offers over 4,300 sq ft of thoughtfully designed living space across three levels. This beautiful Colonial offers 4 bedrooms and 2.5 bathrooms Main Level Highlights: Open-concept floor plan with hardwood flooringFormal living and

    Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

    325 Devon Dr, Chestertown, MD 21620
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $312,000 Sold Jun 13, 2025

    • 1,404 Sq Ft
    • $222/SF
    • 55 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1959

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

    $360,000 Sold Jun 12, 2025

    • 1,724 Sq Ft
    • $209/SF
    • 16 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2022

    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
  • 1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    /8

    $86,000 Sold Jun 09, 2025

    • 973 Sq Ft
    • $88/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1974

    1814 Pondtown Rd, Chestertown, MD 21620

    INVESTOR & BUILDER ALERT! 2.69 Acres | No HOA | Unlock the potential of this prime 2.69-acre property in beautiful Queen Anne’s County! A rare opportunity with no HOA and no restrictions, giving you full creative freedom to bring your vision to life. Whether you're a savvy investor, builder, or contractor looking for your next project, this is the blank canvas you've been waiting for.The existing

    Joelle Dolch Cross Street Realtors LLC

    1814 Pondtown Rd, Chestertown, MD 21620
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    /27

    $280,000 Sold Jun 09, 2025

    • 1,930 Sq Ft
    • $145/SF
    • 164 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    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
  • 508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    /20

    $150,000 Sold Jun 06, 2025

    • 2,240 Sq Ft
    • $67/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1921

    508 Cannon St, Chestertown, MD 21620

    Duplex in the Historic District of Chestertown located near the rails to trails.

    Deborah Dawkins Coldwell Banker Realty

    508 Cannon St, 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

    $575,000 Sold Jun 06, 2025

    • 2,296 Sq Ft
    • $250/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1920

    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
  • 22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    /4

    $15,000 Sold Jun 02, 2025

    • Land
    • 0.48 Acre
    • $31,250 per Acre
    • 4 Days On Market

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

    $262,500 Sold May 29, 2025

    • 2,106 Sq Ft
    • $125/SF
    • 87 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1988

    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
  • 23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    /37

    $295,000 Sold May 29, 2025

    • 1,272 Sq Ft
    • $232/SF
    • 120 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1973

    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
  • 716 Aldora Dr, Chestertown, MD 21620
    716 Aldora Dr, Chestertown, MD 21620
    716 Aldora Dr, Chestertown, MD 21620
    /35

    $510,184 Sold May 29, 2025

    • 2,120 Sq Ft
    • $241/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    716 Aldora Dr, Chestertown, MD 21620

    DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout 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 bath for family and

    Terri Hill Builder Solutions Realty

    716 Aldora 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

    $11,000 Sold May 29, 2025

    • Land
    • 0.34 Acre
    • $32,353 per Acre
    • 371 Days On Market

    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
  • 5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    /40

    $750,000 Sold May 22, 2025

    • 1,682 Sq Ft
    • $446/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1956

    5594 Langford Bay Rd, Chestertown, MD 21620

    Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.The heart

    Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, 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

    $250,000 Sold May 22, 2025

    • 1,248 Sq Ft
    • $200/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    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
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /22

    $490,000 Sold May 21, 2025

    • 1,476 Sq Ft
    • $332/SF
    • 14 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1900

    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
  • 108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    /40

    $600,000 Sold May 16, 2025

    • 2,536 Sq Ft
    • $237/SF
    • 5 Beds
    • 2.5 Baths
    • Built 1920

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /8

    $50,000 Sold May 16, 2025

    • Land
    • 2.20 Acres
    • $22,727 per Acre
    • 159 Days On Market

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land

    William Norris Select Land & Homes, LLC

    0 Fairlee Rd, Chestertown, MD 21620
  • 308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    /32

    $782,500 Sold May 09, 2025

    • 2,204 Sq Ft
    • $355/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    308 Landing Ln, Chestertown, MD 21620

    Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for

    John Burke Gunther-McClary Real Estate

    308 Landing Ln, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 5

Maryland Chestertown

Recently Sold Real Estate & Homes in Chestertown, MD

Frequently Asked Questions Why Live in Chestertown

What is the average home price in Chestertown, MD?
Homes for sale in Chestertown, MD have an average home price of $510,588.
What is the average time to sell a house in Chestertown, MD?
The houses for sale in Chestertown, MD spend an average of 48 days on the market.
What is the number of active homes for sale in Chestertown, MD?
There are 5 active homes for sale in Chestertown, MD.
How many homes have sold over the last 12 months in Chestertown, MD?
57 homes have sold in Chestertown, MD over the last 12 months.
Learn more about living in Chestertown

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 48 days on the market compared to the national average of 70 days. The median sale price for homes in Chestertown, MD over the last 12 months is $495,000, up 82% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$495,000
Median Single Family Sale Price
$495,000
Median Townhouse Sale Price
$569,990
Median 2 Bedroom Sale Price
$565,000
Average Price Per Sq Ft
$303
Number of Homes for Sale
5
Last 12 months Home Sales
57
Months of Supply
1.10
Median List Price
$495,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
82%
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