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Chestertown Homes for Sale

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  • /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
  • /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
  • /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
  • /31

    $209,900

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft

    304 Hilltop Ln, Chestertown, MD 21620

    The townhouse is the second from the end and has three bedrooms and 2.5 baths. The slider door provides easy access to the patio and there is a stack washer on the main level, kitchen has the needed appliances. Located in Chestertown you can enjoy all of the amenities of this historic town, the Farmer's Market, Washington College is only a couple of minutes away, the many parks, marinas, and

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 824-5679

    304 Hilltop Ln, Chestertown, MD 21620
  • /22

    $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
  • /23

    $898,000 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
  • /23

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft

    205 Pine St, Chestertown, MD 21620

    Chestertown -Charming well maintained, landscaped, brick ranch home located in College Heights. Several blocks from Washington College, Hospital, Churches , restaurants, shopping, downtown, and the Chester River. Full basement with a portion used as a garage and the balance used for mechanical and laundry. There is a chair lift from the basement to the first floor, three bedrooms, living room,

    Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, Chestertown, MD 21620
  • /15

    $625,000

    • 1,600 Sq Ft

    26933 Mallard Rd, Chestertown, MD 21620

    Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • /38

    $648,750

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Four Baths! LOTS of storage in this nearly new construction! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This historic home located at Chestertown Marina has seen extensive remodel as recently as 2021. The first floor bedroom suite addition has a full bath, a sitting room, a walk-in closet, and a separate

    Beth Ostrander Doug Ashley Realtors, LLC

    206 S Water St, Chestertown, MD 21620
  • /23

    $495,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • /35

    $480,000

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    206 Barroll Dr, Chestertown, MD 21620

    Charming Rancher with Private Backyard Oasis in Byford Estates206 Barroll Drive, Chestertown, MDLocated in the highly desirable Byford Estates community, this well-maintained rancher offers a rare combination of one-level living, thoughtful layout, and exceptional outdoor space—all within walking distance to historic downtown Chestertown. Enjoy access to festivals, the renowned farmers

    Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
  • /22

    $549,000

    • 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 Encapsulated Crawl Space, New Roof with 50-year shingles and a transferable warranty, new water and sewer lines

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • /4

    $325,000 Coming Soon

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Cute as a button in the historic district on South Kent St. This 1 bedroom, 1.5 bath home is in the center of town within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown"s waterfront promonad. There is potential for a second bedroom upstairs if you add a wall between the bedroom and the sitting area. Adorable backyard. Perfect for one or

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, Chestertown, MD 21620
  • /16

    $175,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, Chestertown, MD 21620
  • /34

    $299,000

    • Studio
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    This duplex is a prime investment located on Washington Avenue in historic Chestertown, Maryland, offering many amenities. It is within walking distance of shopping, entertainment, schools, and medical facilities. Unit A is freshly updated with a spacious living room and dining room. The kitchen offers lots of storage and a stackable washer/dryer. It is a 2-bedroom apartment with a full bath. The

    Kathleen Brenton Brenton Realty Group

    866 Washington Ave, Chestertown, MD 21620
  • /10

    $64,890

    • 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
  • /3

    $240,000

    • 2 Beds
    • 1 Bath
    • 1,290 Sq Ft

    624 High St, Chestertown, MD 21620

    Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or

    Nicole Stephens Tesla Realty Group, LLC

    624 High St, Chestertown, MD 21620
  • /10

    $74,900

    • 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
  • /42

    $1,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,789 Sq Ft

    26875 Mallard Rd, Chestertown, MD 21620

    Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, you’re immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom.The fully renovated chef’s kitchen features

    Lynn Hilfiker Gunther-McClary Real Estate

    26875 Mallard Rd, Chestertown, MD 21620
  • /20

    $220,000

    • 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

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • /52

    $1,395,500

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

    105 High St, Chestertown, MD 21620

    Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /22

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • /5

    $225,000

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • /7

    $250,000

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • /33

    $395,000

    • 7 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    349 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 High St, Chestertown, MD 21620
  • /47

    $395,000

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • /3

    $20,000

    • Land
    • 0.09 Acre
    • $222,222 per Acre

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
  • /9

    $1,150,000

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620
  • /6

    $280,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to the back yard. A new shed was just installed for extra

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • /3

    $199,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location!Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation

    Anastasia Zivkovic Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620

Frequently Asked Questions Why Live in Chestertown

Is Chestertown a good place to live?
Chestertown is a good place to live. Chestertown is considered very car-dependent and somewhat bikeable. Chestertown is a neighborhood with a crime score of 4, on par with the average neighborhood in the U.S. Chestertown has 3 parks for recreational activities. It has a median age of 38. The average household income is $84,271 which is below the national average. College graduates make up 40.5% of residents. A majority of residents in Chestertown are renters, with 50.5% of residents renting and 49.5% of residents owning their home. A local real estate agent serving Chestertown can help you decide if this neighborhood is the right one for you. Learn more on our Chestertown neighborhood guide.
Is Chestertown, MD a safe neighborhood?
Chestertown, MD is a safe neighborhood and is on par with the average neighborhood in the United States. It received a crime score of 4 out of 10.
How much do you need to make to afford a house in Chestertown?
The median home price in Chestertown is $940,915. If you put a 20% down payment of $188,200 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $4,870 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $209K a year to afford the median home price in Chestertown. The average household income in Chestertown is $84K.
What are the best public schools in Chestertown?
The best public schools that serve Chestertown are:
What are the best private schools in Chestertown?
The best private schools that serve Chestertown are:
What are the most popular zip codes in Chestertown, Chestertown, MD?
The most popular zip codes in Chestertown, Chestertown, MD include 21620, 21678, 21623, 21645 and 21667.
What are the most popular neighborhoods near Chestertown, Chestertown, MD?
The most popular neighborhoods near Chestertown, Chestertown, MD are Kingstown, Evergreen Park/Holly Beach, Old Philadelphia, Stepney and Hollywoods.

Home Trends in Chestertown, MD

Housing Trends

Median Sale Price
$359,990
Median Townhouse Sale Price
$359,990
Average Price Per Sq Ft
$247
Number of Homes for Sale
1
Last 12 months Home Sales
1
Months of Supply
12.00
Median List Price
$940,915
Median Change From 1st List Price
6%
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