34

Chestertown Homes for Sale

Section Image Section Image
  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $519,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

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

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

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

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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, 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

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    /27

    $290,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    107 Malone Ave, Chestertown, MD 21620

    Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay

    Agent Photo

    Barbara McPhail

    Douglas Realty LLC

    (410) 705-2953

    107 Malone Ave, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

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

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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

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

    $185,000

    • Land
    • 1.95 Acres
    • $94,872 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
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /20

    $165,000

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /26

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Cross Street Realtors LLC

    109 S College Ave, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /46

    $619,000

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

    206 S Water St, Chestertown, MD 21620

    Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $499,999

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

    101 Birch Run Rd, Chestertown, MD 21620

    Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 AcresDiscover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout.Step inside to find a

    Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
  • 206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    /37

    $615,000

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft

    206 Valley Rd, Chestertown, MD 21620

    Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
  • 100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    /71

    $515,000

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /37

    $499,900

    • 4 Beds
    • 2 Baths
    • 2,220 Sq Ft

    515 N Kent St, Chestertown, MD 21620

    Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming

    Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $695,000

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /23

    $470,000

    • 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
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /9

    $499,999 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    LOCATION! This stunning 4-bedroom, 2-full-bath home is just steps from Washington College and a short stroll to downtown Chestertown. This treasure is full of historic character blended with modern updates!Sellers have INVESTED 60,000 IN RECENT UPGRADES this year, including a brand NEW roof, new electric wiring throughout the entire house, privacy fencing, fresh interior paint, and crawl

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /2

    $425,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    /43

    $250,000

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft

    112 Silver Heel Dr, Chestertown, MD 21620

    AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a

    Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /20

    $269,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $389,900

    • Studio
    • 1,728 Sq Ft

    517 High St, Chestertown, MD 21620

    Fantastic investment opportunity. Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit-

    Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
  • 112 Silver Heel Rd, Chestertown, MD 21620
    112 Silver Heel Rd, Chestertown, MD 21620
    112 Silver Heel Rd, Chestertown, MD 21620
    /43

    $374,900

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft

    112 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space.The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped

    Federico Busacca EXP Realty, LLC

    112 Silver Heel Rd, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    /19

    $315,000

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Price improvement! 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 promenade. Upstairs is a large, sun-filled room with a spacious closet that serves as an office. It could also be a den or sitting room.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /20

    $249,950

    • 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 a spacious back yard. A new shed recently installed for

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $167,000

    • 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
  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    /10

    $62,400

    • 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
  • 624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    624 High 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
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /52

    $1,395,500

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

    105 High St, Chestertown, MD 21620

    ***Photos reflect the progress as of 3 months ago. The property is now completed and is simply awaiting a the gas log sets for the fireplaces. A superb level of craftsmanship and scope of work not to be missed.*** Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy home on Chestertown Historic District’s most prominent

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, 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
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, 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
  • 0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, 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
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /25

    $259,900 New Construction

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

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this October. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
Maryland Kent County Chestertown Chestertown

Real Estate & Homes for Sale in Chestertown, Chestertown

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 $402,000. If you put a 20% down payment of $80,400 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $1,960 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $84K 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 and Long Bar Harbor.
Learn more about living in Chestertown

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 53 days on the market compared to the national average of 53 days. The median sale price for homes in Chestertown, MD over the last 12 months is $370,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$455,000
Median Townhouse Sale Price
$263,750
Median 2 Bedroom Sale Price
$399,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
28
Last 12 months Home Sales
58
Months of Supply
5.80
Median List Price
$402,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group