25

Chestertown, MD Homes for Sale with Garage

Section Image Section Image
  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    102 Little Harbor Way, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    104 Landing Ln, Chestertown, MD 21620
  • 204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    /46

    $565,000

    $47K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, Chestertown, MD 21620
  • 123 Heath Rd, Chestertown, MD 21620
    123 Heath Rd, Chestertown, MD 21620
    123 Heath Rd, Chestertown, MD 21620
    /54

    $349,000

    Open Thu 2PM - 4PM
    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    123 Heath Rd, Chestertown, MD 21620

    Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive

    Erin Anderson Chesapeake Real Estate Associates, LLC

    123 Heath Rd, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /44

    $1,245,500

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

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    /50

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    /26

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    104 Acorn Dr, Chestertown, MD 21620

    Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car

    Sarah King Cross Street Realtors LLC

    104 Acorn Dr, Chestertown, MD 21620
  • 218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    /45

    $499,999

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $385,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 10720 Foreston Rd, Chestertown, MD 21620
    10720 Foreston Rd, Chestertown, MD 21620
    10720 Foreston Rd, Chestertown, MD 21620
    /42

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    10720 Foreston Rd, Chestertown, MD 21620

    Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow

    Kathleen Eder Compass

    10720 Foreston Rd, Chestertown, MD 21620
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • 25750 Collins Ave, Chestertown, MD 21620
    25750 Collins Ave, Chestertown, MD 21620
    25750 Collins Ave, Chestertown, MD 21620
    /50

    $468,000

    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Charming Brick Rancher Near the Chester RiverThis custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home...Living Room: Walk

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /92

    $829,000

    $36K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic DistrictThe Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    /74

    $824,900

    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 7903 Radcliffe Rd, Chestertown, MD 21620
    7903 Radcliffe Rd, Chestertown, MD 21620
    7903 Radcliffe Rd, Chestertown, MD 21620
    /5

    $625,000

    Coming Soon
    • 3 Beds
    • 4 Baths
    • 4,037 Sq Ft

    7903 Radcliffe Rd, Chestertown, MD 21620

    This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to

    Erin Anderson Chesapeake Real Estate Associates, LLC

    7903 Radcliffe Rd, Chestertown, MD 21620
  • 21146 Montana Ave, Chestertown, MD 21620
    21146 Montana Ave, Chestertown, MD 21620
    21146 Montana Ave, Chestertown, MD 21620
    /56

    $289,900

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    21146 Montana Ave, Chestertown, MD 21620

    Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom,

    Jody Baker Cross Street Realtors LLC

    21146 Montana Ave, Chestertown, MD 21620
Maryland Kent County

Homes for Sale with Garage in Chestertown, MD

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $361,950, down 5% year-over-year. Homes in Chestertown sell in 42 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$361,950
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$262,400
Median 2 Bedroom Sale Price
$323,250
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
31
Last 12 months Home Sales
96
Months of Supply
3.90
Median List Price
$355,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 25 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chestertown, MD and find the perfect place to call 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 © 2026 CoStar Group