44

Chestertown, MD Houses for Sale

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  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,297,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory Ln, Chestertown, MD 21620
  • 9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    /45

    $698,000

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft

    9194 N Bayview Ave, Chestertown, MD 21620

    Stunning home and property with 180-degree views of the Chesapeake Bay.The home was completely remodeled in 2017 by Taylor Loughry Construction. Boasting a bright open floor plan with high-end finishing, vaulted ceilings with skylights, and beautifully landscaped outdoor space. Two bedrooms and two full bathrooms, open living space with a gourmet kitchen, and a large deck overlooking the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 650-6367

    9194 N Bayview Ave, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    /33

    $797,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    7514 Muirfield Dr, Chestertown, MD 21620

    Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 206-3727

    7514 Muirfield Dr, Chestertown, MD 21620
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    /66

    $868,000

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    Welcome to a rare opportunity for luxury waterfront living on the Chester River. This beautifully maintained 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space, thoughtfully designed to embrace both comfort and elegance. Set on 1.08 acres of lush, well-landscaped grounds, this exceptional 2001-built two-story residence offers a park-like, deep, well-landscaped and level

    Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /18

    $635,000

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    7729 Country Club Ln, Chestertown, MD 21620

    Country Club Estates - Live Where You Play – Just 1.5 Miles from Downtown Chestertown!Enjoy the ease of one-level living in a prime location near the Chester River Yacht & Country Club, where club members enjoy golf, poolside afternoons, and clubhouse dining are just a short walk away. The interior spanning 2,280 square feet offers a comfortable, continuous flow that makes everyday living

    Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /28

    $440,000 Open House 8/23

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    907 N Meadowview Dr, Chestertown, MD 21620

    COMING SOON!!Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /45

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Great opportunity to own a waterfront property on the scenic Chester River! This beautifully landscaped 3 bedroom, 2 bath home with a wraparound porch offers stunning views. There is an additional partially finished 700+/- sq ft space over the garage, filled with natural light and river views, ideal for extra bedrooms with bath, master bedroom or an in-law suite. Tucked away in a peaceful,

    Leo Kuneman Meredith Fine Properties

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • 10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    /20

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    10165 John Carvill Rd, Chestertown, MD 21620

    Beautiful Brick Rancher in Great Oak Estates – Chestertown, MDNestled on 1.33 acres in the desirable Great Oak Estates community, just a short walk or golf cart drive to Safe Harbor Great Oak Landing marina, restaurant and golf course. This spacious 2,700 sq. ft. brick rancher blends timeless craftsmanship with classic Eastern Shore charm. Built with solid construction, the home features

    Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /49

    $470,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 3,096 Sq Ft

    201 Boundary Ave, Chestertown, MD 21620

    Discover this spacious 4 BR 3 BA home offering 3,100 sq ft of living space on a 1⁄2 acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom,

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary 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
  • 209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    /62

    $815,000

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft

    209 Rivershore Rd, Chestertown, MD 21620

    WELCOME TO 209 RIVERSHORE RD., CHESTERTOWN MD.,, Your natural waterfront retreat on the Chester River. Enjoy your time outside or inside of this tranquil property. As you step inside of this open flowy home with natural wood floors you will see the kitchen which has been partially remodeled with SS appliances, new counters and plenty of cabinet space. Overlooking the large spacious dining area

    Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /58

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living.This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, 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
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, 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
  • 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
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, 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
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $559,900

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    $20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 224 Valley Rd, Chestertown, MD 21620
    224 Valley Rd, Chestertown, MD 21620
    /2

    $450,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft

    224 Valley Rd, Chestertown, MD 21620

    Impeccably maintained! One-level home offers easy living on a quiet street. Thoughtful updates and meticulous care are evident throughout, including a new vapor barrier in the crawl space, new attic fans, the list goes on and on! The spacious primary bedroom features a full en-suite bath, while the exterior boasts a beautifully landscaped yard and a new concrete patio surrounding the in-ground

    Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    /7

    $125,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    5700 Johnsontown Rd, Chestertown, MD 21620

    Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless.Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold

    Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown 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

    $325,000 Open Sat 11AM - 1PM

    • 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
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /36

    $424,000

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft

    600 Rosin Dr, Chestertown, MD 21620

    Nestled along the peaceful shores of Rosin Creek, this charming 3-bedroom, 2-bathroom waterfront cottage combines classic character with modern updates. Inside, the open floor plan creates a warm, inviting flow—perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas, all enhanced by updated flooring and

    Sarah King Cross Street Realtors LLC

    600 Rosin Dr, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect 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
  • 205 Pine St, Chestertown, MD 21620
    205 Pine St, Chestertown, MD 21620
    205 Pine 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
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /34

    $299,000

    • 3 Beds
    • 2 Baths
    • 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
  • 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
  • 10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    /34

    $309,999

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft

    10674 Kasota Rd, Chestertown, MD 21620

    Welcome to 10674 Kasota Rd – Your Tranquil Masterpiece on the Chesapeake's Edge. Nestled in the serene enclave of Chesapeake Landing near Chestertown, this charming 2-bed, 1-bath ranch-style home invites you to reimagine rural living on nearly 0.6 acres of lush landscape. With 1,350 sq ft of one–level living, the brick exterior and detached 2–car garage offers timeless appeal and solid bones with

    Andrew Kruzienski Long & Foster Real Estate, Inc.

    10674 Kasota Rd, 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
  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect 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
  • 26875 Mallard Rd, Chestertown, MD 21620
    26875 Mallard Rd, Chestertown, MD 21620
    26875 Mallard Rd, 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
  • 7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    /93

    $1,550,000

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft

    7961 Quaker Neck Rd, Chestertown, MD 21620

    **Exquisite Waterfront Retreat on Chester River**Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre

    Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, 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

    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
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /16

    $232,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /77

    $4,850,000

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

    23620 Lands End Rd, Chestertown, MD 21620

    80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, 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
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 2

Maryland Kent County Chestertown

Houses for Sale in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 60 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 $559,250, up 106% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$559,250
Median Single Family Sale Price
$495,000
Median Townhouse Sale Price
$680,000
Median 2 Bedroom Sale Price
$565,000
Average Price Per Sq Ft
$303
Number of Homes for Sale
6
Last 12 months Home Sales
86
Months of Supply
0.80
Median List Price
$565,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
106%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 44 houses for sale, offering an array of options for potential buyers. With houses priced between $62,400 to $4,850,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Chestertown is $565,000, while the average sale price is $540,763, offering insights into the local housing market. On average, houses spend 60 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chestertown, MD and find the perfect place to call home.

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