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Newest Homes for Sale in Chestertown, MD

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  • 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 read 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
  • 109 Cedar St, Chestertown, MD 21620
    109 Cedar St, Chestertown, MD 21620
    109 Cedar St, Chestertown, MD 21620
    /22

    $325,000

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 1,397 Sq Ft

    109 Cedar St, Chestertown, MD 21620

    Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind

    Liddy Campbell TTR Sotheby's International Realty

    109 Cedar St, Chestertown, MD 21620
  • 409 Calvert St, Chestertown, MD 21620
    409 Calvert St, Chestertown, MD 21620
    409 Calvert St, Chestertown, MD 21620
    /9

    $155,000

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    409 Calvert St, Chestertown, MD 21620

    Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    409 Calvert St, Chestertown, MD 21620
  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    Open Sun 11AM - 1PM
    • 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
  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $344,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
  • 896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    /34

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

    A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • 210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    /12

    $735,000

    Open House 7/18 Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    210 N Queen St, Chestertown, MD 21620

    Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    210 N Queen St, Chestertown, MD 21620
  • 105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    /49

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, Chestertown, MD 21620
  • 22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    /88

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    22481 Goose Hollow Dr, Chestertown, MD 21620

    AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of

    Tom Atwood Keller Williams Legacy

    22481 Goose Hollow Dr, 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
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /39

    $515,000

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    101 S Mill St, Chestertown, MD 21620

    This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • 517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    /28

    $299,900

    $50K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    517 Round Top Rd, Chestertown, MD 21620

    An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been

    Barry Hess Keller Williams Flagship

    517 Round Top Rd, Chestertown, MD 21620
  • 104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    /27

    $239,900

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    104 Conley Dr, Chestertown, MD 21620

    Price Improvement! Now offered at $239,900Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a

    Heather Kooser Cummings & Co. Realtors

    104 Conley Dr, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • 104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    /26

    $284,900

    • 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
  • 234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    /3

    $100,000

    $20K PRICE DROP
    • 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 or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • 110 Prospect St, Chestertown, MD 21620
    110 Prospect St, Chestertown, MD 21620
    110 Prospect St, Chestertown, MD 21620
    /6

    $79,900

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft

    110 Prospect St, Chestertown, MD 21620

    Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This

    Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,650,000

    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • 1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    /4

    $110,000

    • Land
    • 1.93 Acres
    • $56,995 per Acre

    1906 Pondtown Rd, Chestertown, MD 21620

    Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes.

    Lonnie Gilmore Keller Williams Flagship

    1906 Pondtown Rd, Chestertown, MD 21620
  • 1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    /11

    $265,000

    • 3 Beds
    • 1 Bath
    • 1,967 Sq Ft

    1904 Pondtown Rd, Chestertown, MD 21620

    Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and privacy of a rural setting while still being conveniently located near Chestertown, Millington, and major commuter routes. The spacious lot provides room for gardening, recreation, hobbies, or simply enjoying the outdoors.

    Lonnie Gilmore Keller Williams Flagship

    1904 Pondtown Rd, Chestertown, MD 21620
  • 10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    /54

    $429,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10781 Fermoy Rd, Chestertown, MD 21620

    Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country

    David Moore Real Broker, LLC

    10781 Fermoy Rd, Chestertown, MD 21620
  • 213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    /39

    $380,000

    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • 21172 Wyoming Ave, Chestertown, MD 21620
    21172 Wyoming Ave, Chestertown, MD 21620
    /2

    $200,000

    • 4 Beds
    • 1 Bath
    • 2,920 Sq Ft

    21172 Wyoming Ave, Chestertown, MD 21620

    Great area and lot walking distance to the Chesapeake bay and Tolchester Marina. House is in need of rehab but offers quite a bit of upside in the lot and location. Buyer to verify all info

    Keith French Blue Star Real Estate, LLC

    21172 Wyoming Ave, Chestertown, MD 21620
  • 22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    /54

    $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
  • 522 High St, Chestertown, MD 21620
    522 High St, Chestertown, MD 21620
    522 High St, Chestertown, MD 21620
    /15

    $399,900

    $50K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,518 Sq Ft

    522 High St, Chestertown, MD 21620

    Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3

    Taylor Leaverton Benson & Mangold, LLC

    522 High St, Chestertown, MD 21620
  • 23741 L Rd, Chestertown, MD 21620
    23741 L Rd, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • 956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    /29

    $285,000

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • 0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
  • 102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    /41

    $329,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    102 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large

    Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
  • 240 Merganser Dr, Chestertown, MD 21620
    240 Merganser Dr, Chestertown, MD 21620
    240 Merganser Dr, Chestertown, MD 21620
    /55

    $365,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    240 Merganser Dr, Chestertown, MD 21620

    Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting.Enjoy easy access to

    Erin Anderson Chesapeake Real Estate Associates, LLC

    240 Merganser Dr, Chestertown, MD 21620
  • 23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    /4

    $6,000

    • Land
    • 30,056 Sq Ft
    • $8,696 per Acre

    23683 L Rd, Chestertown, MD 21620

    List Price is opening bid at online auction. Auction at or above $6,000. Bidding begins Saturday, July 4th, and ends Thursday, July 9, 2026 at 2:30 PM. 0.69± Acres of Unimproved Land in Chestertown, Kent County Zoning - Village (V) district. Is intended for:• Small, historic, or traditional rural villages• A mix of residential uses (mostly single-family homes, sometimes limited

    Larry Cooper Alex Cooper Auctioneers, Inc.

    23683 L Rd, Chestertown, MD 21620
  • 107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    /51

    $375,000

    $20K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • 228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    /13

    $59,999

    $39K PRICE DROP
    • Land
    • 22,215 Sq Ft
    • $117,645 per Acre

    228 Merganser Dr, Chestertown, MD 21620

    Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown

    Mae Nordhoff Benson & Mangold, LLC

    228 Merganser Dr, Chestertown, MD 21620
  • 214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    /26

    $340,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /2

    $135,000

    $15K PRICE DROP
    • Land
    • 1.8 Acres
    • $75,000 per Acre

    109 2nd St, Chestertown, MD 21620

    Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton,

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /22

    $259,900

    New Construction Open Sat 12PM - 4PM
    • 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 now. 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 walk-in

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /7

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    /16

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    208 Central Dr, Chestertown, MD 21620

    Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring

    Jennifer Pogoda Redfin Corp

    208 Central Dr, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring 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. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    226 S Water St, 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

Showing Results 1 - 40, Page 1 of 3

Maryland Kent County Chestertown

Newest Listings for Sale in Chestertown, MD

Frequently Asked Questions

What is the average home price in Chestertown, MD?
Homes for sale in Chestertown, MD have an average home price of $431,498.
Are home prices dropping in Chestertown?
Yes, home prices in Chestertown are down 11% in the last 12 months.
How many homes have sold over the last 12 months in Chestertown, MD?
96 homes have sold in Chestertown, MD over the last 12 months.
Is Chestertown, MD a safe city?
In general, the safest neighborhood in Chestertown, MD with lower crime scores is Kingstown.
What are the most popular zip codes in Chestertown, MD?
The most popular zip codes in Chestertown, MD include 21620, 21678, 21623, 21645 and 21661.
What are the most popular neighborhoods in Chestertown, MD?
The most popular neighborhood in Chestertown, MD with the most homes for sale is Kingstown.
How much do you need to make to afford a house in Chestertown?
The median home price in Chestertown is $357,450. If you put a 20% down payment of $71,500 and had a 30-year fixed mortgage with an interest rate of 6.43%, your estimated principal and interest payment would be $1,790 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $77K a year to afford the median home price in Chestertown. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chestertown, MD?
Chestertown, MD has highly rated public and private schools. Some of the best schools in Chestertown based on Niche Grades are Radcliffe Creek School, H.H. Garnett Elementary School and Kent County High School. The neighborhood in Chestertown with the highest rated schools is Kingstown. Browse all the schools in Chestertown, MD to learn more.

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $352,500, down 8% year-over-year. Homes in Chestertown sell in 49 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$352,500
Median Single Family Sale Price
$379,000
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$352,500
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$219
Number of Homes for Sale
32
Last 12 months Home Sales
96
Months of Supply
4.00
Median List Price
$357,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-8%
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