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Newest Homes for Sale in Chestertown, MD

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

    $449,900

    • 3 Beds
    • 3 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
  • 10572 Watonga Rd, Chestertown, MD 21620
    10572 Watonga Rd, Chestertown, MD 21620
    10572 Watonga Rd, Chestertown, MD 21620
    /20

    $325,000

    Open House 6/13 Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10572 Watonga Rd, Chestertown, MD 21620

    Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the

    Samantha Zarnes Serhant

    10572 Watonga Rd, Chestertown, MD 21620
  • 25440 Learman Rd, Chestertown, MD 21620
    25440 Learman Rd, Chestertown, MD 21620
    25440 Learman Rd, Chestertown, MD 21620
    /70

    $3,000,000

    • 3 Beds
    • 4 Baths
    • 3,142 Sq Ft

    25440 Learman Rd, Chestertown, MD 21620

    Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2

    Liddy Campbell TTR Sotheby's International Realty

    25440 Learman Rd, Chestertown, MD 21620
  • 100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    /21

    $215,000

    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft

    100 Prospect St, Chestertown, MD 21620

    Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything.Most homes in this price range make you choose: updated systems or a great location. This one delivers both.Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the

    David Moore Real Broker, LLC

    100 Prospect 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
    /49

    $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 a deeded 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 deeded 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
  • 202 Royston Shores Rd, Chestertown, MD 21620
    202 Royston Shores Rd, Chestertown, MD 21620
    202 Royston Shores Rd, Chestertown, MD 21620
    /72

    $1,200,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    202 Royston Shores Rd, Chestertown, MD 21620

    Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living.Unlike many waterfront properties, the level lot provides easy access from the home to

    Jody Baker Cross Street Realtors LLC

    202 Royston Shores Rd, Chestertown, MD 21620
  • 1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    /5

    $265,000

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

    1904 Pondtown Rd, Chestertown, MD 21620

    Welcome to country living at its finest! Nestled on approximately 2.64 acres, this solid brick rancher offers nearly 2,000 square feet of living space and endless 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

    Lonnie Gilmore Keller Williams Flagship

    1904 Pondtown Rd, Chestertown, MD 21620
  • 1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    /2

    $110,000

    Coming Soon
    • 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
  • 522 High St, Chestertown, MD 21620
    522 High St, Chestertown, MD 21620
    522 High St, Chestertown, MD 21620
    /15

    $450,000

    • 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
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,650,000

    Coming Soon
    • 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
  • 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
  • 24295 Langford Rd, Chestertown, MD 21620
    24295 Langford Rd, Chestertown, MD 21620
    24295 Langford Rd, Chestertown, MD 21620
    /73

    $445,000

    Open Sat 2:30PM - 4:30PM
    • 2 Beds
    • 2.5 Baths
    • 1,857 Sq Ft

    24295 Langford Rd, Chestertown, MD 21620

    Welcome to 24295 Langford Road in Chestertown, Maryland—a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you’ve been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    24295 Langford Rd, Chestertown, MD 21620
  • 110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    /30

    $525,000

    • 3 Beds
    • 1.5 Baths
    • 1,785 Sq Ft

    110 S Queen St, Chestertown, MD 21620

    Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

    J.P. Graham Cross Street Realtors LLC

    110 S Queen St, 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

    $339,900

    • 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
    /51

    $399,000

    Open Sat 12PM - 2PM $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    240 Merganser Dr, Chestertown, MD 21620

    Practically brand new and just 2 years young, 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 the Chester River—you can drive

    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
    /3

    $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 Wednesday, June 3rd, and ends Monday, June 8, 2026 at 1:30PM. 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

    $395,000

    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to this stunning 2023-built home with well-designed architectural elevations! The curb appeal captures your attention and the moment you arrive, the welcoming front porch invites you to slow down, relax; imagine enjoying a glass of iced tea from your favorite wicker chair! Step through the Craftsman style front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /38

    $322,500

    $7K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas

    Dawn Kane Redfin Corporation

    304 Hadaway Dr, Chestertown, MD 21620
  • 228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    /13

    $75,000

    $24K PRICE DROP
    • Land
    • 22,215 Sq Ft
    • $147,059 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
  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /57

    $798,000

    $30K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • 103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    /66

    $419,900

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,944 Sq Ft

    103 Trafford Dr, Chestertown, MD 21620

    PRICE IMPROVEMENT: exceptional value! Priced BELOW 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Trafford Dr, Chestertown, MD 21620
  • 116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    /9

    $109,999

    • Land
    • 7,840 Sq Ft
    • $611,106 per Acre

    116 N Cross St, Chestertown, MD 21620

    Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing

    Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
  • 24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    /29

    $229,990

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    24581 Willow Oak Ln, Chestertown, MD 21620

    If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

    Michele Palmer Doug Ashley Realtors, LLC

    24581 Willow Oak Ln, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /72

    $899,500

    New Construction $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft

    205 River Rd, Chestertown, MD 21620

    New price, same stunning home!!! Stop scrolling — this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly

    Karen Clark Clark & Co Realty, LLC

    205 River Rd, 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
    • 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
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $244,500

    $21K PRICE DROP
    • 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, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, 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

    (410) 936-3661

    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
  • 104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    /30

    $394,900

    $5K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,535 Sq Ft

    104 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,500 square feet of thoughtfully designed living space. With five bedrooms and three and a half bathrooms, this home provides the perfect balance of comfort, functionality, and flexibility for modern living.Step inside to an inviting foyer that leads to the bright and open main living area, where the family room

    David Moore Real Broker, LLC

    104 Flying Cloud Dr, 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

    $865,000

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 108 Pine St, Chestertown, MD 21620
    108 Pine St, Chestertown, MD 21620
    /2

    $115,000

    $28K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 910 Sq Ft

    108 Pine St, Chestertown, MD 21620

    Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+,

    David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
  • 139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    /28

    $225,000

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

    139 Prospect St, Chestertown, MD 21620

    Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

    Barbara McCaffrey Redfin Corp

    139 Prospect St, 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 $443,971.
Are home prices dropping in Chestertown?
Yes, home prices in Chestertown are down 7% in the last 12 months.
How many homes have sold over the last 12 months in Chestertown, MD?
103 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 $377,000. If you put a 20% down payment of $75,400 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,870 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K 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 $364,900, down 1% year-over-year. Homes in Chestertown sell in 51 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$364,900
Median Single Family Sale Price
$396,500
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
$211
Number of Homes for Sale
35
Last 12 months Home Sales
103
Months of Supply
4.10
Median List Price
$377,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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