115

Homes for Sale in 21620

Section Image
  • 0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    /2

    $8,000

    • Land
    • 14,810 Sq Ft
    • $23,529 per Acre

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620

    Build Your Dream Home on Two Expansive Lots in Chesapeake Landing!15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks!Enjoy the charm of Chestertown living, just

    Rena Champaco EXP Realty, LLC

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    /9

    $450,000

    • Land
    • 12,477 Sq Ft
    • $1,570,925 per Acre

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620

    Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

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

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Listing will be removed September 30 until Spring 2027. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

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

    $829,000

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

    106 S Queen St, Chestertown, MD 21620

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

    Maryn LeClair Chesapeake Real Estate Associates, LLC

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

    $824,900

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

    8999 Orchard Dr, Chestertown, MD 21620

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

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • 329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    /10

    $568,900

    Coming Soon Sep 28
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    329 Union Church Rd, Chestertown, MD 21620

    Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own!Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a

    Heather Dolan Chesapeake Real Estate Associates, LLC

    329 Union Church Rd, Chestertown, MD 21620
  • 213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    /39

    $372,000

    $8K PRICE DROP
    • 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
  • 0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    /7

    $5,000

    • Land
    • 16,117 Sq Ft
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:10 AM. The list price is the suggested opening bid. Deposit: $5,000.This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    /32

    $304,000

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

    7464 Shortall St, Chestertown, MD 21620

    Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7464 Shortall St, 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

    $85,000

    $35K 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
  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $5,000

    $7K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable. Investors- this lot could possibly have public utilities available in the future!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $750,000

    $45K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $7,500,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 8276 Broad Neck Rd, Chestertown, MD 21620
    8276 Broad Neck Rd, Chestertown, MD 21620
    8276 Broad Neck Rd, Chestertown, MD 21620
    /82

    $1,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally well-maintained property offers a rare combination of privacy, space, versatility, and convenience.At the heart of the property is a beautifully maintained brick residence overlooking a picturesque private pond, creating a

    Hayley Norris Select Land & Homes, LLC

    8276 Broad Neck Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • 7712 Waterview Ln, Chestertown, MD 21620
    7712 Waterview Ln, Chestertown, MD 21620
    /2

    $659,999

    Open Sat 10AM - 2PM Coming Soon Sep 23
    • 3 Beds
    • 4 Baths
    • 2,716 Sq Ft

    7712 Waterview Ln, Chestertown, MD 21620

    Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre of land, this wonderfully renovated and well-maintained cape cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main floor primary suite and practical indoor / outdoor living spaces make this the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    7712 Waterview Ln, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900

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

    104 Little Harbor Way, Chestertown, MD 21620

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

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    /9

    $99,999

    • Land
    • 3,096 Sq Ft
    • $1,406,963 per Acre

    620 Cannon St, Chestertown, MD 21620

    Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available.

    Julie Santoboni Taylor Properties

    620 Cannon St, Chestertown, MD 21620
  • 8732 Elm Rd, Chestertown, MD 21620
    8732 Elm Rd, Chestertown, MD 21620
    8732 Elm Rd, Chestertown, MD 21620
    /22

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    8732 Elm Rd, Chestertown, MD 21620

    Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay,

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8732 Elm Rd, 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
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,495,000

    $155K PRICE DROP
    • 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
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, 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
  • 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
  • 124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    /23

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis

    Beth Green Doug Ashley Realtors, LLC

    124 Wilton Rd, Chestertown, MD 21620
  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    $23K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $314,000

    $30K PRICE DROP
    • 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

Showing Results 81 - 115, Page 3 of 3

Maryland Kent County Chestertown

Real Estate & Homes for Sale in 21620

How to Buy a Home How to Finance a Home How to Sell a Home

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

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group