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Chestertown, MD Homes for Sale

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  • 404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    /11

    $19,500

    • Land
    • 43,124 Sq Ft
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Queen

    Dustin Parker The Parker Group

    404 Spring Rd, 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
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /2

    $150,000

    • Land
    • 1.8 Acres
    • $83,333 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
  • 0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:50 PM. 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 the Chester River. The area provides easy access to the major

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
  • 107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    /2

    $395,000 Coming Soon

    • 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, and imagine enjoying a glass of iced tea from your favorite wicker chair. Step through the handsome 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
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $9,500

    • Land
    • 14,810 Sq Ft
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

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

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    /73

    $1,600,000

    • 7 Beds
    • 5 Baths
    • 5,400 Sq Ft

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

    **Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 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

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    /6

    $8,000

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

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:55 PM. This auction takes place on the Ashland Auction Group Website Bidding Platform. List Price is Suggested Opening Bid. Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, 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

    $1,495,000

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

    8276 Broad Neck Rd, Chestertown, MD 21620

    Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8276 Broad Neck Rd, Chestertown, MD 21620
  • 0 Beltram Rd, Chestertown, MD 21620
    0 Beltram Rd, Chestertown, MD 21620
    0 Beltram Rd, Chestertown, MD 21620
    /6

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/1/2026 @ 10:00 AM. Bidding ends 6/3/2026 @ 12:30 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900 New Construction

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

    106 Landing Ln, Chestertown, MD 21620

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

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

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

    109 Wilton Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $385,000

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

    23043 Bay Shore Spur, Chestertown, MD 21620

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

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 22681 Wood Yard Ln, Chestertown, MD 21620
    22681 Wood Yard Ln, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 22,651 Sq Ft
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • 0 Kinglet Rd, Chestertown, MD 21620
    0 Kinglet Rd, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

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

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • 117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    /23

    $350,000

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft

    117 N Water St Unit 2B, 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 2B, 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

    $399,900

    • 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
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:45 PM. 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 the Chester River. The area provides easy access to the major

    Adam Shpritz Ashland Auction Group LLC

    0 Lenapah Rd, 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

    $130,000

    • 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
  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $384,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • 0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 4,791 Sq Ft
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • 0 Sheldrake Dr, Chestertown, MD 21620
    0 Sheldrake Dr, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 14,810 Sq Ft
    • $44,118 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, Chestertown, MD 21620
  • 23710 L Rd, Chestertown, MD 21620
    23710 L Rd, Chestertown, MD 21620
    /2

    $24,000

    • Land
    • 21,780 Sq Ft
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    23710 L Rd, 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

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    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 systems like the roof, HVAC, and water heater are all just a few years old,

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • 231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    /51

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 23,958 Sq Ft
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing 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 Open Sun 1PM - 3PM

    • 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
  • 0 Spinnaker Rd, Chestertown, MD 21620
    0 Spinnaker Rd, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900 New Construction

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

    35 Landing Ln, Chestertown, MD 21620

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

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 103 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
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • 0 Cromwell Clark Rd, Chestertown, MD 21620
    0 Cromwell Clark Rd, Chestertown, MD 21620
    0 Cromwell Clark Rd, Chestertown, MD 21620
    /19

    $3,000,000

    • Land
    • 87.34 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community.

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, Chestertown, MD 21620
  • 0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 14,810 Sq Ft
    • $29,412 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 Samson Properties

    0 Clarissa Rd Unit MDKE2005786, 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
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

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

    103 Landing Ln, Chestertown, MD 21620

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

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    /2

    $215,000 Coming Soon

    • 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
  • 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 6/1/2026 @ 10:00 AM. Bidding ends 6/3/2026 @ 12:40 PM. 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 easy

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

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

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

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