33

Chestertown, MD Land & Home Lots for Sale

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  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    /3

    $3,000

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

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 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 the Chester River. The area provides easy access to the major

    Adam Shpritz Ashland Auction Group LLC

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $35,000

    • Land
    • 39,204 Sq Ft
    • $38,889 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± 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

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, 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
  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, 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
  • 0 Melitota Ln, Chestertown, MD 21620
    0 Melitota Ln, Chestertown, MD 21620
    /2

    $29,000

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, 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 Long & Foster Real Estate, Inc.

    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
  • 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
  • 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 4/24/2026 @ 10:00 AM. Bidding ends 4/28/2026 @ 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
  • 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
  • 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
  • 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 Long & Foster Real Estate, Inc.

    23710 L Rd, 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
  • 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 Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, 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
  • 23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    /5

    $20,750

    • Land
    • 2.6 Acres
    • $7,981 per Acre

    23698 L Rd, Chestertown, MD 21620

    Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

    Joe Howerton Taylor Properties

    23698 L Rd, 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 4/24/2026 @ 10:00 AM. Bidding ends 4/28/2026 @ 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
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $795,000

    • Land
    • 4,356 Sq Ft
    • $7,950,000 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
  • 0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, 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
  • 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
  • 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. The rear portion of the property is designated forested shrub wetlands, though it’s been

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 206 Burchard Sawmill Rd, Chestertown, MD 21620
    206 Burchard Sawmill Rd, Chestertown, MD 21620
    /2

    $29,000

    • Land
    • 1.05 Acres
    • $27,619 per Acre

    206 Burchard Sawmill Rd, Chestertown, MD 21620

    Rare opportunity to own 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown! The property sell AS IS. Buyer will need to verify zoning and utilities.

    Norman Domingo XRealty.NET LLC

    206 Burchard Sawmill Rd, Chestertown, MD 21620
  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
Maryland Kent County Chestertown

Land & Lots for Sale in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 49 days on the market compared to the national average of 56 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$396,500
Median Townhouse Sale Price
$292,250
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$213
Number of Homes for Sale
36
Last 12 months Home Sales
101
Months of Supply
4.30
Median List Price
$379,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 33 parcels of land for sale, offering a unique opportunity for potential buyers to build their dream home or invest in private land. Whether you're in the market for a lot for sale to construct a custom home or looking to invest in substantial acreage, there are options to cater to different needs. With the chance to build your dream home on private acreage, explore land for sale in Chestertown, MD and turn your vision into reality.

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