26

Chestertown, MD Homes for Sale under $100,000

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  • 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

    Multi-lot online auction featuring 4 residential land parcels located throughout Chestertown, Maryland in Kent County. Multi-lot Auction Begins: June 1, 2026 at 10:00 AM ET. Auction Ends: June 3, 2026 from 12:50 PM through 1:05 PM ET. List Price is Suggested Opening Bid. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River.

    Adam Shpritz Ashland Auction Group LLC

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
  • 228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    /13

    $99,000

    • Land
    • 22,215 Sq Ft
    • $194,118 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
  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $25,000

    • Land
    • 39,204 Sq Ft
    • $27,778 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
  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    $22K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 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
  • 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

    Multi-lot online auction featuring 4 residential land parcels located throughout Chestertown, Maryland in Kent County. Multi-lot Auction Begins: June 1, 2026 at 10:00 AM ET. Auction Ends: June 3, 2026 from 12:50 PM through 1:05 PM ET. List Price is Suggested Opening Bid. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River.

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, 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. Absolute 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
  • 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
  • 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

    Multi-lot online auction featuring 4 residential land parcels located throughout Chestertown, Maryland in Kent County. Multi-lot Auction Begins: June 1, 2026 at 10:00 AM ET. Auction Ends: June 3, 2026 from 12:50 PM through 1:05 PM ET. List Price is Suggested Opening Bid. Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton

    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 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
  • 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

    $3K PRICE DROP
    • 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
  • 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

    Multi-lot online auction featuring 4 residential land parcels located throughout Chestertown, Maryland in Kent County. Multi-lot Auction Begins: June 1, 2026 at 10:00 AM ET. Auction Ends: June 3, 2026 from 12:50 PM through 1:05 PM ET. List Price is Suggested Opening Bid. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River.

    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

    $4K PRICE INCREASE
    • 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
  • 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

    $17K PRICE INCREASE
    • 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
  • 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
  • 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

    $3K PRICE DROP
    • 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
  • 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 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
  • 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

    $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
Maryland Kent County Chestertown

Real Estate & Homes in Chestertown, MD under $100,000

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 50 days on the market compared to the national average of 58 days. The median sale price for homes in Chestertown, MD over the last 12 months is $370,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$398,000
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$210
Number of Homes for Sale
37
Last 12 months Home Sales
101
Months of Supply
4.40
Median List Price
$377,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 26 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Chestertown, MD. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

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