36

Chestertown, MD Homes for Sale under $100,000

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  • /9

    $65,000

    • Land
    • 3 Acres
    • $21,667 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • /11

    $19,500

    • Land
    • 0.99 Acre
    • $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 Kent

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • /5

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 per Acre

    23628 Canvasback Rd, Chestertown, MD 21620

    Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.

    Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
  • /2

    $15,000

    • Land
    • 0.35 Acre
    • $42,706 per Acre

    0 Elbon Rd, Chestertown, MD 21620

    Create your dream home or capitalize on a prime investment opportunity with this exceptional parcel of land. Nestled in a serene setting, it’s a blank canvas for luxury living or profitable development. Whether designing a private retreat or building for resale, the possibilities are endless.

    Waylon Yuan Signature Home Realty LLC

    0 Elbon Rd, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 0.55 Acre
    • $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
  • /2

    $40,000

    • Land
    • 0.34 Acre
    • $117,647 per Acre

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620

    Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

    Jo Ann Edwards The Hogans Agency

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
  • /16

    $35,000

    • Land
    • 0.9 Acre
    • $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

    $9,000

    • Land
    • 0.61 Acre
    • $14,754 per Acre

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620

    Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
  • /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land

    Lori Sample EXIT Preferred Realty

    0 Fairlee Rd, Chestertown, MD 21620
  • /3

    $10,000

    • Land
    • 0.69 Acre
    • $14,493 per Acre

    23683 L Rd, Chestertown, MD 21620

    This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront attractions just minutes from the town of Chestertown, Worton Creek Marina, and Great Oak Landing.

    Alyson Anderson Allfirst Realty, Inc.

    23683 L Rd, Chestertown, MD 21620
  • /32

    $49,900

    • Land
    • 1.51 Acres
    • $33,046 per Acre

    0 Cloquet Rd Unit MDKE2004960, 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 MDKE2004960, Chestertown, MD 21620
  • /2

    $15,000

    • Land
    • 0.51 Acre
    • $29,412 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. The 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. There is a 16' right of way to access which has not been maintained. Buyer to do any due diligence. Could be a great hunting property!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • /3

    $20,000

    • Land
    • 0.09 Acre
    • $222,222 per Acre

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
  • /3

    $55,000

    • Land
    • 0.7 Acre
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2003624, Chestertown, MD 21620

    Exciting opportunity awaits with this open lot located in Fairlee, Md. This parcel of land offers the perfect canvas for your dream home or investment project. .69 acres provides ample space for your vision to flourish. The property is allocated for public water and sewer, so the new owner won’t have to worry about drilling a well or paying for and maintaining a septic system! Allocations are

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2003624, Chestertown, MD 21620
  • /2

    $15,000

    • Land
    • 0.34 Acre
    • $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
  • /2

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 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
  • /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

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

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    Discover your own piece of paradise in Lenapah, Chestertown, MD! This expansive 14,500 square foot lot offers endless possibilities for your dream home or investment vision. Nestled in a serene setting, this raw land is ready for your creative touch. Embrace the tranquility of nature while being just a short drive from local amenities. Whether you’re looking to build your dream oasis or a savvy

    Solomon Zaldivar Compass

    0 Lenapah Rd, Chestertown, MD 21620
  • /2

    $59,000

    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • /2

    $40,000

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • /2

    $40,000

    • Land
    • 0.11 Acre
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

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

    $28,000

    • Land
    • 2 Acres
    • $14,000 per Acre

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • /2

    $38,000

    • Land
    • 0.34 Acre
    • $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
  • /2

    $24,000

    • Land
    • 0.5 Acre
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23710 L Rd, Chestertown, MD 21620
  • /2

    $37,000

    • Land
    • 0.34 Acre
    • $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
  • /2

    $38,000

    • Land
    • 0.56 Acre
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, Chestertown, MD 21620
  • /2

    $9,500

    • Land
    • 0.34 Acre
    • $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
  • /4

    $50,000 Coming Soon

    • Land
    • 0.5 Acre
    • $100,000 per Acre

    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620

    The building lot you’ve been waiting for!Half-acre, mostly cleared, and wonderfully private, tucked down a quiet gravel road with few neighbors. A survey has been ordered and the county confirms a water/sewer allocation is available for $16,200 at buyer's expense. Conveniently located just outside the small town of Fairlee and close to Chestertown, Rock Hall, and multiple boat ramps for all

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620
  • /9

    $15,000

    • Land
    • 1.8 Acres
    • $8,333 per Acre

    109 2nd St, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 10/15/2025 @ 10:00 AM. Bidding ends 10/17/2025 @ 12:40 PM. List Price is Suggested Opening Bid. Deposit: $5,000+/- 1.80 AC lot in Chestertown (Kent County). Existing structure is uninhabitable; offered as land only. Short distance to the Chester River with convenient access to nearby marinas, parks, and in-town amenities. Buyer to verify utilities, access,

    Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
  • /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    POST AUCTION! Make an offer, buy it now! 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to Worton Creek Marina, and all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /7

    $10,000

    • Land
    • 0.37 Acre
    • $27,027 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    POST AUCTION - Make an offer, buy it now! 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown

    Adam Shpritz Ashland Auction Group LLC

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

    $10,000

    • Land
    • 0.09 Acre
    • $111,111 per Acre

    0 Texas Ave, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    0 Texas Ave, Chestertown, MD 21620
  • /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! 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 Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

Home Trends in Chestertown, MD

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$385,000
Median Townhouse Sale Price
$263,750
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$220
Number of Homes for Sale
35
Last 12 months Home Sales
90
Months of Supply
4.70
Median List Price
$367,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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