Chestertown MD Real Estate & Land for Sale

38 Properties Found

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Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006672
Type:
Land
Lot size:
2.2 Acres
Courtesy: RE/MAX Chesapeake 410-398-9200
View additional info

ADDITIONAL INFORMATION

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. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. 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 Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2017476
Type:
Land
Lot size:
1.93 Acres
Courtesy: Keller Williams Flagship 410-729-7700
View additional info

ADDITIONAL INFORMATION

Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes. Whether you're planning a custom residence, weekend getaway, or future investment, this property provides the ideal setting to bring your vision to life. With a perc approval already in place, this is an outstanding opportunity to create the home you've always wanted in a picturesque rural setting.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006634
Type:
Land
Lot size:
4.03 Acres
Courtesy: Samson Properties 443-317-8125
View additional info

ADDITIONAL INFORMATION

Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a rare combination of privacy, recreation, and convenience. Whether you're seeking a peaceful retreat, hunting property, or camping getaway, this versatile parcel offers endless opportunities. Enjoy the tranquility of nature, abundant wildlife, and the privacy of a secluded setting. A small portion near the middle of the parcel is designated as non-tidal wetlands; however, it has never been observed with standing water, even after substantial rainfall.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006622
Type:
Land
Lot size:
1 Acres
Courtesy: Benson & Mangold, LLC 410-822-6665
View additional info

ADDITIONAL INFORMATION

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.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006592
Type:
Land
Lot size:
0.7 Acres
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

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. Nestled off the main road and deeded with a right-of-way for access, this parcel offers a peaceful, private setting while remaining conveniently close to local amenities, recreation, and the waterfront charm of the Eastern Shore. Public water and sewer may be available, offering the potential convenience of public utilities without the expense and maintenance of a private well or septic system. Buyer to verify availability of allocations and is responsible for any associated fees. Don’t miss this chance to own a versatile piece of land in a desirable location with great potential for future growth and development!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006580
Type:
Land
Lot size:
0.69 Acres
Courtesy: Alex Cooper Auctioneers, Inc. 410-828-4838
View additional info

ADDITIONAL INFORMATION

List Price is opening bid at online auction. Auction at or above $6,000. Bidding begins Saturday, June 20th, and ends Thursday, June 25, 2026 at 11:30am. 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 multi-family) • Low-intensity commercial uses (like small shops, offices, or services) • Walkable, community-centered development (more dense than rural zones, but less than commercial corridors) It’s basically a transitional zoning category between rural/residential land and more developed commercial areas—meant to preserve the “small-town village” character. (information from a Kent County Government site) Important Note: Location shown in aerial images is approximate. Please refer to the plat available in the documents section for accurate parcel boundaries. The information contained herein was obtained from sources deemed to be reliable, but is offered for informational purposes only. Neither the auctioneer, or the owner make any representations or warranties with respect to the accuracy of information. Buyer's are encouraged to conduct their own due diligence to determine the best use for the property.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006554
Type:
Land
Lot size:
1.95 Acres
Courtesy: Village Real Estate Company LLC 410-648-6844
View additional info

ADDITIONAL INFORMATION

Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of mature trees and a partially open entrance area, this property is ideal for camping, hunting, recreation, or simply enjoying nature in a tranquil setting. Bring your RV or pitch a tent and enjoy the great outdoors! Electric is available at the road, and the seller has marked the approximate property corners and boundaries for convenience (no survey on file). A seasonal hand-dug well is also located on the property. Whether you're looking for a weekend getaway, a place to gather around bonfires, or your own private retreat in nature, this property offers endless possibilities to relax and unwind outdoors.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2017240
Type:
Land
Subdivision:
Ducks Neck
Lot size:
0.51 Acres
Courtesy: Benson & Mangold, LLC 410-822-6665
View additional info

ADDITIONAL INFORMATION

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 Chestertown. A mobile home currently exists on the property and is believed to be approximately 60 years old. Buyer to verify condition and habitability of the mobile home or remove at buyer’s discretion. Seller has no knowledge or information regarding the mobile home. Original well and septic are present on the property; buyer to verify condition and functionality of both.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2017232
Type:
Land
Lot size:
1.8 Acres
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

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, and Middletown easy. Quotes are already available for septic installation, well installation, and clearing of the existing structure and brush.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006420
Type:
Land
Lot size:
0.18 Acres
Courtesy: Select Land & Homes, LLC 410-810-3900
View additional info

ADDITIONAL INFORMATION

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 by. Whether you’re envisioning a commercial storefront, office space, investment rental, or even a mixed-use concept, the flexibility here is hard to beat. Offered at an attractive price point, this is a rare chance to secure a well-located parcel in one of the Eastern Shore’s most charming and active downtown settings.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006304
Type:
Land
Lot size:
0.34 Acres
Courtesy: Ashland Auction Group LLC 410-488-3124
View additional info

ADDITIONAL INFORMATION

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/30/2026, 10:00 AM. Bidding ends 7/2/2026, 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 traffic artery, Fairlee Rd, connecting to the surrounding areas.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006274
Type:
Land
Lot size:
0.87 Acres
Courtesy: Select Land & Homes, LLC 410-810-3900
View additional info

ADDITIONAL INFORMATION

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 potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006290
Type:
Land
Lot size:
0.85 Acres
Courtesy: Select Land & Homes, LLC 410-810-3900
View additional info

ADDITIONAL INFORMATION

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 potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006286
Type:
Land
Subdivision:
Chestertown
Lot size:
0.34 Acres
Courtesy: Ashland Auction Group LLC 410-488-3124
View additional info

ADDITIONAL INFORMATION

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/30/2026, 10:00 AM. Bidding ends 7/2/2026, 1:00 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 traffic artery, Fairlee Rd, connecting to the surrounding areas.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006284
Type:
Land
Lot size:
0.34 Acres
Courtesy: Ashland Auction Group LLC 410-488-3124
View additional info

ADDITIONAL INFORMATION

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/30/2026, 10:00 AM. Bidding ends 7/2/2026, 12:55 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 traffic artery, Morgnec Rd, connecting to the surrounding areas.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2016578
Type:
Land
Lot size:
5.81 Acres
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

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.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006144
Type:
Land
Subdivision:
Chestertown
Lot size:
0.1 Acres
Courtesy: RE/MAX Associates-Hockessin 302-234-3800
View additional info

ADDITIONAL INFORMATION

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.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006032
Type:
Land
Lot size:
0.52 Acres
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

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!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005844
Type:
Land
Lot size:
3.92 Acres
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

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 will need to install a driveway and connect to utilities.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005902
Type:
Land
Subdivision:
Chester River Landing
Lot size:
0.09 Acres
Courtesy: Gunther-McClary Real Estate 410-275-2118
View additional info

ADDITIONAL INFORMATION

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 water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Enjoy the close proximity to ample shops, dining options, and Chestertown’s year-round farmers market.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005786
Type:
Land
Lot size:
0.34 Acres
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

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 minutes from Historic Downtown Chestertown, the scenic Chesapeake Bay, and Washington College. Conveniently close to local parks, restaurants, and waterfront amenities, this location combines tranquility with accessibility. Don’t miss this incredible chance to secure your lot and bring your dream home to life. Opportunities like this don’t come often—act now and make your vision a reality!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2014990
Type:
Land
Lot size:
0.99 Acres
Courtesy: The Parker Group 302-217-6692
View additional info

ADDITIONAL INFORMATION

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 Anne's County with room to make it your own.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005550
Type:
Land
Lot size:
0.9 Acres
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-464-5500
View additional info

ADDITIONAL INFORMATION

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

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005120
Type:
Land
Lot size:
2 Acres
Courtesy: RE/MAX Allegiance 703-237-9500
View additional info

ADDITIONAL INFORMATION

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2005076
Type:
Land
Lot size:
2 Acres
Courtesy: RE/MAX Allegiance 703-237-9500
View additional info

ADDITIONAL INFORMATION

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 the beautiful Chester River, which flows right through Chestertown. Whether you're looking for a peaceful retreat or a place to create your forever home, this is an opportunity you don’t want to miss!

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



Chestertown Real Estate

Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.

The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.

Chestertown Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.

Chestertown Map

Chestertown Real Estate Market Conditions

  • Median sales price

    $250,000
    14.5%
    change since last quarter
  • # Active listings

    121
    30-day change

Chestertown Schools and Demographics

Education near Chestertown, MD

City County
High School Graduates 88.37 90.6
College Degree - 2 year 5.13 5.64
College Degree - 4 year 42.33 37.48
Graduate Degree 16.24 9.64
Expenditures per Student 19,095 19,095
Students per Teacher 10.4 10.4

Elementary Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Elementary School PK - 02 550 17.4 21617
Church Hill Elementary School PK - 04 314 15.2 21623
H. H. Garnett Elementary PK - 05 233 11.5 21620
Kennard Elementary School 03 - 05 513 17.7 21617
Rock Hall Elementary School PK - 05 187 14.3 21661
Worton Elementary School PK - 05 277 12.7 21678

Middle Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Middle School 06 - 08 537 14.9 21617
Kent County Middle School 06 - 08 439 12.9 21620

High Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Kent County High School 09 - 12 594 13.8 21678
Queen Anne's County High School 09 - 12 1,102 14.3 21617

Demographics near Chestertown, MD

City County
Neighborhood Type Small Town
Population 5,557 19,335
Population Density 2,016 70
Median Age 39.1 47.1
People per Household 1.7 2.1
Median Household Income 44,665 64,451
Average Income per Capita 28,645 39,658

Real estate near Chestertown