The median home value in Chestertown, MD is $359,900.
This is
higher than
the county median home value of $249,900.
The national median home value is $308,980.
The average price of homes sold in Chestertown, MD is $359,900.
Approximately 44% of Chestertown homes are owned,
compared to 42% rented, while
14% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chestertown real estate agent to arrange a tour
today! Learn more about Chestertown Real Estate.
Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and sewer has been confirmed as available to purchase for each lot. Lot #2 - .286 acres Lot #3 - .268 acres Lot #4 - .431 acres Lot #5 - .452 acres
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.
Court ordered sale - all offers subject to third party approval. Lot does not have a water/sewer allocation. All parties must do their due diligence with county to determine use of lot. Currently wooded 0.73 acre lot on right corner of Iowa, Elm/Cumberland & Montgomery Avenues.
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 relaxed lifestyle. Don't miss the opportunity to make it yours!
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 relaxed lifestyle. Don't miss the opportunity to make it yours!
(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!
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 extra fee.
ONLINE AUCTION: Bidding begins 4/22/2025 @ 10:00 AM. Bidding ends 4/23/2025 @ 12:40 PM. List Price is Suggested Opening Bid. 4 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 Road. Deposit: $5,000.
Extremely Rare offering! 2 acre recorded waterfront parcel in Quaker Neck on Walnut Point Road with 211 feet of frontage on the East Fork Of Langford Creek. Parcel was perc evaluated years ago and require re-evaluation which has been applied for, please see documents. Partially wooded and partially cleared with gorgeous views of the Langford Creek. Dock is allowed by the County. Possibility of 4" water depth (see navigation chart). Private road to be installed and maintained at buyers expense. (see documents). If you are searching for a place to build your dream waterfront home close to Chestertown in a highly desirable location, this is it! Subject to first right of refusal. Absolutely no drive-byes!!! Appointment must be arranged with listing agent 36 hours prior to showing and listing agent is required to be present. DO NOT GO DOWN BELLE GROVE LANE!
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.
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. Lot failed percolation Test in March of 1989.
Prime 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd, this versatile property offers a fantastic opportunity to build your dream home or investment property in a peaceful, scenic setting. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Dont miss out on this rare chance to own land in historic Chestertown!
ONLINE AUCTION: Bidding begins 4/22/2025 @ 10:00 AM. Bidding ends 4/23/2025 @ 12:20 PM. List Price is Suggested Opening Bid. 4 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 Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 4/22/2025 @ 10:00 AM. Bidding ends 4/23/2025 @ 12:30 PM. List Price is Suggested Opening Bid. 4 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 Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 4/22/2025 @ 10:00 AM. Bidding ends 4/23/2025 @ 12:10 PM. List Price is Suggested Opening Bid. 4 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 Road Deposit: $5,000.
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!
This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether youre looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Dont miss out on this rare opportunity!
This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether youre looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Dont miss out on this rare opportunity!
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 Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.
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.
Property in Tolchester Estates! Walking distance to the Chesapeake Bay, Tolchester beach, marina and Shanty. The county says sewer allocation is available. Buyer to confirm lot is buildable regarding setbacks, sewer allocation, and utility hookups. Buyer responsible for sewer allocation fees estimated to be $12,800. Lot next door is also for sale MDKE2003418. All offers considered!
Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.
Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.
