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108 Little Harbor Way, Chestertown

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.

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.

108 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

105 High St, Chestertown

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

5 Beds ⋅ 5 Baths

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

105 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

222 Dutchess Rd, Chestertown

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

3 Beds ⋅ 2 Baths

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

404 Spring Rd, Chestertown

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.

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.

404 Spring Rd, Chestertown

Listing courtesy of The Parker Group. Contact:

23043 Bay Shore Spur, Chestertown

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Parcel Parcel Buck Neck Ldg Road, Chestertown

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. 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.

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. 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.

Parcel Parcel Buck Neck Ldg Road, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Buck Neck Road, Chestertown

Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable. 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. Investors- this lot could possibly have public utilities available in the future!

Buck Neck Road, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Kinglet Road, Chestertown

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.

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.

Kinglet Road, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Buck Neck Landing Road, Chestertown

Buck Neck Landing Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

Georgetown Rd, Chestertown

Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

Georgetown Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Fish Hatchery Road, Chestertown

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:40 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 access to major traffic arteries including Chestertown Road.

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:40 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 access to major traffic arteries including Chestertown Road.

Fish Hatchery Road, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Beltram Rd, Chestertown

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:30 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 vacant. The area provides easy access to the major traffic artery Chestertown Road.

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:30 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 vacant. The area provides easy access to the major traffic artery Chestertown Road.

Beltram Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Towhee Road, Chestertown

ONLINE AUCTION: Bidding begins 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:30 PM. This auction takes place on the Ashland Auction Group bidding platform. 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 access to major traffic arteries including Chestertown Road

ONLINE AUCTION: Bidding begins 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:30 PM. This auction takes place on the Ashland Auction Group bidding platform. 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 access to major traffic arteries including Chestertown Road

Towhee Road, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Bunting Road, Chestertown

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:35 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 access to major traffic arteries including Chestertown Road

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:35 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 access to major traffic arteries including Chestertown Road

Bunting Road, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Sheldrake Drive, Chestertown

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.

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.

Sheldrake Drive, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

515 Washington Ave, Chestertown

Commercial Development Site on busy MD Rte 213, Prime location across from new Starbucks and Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available.

Commercial Development Site on busy MD Rte 213, Prime location across from new Starbucks and Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available.

515 Washington Ave, Chestertown

Listing courtesy of EShore. Contact:

23710 L Rd, Chestertown

23710 L Rd, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

Fish Hatchery Road, Chestertown

Fish Hatchery Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

Spinnaker Road, Chestertown

Spinnaker Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

Redfield Road, Chestertown

Redfield Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

Old Morgnec Road, Chestertown

(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. Unsuccessful land evaluation completed on May 26,2026 for a conventional septic. You will need to reach out to the County for highest and best use or to talk about an alternative septic system. Lots being sold together!

(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. Unsuccessful land evaluation completed on May 26,2026 for a conventional septic. You will need to reach out to the County for highest and best use or to talk about an alternative septic system. Lots being sold together!

Old Morgnec Road, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

no property photo

*2-Acres of land. *Only 1.7 miles to the Chesapeake Bay *10-mins to the lively town of Rock Hall *14-mins to Chestertown *1-hr and 10-mins to Annapolis *1-hr and 10-mins to Wilmington, DE *Don't miss Betterton Beach which is only 25-mins away. This property is now active in an online auction. All offers must be submitted through the property’s listing page. PLEASE CALL OR EMAIL LISTING AGENT OR BROKERAGE FOR WEBSITE INFO! The sale will be subject to a 5% buyer’s premium pursuant to the Auction Terms and Conditions (minimums may apply). All auction bids will be processed subject to seller approval. RECOMMENDED STARTING BID $9900. PROPERTY WILL BE AUCTIONED MAY 21, 2024 BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

*2-Acres of land. *Only 1.7 miles to the Chesapeake Bay *10-mins to the lively town of Rock Hall *14-mins to Chestertown *1-hr and 10-mins to Annapolis *1-hr and 10-mins to Wilmington, DE *Don't miss Betterton Beach which is only 25-mins away. This property is now active in an online auction. All offers must be submitted through the property’s listing page. PLEASE CALL OR EMAIL LISTING AGENT OR BROKERAGE FOR WEBSITE INFO! The sale will be subject to a 5% buyer’s premium pursuant to the Auction Terms and Conditions (minimums may apply). All auction bids will be processed subject to seller approval. RECOMMENDED STARTING BID $9900. PROPERTY WILL BE AUCTIONED MAY 21, 2024 BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Caulks Field Rd, Chestertown

Listing courtesy of Meredith Fine Properties. Contact:

no property photo

0.39-Acres in Chesapeake Landing Subdivision *Access to 2 private marinas in the neighborhood * The larger community marina has 36 boat slips with water and electrical service, shower facilities, and a launching ramp. * Potential for public sewer connection in the future. This property is now active in an online auction. All offers must be submitted through the property’s listing page. PLEASE CALL OR EMAIL LISTING AGENT OR BROKERAGE FOR WEBSITE INFO! The sale will be subject to a 5% buyer’s premium pursuant to the Auction Terms and Conditions (minimums may apply). All auction bids will be processed subject to seller approval. RECOMMENDED STARTING BID $7700. PROPERTY WILL BE AUCTIONED MAY 21, 2024 BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

0.39-Acres in Chesapeake Landing Subdivision *Access to 2 private marinas in the neighborhood * The larger community marina has 36 boat slips with water and electrical service, shower facilities, and a launching ramp. * Potential for public sewer connection in the future. This property is now active in an online auction. All offers must be submitted through the property’s listing page. PLEASE CALL OR EMAIL LISTING AGENT OR BROKERAGE FOR WEBSITE INFO! The sale will be subject to a 5% buyer’s premium pursuant to the Auction Terms and Conditions (minimums may apply). All auction bids will be processed subject to seller approval. RECOMMENDED STARTING BID $7700. PROPERTY WILL BE AUCTIONED MAY 21, 2024 BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Colfax Rd, Chestertown

Listing courtesy of Meredith Fine Properties. Contact:

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