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1906 Pondtown Rd, Chestertown

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.

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.

1906 Pondtown Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

Georgetown Road, Chestertown

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.

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.

Georgetown Road, Chestertown

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

620 Cannon St, Chestertown

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available. Buyer to confirm with the Town of Chestertown allowable uses and the use of the previous water/sewer allocation.

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available. Buyer to confirm with the Town of Chestertown allowable uses and the use of the previous water/sewer allocation.

620 Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

234 N College Ave, Chestertown

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

2 Beds ⋅ 1 Baths

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

Fairlee Road, Chestertown

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.

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.

Fairlee Road, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

8886 Georgetown Rd, Chestertown

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.

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.

8886 Georgetown Rd, Chestertown

Listing courtesy of Samson Properties. Contact:

233 Merganser Dr, Chestertown

Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. 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:

Map 36 Parcel 80 Watertower Road, Chestertown

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!

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!

Map 36 Parcel 80 Watertower Road, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. 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:

Sandy Bottom Road, Chestertown

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.

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.

Sandy Bottom Road, Chestertown

Listing courtesy of Village Real Estate Company LLC. Contact:

305 Roosevelt Dr, Chestertown

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

305 Roosevelt Dr, Chestertown

Listing courtesy of Taylor Properties. Contact:

Towhee Road, Chestertown

This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. 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.

This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. 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.

Towhee Road, Chestertown

Listing courtesy of The Parker Group. Contact:

Montgomery Avenue, Chestertown

Montgomery Avenue, Chestertown

Listing courtesy of The Hogans Agency. 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:

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:

Fish Hatchery Road, Chestertown

Fish Hatchery Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

23741 L Rd, Chestertown

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.

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.

23741 L Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

22681 Wood Yard Ln, Chestertown

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!

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!

22681 Wood Yard Ln, Chestertown

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

23710 L Rd, Chestertown

23710 L Rd, Chestertown

Listing courtesy of Paul Wesley Real Estate. 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:

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:

Buck Neck Landing Road, Chestertown

Buck Neck Landing Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. 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:

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:

Fish Hatchery 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, 12:25 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 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:25 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 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:55 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 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:55 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:

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