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Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$264,900

*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

121 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$259,900

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

3 Beds ⋅ 3 Baths

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$259,900

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$259,000

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

$255,600

Ranch style home offering plenty of parking, three bedrooms and two full baths and a lot of outdoor living space on decks and the covered front porch. Located at end of cul-de-sac for privacy. Not much to do here to make this your new home! Property strictly sold as is. HUD CASE#241-778774 . Please see website hudhomestore for details.

Ranch style home offering plenty of parking, three bedrooms and two full baths and a lot of outdoor living space on decks and the covered front porch. Located at end of cul-de-sac for privacy. Not much to do here to make this your new home! Property strictly sold as is. HUD CASE#241-778774 . Please see website hudhomestore for details.

25690 Meadow Rd, Worton

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot, .36 acres, plus a large garage/ workshop with electric! Step inside to discover a warm and inviting interior. Original solid hardwood floors throughout, traditional floor plan with classic build-ins. The heart of the home is the large country-style kitchen, with ample table space and a pantry. The adjoining family room has a cozy propane fireplace with glass doors, which keeps this home very cozy! The formal dining room gets lots of natural light and leads to a large mudroom/ rear entry. There are three spacious bedrooms upstairs, as well as a half bathroom. There is a full bathroom downstairs. This home is ready for its next chapter. A great opportunity to renovate a property with solid bones in the heart of town! The large yard gives you privacy and room for activities while still being downtown. Walking distance to all Rock Hall has to offer, marinas, restaurants, Main Street shops, public boat launches, Ferry Park beach, and a front seat for the Rock Hall 4th of July parade! Additionally, this home is right across from the Rock Hall Civic Center. New water heater and plumbing throughout the home.

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot, .36 acres, plus a large garage/ workshop with electric! Step inside to discover a warm and inviting interior. Original solid hardwood floors throughout, traditional floor plan with classic build-ins. The heart of the home is the large country-style kitchen, with ample table space and a pantry. The adjoining family room has a cozy propane fireplace with glass doors, which keeps this home very cozy! The formal dining room gets lots of natural light and leads to a large mudroom/ rear entry. There are three spacious bedrooms upstairs, as well as a half bathroom. There is a full bathroom downstairs. This home is ready for its next chapter. A great opportunity to renovate a property with solid bones in the heart of town! The large yard gives you privacy and room for activities while still being downtown. Walking distance to all Rock Hall has to offer, marinas, restaurants, Main Street shops, public boat launches, Ferry Park beach, and a front seat for the Rock Hall 4th of July parade! Additionally, this home is right across from the Rock Hall Civic Center. New water heater and plumbing throughout the home.

5661 S Main St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Nestled in a serene enclave, this exceptional 0.55-acre lot offers a rare opportunity to create your dream retreat, perfectly positioned just a block away from the tranquil waters of Swan Creek and The Chesapeake Bay. and just across the street from The Haven on Swan Creek. The property boasts a level, cleared landscape, with water-views of The Haven. Perfect for a permanent residence or a seasonal escape. Keep your boat at any one of several marinas nearby, just a stroll or bike ride away. Town water and sewer both available on Hynson Road. The lot is flagged. A survey plat is available upon request.

Hynson Rd., Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

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.

Scheeler Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

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.

Scheeler Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$249,000

Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous updates, a full, unfinished walk-out basement, and plenty of possibilities! Situated on .63 acres with Village zoning and NO HOA, this property offers the freedom and flexibility you’ve been looking for! Bring your boat, RV, or recreational toys—there’s room to enjoy your property your way! Inside, you’ll appreciate the many improvements, including an updated roof, windows, water heater, water softener, and luxury vinyl plank (LVP) flooring. Step outside onto the beautiful Trex deck with low-maintenance vinyl railings, perfect for relaxing or entertaining. The full unfinished walk-out basement offers excellent storage and potential for additional living space. Conveniently located just minutes from Chestertown, Betterton, and Still Pond, you’ll enjoy peaceful country living while remaining close to shopping, dining, boating, beaches, and everything Kent County has to offer! Whether you’re searching for your first home, looking to downsize, or wanting a weekend getaway, this one deserves a look! Affordable living and valuable updates-all on your own .63-acre property!

1 Beds ⋅ 1 Baths

Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous updates, a full, unfinished walk-out basement, and plenty of possibilities! Situated on .63 acres with Village zoning and NO HOA, this property offers the freedom and flexibility you’ve been looking for! Bring your boat, RV, or recreational toys—there’s room to enjoy your property your way! Inside, you’ll appreciate the many improvements, including an updated roof, windows, water heater, water softener, and luxury vinyl plank (LVP) flooring. Step outside onto the beautiful Trex deck with low-maintenance vinyl railings, perfect for relaxing or entertaining. The full unfinished walk-out basement offers excellent storage and potential for additional living space. Conveniently located just minutes from Chestertown, Betterton, and Still Pond, you’ll enjoy peaceful country living while remaining close to shopping, dining, boating, beaches, and everything Kent County has to offer! Whether you’re searching for your first home, looking to downsize, or wanting a weekend getaway, this one deserves a look! Affordable living and valuable updates-all on your own .63-acre property!

25705 Meadow Rd, Worton

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

$245,000

A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. ft., featuring a completed exterior and an unfinished interior that gives the next owner the opportunity to finish and customize the home to their own style. Designed for 3 bedrooms and 3 full bathrooms, with the potential for a 4th bedroom or additional living space above the garage. The unfinished interior features open stud walls with roughed-in plumbing and electric, underground electric with 200-amp service, 2x6 exterior walls, 9-foot ceilings on the first floor and basement, Andersen windows, steel entry doors, and an oversized garage door. A beautiful wrap-around porch, attached side-entry garage, and cleared, level 0.24-acre lot add to the possibilities. Located just 3 short blocks from the Chesapeake Bay and a short walk to Betterton Beach, enjoy convenient access to the beach, boardwalk, boat ramp, fishing, swimming, basketball and tennis courts, picnic pavilions, and a town playground. Whether you're envisioning a year-round residence, vacation getaway, or investment opportunity, much of the vision is already in place. Bring your ideas and make this unique property near the Bay your own!

3 Beds ⋅ 3 Baths

A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. ft., featuring a completed exterior and an unfinished interior that gives the next owner the opportunity to finish and customize the home to their own style. Designed for 3 bedrooms and 3 full bathrooms, with the potential for a 4th bedroom or additional living space above the garage. The unfinished interior features open stud walls with roughed-in plumbing and electric, underground electric with 200-amp service, 2x6 exterior walls, 9-foot ceilings on the first floor and basement, Andersen windows, steel entry doors, and an oversized garage door. A beautiful wrap-around porch, attached side-entry garage, and cleared, level 0.24-acre lot add to the possibilities. Located just 3 short blocks from the Chesapeake Bay and a short walk to Betterton Beach, enjoy convenient access to the beach, boardwalk, boat ramp, fishing, swimming, basketball and tennis courts, picnic pavilions, and a town playground. Whether you're envisioning a year-round residence, vacation getaway, or investment opportunity, much of the vision is already in place. Bring your ideas and make this unique property near the Bay your own!

14 Third Ave, Betterton

Listing courtesy of Foraker Realty Co.. Contact:

11989 Augustine Herman Hwy, Kennedyville

$245,000

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

2 Baths

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$245,000

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$239,900

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

$239,000

Get settled in before cooler weather. Renovated from top to bottom. Pictures say it all. Outside, we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. The quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

Get settled in before cooler weather. Renovated from top to bottom. Pictures say it all. Outside, we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. The quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

11106 Plum Dr, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$229,900

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

317 Rolling Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$225,000

This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, 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.

Haacke Dr, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$225,000

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.

Haacke Dr, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$224,900

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

28036 Creamery St, Kennedyville

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

$222,000

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$210,000

Price Reduced! Three bedroom home in Still Pond. This renovated home has new kitchen, HVAC, baths, carpet, paint flooring and more! Located on .38 acres amenities include covered front and side porch, shed, 1.5 baths, Chestertown is a short drive away with restaurants and shopping. This is a Fannie Mae home, submit all offers on Homepath site.

Price Reduced! Three bedroom home in Still Pond. This renovated home has new kitchen, HVAC, baths, carpet, paint flooring and more! Located on .38 acres amenities include covered front and side porch, shed, 1.5 baths, Chestertown is a short drive away with restaurants and shopping. This is a Fannie Mae home, submit all offers on Homepath site.

26663 Maple Ave, Still Pond

Listing courtesy of Real Estate Consultants. Contact:

$200,000

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 bedroom downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Currently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash only!

4 Beds ⋅ 1 Baths

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 bedroom downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Currently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash only!

223 Mount Vernon Ave, Chestertown

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

$200,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

1 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 1B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$199,000

Unique opportunity to restore and customize the historic former "Rock Hall Shirt Factory!" This 5,558± sq. ft. building is situated on a 0.31± acre in-town lot and offers endless potential for investors, developers, or buyers looking for a one-of-a-kind project. The interior has been framed and studded for rooms, providing a head start on the renovation process while allowing you to complete the layout to suit your vision. Zoned R-3 High Density Residential, the property may offer the potential for multiple apartments or conversion into duplex or triplex units, subject to Town of Rock Hall approval and all applicable zoning and building requirements. The property features two separate driveways, a one-car garage, and all remaining contents will convey with the sale, potentially including valuable construction materials to assist with completing the project. Conveniently located just a short walk from Rock Hall's charming Main Street, you'll enjoy easy access to local shops, restaurants, the harbor, and community events. Bring your imagination and transform this historic property into something truly special!

5804 Downey Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$196,000

Major price reduction! Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. The adjacent lot at the corner of Cannon and Lynchburg is also available for purchase. No property address has yet been assigned to this lot. Buyer to verify zoning, permitted uses, building requirements, and utility availability.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

$195,000

15.5 + Acres- Build, Hunt, or Escape! Enjoy approximately 15.5 acres of beautiful open land in a peaceful setting. Previously perced by the prior owner, this property offers incredible potential for your future home, weekend getaway, or private hunting and recreational retreat. Whether you’re looking to build now or invest for the future, this versatile parcel is ready for your vision. A rare opportunity with endless possibilities!

Chestervl-Millington Road, Millington

Listing courtesy of Keller Williams Realty Wilmington. Contact:

$175,000

Needs work. Sold as is