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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.

3 Beds ⋅ 1 Baths

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:

$679,900

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

3 Beds ⋅ 4 Baths

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

$300,000

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

5 Beds ⋅ 2 Baths

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

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

$281,500

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

3 Beds ⋅ 2 Baths

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$1,800,000

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

4 Beds ⋅ 4 Baths

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Little Harbor Way Unit 1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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:

$155,000

Build your Eastern Shore home on this .79-acre lot located within Rock Hall town limits, just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek. The property offers easy access to marinas, restaurants, shops, community beach and everything Rock Hall has to offer. Much of the preliminary work has already been completed. Public water and sewer allocations have been paid, and an elevation certificate is available with a benchmark placed on the property. A building permit has been issued for a 1,650-square-foot home, with all required engineering completed and the proposed house location already staked. The driveway entrance has also been approved and installed to the homesite. There is no builder tie-in, giving buyers the flexibility to bring their own builder and plans, subject to applicable approvals and permitting. For buyers looking for an even more streamlined option, the property is also listed as a new construction package starting at $599,900.

21008 Rock Hall Ave, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. 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:

$325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Fully finished basement. Plenty of parking. A great place for a centrally located home or office.

896 Washington Ave, Chestertown

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

$849,000

This former West Marine commercial property, constructed in 2001, presents a compelling investment opportunity in a rural location, characterized by its solid construction of metal and vinyl siding. With a lot size of 0.68 acres and 61,00 sqare foot building, the property offers ample space for various commercial ventures, enhancing its potential for rental income or resale value. The good condition of the building ensures minimal immediate capital expenditure, allowing investors to focus on maximizing returns. The rural setting provides a unique advantage, as it often attracts businesses seeking lower operational costs and a tranquil environment. The availability of parking facilities further enhances accessibility for clients and customers. This property is strategically positioned to capitalize on the growing demand for commercial spaces in less urbanized areas, making it an attractive option for investors looking to diversify their portfolios. The potential for appreciation in value, coupled with the benefits of lower competition, positions this property as a prudent investment choice.

21386 Rock Hall Ave, Rock Hall

Listing courtesy of Benson & Mangold, LLC. Contact:

$425,000

10k BONUS OFFER!!! NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, comfortable living, and small-town Eastern Shore charm. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this thoughtfully designed home boasts an inviting open floor plan that creates an easy flow between the living, dining, and kitchen areas. Step inside from the cozy front porch and appreciate the quality and efficiency built into this home. Energy-conscious features include high-efficiency windows and doors, quality insulation, and a professionally conditioned, watertight crawl space designed to provide a cleaner, drier, more efficient foundation for years to come. For added convenience, laundry is located on the top floor, making everyday living and household chores that much easier. Parking is plentiful, with a spacious driveway in the front as well as convenient additional access from the side entrance off Cottage Street. Situated on a large lot, there is plenty of room to enjoy the outdoors and even the potential to add an approximately 1,200-square-foot outbuilding—perfect for a workshop, garage, storage, studio, or other future needs (subject to applicable approvals and zoning). Located in the wonderful waterfront community of Rock Hall, Maryland, you'll be close to the area's marinas, restaurants, shops, and the Chesapeake Bay while enjoying the relaxed lifestyle that makes Rock Hall such a special Eastern Shore destination. Seller to Credit any BUYER 10k towards buyers choice: Purchase price, Seller Assist, Construction of : Deck, Fence, Etc... at time of closing.

3 Beds ⋅ 3 Baths

10k BONUS OFFER!!! NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, comfortable living, and small-town Eastern Shore charm. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this thoughtfully designed home boasts an inviting open floor plan that creates an easy flow between the living, dining, and kitchen areas. Step inside from the cozy front porch and appreciate the quality and efficiency built into this home. Energy-conscious features include high-efficiency windows and doors, quality insulation, and a professionally conditioned, watertight crawl space designed to provide a cleaner, drier, more efficient foundation for years to come. For added convenience, laundry is located on the top floor, making everyday living and household chores that much easier. Parking is plentiful, with a spacious driveway in the front as well as convenient additional access from the side entrance off Cottage Street. Situated on a large lot, there is plenty of room to enjoy the outdoors and even the potential to add an approximately 1,200-square-foot outbuilding—perfect for a workshop, garage, storage, studio, or other future needs (subject to applicable approvals and zoning). Located in the wonderful waterfront community of Rock Hall, Maryland, you'll be close to the area's marinas, restaurants, shops, and the Chesapeake Bay while enjoying the relaxed lifestyle that makes Rock Hall such a special Eastern Shore destination. Seller to Credit any BUYER 10k towards buyers choice: Purchase price, Seller Assist, Construction of : Deck, Fence, Etc... at time of closing.

5855 Cottage Ave, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

$50,000

Nearly 4 acres of privacy and natural beauty tucked away down a quiet, secluded road just outside the charming town of Galena. This wooded parcel offers favorable soils and was recently perc approved, providing the potential for a future homesite. Access to the buildable area will require construction of a bridge or culvert over an existing ravine. Beyond residential possibilities, the property could also make an excellent recreational retreat for hunting, ATV riding, hiking, nature trails, or simply enjoying the peace and privacy of the outdoors. Enjoy the best of both worlds—seclusion and convenience. Galena offers small-town charm, local shops, and access to the Sassafras River, while Middletown, Delaware is just a short drive up Route 301 for additional shopping, dining, and amenities. A unique opportunity for a buyer willing to take on the access improvements and unlock the potential of this secluded parcel.

Olivet Hill Rd, Galena

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

$495,000

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

3 Beds ⋅ 3 Baths

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$2,895,000

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

5 Beds ⋅ 4 Baths

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

6324 Quaker Neck Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$315,000

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

2 Beds ⋅ 2 Baths

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

$459,000

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

2 Beds ⋅ 2 Baths

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

105 N Water St Unit 3, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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.

3 Beds ⋅ 2 Baths

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:

$535,000

Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. Great for all the toys, Shop, or Storage. Mature Landscaping, All Situated on 9.28 Acres located close to the Sassafras River. Wow! Call for your private showing.

4 Beds ⋅ 2 Baths

Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. Great for all the toys, Shop, or Storage. Mature Landscaping, All Situated on 9.28 Acres located close to the Sassafras River. Wow! Call for your private showing.

13984 Mill Creek Ln, Galena

Listing courtesy of Key Realty, Incorporated. Contact:

$289,000

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

3 Beds ⋅ 2 Baths

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

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

$1,050,000

104 Maple Ave, Chestertown

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

$175,000

Charming "TINY" house within quiet community of Worton off the main thoroughfare. Woods, public water and sewer, mature trees, deck with view of woods. One bedroom and bath, eat-in kitchen. Separate laundry/utility room. Not fancy by delightful on large lot. Only ten minutes from Historic Chestertown where one can find all daily needs plus many year-round cultural events including live performances. Washington College, tenth oldest college in America, offers programs and events continually. Minutes from Lockbriar (Pick Your Own) Farm and rest of beautiful County of Kent. Bettertown sandy Public beach on Chesapeake Bar and modern playground is nearby. Weekends? Year-round living?

1 Beds ⋅ 1 Baths

Charming "TINY" house within quiet community of Worton off the main thoroughfare. Woods, public water and sewer, mature trees, deck with view of woods. One bedroom and bath, eat-in kitchen. Separate laundry/utility room. Not fancy by delightful on large lot. Only ten minutes from Historic Chestertown where one can find all daily needs plus many year-round cultural events including live performances. Washington College, tenth oldest college in America, offers programs and events continually. Minutes from Lockbriar (Pick Your Own) Farm and rest of beautiful County of Kent. Bettertown sandy Public beach on Chesapeake Bar and modern playground is nearby. Weekends? Year-round living?

25373 Worton Lynch Rd, Worton

Listing courtesy of Maryland Heritage Properties. 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:

$160,000

Escape to Little Neck Farm, an exceptional 350-acre waterfront community on Maryland’s Eastern Shore, where natural beauty, privacy, and access to the Chesapeake Bay come together. This 1.24-acre building lot offers the opportunity to create your own Eastern Shore retreat within a thoughtfully designed community surrounded by abundant wildlife and peaceful natural scenery. Little Neck Farm features approximately four miles of protected shoreline, with more than 200 acres preserved as community open space, creating a wonderfully private and uncrowded setting with only 28 total homesites. Adding to the appeal, this property conveys with a deeded deep-water boat slip at the private community marina, providing convenient access to the Chesapeake Bay and beyond. Build the home you've envisioned and enjoy a lifestyle centered around boating, nature, open space, and the tranquility of Maryland’s Eastern Shore.

Hagy Road, Rock Hall

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

$695,000

Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportunity to create your own private estate while enjoying outstanding recreational and hunting opportunities. The current owners have strategically developed and maintained the property for exceptional deer and turkey hunting through their partnership with HuntingPlots.com. Thoughtful habitat and land management includes established travel corridors, bedding areas, food plots, an artificial water pond, and carefully planned tree management, creating an ideal environment for wildlife. The property is subject to a Maryland Environmental Trust conservation easement; however, the easement permits the construction of one homestead, offering the opportunity to build a private residence surrounded by acreage and natural beauty. Please refer to the Kent County Health Department percolation letter and additional easement information included in the documents. Location is truly a standout feature of this rare offering. Situated within approximately 1.5 miles of downtown Chestertown, the property provides convenient access to Chester River boat ramps, Washington College, the Chester River Yacht & Country Club, shopping, dining, and all that Chestertown has to offer. Included are 3 Ten Point box deer stands, several tacticam deer cameras, and several other ladder stands. A rare combination of acreage, privacy, recreational value, and proximity to town, an exceptional opportunity on Maryland’s Upper Eastern Shore.

Chestertown

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

$40,000

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:

$50,000

Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

1 Beds ⋅ 1 Baths

Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

34155 Bradford Johnson Rd, Galena

Listing courtesy of Taylor Properties. Contact:

$325,000

ONE-LEVEL LIVING IN GALENA—SELLER WELCOMES ALL REASONABLE OFFERS! This three-bedroom, two-bath ranch offers a practical layout, manageable homesite, and the opportunity to make it your own. Built in 2007 and situated on a cleared 0.47-acre lot in the Sassafras subdivision, the home features luxury vinyl plank flooring, abundant natural light, and an open living area that connects easily to the kitchen and breakfast space. The country-style kitchen includes generous cabinet storage, an electric range, built-in microwave, and dishwasher. The primary bedroom features a private bath with a soaking tub and separate stall shower, while the remaining bedrooms can accommodate additional sleeping space, an office, hobbies, or other needs. Outside, the front, side, and rear yards provide room for gardening, recreation, outdoor gatherings, or relaxing in the peaceful surroundings. A detached shed offers convenient storage for tools, lawn equipment, and seasonal belongings. Schedule your private showing and bring the seller your reasonable offer!

3 Beds ⋅ 2 Baths

ONE-LEVEL LIVING IN GALENA—SELLER WELCOMES ALL REASONABLE OFFERS! This three-bedroom, two-bath ranch offers a practical layout, manageable homesite, and the opportunity to make it your own. Built in 2007 and situated on a cleared 0.47-acre lot in the Sassafras subdivision, the home features luxury vinyl plank flooring, abundant natural light, and an open living area that connects easily to the kitchen and breakfast space. The country-style kitchen includes generous cabinet storage, an electric range, built-in microwave, and dishwasher. The primary bedroom features a private bath with a soaking tub and separate stall shower, while the remaining bedrooms can accommodate additional sleeping space, an office, hobbies, or other needs. Outside, the front, side, and rear yards provide room for gardening, recreation, outdoor gatherings, or relaxing in the peaceful surroundings. A detached shed offers convenient storage for tools, lawn equipment, and seasonal belongings. Schedule your private showing and bring the seller your reasonable offer!

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. Contact:

$1,500,000

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertaining alike! Perfectly perched above the creek, this home offers an outdoor wonderland! It showcases a long dock with 2 lifts perfect for boating or kayaking or canoeing, an inground pool, 2 decks and magical water views! A bird loverś paradise, Swantown Creek and the connecting Sassafras River sit on the upper Chesapeake Bay watershed, making it a thoroughfare for resident species and migratory birds traveling the Atlantic Flyway! You will see Bald Eagles all year long! Inside this completely renovated Masterpiece, the fine details will fascinate even the most discerning buyers, from the gorgeous hardwood flooring to the gourmet kitchen to the double sided fireplace! The very spacious open floor plan is ideal for entertaining with multiple living and dining areas that simultaneously offer those lovely views! The luxurious kitchen has been beautifully appointed with premium countertops, a suite of super high end Forno Stainless Steel appliances including a 48" Dual Fuel Double Oven, 48" wall mounted hood, 60" 2-piece, convertible, built-in fridge, super quiet dishwasher and 24" microwave drawer, stunning cabinetry & hardware, a radiant island and a splendid butler bar! A split bedroom floor plan allows for some seclusion for the primary suite! The primary suite is intoxicating! It has its own deck, an awesome walk through closet with a ready made closet system, a palatial luxurious tiled shower, dazzling double sinks and separate water closet! The other two bedrooms are nicely situated at the other end of the home with a Jack & Jill bath! There is also a flexible bonus room off the living room perfect for a home office/study. The laundry area is sweetly tucked away behind the kitchen and flanking the stacked washer/dryer is lovely cabinetry and a useful sink! No detail has been overlooked namely the interior plantation shutters, ceiling fans, led lighting and fixtures and so much more! The large driveway and cul-de-sac location translates to lots of parking and you will also appreciate the side yard storage shed. Come be awed by this Shorewood Estates Showpiece!

3 Beds ⋅ 3 Baths

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertaining alike! Perfectly perched above the creek, this home offers an outdoor wonderland! It showcases a long dock with 2 lifts perfect for boating or kayaking or canoeing, an inground pool, 2 decks and magical water views! A bird loverś paradise, Swantown Creek and the connecting Sassafras River sit on the upper Chesapeake Bay watershed, making it a thoroughfare for resident species and migratory birds traveling the Atlantic Flyway! You will see Bald Eagles all year long! Inside this completely renovated Masterpiece, the fine details will fascinate even the most discerning buyers, from the gorgeous hardwood flooring to the gourmet kitchen to the double sided fireplace! The very spacious open floor plan is ideal for entertaining with multiple living and dining areas that simultaneously offer those lovely views! The luxurious kitchen has been beautifully appointed with premium countertops, a suite of super high end Forno Stainless Steel appliances including a 48" Dual Fuel Double Oven, 48" wall mounted hood, 60" 2-piece, convertible, built-in fridge, super quiet dishwasher and 24" microwave drawer, stunning cabinetry & hardware, a radiant island and a splendid butler bar! A split bedroom floor plan allows for some seclusion for the primary suite! The primary suite is intoxicating! It has its own deck, an awesome walk through closet with a ready made closet system, a palatial luxurious tiled shower, dazzling double sinks and separate water closet! The other two bedrooms are nicely situated at the other end of the home with a Jack & Jill bath! There is also a flexible bonus room off the living room perfect for a home office/study. The laundry area is sweetly tucked away behind the kitchen and flanking the stacked washer/dryer is lovely cabinetry and a useful sink! No detail has been overlooked namely the interior plantation shutters, ceiling fans, led lighting and fixtures and so much more! The large driveway and cul-de-sac location translates to lots of parking and you will also appreciate the side yard storage shed. Come be awed by this Shorewood Estates Showpiece!

13876 Swantown Creek Rd, Galena

Listing courtesy of Patterson-Schwartz - Greenville. Contact:

$897,000

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

3 Beds ⋅ 3 Baths

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

25411 Paradise Point Ln, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$340,000

Nestled in charming Watermans Estates, this traditional duplex home offers a perfect blend of comfort and style. With 1,720 sq ft, the inviting interior features warm wood flooring throughout the main level. Nine foot ceilings, crown molding and fresh paint give the living areas an open, airy feel. Stainless kitchen appliances and solid wood cabinets are complemented by Corian countertops in the kitchen. Upstairs you'll find an inviting primary suite with jetted tub and separate tile shower, plus two generous size bedrooms and another full bath. Step outside to a covered front porch or screened patio, both ideal for morning coffee or evening relaxation. The community is known for its friendly atmosphere and close proximity to the town's waterfront harbor and amenities. Experience the warmth and charm of Watermans Estates.

3 Beds ⋅ 3 Baths

Nestled in charming Watermans Estates, this traditional duplex home offers a perfect blend of comfort and style. With 1,720 sq ft, the inviting interior features warm wood flooring throughout the main level. Nine foot ceilings, crown molding and fresh paint give the living areas an open, airy feel. Stainless kitchen appliances and solid wood cabinets are complemented by Corian countertops in the kitchen. Upstairs you'll find an inviting primary suite with jetted tub and separate tile shower, plus two generous size bedrooms and another full bath. Step outside to a covered front porch or screened patio, both ideal for morning coffee or evening relaxation. The community is known for its friendly atmosphere and close proximity to the town's waterfront harbor and amenities. Experience the warmth and charm of Watermans Estates.

5815 Clam Cv, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

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