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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:

$312,500

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:

$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:

$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:

$535,000

Custom-built rancher situated on more than 1.8 acres in the Kentfield community of Worton. Designed for one-floor living, the home offers a spacious, functional layout along with an unfinished basement that provides plenty of room for storage, a workshop, or other possibilities. The large kitchen features a breakfast area, generous cabinet and counter space, and a center island with propane cooktop. The living room includes built-in cabinetry, a propane fireplace, and a slider door leading to the screened porch overlooking the private backyard. The living room opens to the dining area and entry, creating an easy flow through the main living spaces. The primary suite includes an en-suite bath with two walk-in closets, dual vanities, a separate shower, and jetted tub. Two additional bedrooms share a full hall bath, while a separate office offers flexible space and could serve as a fourth bedroom. The two car, side entry garage has access to the basement. Outside, the large backyard is surrounded by mature trees and includes split-rail fencing, a storage shed, and covered pergola. The 1.8+ acre lot offers plenty of room for a future pool, larger outbuilding, gardens, or additional outdoor living space. Located near Still Pond Creek and just five minutes from Worton Elementary School and Kent County High School, the property offers a peaceful setting while remaining convenient to both Chestertown and Rock Hall. Middletown, Delaware is approximately 35 minutes away. Schedule a showing today.

3 Beds ⋅ 3 Baths

Custom-built rancher situated on more than 1.8 acres in the Kentfield community of Worton. Designed for one-floor living, the home offers a spacious, functional layout along with an unfinished basement that provides plenty of room for storage, a workshop, or other possibilities. The large kitchen features a breakfast area, generous cabinet and counter space, and a center island with propane cooktop. The living room includes built-in cabinetry, a propane fireplace, and a slider door leading to the screened porch overlooking the private backyard. The living room opens to the dining area and entry, creating an easy flow through the main living spaces. The primary suite includes an en-suite bath with two walk-in closets, dual vanities, a separate shower, and jetted tub. Two additional bedrooms share a full hall bath, while a separate office offers flexible space and could serve as a fourth bedroom. The two car, side entry garage has access to the basement. Outside, the large backyard is surrounded by mature trees and includes split-rail fencing, a storage shed, and covered pergola. The 1.8+ acre lot offers plenty of room for a future pool, larger outbuilding, gardens, or additional outdoor living space. Located near Still Pond Creek and just five minutes from Worton Elementary School and Kent County High School, the property offers a peaceful setting while remaining convenient to both Chestertown and Rock Hall. Middletown, Delaware is approximately 35 minutes away. Schedule a showing today.

12200 Azalea Ct, Worton

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

$410,000

Welcome 14 1st Avenue - a charming Victorian just steps from the Betterton bluff and public beach and with water views from the back deck and primary bedroom. Known as the Jewel of the Chesapeake, Betterton is located at the confluence of the Sassafras River and Chesapeake Bay and got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This four bedroom, two full bathroom home has been lovingly maintained and is full of historic charm: hardwood floors throughout both levels, crown, baseboard, and bullseye moldings, transom windows, the list goes on. Brand new architectural shingle roof in 2025. Geothermal heating and cooling systems are energy efficient and cost effective. The first floor layout is all about convenience with an open layout and full bath. Natural light abounds the living, dining and kitchen spaces. Moving upstairs you will love the spacious primary bedroom with vaulted ceiling and water views out the back window. A full bath, three more bedrooms and a large attic / storage space complete the second floor. Large walkout basement providing easy access for bikes, kayaks, paddle boards, you name it! Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

4 Beds ⋅ 2 Baths

Welcome 14 1st Avenue - a charming Victorian just steps from the Betterton bluff and public beach and with water views from the back deck and primary bedroom. Known as the Jewel of the Chesapeake, Betterton is located at the confluence of the Sassafras River and Chesapeake Bay and got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This four bedroom, two full bathroom home has been lovingly maintained and is full of historic charm: hardwood floors throughout both levels, crown, baseboard, and bullseye moldings, transom windows, the list goes on. Brand new architectural shingle roof in 2025. Geothermal heating and cooling systems are energy efficient and cost effective. The first floor layout is all about convenience with an open layout and full bath. Natural light abounds the living, dining and kitchen spaces. Moving upstairs you will love the spacious primary bedroom with vaulted ceiling and water views out the back window. A full bath, three more bedrooms and a large attic / storage space complete the second floor. Large walkout basement providing easy access for bikes, kayaks, paddle boards, you name it! Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

14 1st Ave, Betterton

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

$499,999

Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

4 Beds ⋅ 4 Baths

Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

331 Devon Dr, Chestertown

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

$425,000

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. Coming to market October 1st — don't miss your opportunity to tour this beautiful new home!

3 Beds ⋅ 3 Baths

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. Coming to market October 1st — don't miss your opportunity to tour this beautiful new home!

5855 Cottage Ave, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

$389,000

Nestled in the community of Reeds Meadows, this contemporary residence offers a blend of modern convenience and comfortable living. Built in 2020, this meticulously maintained home spans 1,974 square feet, providing ample space for relaxation and entertainment. As you approach the property, you are greeted by a charming exterior with durable vinyl siding, complemented by well-maintained entry. The newly paved road invites leisurely strolls in a pleasant setting. An asphalt driveway leads to an attached garage featuring convenient inside access as well as access to the rear of the property. A garage door with remote opener ensures effortless entry and exit. Step inside to discover a thoughtfully designed layout that emphasizes both functionality and style. The heart of the home is the kitchen, equipped with stainless appliances including a built-in microwave, sleek dishwasher, and a classic range hood. The new refrigerator and stove make meal preparation a delight, while the adjacent laundry area with half bath is conveniently located on the main floor. Natural light pours through large windows, enhancing the warm ambiance throughout. The absence of a fireplace allows for a clean, modern aesthetic, while the contemporary design elements provide a timeless appeal. Retreat to the tranquil first floor master suite, complete with an en-suite bathroom featuring luxurious finishes. Two additional bedrooms, a bonus room, and a well-appointed full-bath ensure comfort and privacy for all. Step outside onto the custom deck, perfect for alfresco dining or simply enjoy the peaceful surroundings of your 0.32-acre lot. This outdoor space is ideal for hosting summer barbecues or unwinding with a good book in the fresh air. Experience the lifestyle that you deserve. Don't miss the opportunity to make this residence your own. Located about 10 minutes from historic Chestertown on the Chester River, this tidy subdivision 's location offers quick access to public landings for fishing and boating fun, beautiful farms, including Red Acres, which offers beautiful produce, flowers, and retail products. Located between Chestertown/Galena, and Betterton, and also close to Rock Hall which boasts good shopping, restaurants and loads of fun on the Chesapeake Bay.

3 Beds ⋅ 3 Baths

Nestled in the community of Reeds Meadows, this contemporary residence offers a blend of modern convenience and comfortable living. Built in 2020, this meticulously maintained home spans 1,974 square feet, providing ample space for relaxation and entertainment. As you approach the property, you are greeted by a charming exterior with durable vinyl siding, complemented by well-maintained entry. The newly paved road invites leisurely strolls in a pleasant setting. An asphalt driveway leads to an attached garage featuring convenient inside access as well as access to the rear of the property. A garage door with remote opener ensures effortless entry and exit. Step inside to discover a thoughtfully designed layout that emphasizes both functionality and style. The heart of the home is the kitchen, equipped with stainless appliances including a built-in microwave, sleek dishwasher, and a classic range hood. The new refrigerator and stove make meal preparation a delight, while the adjacent laundry area with half bath is conveniently located on the main floor. Natural light pours through large windows, enhancing the warm ambiance throughout. The absence of a fireplace allows for a clean, modern aesthetic, while the contemporary design elements provide a timeless appeal. Retreat to the tranquil first floor master suite, complete with an en-suite bathroom featuring luxurious finishes. Two additional bedrooms, a bonus room, and a well-appointed full-bath ensure comfort and privacy for all. Step outside onto the custom deck, perfect for alfresco dining or simply enjoy the peaceful surroundings of your 0.32-acre lot. This outdoor space is ideal for hosting summer barbecues or unwinding with a good book in the fresh air. Experience the lifestyle that you deserve. Don't miss the opportunity to make this residence your own. Located about 10 minutes from historic Chestertown on the Chester River, this tidy subdivision 's location offers quick access to public landings for fishing and boating fun, beautiful farms, including Red Acres, which offers beautiful produce, flowers, and retail products. Located between Chestertown/Galena, and Betterton, and also close to Rock Hall which boasts good shopping, restaurants and loads of fun on the Chesapeake Bay.

25094 Reeds Mdw, Worton

Listing courtesy of Doug Ashley Realtors, 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:

$329,900

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:

$489,000

Welcome to 32050 River Road in Millington! This fully renovated brick ranch-style home offers the perfect blend of modern updates, comfortable living, and peaceful country living. Situated on approximately 1.6 acres, this spacious property features 4 bedrooms and 2 full bathrooms, providing plenty of room for family and guests. Step inside to discover a beautifully updated interior with a fresh, modern feel throughout. The renovated kitchen features stainless-steel appliances and offers a functional space for everyday cooking and entertaining. The main-level layout provides convenient one-level living with generously sized bedrooms and updated bathrooms. Enjoy the outdoors from the inviting screened-in back porch — the perfect spot to relax, entertain, or take in the peaceful surroundings while enjoying protection from the elements. The expansive 1.6-acre lot provides plenty of room to enjoy the outdoors and create your own private retreat. The full basement offers valuable additional space and endless possibilities for storage, recreation, a workshop, or future finished living space. With its classic brick exterior, extensive renovations, spacious floor plan, screened-in back porch, full basement, and beautiful acreage, this home is move-in ready and waiting for its next owner.

4 Beds ⋅ 2 Baths

Welcome to 32050 River Road in Millington! This fully renovated brick ranch-style home offers the perfect blend of modern updates, comfortable living, and peaceful country living. Situated on approximately 1.6 acres, this spacious property features 4 bedrooms and 2 full bathrooms, providing plenty of room for family and guests. Step inside to discover a beautifully updated interior with a fresh, modern feel throughout. The renovated kitchen features stainless-steel appliances and offers a functional space for everyday cooking and entertaining. The main-level layout provides convenient one-level living with generously sized bedrooms and updated bathrooms. Enjoy the outdoors from the inviting screened-in back porch — the perfect spot to relax, entertain, or take in the peaceful surroundings while enjoying protection from the elements. The expansive 1.6-acre lot provides plenty of room to enjoy the outdoors and create your own private retreat. The full basement offers valuable additional space and endless possibilities for storage, recreation, a workshop, or future finished living space. With its classic brick exterior, extensive renovations, spacious floor plan, screened-in back porch, full basement, and beautiful acreage, this home is move-in ready and waiting for its next owner.

32050 River Rd, Millington

Listing courtesy of Crown Homes Real Estate. Contact:

$131,000

Welcome to peaceful country living in this cozy 2-bedroom, 1-bath manufactured home. Nestled in a serene setting, this home offers several recent improvements. Major updates include a new roof installed in 2026 with a lifetime warranty, newly installed storm door, insulated pipes, hot water heater, and gutters. Step outside and enjoy the covered rear porch—perfect for relaxing and taking in the tranquil surroundings. The partially fenced backyard provides additional outdoor space, while the detached shed offers convenient storage and is equipped with electricity and cable-ready connections. With its recent updates, peaceful setting, and outdoor amenities, this home is ready for its next owner to make it their own. Property is being sold strictly as-is.

2 Beds ⋅ 1 Baths

Welcome to peaceful country living in this cozy 2-bedroom, 1-bath manufactured home. Nestled in a serene setting, this home offers several recent improvements. Major updates include a new roof installed in 2026 with a lifetime warranty, newly installed storm door, insulated pipes, hot water heater, and gutters. Step outside and enjoy the covered rear porch—perfect for relaxing and taking in the tranquil surroundings. The partially fenced backyard provides additional outdoor space, while the detached shed offers convenient storage and is equipped with electricity and cable-ready connections. With its recent updates, peaceful setting, and outdoor amenities, this home is ready for its next owner to make it their own. Property is being sold strictly as-is.

21899 Lovers Ln, Rock Hall

Listing courtesy of Coldwell Banker Realty. Contact:

$489,000

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:

$284,000

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:

$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:

$55,000

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

SELLER WELCOMES ALLREASONABLE OFFERS! Discover easy one-level living at this three-bedroom, two-bath ranch home located in Galena’s Sassafras subdivision. Set on a cleared 0.47-acre lot, the property offers spacious front, side, and rear yards with room for outdoor entertaining, recreation, gardening, or future improvements. Inside, the open layout creates a natural flow between the light-filled living area, country-style kitchen, and adjoining breakfast space. The kitchen is equipped with ample cabinetry, an electric range, built-in microwave, and dishwasher, while luxury vinyl plank flooring adds durability and a cohesive look throughout the main living areas. The primary bedroom includes a private bath with a soaking tub and separate stall shower. Two additional bedrooms provide flexibility for sleeping space, an office, hobbies, or storage. A detached shed provides additional space for lawn equipment and outdoor items. Built in 2007 and surrounded by peaceful garden and lawn views, this home offers comfortable living with convenient access to Galena and the surrounding Eastern Shore area. Schedule your private showing and submit your offer for the seller’s consideration.

3 Beds ⋅ 2 Baths

SELLER WELCOMES ALLREASONABLE OFFERS! Discover easy one-level living at this three-bedroom, two-bath ranch home located in Galena’s Sassafras subdivision. Set on a cleared 0.47-acre lot, the property offers spacious front, side, and rear yards with room for outdoor entertaining, recreation, gardening, or future improvements. Inside, the open layout creates a natural flow between the light-filled living area, country-style kitchen, and adjoining breakfast space. The kitchen is equipped with ample cabinetry, an electric range, built-in microwave, and dishwasher, while luxury vinyl plank flooring adds durability and a cohesive look throughout the main living areas. The primary bedroom includes a private bath with a soaking tub and separate stall shower. Two additional bedrooms provide flexibility for sleeping space, an office, hobbies, or storage. A detached shed provides additional space for lawn equipment and outdoor items. Built in 2007 and surrounded by peaceful garden and lawn views, this home offers comfortable living with convenient access to Galena and the surrounding Eastern Shore area. Schedule your private showing and submit your offer for the seller’s consideration.

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. 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:

$229,000

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.

3 Beds ⋅ 1 Baths

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:

$363,000

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

3 Beds ⋅ 3 Baths

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

$320,000

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Hall’s restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall.

4 Beds ⋅ 1 Baths

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Hall’s restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall.

20705 Wilkins Ave, Rock Hall

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

$315,000

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

3 Beds ⋅ 1 Baths

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$285,000

**OPEN HOUSE Saturday October 3rd 10AM-12PM** This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own. Three comfortably sized bedrooms provide flexibility for sleeping, working from home or creating a dedicated hobby space. The updated full bathroom continues the fresh aesthetic with tile flooring and a coordinating white vanity. Even the everyday necessities have been thoughtfully considered with a dedicated laundry closet featuring a full-size washer and dryer plus shelving for additional storage. Outside, the large corner lot gives you room to spread out without sacrificing that familiar neighborhood feel. Step through the rear entry onto the newer paver patio, perfect for grilling, outdoor dining or relaxing while overlooking the playset and backyard. Vinyl privacy fencing, a storage shed, long driveway and plenty of usable outdoor space round out the property. With main level living, thoughtful updates and neighborhood vibes without the community HOA, this home offers an easy, comfortable lifestyle with plenty of opportunity to make it your own.

3 Beds ⋅ 1 Baths

**OPEN HOUSE Saturday October 3rd 10AM-12PM** This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own. Three comfortably sized bedrooms provide flexibility for sleeping, working from home or creating a dedicated hobby space. The updated full bathroom continues the fresh aesthetic with tile flooring and a coordinating white vanity. Even the everyday necessities have been thoughtfully considered with a dedicated laundry closet featuring a full-size washer and dryer plus shelving for additional storage. Outside, the large corner lot gives you room to spread out without sacrificing that familiar neighborhood feel. Step through the rear entry onto the newer paver patio, perfect for grilling, outdoor dining or relaxing while overlooking the playset and backyard. Vinyl privacy fencing, a storage shed, long driveway and plenty of usable outdoor space round out the property. With main level living, thoughtful updates and neighborhood vibes without the community HOA, this home offers an easy, comfortable lifestyle with plenty of opportunity to make it your own.

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

$359,000

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

3 Beds ⋅ 2 Baths

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

374 Hurtt Ave, Millington

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

$270,000

Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for gatherings and everyday living. The spacious kitchen features a convenient island, perfect for casual meals or entertaining guests. Equipped with stainless steel appliances, including a built-in microwave, dishwasher, and washer/dryer, this kitchen is both stylish and practical. The breakfast area is a lovely spot to enjoy your morning coffee while basking in the natural light that fills the space. This home boasts three well-appointed bedrooms, including a primary suite with an en-suite bathroom that features a tub shower, providing a serene retreat at the end of the day. Ceiling fans throughout the home ensure comfort year-round, while the combination of living and dining spaces enhances the sense of togetherness. Outside, the property is equally inviting. The exterior is adorned with low-maintenance vinyl siding and features exterior lighting that adds a warm glow to the evenings. A spacious deck invites you to enjoy outdoor living, whether it's hosting summer barbecues or simply unwinding with a good book. The lot backs to trees, offering a peaceful backdrop and a sense of privacy that is hard to find. The 0.14-acre lot provides ample space for gardening or play, while a handy shed offers additional storage for tools and outdoor equipment. Parking is a breeze with a dedicated driveway, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where comfort meets functionality. With its excellent condition and modern amenities, it's ready for you to make it your own. Don't miss the opportunity to experience the warmth and charm of this beautiful property in WORTON.

3 Beds ⋅ 2 Baths

Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for gatherings and everyday living. The spacious kitchen features a convenient island, perfect for casual meals or entertaining guests. Equipped with stainless steel appliances, including a built-in microwave, dishwasher, and washer/dryer, this kitchen is both stylish and practical. The breakfast area is a lovely spot to enjoy your morning coffee while basking in the natural light that fills the space. This home boasts three well-appointed bedrooms, including a primary suite with an en-suite bathroom that features a tub shower, providing a serene retreat at the end of the day. Ceiling fans throughout the home ensure comfort year-round, while the combination of living and dining spaces enhances the sense of togetherness. Outside, the property is equally inviting. The exterior is adorned with low-maintenance vinyl siding and features exterior lighting that adds a warm glow to the evenings. A spacious deck invites you to enjoy outdoor living, whether it's hosting summer barbecues or simply unwinding with a good book. The lot backs to trees, offering a peaceful backdrop and a sense of privacy that is hard to find. The 0.14-acre lot provides ample space for gardening or play, while a handy shed offers additional storage for tools and outdoor equipment. Parking is a breeze with a dedicated driveway, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where comfort meets functionality. With its excellent condition and modern amenities, it's ready for you to make it your own. Don't miss the opportunity to experience the warmth and charm of this beautiful property in WORTON.

25213 Porters Grove Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact:

$675,000

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

5 Beds ⋅ 3 Baths

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

212 Washington Ave, Chestertown

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

$339,000

Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

2 Beds ⋅ 2 Baths

Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

1 Bayview Rd Unit 19A, Betterton

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