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Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to find anything on the water this cute and in this price range so come take a look and decide for yourself!

2 Beds ⋅ 1 Baths

Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to find anything on the water this cute and in this price range so come take a look and decide for yourself!

31673 W Edge Rd, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,000

Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

4 Beds ⋅ 2 Baths

Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$275,000

Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

3 Beds ⋅ 1 Baths

Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

956 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$349,900

ROCK HALL — ON THE GRID, NOT OFF THE GRID! NEW PRICE and an incredible opportunity to enjoy Eastern Shore living with 2,040+ sq ft, a flexible floor plan, premium oversized lot and NO HOA! This beautifully maintained end-unit townhome offers 3 bedrooms plus an impressive oversized sunroom/flex space—larger than the primary suite—with its own private exterior entrance and direct kitchen access. Use it as a 4th bedroom, guest suite, home office, studio or additional living space. Inside you’ll find abundant natural light, hardwood flooring, a gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your finishing touches. Outside offers low-maintenance living, plenty of parking and room for the golf cart. And the location is what Rock Hall living is all about! Enjoy nearby marinas, the harbor, boating, fishing, restaurants, coffee shops, live music, a brewery, markets and more. Spend less time maintaining and more time enjoying the Chesapeake Bay lifestyle. NO HOA, MORE SPACE and a NEW PRICE—come see why Rock Hall is one of the Eastern Shore’s best-kept secrets!

3 Beds ⋅ 3 Baths

ROCK HALL — ON THE GRID, NOT OFF THE GRID! NEW PRICE and an incredible opportunity to enjoy Eastern Shore living with 2,040+ sq ft, a flexible floor plan, premium oversized lot and NO HOA! This beautifully maintained end-unit townhome offers 3 bedrooms plus an impressive oversized sunroom/flex space—larger than the primary suite—with its own private exterior entrance and direct kitchen access. Use it as a 4th bedroom, guest suite, home office, studio or additional living space. Inside you’ll find abundant natural light, hardwood flooring, a gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your finishing touches. Outside offers low-maintenance living, plenty of parking and room for the golf cart. And the location is what Rock Hall living is all about! Enjoy nearby marinas, the harbor, boating, fishing, restaurants, coffee shops, live music, a brewery, markets and more. Spend less time maintaining and more time enjoying the Chesapeake Bay lifestyle. NO HOA, MORE SPACE and a NEW PRICE—come see why Rock Hall is one of the Eastern Shore’s best-kept secrets!

21123 Striper Run, Rock Hall

Listing courtesy of Chaney Homes, LLC. Contact:

$359,900

Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The level of craftsmanship, custom finishes, thoughtful details, and high-end touches throughout this home are the kind buyers WANT but rarely get from a builder at this price point. Simply put, you will NOT find these upgrades in new construction without spending significantly more. The stunning kitchen is the heart of the home, featuring upgraded finishes, custom details, and a layout designed perfectly for entertaining and everyday coastal living. Every space throughout the home feels warm, inviting, and move-in ready with details that immediately stand out. Whether you’re searching for a full-time residence, weekend getaway, vacation home, Airbnb investment opportunity, or second home near the Chesapeake Bay, this property checks every box. -High-end upgrades throughout -Stunning kitchen with custom finishes -Spacious layout designed for entertaining -Move-in ready with luxury details throughout -Golf cart or bike ride to marinas, restaurants, and downtown Rock Hall -Minutes to waterfront dining, boating, and the Chesapeake Bay -The perfect blend of location, lifestyle, and luxury upgrades Homes with THIS location and THIS level of upgrades rarely hit the market in Rock Hall… and when they do, buyers move FAST. If you’ve been searching for a beautifully upgraded home in Rock Hall, Maryland with close access to marinas, boating, waterfront restaurants, and Chesapeake Bay living, this is the one you do not want to miss.

3 Beds ⋅ 3 Baths

Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The level of craftsmanship, custom finishes, thoughtful details, and high-end touches throughout this home are the kind buyers WANT but rarely get from a builder at this price point. Simply put, you will NOT find these upgrades in new construction without spending significantly more. The stunning kitchen is the heart of the home, featuring upgraded finishes, custom details, and a layout designed perfectly for entertaining and everyday coastal living. Every space throughout the home feels warm, inviting, and move-in ready with details that immediately stand out. Whether you’re searching for a full-time residence, weekend getaway, vacation home, Airbnb investment opportunity, or second home near the Chesapeake Bay, this property checks every box. -High-end upgrades throughout -Stunning kitchen with custom finishes -Spacious layout designed for entertaining -Move-in ready with luxury details throughout -Golf cart or bike ride to marinas, restaurants, and downtown Rock Hall -Minutes to waterfront dining, boating, and the Chesapeake Bay -The perfect blend of location, lifestyle, and luxury upgrades Homes with THIS location and THIS level of upgrades rarely hit the market in Rock Hall… and when they do, buyers move FAST. If you’ve been searching for a beautifully upgraded home in Rock Hall, Maryland with close access to marinas, boating, waterfront restaurants, and Chesapeake Bay living, this is the one you do not want to miss.

21124 Striper Run, Rock Hall

Listing courtesy of RE/MAX Executive. Contact:

$399,000

Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From the moment you arrive, it feels like your own private retreat. Inside, the open floor plan is filled with warmth and character, featuring exposed beams, rich hickory flooring, and beautiful wood accents throughout. Skylights and expansive windows bring in natural light and showcase the ever-changing scenery just outside—whether it’s wildlife passing through or the quiet beauty of the woods. The kitchen is truly the heart of the home, designed with both function and gathering in mind. Custom solid cherry cabinetry with soft-close doors and drawers, a spacious walk-in pantry, and an oversized island with seating, shelving, and a propane cooktop make it as practical as it is inviting. A charming bay window over the sink offers the perfect view of the backyard. Just steps away, the screened porch and private deck create seamless indoor-outdoor living—ideal for morning coffee, entertaining, or simply unwinding in the peaceful surroundings. The first-floor primary suite offers comfort and convenience, complete with its own private deck, walk-in closet, and a spa-like bath featuring a soaking tub and separate shower. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft space perfect for a home office, reading nook, or play area. Built with efficiency and quality in mind, the home features Structural Insulated Panels (SIPs) for enhanced insulation and comfort, along with a conditioned crawl space with concrete flooring and lighting for easy-access storage. The newly installed roof includes a 5-year workmanship warranty from Monarch Roofing and a 50-year material defect warranty from Owens Corning Roofing. A generator adds an extra layer of peace of mind. Located in a quiet rural setting with access to Herringtown Creek, you’re also just minutes from Rock Hall—known for its charming restaurants, marinas, shops, and waterfront at Ferry Park. For even more outdoor exploration, Eastern Neck National Wildlife Refuge is just a short drive away. If you’ve been dreaming of a home that offers privacy, comfort, and a true connection to nature, this one is worth experiencing in person. One year home warranty included!

3 Beds ⋅ 2 Baths

Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From the moment you arrive, it feels like your own private retreat. Inside, the open floor plan is filled with warmth and character, featuring exposed beams, rich hickory flooring, and beautiful wood accents throughout. Skylights and expansive windows bring in natural light and showcase the ever-changing scenery just outside—whether it’s wildlife passing through or the quiet beauty of the woods. The kitchen is truly the heart of the home, designed with both function and gathering in mind. Custom solid cherry cabinetry with soft-close doors and drawers, a spacious walk-in pantry, and an oversized island with seating, shelving, and a propane cooktop make it as practical as it is inviting. A charming bay window over the sink offers the perfect view of the backyard. Just steps away, the screened porch and private deck create seamless indoor-outdoor living—ideal for morning coffee, entertaining, or simply unwinding in the peaceful surroundings. The first-floor primary suite offers comfort and convenience, complete with its own private deck, walk-in closet, and a spa-like bath featuring a soaking tub and separate shower. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft space perfect for a home office, reading nook, or play area. Built with efficiency and quality in mind, the home features Structural Insulated Panels (SIPs) for enhanced insulation and comfort, along with a conditioned crawl space with concrete flooring and lighting for easy-access storage. The newly installed roof includes a 5-year workmanship warranty from Monarch Roofing and a 50-year material defect warranty from Owens Corning Roofing. A generator adds an extra layer of peace of mind. Located in a quiet rural setting with access to Herringtown Creek, you’re also just minutes from Rock Hall—known for its charming restaurants, marinas, shops, and waterfront at Ferry Park. For even more outdoor exploration, Eastern Neck National Wildlife Refuge is just a short drive away. If you’ve been dreaming of a home that offers privacy, comfort, and a true connection to nature, this one is worth experiencing in person. One year home warranty included!

22300 Frazier Rd, Rock Hall

Listing courtesy of Cross Street Realtors LLC. Contact:

$379,000

WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

4 Beds ⋅ 3 Baths

WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

122 Main St, Galena

Listing courtesy of Village Real Estate Company LLC. Contact:

$315,000

* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

3 Beds ⋅ 2 Baths

* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$379,900

Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd floor is another bedroom that could also be used as a family room, hobby room or office. Out back, there is a driveway with parking for 2 cars. The rear yard is perfect for entertaining with a deck, patio and covered pergola. Brand new oil furnace. Mini splits in most of the rooms. This property is quaint and charming and would be perfect as a beach home or a full time residence.

4 Beds ⋅ 2 Baths

Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd floor is another bedroom that could also be used as a family room, hobby room or office. Out back, there is a driveway with parking for 2 cars. The rear yard is perfect for entertaining with a deck, patio and covered pergola. Brand new oil furnace. Mini splits in most of the rooms. This property is quaint and charming and would be perfect as a beach home or a full time residence.

104 Main St, Betterton

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

$269,900

Move-in ready and packed with updates, this 3-bedroom, 1-bath home offers an affordable opportunity to enjoy Eastern Shore living without a long list of projects waiting for you. Major improvements include a newer roof, HVAC system, water heater, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, plus a vapor barrier and insulation in the crawlspace. Inside, the home feels bright, clean, and refreshed, making it an easy choice for buyers looking for comfort, convenience, and low-maintenance living. The location makes it even better. In approximately 12 minutes, you can be exploring historic Chestertown, spending the day at Betterton Beach, or enjoying waterfront dining, boating, and sunsets at Great Oak Landing. With its extensive updates, convenient location, and newly improved price, this home offers a lot of value for buyers.

3 Beds ⋅ 1 Baths

Move-in ready and packed with updates, this 3-bedroom, 1-bath home offers an affordable opportunity to enjoy Eastern Shore living without a long list of projects waiting for you. Major improvements include a newer roof, HVAC system, water heater, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, plus a vapor barrier and insulation in the crawlspace. Inside, the home feels bright, clean, and refreshed, making it an easy choice for buyers looking for comfort, convenience, and low-maintenance living. The location makes it even better. In approximately 12 minutes, you can be exploring historic Chestertown, spending the day at Betterton Beach, or enjoying waterfront dining, boating, and sunsets at Great Oak Landing. With its extensive updates, convenient location, and newly improved price, this home offers a lot of value for buyers.

11167 Oak Ln, Worton

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

5656 Circle Park Dr Park Unit #5594, Rock Hall

$89,000

Brand new 2025 Clayton Ruby Z located in the Circle Park mobile home community in Rock Hall. This 2-bedroom, 2-bathroom home features a spacious open floor plan with a full bedroom and bathroom on either end, offering privacy and flexibility. The home comes complete with brand-new appliances and is ready for its first owners. Public water and sewer. Financing available through Clayton Homes, subject to credit score and financing approval. Offered at $110,000. Buyer must be approved by the park. Ground rent is $550/month (buyer to verify). Contact us to schedule a tour.

2 Beds ⋅ 2 Baths

Brand new 2025 Clayton Ruby Z located in the Circle Park mobile home community in Rock Hall. This 2-bedroom, 2-bathroom home features a spacious open floor plan with a full bedroom and bathroom on either end, offering privacy and flexibility. The home comes complete with brand-new appliances and is ready for its first owners. Public water and sewer. Financing available through Clayton Homes, subject to credit score and financing approval. Offered at $110,000. Buyer must be approved by the park. Ground rent is $550/month (buyer to verify). Contact us to schedule a tour.

5656 Circle Park Dr Park Unit #5594, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

11944 Augustine Herman Hwy, Kennedyville

$399,000

Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm. Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat. Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage. Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

4 Beds ⋅ 2 Baths

Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm. Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat. Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage. Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

11944 Augustine Herman Hwy, Kennedyville

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

$210,000

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

3 Beds ⋅ 2 Baths

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

26663 Maple Ave, Still Pond

Listing courtesy of Real Estate Consultants. Contact:

$399,900

REDUCED!! Nestled in the charming Betterton community, this delightful farmhouse-style home offers a perfect blend of rustic charm and modern comfort. With 3 spacious bedrooms and 1.5 bathrooms, the interior features warm wood flooring and a cozy brick fireplace, creating an inviting atmosphere for gatherings. The attic provides additional storage or potential for creative use, while the partial basement adds practicality to your living space. Set on a generous 3.75-acre lot, this property boasts a serene backdrop of trees and open spaces, ensuring privacy and tranquility. Enjoy panoramic views of the surrounding woods, perfect for nature lovers and those seeking a peaceful retreat. The outdoor space is ideal for gardening, play, or simply unwinding in the fresh air. Located in a rural setting, this home is just a short walk from local amenities, including r Betterton beach and boat ramp. The community is known for its friendly atmosphere and strong sense of belonging. Public services are readily available, ensuring convenience and peace of mind. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle that Betterton offers, where comfort meets community. Lot does have subdivision possibilities. Check with the town manager.

3 Beds ⋅ 2 Baths

REDUCED!! Nestled in the charming Betterton community, this delightful farmhouse-style home offers a perfect blend of rustic charm and modern comfort. With 3 spacious bedrooms and 1.5 bathrooms, the interior features warm wood flooring and a cozy brick fireplace, creating an inviting atmosphere for gatherings. The attic provides additional storage or potential for creative use, while the partial basement adds practicality to your living space. Set on a generous 3.75-acre lot, this property boasts a serene backdrop of trees and open spaces, ensuring privacy and tranquility. Enjoy panoramic views of the surrounding woods, perfect for nature lovers and those seeking a peaceful retreat. The outdoor space is ideal for gardening, play, or simply unwinding in the fresh air. Located in a rural setting, this home is just a short walk from local amenities, including r Betterton beach and boat ramp. The community is known for its friendly atmosphere and strong sense of belonging. Public services are readily available, ensuring convenience and peace of mind. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle that Betterton offers, where comfort meets community. Lot does have subdivision possibilities. Check with the town manager.

201 Ericsson Ave, Betterton

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$350,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

1 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 2B, Chestertown

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

$375,000

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

2 Beds ⋅ 1 Baths

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

117 Water St N Unit 2A, Chestertown

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

$200,000

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

1 Beds ⋅ 1 Baths

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

117 Water St N Unit 1B, Chestertown

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

$369,000

REICE REDUCED!! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, you’ll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area — perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from town, marinas, restaurants, and waterfront attractions.

3 Beds ⋅ 3 Baths

REICE REDUCED!! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, you’ll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area — perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from town, marinas, restaurants, and waterfront attractions.

6416 Edesville Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$210,000

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by. Seller is offering a $5,000 credit to the buyer !! Property sold AS- IS Seller will make NO REPAIRS

3 Beds ⋅ 2 Baths

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by. Seller is offering a $5,000 credit to the buyer !! Property sold AS- IS Seller will make NO REPAIRS

25044 Travis Trl, Worton

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

$339,000

5 Beds ⋅ 3 Baths

6746 Quaker Neck Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$385,000

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

4 Beds ⋅ 3 Baths

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

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$290,000

The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and .5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed Reference 249/96 . Both homes are in need of major repair however the parcels are lovely. These residentially zoned properties present a great investment opportunity. The parcels are of a generous size, featuring front and side yards that offers great outdoor space. Still Pond is just minutes from Betterton Beach. Total size of three parcels is 1.66 +/- acre.

3 Beds ⋅ 2 Baths

The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and .5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed Reference 249/96 . Both homes are in need of major repair however the parcels are lovely. These residentially zoned properties present a great investment opportunity. The parcels are of a generous size, featuring front and side yards that offers great outdoor space. Still Pond is just minutes from Betterton Beach. Total size of three parcels is 1.66 +/- acre.

26670-26680 Maple Ave, Still Pond

Listing courtesy of Doug Ashley Realtors, LLC. Contact: