easternshoremdfineproperties.com Search Results

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:

$2,150,000

Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private deep-water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

4 Beds ⋅ 4 Baths

Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private deep-water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

31436 Sassafras River Ave, Galena

Listing courtesy of EXP Realty, LLC. 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:

$799,000

This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at the rear of the property could remain in ag use as tilled land and/or be used for hunting or as a horse farm. With ample room to customize, this home is a canvas for your personal touch. Located in Kent County, you'll enjoy a peaceful retreat while still being close to local amenities. This property is not just a house; it's a place where you can truly feel at home. Don't miss the opportunity to make this inviting space your own! This property is being sold as-is.

4 Beds ⋅ 2 Baths

This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at the rear of the property could remain in ag use as tilled land and/or be used for hunting or as a horse farm. With ample room to customize, this home is a canvas for your personal touch. Located in Kent County, you'll enjoy a peaceful retreat while still being close to local amenities. This property is not just a house; it's a place where you can truly feel at home. Don't miss the opportunity to make this inviting space your own! This property is being sold as-is.

4020 Eastern Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$349,900

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:

$499,000

Amazing waterfront community on the Sassafras river. This Kentmore Park home was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect year round get away or primary residence. Well maintained. Four bedrooms and two baths. Lower level garage and walk out basement. Enclosed lawn and yard equipment storage space. Rear yard gathering area and room for a garden. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park Community areas. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, sailing, power boating, jet skis. Friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

4 Beds ⋅ 2 Baths

Amazing waterfront community on the Sassafras river. This Kentmore Park home was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect year round get away or primary residence. Well maintained. Four bedrooms and two baths. Lower level garage and walk out basement. Enclosed lawn and yard equipment storage space. Rear yard gathering area and room for a garden. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park Community areas. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, sailing, power boating, jet skis. Friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

14136 Kentmore Park Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. 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:

$425,000

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

3 Beds ⋅ 2 Baths

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

6202 Rock Hall Rd, Rock Hall

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

11944 Augustine Herman Hwy, Kennedyville

$379,000

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:

$799,900

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

3 Beds ⋅ 4 Baths

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

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

$210,000

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

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:

$750,000

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

2 Baths

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. 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:

$1,750,000

Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

5 Beds ⋅ 3 Baths

Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

14183 Roberts Dr, Golts

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,195,000

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

5 Beds ⋅ 5 Baths

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

105 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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:

How much is your home worth?

How much is your home worth?