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$1,399,000

Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property designed for gathering generations of family and friends. A long private approach welcomes you to a setting where nature and waterfront living take center stage. Inside, hardwood floors, timeless architecture, and expansive Bay views create a warm yet elegant atmosphere. The waterfront family room features a striking stone fireplace with wood-burning insert and opens seamlessly to both the screened porch and covered deck, creating effortless indoor-outdoor living. The spacious kitchen was designed with entertaining in mind, offering a center island, breakfast bar, abundant cabinetry, stainless steel appliances, double wall ovens, pantry storage, and an oversized breakfast room ideal for casual mornings by the water. Formal living and dining rooms provide additional space for hosting holidays and special occasions. The first-floor primary suite serves as a private waterfront sanctuary with direct access to the covered porch and peaceful Chesapeake Bay views. Upstairs, five spacious guest bedrooms and three full baths—including a private en-suite—offer flexibility for large families, guests, or vacation rental potential. Vaulted ceilings and dormer windows add architectural charm and natural light throughout the second level. Outside, the lifestyle only gets better. Spend summer days around the inground pool, rinse off in the outdoor shower after boating or kayaking, enjoy crab feasts on the screened porch, or gather around the waterside fire pit as the sun sets across the Bay. The partially wooded acreage provides exceptional privacy while attracting an abundance of wildlife including bald eagles, deer, ducks, geese, and shorebirds—an everyday reminder of the natural beauty that surrounds you. Located on Ragged Point with Eastern Shore favorites like Soft & Salty Seafood and Danny's Seafood, this property offers easy access to fresh seafood, marinas, boating, and some of the finest fishing and crabbing waters on the Chesapeake Bay. The nearby Neck District Grill is a great spot for breakfast, lunch or weekend dinner. Whether you are searching for a full-time waterfront residence, luxury weekend escape, or investment opportunity with proven vacation rental appeal, this extraordinary property delivers the privacy, waterfront lifestyle, and authentic charm that buyers are seeking on Maryland’s Eastern Shore.

6 Beds ⋅ 5 Baths

Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property designed for gathering generations of family and friends. A long private approach welcomes you to a setting where nature and waterfront living take center stage. Inside, hardwood floors, timeless architecture, and expansive Bay views create a warm yet elegant atmosphere. The waterfront family room features a striking stone fireplace with wood-burning insert and opens seamlessly to both the screened porch and covered deck, creating effortless indoor-outdoor living. The spacious kitchen was designed with entertaining in mind, offering a center island, breakfast bar, abundant cabinetry, stainless steel appliances, double wall ovens, pantry storage, and an oversized breakfast room ideal for casual mornings by the water. Formal living and dining rooms provide additional space for hosting holidays and special occasions. The first-floor primary suite serves as a private waterfront sanctuary with direct access to the covered porch and peaceful Chesapeake Bay views. Upstairs, five spacious guest bedrooms and three full baths—including a private en-suite—offer flexibility for large families, guests, or vacation rental potential. Vaulted ceilings and dormer windows add architectural charm and natural light throughout the second level. Outside, the lifestyle only gets better. Spend summer days around the inground pool, rinse off in the outdoor shower after boating or kayaking, enjoy crab feasts on the screened porch, or gather around the waterside fire pit as the sun sets across the Bay. The partially wooded acreage provides exceptional privacy while attracting an abundance of wildlife including bald eagles, deer, ducks, geese, and shorebirds—an everyday reminder of the natural beauty that surrounds you. Located on Ragged Point with Eastern Shore favorites like Soft & Salty Seafood and Danny's Seafood, this property offers easy access to fresh seafood, marinas, boating, and some of the finest fishing and crabbing waters on the Chesapeake Bay. The nearby Neck District Grill is a great spot for breakfast, lunch or weekend dinner. Whether you are searching for a full-time waterfront residence, luxury weekend escape, or investment opportunity with proven vacation rental appeal, this extraordinary property delivers the privacy, waterfront lifestyle, and authentic charm that buyers are seeking on Maryland’s Eastern Shore.

5332 Ragged Point Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$615,000

This recently renovated home offers unique flexibility. It sits on a rare TRIPLE corner lot, and the expansive backyard spans two additional lots that may be subdivided. The first floor is beautifully finished with a new kitchen, scullery/laundry, parlor, great room, 3 bedrooms (including primary ensuite) and 2 more bathrooms. Nine rooms on the 2nd floor are ready to be finished as bedrooms, bathrooms, office/gym, etc. The 3rd floor includes additional heated space and storage. Historic charm is showcased throughout with grand front and rear staircases, built-in cabinetry, millwork, wainscoting, pocket doors, architectural radiators, and two original Rumford corner fireplaces. Major upgrades include a new two-zoned central HVAC system along with a high efficiency boiler for hot water and adjustable radiant heating, upgraded 320 Amp electric service (the whole home has been rewired), and updated plumbing. The front entrance has been brought back to the original woodwork with restored leaded glass sidelights and transom. The large front and side wrapped porch have been refreshed. Enjoy ample off-street parking from Choptank Avenue where there is also room for a "carriage house"/garage, workshop, boat storage and/or pool. Are you thinking Country Inn or Bed and Breakfast? A handicap ramp gives access to the porch and front entrance. There is an existing sprinkler system. Within blocks of historic downtown shopping and dining, water access, the Yacht Club, city marina, and waterfront parks. Also, there are nearby marinas that offer travel lifts, maintenance, and offseason storage. Nearby beaches and commuting distances: Assateague Island (61 miles), Rehoboth (65 miles), Ocean City (69 miles), Lewes with ferry to Cape May, and Cape Henlopen (61 miles). Distances to other areas of interest: Blackwater National Wildlife Refuge and Harriet Tubman Museum (11 miles), Saint Michaels (26 miles), Annapolis (58 miles), Washington DC (86 miles), Newark DE (88 miles), Wilmington (98 miles), NY, NY (414 miles). Washington, Newark and Wilmington have Amtrack train stations. Airports and distances: BWI (78 miles), Dulles (117 miles), PHL (115 miles).

8 Beds ⋅ 3 Baths

This recently renovated home offers unique flexibility. It sits on a rare TRIPLE corner lot, and the expansive backyard spans two additional lots that may be subdivided. The first floor is beautifully finished with a new kitchen, scullery/laundry, parlor, great room, 3 bedrooms (including primary ensuite) and 2 more bathrooms. Nine rooms on the 2nd floor are ready to be finished as bedrooms, bathrooms, office/gym, etc. The 3rd floor includes additional heated space and storage. Historic charm is showcased throughout with grand front and rear staircases, built-in cabinetry, millwork, wainscoting, pocket doors, architectural radiators, and two original Rumford corner fireplaces. Major upgrades include a new two-zoned central HVAC system along with a high efficiency boiler for hot water and adjustable radiant heating, upgraded 320 Amp electric service (the whole home has been rewired), and updated plumbing. The front entrance has been brought back to the original woodwork with restored leaded glass sidelights and transom. The large front and side wrapped porch have been refreshed. Enjoy ample off-street parking from Choptank Avenue where there is also room for a "carriage house"/garage, workshop, boat storage and/or pool. Are you thinking Country Inn or Bed and Breakfast? A handicap ramp gives access to the porch and front entrance. There is an existing sprinkler system. Within blocks of historic downtown shopping and dining, water access, the Yacht Club, city marina, and waterfront parks. Also, there are nearby marinas that offer travel lifts, maintenance, and offseason storage. Nearby beaches and commuting distances: Assateague Island (61 miles), Rehoboth (65 miles), Ocean City (69 miles), Lewes with ferry to Cape May, and Cape Henlopen (61 miles). Distances to other areas of interest: Blackwater National Wildlife Refuge and Harriet Tubman Museum (11 miles), Saint Michaels (26 miles), Annapolis (58 miles), Washington DC (86 miles), Newark DE (88 miles), Wilmington (98 miles), NY, NY (414 miles). Washington, Newark and Wilmington have Amtrack train stations. Airports and distances: BWI (78 miles), Dulles (117 miles), PHL (115 miles).

709 Church St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800

$1,995,000

Nestled on the private four-acre waterfront enclave of Three Creeks Point, this extraordinary estate offers breathtaking sunrises and sunsets over Fishing Creek with sweeping southerly views of Church Creek spanning more than 180 degrees. The primary residence features 5 bedrooms, 4.5 baths, and over 5,400 square feet of thoughtfully designed living space, complemented by an expansive maintenance-free wraparound deck providing panoramic water views from nearly every angle. Enhancing the main residence is a separate 2-bedroom, 1.5-bath guest home featuring a Primary Bedroom on the 1st floor with full bath and additional bedroom in the loft with adjoining half bath. The guest home is complete with a full kitchen, laundry, private deck, and tranquil water vistas — ideal for hosting guests or multi-generational living. Just minutes from the open Chesapeake Bay, this property boasts approximately 6 feet mean low water (MLW) along the protected waters of Fishing Creek, creating exceptional opportunities for boating, fishing, crabbing, paddleboarding, and kayaking along the quiet creeks of the Little Choptank River. The L-shaped pier is fully equipped with an electric boat lift, jet ski lift, and multiple slips, offering ease of waterfront access. Recent extensive exterior improvements and renovations have enhanced both the low-maintenance appeal of the property and maximized the stunning waterfront views. Inside, the home showcases a spacious open layout perfect for everyday living and entertaining. The Great Room is filled with natural light and opens seamlessly to the wraparound deck, creating a remarkable indoor-outdoor flow. The Brand-New 2025 Kitchen is the heart of the home, completely remodeled with high-end finishes and designed to serve both the casual homeowner and the enthusiastic entertainer alike. New hardwood flooring throughout the first floor elevates the living spaces while maintaining warmth and coastal elegance. Formal living and dining areas provide refined entertaining space anchored by a stunning stone fireplace, while the sunroom, spanning the width of the home, delivers captivating eastern, western, and southern water views that shift beautifully throughout the day. The main level includes two bedrooms and a full bath tucked into a private alcove, offering comfortable guest accommodations or flexible living options. The upper level hosts the impressive primary suite, complete with vaulted ceiling, fireplace, private waterside balcony, spa-inspired ceramic tile bath with walk-in shower, and spacious walk-in closet. Two additional bedrooms and a full bath are also located on the second floor. An oversized office with vaulted ceiling and its own balcony provides an inspiring remote workspace overlooking the water. The guest house is equally inviting, featuring a first-floor bedroom and bath, full kitchen, stacked washer and dryer, and a second-floor bedroom with loft area — perfect for extended stays. A detached four-car garage offers ample storage for vehicles, water toys, and workshop needs. With its unrivaled waterfront views, deep water access, private setting, generous living spaces, updated interior features, guest accommodations, and extensive dock amenities, this exceptional property represents the pinnacle of luxury Eastern Shore living.

7 Beds ⋅ 7 Baths

Nestled on the private four-acre waterfront enclave of Three Creeks Point, this extraordinary estate offers breathtaking sunrises and sunsets over Fishing Creek with sweeping southerly views of Church Creek spanning more than 180 degrees. The primary residence features 5 bedrooms, 4.5 baths, and over 5,400 square feet of thoughtfully designed living space, complemented by an expansive maintenance-free wraparound deck providing panoramic water views from nearly every angle. Enhancing the main residence is a separate 2-bedroom, 1.5-bath guest home featuring a Primary Bedroom on the 1st floor with full bath and additional bedroom in the loft with adjoining half bath. The guest home is complete with a full kitchen, laundry, private deck, and tranquil water vistas — ideal for hosting guests or multi-generational living. Just minutes from the open Chesapeake Bay, this property boasts approximately 6 feet mean low water (MLW) along the protected waters of Fishing Creek, creating exceptional opportunities for boating, fishing, crabbing, paddleboarding, and kayaking along the quiet creeks of the Little Choptank River. The L-shaped pier is fully equipped with an electric boat lift, jet ski lift, and multiple slips, offering ease of waterfront access. Recent extensive exterior improvements and renovations have enhanced both the low-maintenance appeal of the property and maximized the stunning waterfront views. Inside, the home showcases a spacious open layout perfect for everyday living and entertaining. The Great Room is filled with natural light and opens seamlessly to the wraparound deck, creating a remarkable indoor-outdoor flow. The Brand-New 2025 Kitchen is the heart of the home, completely remodeled with high-end finishes and designed to serve both the casual homeowner and the enthusiastic entertainer alike. New hardwood flooring throughout the first floor elevates the living spaces while maintaining warmth and coastal elegance. Formal living and dining areas provide refined entertaining space anchored by a stunning stone fireplace, while the sunroom, spanning the width of the home, delivers captivating eastern, western, and southern water views that shift beautifully throughout the day. The main level includes two bedrooms and a full bath tucked into a private alcove, offering comfortable guest accommodations or flexible living options. The upper level hosts the impressive primary suite, complete with vaulted ceiling, fireplace, private waterside balcony, spa-inspired ceramic tile bath with walk-in shower, and spacious walk-in closet. Two additional bedrooms and a full bath are also located on the second floor. An oversized office with vaulted ceiling and its own balcony provides an inspiring remote workspace overlooking the water. The guest house is equally inviting, featuring a first-floor bedroom and bath, full kitchen, stacked washer and dryer, and a second-floor bedroom with loft area — perfect for extended stays. A detached four-car garage offers ample storage for vehicles, water toys, and workshop needs. With its unrivaled waterfront views, deep water access, private setting, generous living spaces, updated interior features, guest accommodations, and extensive dock amenities, this exceptional property represents the pinnacle of luxury Eastern Shore living.

5202 Heron Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$535,000

WATERFRONT! WATERFRONT! Direct access to the Chesapeake Bay via Hudson Creek! This sprawling rancher offers 7, yes SEVEN, bedrooms, 3 full baths and 1 half bath. You will marvel at the expansive living and dining areas that flow seamlessly and offer expansive water views. All of this on a 1.84 +/-acre parcel with an in-ground pool, a boat dock and approximately 222' of waterfrontage. This unique property will not last long! Schedule a showing today! Equally impressive views are present from the HUGE recreational room. Seller may contribute up to 3% of buyer’s closing cost. HUD Case #244-000054. Equal Housing Opportunity.

7 Beds ⋅ 4 Baths

WATERFRONT! WATERFRONT! Direct access to the Chesapeake Bay via Hudson Creek! This sprawling rancher offers 7, yes SEVEN, bedrooms, 3 full baths and 1 half bath. You will marvel at the expansive living and dining areas that flow seamlessly and offer expansive water views. All of this on a 1.84 +/-acre parcel with an in-ground pool, a boat dock and approximately 222' of waterfrontage. This unique property will not last long! Schedule a showing today! Equally impressive views are present from the HUGE recreational room. Seller may contribute up to 3% of buyer’s closing cost. HUD Case #244-000054. Equal Housing Opportunity.

5608 Riverton Rd, Cambridge

Listing courtesy of Brokers Realty Group, LLC. Contact: 8556872765

$1,200,000

Escape to this rare waterfront retreat on Brooks Creek in Cambridge, offering Two Thousand ft of water frontage with sandy beaches, Private pier and Pond. The property features a Four Bedroom, Two and One half Bath Colonial-style main home plus a Three Bedroom, Two Bath guest house with great potential. Enjoy a large barn, pond, and multiple outbuildings, ideal for hobbies, storage, or fishing. With serene views, abundant space, and endless opportunities, this property blends waterfront living with country charm.

7 Beds ⋅ 5 Baths

Escape to this rare waterfront retreat on Brooks Creek in Cambridge, offering Two Thousand ft of water frontage with sandy beaches, Private pier and Pond. The property features a Four Bedroom, Two and One half Bath Colonial-style main home plus a Three Bedroom, Two Bath guest house with great potential. Enjoy a large barn, pond, and multiple outbuildings, ideal for hobbies, storage, or fishing. With serene views, abundant space, and endless opportunities, this property blends waterfront living with country charm.

5304 Cassons Neck Rd, Cambridge

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435