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$1,399,000
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:

$1,195,000
4 Beds ⋅ 4 Baths
Welcome to a rare Eastern Shore offering where privacy, income potential, and waterfront lifestyle come together on 23± acres along the Little Choptank River. Currently a successful vacation rental, this property presents an exceptional opportunity for a second home that works for you—enjoy it when you want and generate income when you’re away. The expansive acreage provides a peaceful, private setting with endless possibilities—gardening, small-scale farming, hunting, or enhancing the land with an impoundment or pond to attract waterfowl. The waterfront is fully equipped for enjoying life on the water with a partially rip-rapped shoreline, private pier and approximately 2.5 feet of mean low water depth—ideal for boating, fishing, and crabbing, with easy access to Fishing Creek and the Chesapeake Bay beyond. Outdoor living truly shines with an in-ground pool overlooking the water, offering a serene setting for both quiet relaxation and entertaining. The spacious wooden deck provides ample room for dining and gatherings, while taking full advantage of the surrounding views. An outdoor shower adds a practical touch, making it easy to rinse off after time spent on the water or enjoying the outdoors. The 4-bedroom, 3.5-bath residence is designed for comfort and gatherings, offering an open floor plan with two primary suites, each with private baths. The spacious kitchen is a true centerpiece, featuring a large island with breakfast bar, double wall ovens, cooktop, refrigerator, dishwasher, beverage refrigerator, and separate ice maker—fully equipped to handle everything from intimate dinners to large-scale entertaining. The adjacent dining room easily accommodates gatherings, while the family room, just off the kitchen, captures serene water views and opens to a spacious screened porch for seamless indoor-outdoor living. A sunroom adds additional living space, also overlooking the pool and waterfront, creating the perfect spot to unwind year-round. The home’s low-maintenance brick exterior, attached two-car garage with automatic opener, and thoughtful layout make it as practical as it is inviting. Conveniently located approximately 2 hours from Washington, DC and 1.5 hours from Baltimore, this property offers the perfect escape without sacrificing accessibility. Whether you’re seeking a private retreat, an income-producing investment, or a place to fully embrace the Eastern Shore lifestyle—boating, fishing, crabbing, kayaking, paddleboarding, and more—this property delivers. Don’t miss the opportunity to own a truly unique waterfront estate with everything in place for summer enjoyment—schedule your private tour today and start living the lifestyle you’ve been waiting for.

1661 Town Point Rd, Cambridge

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

$339,000
3 Beds ⋅ 2 Baths
SELLER WILL CONTRIBUTE UP TO FIFTEEN THOUSAND DOLLARS ($15,000) TOWARDS BUYER CLOSING COST. WATER ACCESS - VERY LIMITED "BUT" a small boat could provide you limited duration of access to the Choptank River. A great opportunity to enjoy the charm of Eastern Shore living. This 3 BR, 2 BA home features open layout connecting kitchen to dining and living rooms offering optimal natural lighting. Each boasting large window allowing for scenic outdoor viewing. New kitchen stainless steel appliances and cabinetry along with new countertop and backsplash. Backyard offers large, detached 2 car garage, privacy and solitude overlooking Canal leading to the Choptank River. Located just minutes from downtown historic Cambridge, shopping, and local marinas.

202 Buena Vista Ave, Cambridge

Listing courtesy of Eastern Shore Properties, ESP Inc.. Contact:

$1,035,000
5 Beds ⋅ 5 Baths
MAJOR PRICE IMPROVEMENT of $165K since first listed- HURRY to claim this unmatched waterfront oasis- Set on just shy of 4.5 private acres at the end of a quiet dead-end road, this stunning property boasts over 2,700 square feet, five bedrooms, and an incredible 1,000 feet of water frontage—creating a rare combination of space, privacy, and panoramic views of coveted Little Choptank River. Designed and built by an architect for their own personal retreat, this one-of-a-kind coastal waterfront sanctuary blends thoughtful design with the natural beauty distinct to the Eastern Shore. Enjoy effortless waterfront living with your own private pier featuring 3’ mean low water, a protected lagoon, and endless opportunities for boating, jet ski'ing, crabbing/fishing, kayaking, and exploring nature abound. Surrounded by wildlife and untouched beauty, this is the kind of setting that feels worlds away—yet you’re just minutes from the charm, dining, and shops of downtown Cambridge. And the opportunities don’t stop there!!--NO HOA and strong Airbnb potential make this not only a dream retreat, but a smart investment just in time for summer.

1307 Broadview Dr, Cambridge

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242