Dorchester County Public Schools Homes with Bay View

McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

5207 Brooks Rd, Woolford

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

$665,000

2 Beds ⋅ 1 Baths

Welcome to Fishing Creek, where Chesapeake Bay waterfront living takes center stage. This beautifully renovated coastal retreat offers approximately 138 feet of water frontage, extensive riprap shoreline protection and incredible views in nearly every direction. Step outside and enjoy an impressive 155-foot private pier with boat lift, jet ski lift, electric, lighting and plumbing, creating the perfect setup for boating, fishing, crabbing and everything the Eastern Shore lifestyle has to offer. Inside, the home has been thoughtfully transformed with an updated kitchen and appliances, renovated tile bathroom, updated flooring, recessed lighting, a gorgeous 200+ sq. ft. sunroom surrounded by windows and water views. Wake up to sunrise over the harbor, unwind with sunsets over the Chesapeake, and enjoy the water from nearly every room. The investment into this property goes far beyond what you can see. Major improvements include a new septic field, extensive riprap shoreline stabilization, upgraded pier infrastructure with boat lift, jet ski lift, updated dock, electric on dock and plumbing, a custom Amish built two-story bunkhouse with insulation, flooring and electric, a 200-amp electrical upgrade, renovated bathroom, new kitchen appliances, waterfront hardscape patio, exterior improvements and a new well pump and many more. These are the big-ticket improvements that deliver true peace of mind. Peaceful, private and built to enjoy the Chesapeake, this is more than a waterfront home. It’s your own Eastern Shore escape.

2530 Hoopers Island Rd, Fishing Creek

Listing courtesy of Keller Williams Flagship. Contact:

$899,000

Redevelopment Opportunity L Shaped Lot This commercial property, originally built in 1930 and extensively renovated in 2006, presents a unique investment opportunity. Spanning 1 acre. Three properties, four parcels with Route 50 (Sunburst Highway) access as well as ingress egress from Henry Street. The property is strategically located along a major highway, and also connects with Hensry Street which is an artery into town. The below-average condition offers potential for further improvements or a total demolition and redevelopement. Parking options, including a driveway and parking lot, the property is well-equipped to accommodate high traffic. This asset is ideal for those looking to capitalize on a prime location with significant upside potential in a growing market.

203 Sunburst Hwy, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$849,900

3 Beds ⋅ 2 Baths

Trade Traffic for Tides — Your Waterfront Island Escape Awaits! From the moment you cross the bridge onto Hooper's Island, something changes. A sense of peace settles in. Life slows down. The water sets the schedule, neighbors wave as they pass, and the pace becomes simpler, sweeter, and slower—in the very best way. This beautifully remodeled 3-bedroom, 2-full-bath waterfront home is being offered fully furnished and is already an established, highly successful 5-star Airbnb, renting for $430 per night. Whether you're looking for a personal island retreat, an investment property, or the best of both worlds, this home is ready to enjoy from day one. The entire home has been remodeled from the ground up, so nothing in the home is older than 5 years old- appliances, roof, well, mechanicals -you name it!! Imagine looking out your window and seeing crab boats, dolphins playing in the bay, and cruise ships and container vessels making their way across the horizon. A rear wall of floor-to-ceiling glass doors provides panoramic bay views, bringing the water into nearly every room. Cooking becomes relaxing because the views are amazing, even from the kitchen! Wake in the primary suite, open the blinds with a remote control, and take in the water views from the comfort of your bed. Freshly painted and featuring brand-new flooring throughout, the home combines comfortable coastal living with thoughtful modern updates. The crawl space had spray foam insulation, vapor barrier, and a new sump pump installed in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, wrap around Trex decking, and even paved sidewalks with railings leading the whole way to the dock. Smart technology integrated into so many aspects of the property! Access an app to control the thermostat, garage door, RING cameras, and even view the contents of your fridge so you can remember what you need to get at the grocery store! And then there's the waterfront. A private dock, built just two years ago, is ready for your next adventure and includes a 10,000-pound boat lift. Spend your days kayaking, swimming, boating, jet skiing, fishing, or crabbing—or simply sit by the water and watch island life unfold. Search the shoreline for sea glass and seashells, launch the kayak, or cast a line and see what the day brings. On this island, you won't need your car. Leave it parked and explore by foot, bike, or golf cart. Hooper's Island has a general store stocked with everyday essentials, from fishing tackle to ice cream, and Old Salty's, the island's only restaurant, serves wonderful fresh seafood alongside a laid-back tiki bar. Fun fact about Hooper's Island: Before it started as a culinary legend, it all started on this island in 1914 when Augustus E. Phillips opened the A.E. Phillips & Son packing plant. In 1956, faced with a surplus of crabs, Augustus' son and his wife opened a small 'shack' in Ocean City, MD... and we all know how that exploded with popularity! The original processing plant is still part of the company, and when operational, continues to process blue crabs and soft-shell crabs for regional locations.

1210 Horse Point Rd, Fishing Creek

Listing courtesy of Contigo Real Estate. Contact: 7172694566

$649,000

4 Beds ⋅ 3 Baths

Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz countertops, GE Café appliances, brand-new Bosch high-efficiency inverter heat pumps, new luxury vinyl plank flooring and a large waterfront deck perfect for entertaining or simply relaxing while taking in the scenic water views. Additional features include an attached two-car garage, detached garage/storage building, private deep well and county sewer. Enjoy boating, fishing, kayaking, biking and running right outside your door. Located near Blackwater National Wildlife Refuge and public hunting lands, this property is ideal for outdoor enthusiasts and nature lovers. Conveniently located near the Madison public boat ramp, volunteer fire company and just 15 minutes from Route 50 and Cambridge, with shopping, restaurants and Emily's Produce nearby. Whether you are looking for a full-time residence or private waterfront retreat, this property offers the very best of Maryland's Eastern Shore lifestyle. This property would also work very well as an Airbnb. Motivated sellers, offers are welcome.

4825 Madison Canning House Rd, Madison

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$195,000

2 Beds ⋅ 1 Baths

Nestled in the charming waterfront community of Hoopers Island, this beautifully renovated traditional home is move-in ready and full of modern updates. Completely renovated in 2026, this home offers the perfect combination of comfort, style, and coastal charm. Inside, you'll find 2 spacious bedrooms and 1 full bathroom, featuring brand-new flooring, fresh paint throughout, new kitchen cabinets, and an inviting layout that feels bright and welcoming. The home also includes a brand-new roof, new windows, and a new HVAC system, giving you peace of mind for years to come. Ceiling fans add extra comfort, and the home comes equipped with a refrigerator, stove, washer, and dryer. Step outside onto the balcony and enjoy the peaceful surroundings, or take advantage of the 0.19-acre lot, offering space for gardening, relaxing, and entertaining. A storage shed provides additional room for tools and outdoor equipment. Located just minutes from the water, this home offers easy access to the Chesapeake Bay, making it a great choice for boating, fishing or simply enjoying the laid-back Eastern Shore lifestyle. With driveway and on-street parking available, convenience is built right in. Whether you're looking for a full-time residence, a weekend getaway, or an investment opportunity, this beautifully updated home is ready to welcome its next owner. Don't miss your chance to experience the charm of Hoopers Island living!

1227 Horse Point Rd, Fishing Creek

Listing courtesy of Fairfax Realty Premier. Contact: 3014399500

$3,200,000

Looking for a business opportunity, want to expand your business? This exceptional property offers outstanding income and business potential, including opportunities for a private retreat, vacation rental, event or wedding venue, guided hunting and fishing, sporting clay, kayak, water sports experiences and other outdoor recreational offerings. Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$3,200,000

Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$3,200,000

5 Beds ⋅ 6 Baths

Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$299,000

3 Beds ⋅ 1 Baths

Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

2517 Old House Point Rd, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$1,375,000

4 Beds ⋅ 5 Baths

End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound offering 268 feet of protected, rip-rapped shoreline and 1.12 acres of privacy, ideally positioned with a coveted east-west orientation. A private pier equipped with a boat lift and personal watercraft lift enhances the property’s appeal, delivering immediate access to the water and an effortless boating lifestyle. Designed by renowned architect Burhsar Pathare, the impeccably crafted residence spans over 5,000 square feet across three finished levels, featuring 4 bedrooms and 4.5 baths, all thoughtfully positioned to capture unobstructed water views. Beautiful flooring flows throughout, complementing clean architectural lines and high-end finishes. The entry level welcomes you with a large living space highlighted by high ceilings and an abundance of windows that frame stunning water views. A beautiful, full-service bar—complete with sink, dishwasher, and high-end finishes—creates the perfect setting for entertaining. This level also features a spacious laundry and utility area along with a convenient half bath, and provides direct access to the backyard and waterfront setting for seamless indoor-outdoor living. Take the stairs or the elevator to access the upper levels of the home. The main level is truly striking, showcasing soaring 40-foot ceilings and a dramatic wall of glass capturing panoramic bay views. The open-concept design seamlessly integrates the kitchen, dining, and living areas, anchored by a stone fireplace. The gourmet kitchen features a spacious eat-in area and opens to a full-length wraparound deck overlooking the water—ideal for gatherings of any size. The main-level primary suite offers private deck access and a spa-like bath, with an additional full bath also located on this level. Upstairs, a loft overlooks the main living space, along with three generously sized bedrooms, including two ensuite bedrooms with private baths—each bedroom also features its own private deck overlooking the water, offering a peaceful retreat with breathtaking views. The third secondary bedroom features the added convenience of direct elevator access within the room itself. Outdoor living is equally impressive with multiple decking areas and a beautifully designed paver patio featuring a fire pit and sitting walls—all oriented to take full advantage of the waterfront setting. The property is fully fenced, enhancing both privacy and functionality. A gated entrance with electronic access further enhances privacy and security, while an oversized two-car attached garage provides ample convenience and storage. The property is serviced by public sewer and a private well. The residence is offered as a truly turnkey opportunity, conveying with the majority of its high-quality furnishings for an effortless, move-in-ready experience (select artwork and personal items excluded). The adjoining property at 1250 Old Madison Road is also available for purchase (MDDO2012114), featuring a charming 2-bedroom, 2-bath cottage with additional living space and expansive water views—ideal as a guest house or income-producing rental. An exceptional opportunity to fully embrace the waterfront lifestyle—where every day feels like a retreat and lasting memories are made. Mortgage savings may be available for buyers of this listing.

1252 Old Madison Rd, Madison

Listing courtesy of Redfin Corp. Contact: 3016586186

$320,000

3 Beds ⋅ 2 Baths

$10,000 Price Reduction – Rare Chesapeake Bay Waterfront Opportunity! Waterfront homes under $325,000 are becoming increasingly difficult to find, making this well-maintained island retreat an exceptional value. Enjoy sweeping western views across the Chesapeake Bay, spectacular sunsets, and the peaceful waterfront lifestyle you've been dreaming of. Ideal as a full-time residence, weekend getaway, or a short-term rental investment. The home features an updated kitchen with a center island, gas range, coffee bar, and luxury vinyl plank flooring. Flexible living spaces include a first-floor bedroom and office/playroom, an updated bath, a spacious family room, and a private second-floor owner's suite. Additional highlights include ductless mini-split heating and cooling, hot water baseboard heat, high-speed internet availability, rip-rapped shoreline, and a BAT septic system installed in 2019. A county-owned public boat ramp is just down the street beside a privately owned marina where slips may be available for rent (buyer to verify). A brand-new survey and legal description are available upon request. With a $10,000 price reduction, this is one of the best opportunities to own Chesapeake Bay waterfront without the premium price tag.

1814 Hoopersville Rd, Fishing Creek

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

Dorchester County Public Schools Homes with Bay View

Newest Dorchester County Public Schools Homes with Bay View