Dorchester County Public Schools Homes with Bay View

Dorchester County Public Schools Homes with Bay View

Welcome to the picturesque region of Dorchester County, Maryland, where stunning bay views and a vibrant community await you. One of the crown jewels of this area is the Dorchester County Public Schools, a district dedicated to fostering academic excellence and nurturing the potential of every student. With a commitment to providing a well-rounded education, the district offers a variety of programs and resources designed to support students from early childhood through graduation.

Families moving to this charming area will find a range of educational opportunities that cater to diverse learning styles. The schools prioritize not only academic achievement but also character development, ensuring that students are well-prepared for both college and life beyond the classroom. With dedicated teachers and a supportive community, Dorchester County Public Schools are a cornerstone of this welcoming environment.

In addition to the exceptional educational offerings, the homes in this area boast breathtaking bay views that enhance the allure of living here. Imagine waking up each morning to the serene beauty of the Chesapeake Bay, where the shimmering waters and vibrant sunsets become a part of your daily routine. Whether you’re looking for a cozy cottage or a spacious family home, the real estate options available in Dorchester County cater to various tastes and budgets, all while providing easy access to the natural beauty that surrounds you.

Explore the charm of Dorchester County and discover how the combination of quality education and stunning bay views makes this area an ideal place to call home. Embrace a lifestyle that balances tranquility with community spirit, all while ensuring that your family receives the best in education. Welcome to your new beginning!

Newest Dorchester County Public Schools Homes with Bay View

$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 updated 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, 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 was freshly encapsulated in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, a wrap around deck, 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. Don't wait- grab this home and move in before the Waterman's Rodeo this fall!!

1210 Horse Point Rd, Fishing Creek

Listing courtesy of Contigo Real Estate. Contact: 7172694566
$695,000
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.

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:

$629,900
2 Beds ⋅ 2 Baths
Enjoy breathtaking Honga River and Chesapeake Bay views from this exceptional waterfront property featuring a long private pier with multiple slips and two boat lifts. This well-maintained 2 bedroom, 2 full bath home offers comfortable coastal living with a riprapped shoreline, spacious yard and endless opportunities for boating, fishing, crabbing and embracing the Hoopers Island lifestyle. The expansive waterfront deck offers the perfect place to relax, entertain and enjoy cookouts with family and friends while taking in the panoramic waterfront views. Stunning sunrise and sunsets create the ideal setting for a full-time residence, weekend getaway, a peaceful waterfront retreat. Bring your golf cart and bicycles and enjoy nearby local favorites including Old Salty’s Restaurant and Hooper’s Island General Store. Conveniently located within walking distance to a local marina and public boat ramp.

1709 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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:

$895,000
Spectacular Waterfront Peninsula – 21.87 Acres in Dorchester County Discover a truly rare opportunity to own a breathtaking 21.87acre waterfront peninsula in Dorchester County, offering unmatched privacy, natural beauty, and over 4,000 feet of protected shoreline. Perfect for boating enthusiasts, the property features 3’ MLW and a 200 foot private pier complete with a boatlift, making water access effortless. This expansive property is fully fenced and equipped with an automatic entrance gate, ensuring both security and seclusion. Additional improvements include small outbuildings, a leanto shed, and the convenience of electric service and running water already onsite—ideal for immediate use or future development. Whether you envision creating a private retreat, recreational haven, or future waterfront estate, this oneofakind property

Condon Rd, Cambridge

Listing courtesy of Shore Living Real Estate. Contact: 4102515291
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