Dorchester County Public Schools Homes with Panoramic View

Private Eastern Shore retreat with panoramic water views! This spacious newly renovated 6 bedroom, 4.5 bath home offers an abundance of room for family, guests and entertaining, with beautiful water views and a peaceful, private setting. Currently operating as an Airbnb and family retreat, the property is on track to generate approximately $40,000–$50,000 in rental income this year, with projected earnings of $50,000+ for 2027. This property offers flexibility for continued short-term rental use, a full-time residence and private getaway. The 40' x 60' pole barn with concrete floor and electric provides ample space for boats, vehicles, equipment, hobbies and storage. Close to marinas and public boat ramps for easy access to boating, fishing and crabbing. Property may convey furnished with an acceptable offer. Enjoy the Hoopers Island lifestyle! Bring your bikes and golf cart, enjoy nearby favorites like Old Salty's Restaurant and Blackwater National Wildlife Refuge.

2144 Hoopersville Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,075,000

3 Beds ⋅ 3 Baths

Welcome to the most private wooded parcel of land on Upper Hooper's island , accessed by a private road and bridge from Hooper's Island Road , to the exclusive 8 acres of land with 1200 feet of waterfront on the Chesapeake Bay with a 300 foot long by 100 foot wide all white sand beach with unobstructed southerly views to the Potomac River 19 miles away..The views at night is not one light across the Chesapeake Bay , only Hoopers Island lighthouse blinking at night, as the government owns from the naval air station to the mouth of the Potomac River. The property is so secluded you only hear wind in the trees and wave lapping on the beach. The property has the first house ever built on this land in 2022 having 2000 square feet with 9 foot ceilings and a vaulted ceiling in the living room with stone fireplace. The screen porch overlooking the bay is over 600 square feet of living space and the house contains master bedroom overlooking the bay with walk in closet and bath and two other bedrooms with shared bedroom. The house also includes a large outside enclosed shower .The stone patio next to the house has grill, firepit and 6 lounge chairs to enjoy the fire at night overlooking the vista of the Chesapeake Bay, The expansive beach on the Bay also has a firepit for enjoyment of fires on the beach at night .The property has been totally graded with wrap around berms to protect the property from any flooding conditions. Dorchester County regulations allows an extensive pier to be built if the buyer desires a private dock. Rockfish and Sea Trout are caught off the beach as well as The shoreline is licensed if the buyer wishes to shoot waterfowl from the beach area or construct a offshore blind and the property is covered in White Tail Deer and Sika . The bridge as approved by MDE and Corps was constructed to hold any vehicle up to 100,000 pounds and can accomodate all Hoopers Island Fire equipment .The property also includes a pad site on the property , having 20-30-and 50 amp service and water to the site for either a RV pad with slate terrace, or future building if desired by the buyer ,All electric and water were underground bored from the house to the site, All electric to the house was bored from the road and is also underground.. The property his high speed WiFi and Dish Television.. The kitchen is totally open space with all appliances and full stocked cooking pans and utensils .and a cozy breakfast bulkhead seating eight in the kitchen, The house is being sold totally furnished including towels and sheets except for some private art and two pieces of furniture . One walk in the deep white sand beach and the expansive views will convince you this is a one of a kind property to buy as it has it all and move in ready

2344 Hoopers Island Rd, Fishing Creek

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755

$429,990

2 Beds ⋅ 2 Baths

Immaculate end-unit condo overlooks the Choptank River and the 18th Fairway. Willow Oaks in the Residences at River Marsh - adjacent to the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina - is your vacation-at-home destination, as relaxing or full of adventure as you choose! Enjoy carefree, maintenace-free living in this turn-key 2BR/2BA, with a great floorplan and even greater views. Spacious great room with gorgeous wood floors, crown molding, and loads of natural light through the many windows over the golf course greens and glorious Choptank River. Formal dining room opens to the balcony. Large kitchen features an informal dining area, breakfast bar, pantry, and plentiful cabinetry. Primary bedroom also offers warm hardwood floors, walk-in closet, and a full, en-suite bath - soaking tub, custom tile shower. Welcoming guest bedroom and 2nd full bath with a tub/shower combo. Nice-sized laundry room includes a front-load washer and dryer, and storage space. Assigned parking space in the covered parking garage, and additional parking in the outdoor lot. The common areas in the building are well-maintained and stylishly-appointed. Lush, gorgeous grounds surround the building.Walking trails, lawn maintenace, common area maintenance, exterior building insurance and maintenace, snow removal, water, trash, reserve funds - all included in your monthly condo dues. Residents may choose to secure amenity privileges with the Hyatt Resort and associated businesses - pools and spas, golf memberships, tennis, wellness center / gym memberships, pier / dock, kayaks, paddleboards, jet skis, bikes, multiple restaurants - all just a short stroll from home. Quick drive to Downtown Cambridge - a quintessential waterfront town on the Eastern Shore - full of incredible seafood, unique boutiques, arts and entertainment, tons of history, and local brews and restaurants. On the banks of the Choptank River, you'll be charmed by this gem of the Shore. Great central location - hour West to Annapolis, East to Ocean City beach and boardwalks, Assateague Island or the Delaware Beaches; half hour to Salisbury. Don't miss this unique opportunity to live the good life on the Eastern Shore! Sizes, taxes, distances approximate

2700 Willow Oak Dr Unit #310C, Cambridge

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$299,000

3 Beds ⋅ 3 Baths

Welcome to this charming farmette featuring a 3 bedroom, 2 3/4 bath home that has been elevated and features a conditioned crawl space, includes a 3-stall barn, pole barn and shop/shed. Situated on over 8.5 acres, this property offers open fields, established pastures with fencing, a pond and wooded areas, creating the perfect blend of recreation, hobby farming and peaceful country living for the nature enthusiast and hunters alike. Enjoy Sika deer and waterfowl hunting right in your own backyard, with endless opportunities to enjoy the outdoors. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,690,000

A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,690,000

7 Beds ⋅ 3 Baths

A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$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

$299,000

3 Beds ⋅ 2 Baths

Brand new septic being installed, newly remodeled, new detached garage with living space, orchard, fully furnished, just bring your suitcase and move-in! This furnished 3-bedroom, 2-full-bath home is nestled in the heart of Sika deer country. The home is in excellent condition and features beautiful hardwood and luxury vinyl plank flooring, central heating and air, mini-splits, a pellet stove, and a detached one-car garage with a finished bonus room above, complete with electric, water and a mini-split for heating and air. Outside, enjoy a storage shed, fire pit, established orchard with pin oak, apple and persimmon trees, and a deer feeder that conveys. The nearby public boat ramp and marina provide easy access to the Honga River. Whether you're looking for a full-time residence, weekend getaway or hunting retreat, this turnkey property is ready to enjoy. Backs up to a 350+ acre managed Sika deer/farm property. *new septic system is scheduled to be installed within the next 30-60 days. The existing system is functioning; however, replacement was recommended and the seller is moving forward with installation.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$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

Dorchester County Public Schools Homes with Panoramic View

Newest Dorchester County Public Schools Homes with Panoramic View