Dorchester County Public Schools Homes with Landscaping Lot features

Dorchester County Public Schools Homes with Landscaping Lot features

Welcome to Dorchester County, Maryland, where picturesque landscapes meet exceptional educational opportunities. Nestled along the scenic shores of the Chesapeake Bay, this vibrant community is served by the esteemed Dorchester County Public Schools. Known for their commitment to academic excellence and holistic student development, these schools offer a nurturing environment that fosters both learning and growth. With a range of programs designed to cater to diverse interests and talents, parents can be assured that their children are receiving a quality education that prepares them for future success.

Beyond the classrooms, Dorchester County is a haven for families seeking homes with beautiful landscaping and ample outdoor space. Picture yourself in a charming residence surrounded by lush gardens, vibrant flower beds, and mature trees, creating a serene oasis right in your backyard. These homes not only provide comfort and style but also offer the perfect setting for family gatherings, outdoor play, and peaceful retreats. Whether you’re sipping coffee on your patio or hosting a summer barbecue, the beautifully landscaped lots enhance the overall living experience.

Living in Dorchester County means embracing a lifestyle where education and nature intertwine. The community is rich in history and culture, with easy access to parks, waterways, and recreational activities that promote an active lifestyle. Discover your dream home in this idyllic setting, where quality education and stunning outdoor spaces await you and your family. Come explore the charm of Dorchester County—your new home is just around the corner!

Newest Dorchester County Public Schools Homes with Landscaping Lot features

$1,495,000
7 Beds ⋅ 5 Baths
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:

$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
$295,000
4 Beds ⋅ 2 Baths
Discover the space, character and walkability of downtown Cambridge in this beautifully updated historic home. Offering 2,316 square feet, four bedrooms and two full bathrooms, the property blends distinctive Victorian details with substantial modern improvements. Relax on the covered front porch, complete with a classic porch swing, or enjoy the neighborhood views from either of the home’s two upper-level balconies. Located just blocks from the Choptank River, Cambridge Yacht Club, restaurants, coffee shops and local boutiques, this home places some of the city’s best amenities within an easy walk. Major capital improvements include a new roof, new kitchen appliances, upgraded electrical and plumbing, new sewer connections, storm windows, a Rinnai tankless gas water heater and high-end, two-zone low-profile radiators. Inside, refinished hardwood floors and original architectural details create a warm and inviting atmosphere. The living room features built-in bookcases and a fireplace and opens to a formal dining room with bay windows and an elegant chandelier. The kitchen offers stainless steel appliances, quality countertops and a charming breakfast nook. Two additional flexible rooms provide excellent options for home offices, a nursery, hobby space or additional storage. The main level includes a bedroom and full bathroom, offering flexibility for guests or one-level living. Upstairs, the spacious primary bedroom features a dedicated wardrobe room and convenient access to a full bathroom with a classic clawfoot tub. Two additional bedrooms open to an adjoining balcony. Across the street, the community garden provides an opportunity to grow flowers, herbs and fresh produce while enjoying the convenience of downtown living. Additional highlights include a private driveway, covered carport, rear accessibility ramp, backyard storage shed, no HOA and not located in a flood zone. With generous living space, valuable updates, off-street parking and an exceptional historic-district location, this distinctive Cambridge home is ready for its next chapter.

817 Locust St, Cambridge

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$480,000
4 Beds ⋅ 3 Baths
. Searching for a historic primary residence, vacation home, potential Airbnb or Eastern Shore retreat with modern updates and Chesapeake Bay lifestyle? This is it. Custom remodeled inside and out. Built in 1910 and situated in the Cambridge Historic District on Maryland's Eastern Shore, 1109 Locust Street delivers 2,228 finished square feet of beautifully updated living space across three levels. This 4-bedroom, 3 full-bath home includes a finished attic with a window and closet 7'ceilings, ideal for use as a potential fifth bedroom or home office, and a convenient first-floor bedroom and full bath. The fully reimagined chef's kitchen features a professional style gas range with hood exhaust, counter depth French door refrigerator with freezer drawers, pro-style dishwasher, large porcelain farm sink, premium cabinetry with walnut butcher block countertops, a dedicated beverage and coffee bar with ice machine, wine cooler, and filtered water sink, plus a separate walk-in pantry. Exactly what you want after a day on the water. Custom crown molding. Major updates include a new roof installed August 2023, dual electric heat pumps, natural gas on-demand tankless water heater, and a natural gas fireplace. Second-floor laundry, EV charging station, and off-street parking with rear alley access round out the practical upgrades. Outdoor spaces are built for real life and weekend living. A screened-in rear porch with a built-in grilling station and exhaust hood, a backyard workshop, and a potting shed make this property as functional as it is charming. Located outside the flood zone on a 0.24 acre lot. Lot is ideal for additional building. Steps from the Cambridge Municipal Marina and the Choptank River, with easy access to Blackwater National Wildlife Refuge, downtown Cambridge waterfront dining, boutique shops, and galleries. Whether you are launching a kayak, crabbing, pulling into the marina, or simply watching the sunset over the water, this location delivers the Eastern Shore lifestyle year-round. Only 45 minutes to Annapolis, Maryland, and under two hours to Washington D.C. and Baltimore. This is Eastern Shore living without compromise.

1109 Locust St, Cambridge

Listing courtesy of CENTURY 21 New Millennium. Contact: 7037537910
$849,500
3 Beds ⋅ 3 Baths
Price adjustment! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the rear of the house situated to enjoy the tranquil water views. Roof new in 2026 along with other recent upgrades.

4712 Steamboat Rd, Woolford

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

$998,500
4 Beds ⋅ 4 Baths
Exceptional waterfront estate in Dorchester County offers sweeping panoramic views of Church Creek with direct access to the Chesapeake Bay . Also located in the highly sought after Cambridge South Dorchester School District . Featuring over 470 feet of protected shoreline , a private dock with 4 feet of water depth, and a boat lift , this property is a rare opportunity for true waterfront living . The 3400 square foot , two and a half story home is thoughtfully designed to capture stunning water views from every angle . In side you will find four spacious bedrooms , including a grand primary suite , along with two full baths and a half bath on the upper level. The main floor is ideal for both everyday living and entertaining . offering a large waterfront dining room , a cozy water view den , and an expansive living room with a wood burning fireplace . The modern kitchen is beautifully updated and includes a pantry and a covered side porch. A unique extended screened porch off the dining room provides the perfect setting to relax and take in the serene views of Church Creek. Upstairs, the luxurious master suite features walk in closets, and the master bathroom showcases a vintage inspired clawfoot tub , a standout feature for those drawn to a modern farmhouse aesthetic , along side a walk in shower. Step out onto your private deck from the master bedroom to enjoy breathtaking sunsets over the water. Two additional bedrooms share a well appointed bathroom , spacious laundry room includes a new washer and dryer . The third floor offers flexible space with two large rooms , ideal for additional bedrooms , a home office , office gym, or media room . Additional features include multiple outbuildings : a two car garage, a kennel with three bays ready for future fencing , and a separate structure perfect for storage of a office. The property spans three lots totaling 3.395 acres of land , accessed by a long privately owned driveway that ensures ultimate privacy . This truly remarkable waterfront retreat where privacy, natural beauty, and expansive water views come together , an opportunity that must be experienced to be fully appreciated

4928 Gregory Rd, Cambridge

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$580,000
5 Beds ⋅ 4 Baths
This is a beautifully updated and well-maintained Four Square located in Cambridge's Historic District. It is a grand house for entertaining both inside and out. In addition to the 5 bedrooms and 3.5 baths in the Manor House, the property boasts 2 additional buildings on the .57 acre lot filled with specimen flowers, shrubs and trees. 1 building, originally built as a Montessori school, is well suited as a studio, in-law suite, professional office space or Man cave. It is currently registered and generating income as an Airbnb.

309 Glenburn Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$625,000
3 Beds ⋅ 2 Baths
Situated as the last privately owned property on Maple Dam Road before entering Blackwater National Wildlife Refuge, this 10.54± acre offering occupies an exceptional setting surrounded by refuge lands on all sides. The property lies within thousands of acres of permanently protected public ground, providing unmatched privacy, wildlife presence, and long-term landscape preservation in the heart of Dorchester County. Improvements include a 1,718± square-foot residence powered by a PV solar array, backed by an on-demand 22kw generator delivering efficient and sustainable energy. Climate control is handled by six mini-split systems, with an additional in-box unit conveying with the sale, offering flexibility for future expansion or replacement. The home features two gas fireplaces, with one having an option to burn wood, adding both comfort and versatility. A four-person hot tub is included, creating an ideal space to unwind and watch the sunset. A 30’ x 30’ garage with 14-foot ceilings provides ample room for boats, equipment, and sporting gear. in addition to the large garage, a climate-controlled office/workshop is just steps away from the main house. The land itself is highlighted by natural marsh ponds and wetlands, enhancing habitat and contributing to the area’s outstanding waterfowl hunting and well-established Sika deer population. This property offers a unique opportunity to enjoy legitimate hunting and outdoor recreation from a private home site while being fully immersed within one of Maryland’s most iconic conservation landscapes. Whether used as a full-time residence, weekend retreat, or generational sporting property, Maple Dam Road delivers an exceptional blend of access, privacy, and outdoor heritage that is increasingly difficult to find on the Eastern Shore. A BAT System upgrade plan has been developed to bring BAT/BIP System up to standards. Contact for additional information.

3819 Maple Dam Rd, Cambridge

Listing courtesy of The Land Group. Contact: (410) 934-3478
Start Your Search