Dorchester County Public Schools Homes with Trees/Woods View

Dorchester County Public Schools Homes with Trees/Woods View

Welcome to Dorchester County, Maryland, where the charm of small-town living meets the beauty of nature! Nestled in the heart of this picturesque region is the highly regarded Dorchester County Public Schools district. Known for its commitment to academic excellence and community involvement, this school district is dedicated to fostering a nurturing environment for students. With a variety of educational programs and extracurricular activities, parents can rest assured that their children are receiving a well-rounded education that prepares them for future success.

Imagine coming home to a serene retreat surrounded by the lush greenery of trees and woods. Homes with trees and woods views in Dorchester County offer not just a residence, but a lifestyle. Picture sipping your morning coffee while basking in the tranquility of nature, with the gentle rustle of leaves and the cheerful songs of birds as your backdrop. These homes provide an ideal setting for families who cherish outdoor activities, from hiking and biking to simply enjoying the peace and beauty of their surroundings.

The combination of excellent schools and the natural beauty of tree-lined neighborhoods makes Dorchester County an ideal place to call home. Whether you're a young family looking to plant roots or retirees seeking a peaceful sanctuary, the homes here offer the best of both worlds. Explore your options in this vibrant community, where education and nature harmoniously coexist, and discover the perfect place for you and your family to thrive!

Newest Dorchester County Public Schools Homes with Trees/Woods View

6108 Delaware Line Reliance Rd, Rhodesdale
$700,000
3 Beds ⋅ 2 Baths
Exceptional opportunity to own 33+ acres of private Eastern Shore countryside! This charm-filled 3 BR / 2 BA ranch home delivers easy single-story living with 2,160 sq. ft., an attached 2-car side-entry garage, and spacious main-level accommodations. 3 bedrooms, dining room, den, living room and office. Detached garage/workshop. Highlights include open surrounding views of woods and pastures, ideal for nature lovers, hunting enthusiasts, or those seeking a quiet rural sanctuary. Conveniently located to all Mid Shore locations.

6108 Delaware Line Reliance Rd, Rhodesdale

Listing courtesy of Coldwell Banker Realty. Contact:

2144 Hoopersville Rd, Fishing Creek
$799,000
6 Beds ⋅ 5 Baths
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:

2344 Hoopers Island Rd, Fishing Creek
$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 OWNER FINANCING AT 5% INTEREST ONLY 2 YEARS

2344 Hoopers Island Rd, Fishing Creek

Listing courtesy of Stafford-Stafford Real Estate. Contact:

1610 Winters Ct, Cambridge
$389,900
4 Beds ⋅ 3 Baths
Nestled in the serene enclave of Blackwater Cove, this exquisite traditional home offers a harmonious blend of comfort and elegance, perfect for those seeking a refined lifestyle. Spanning 2,710 square feet, this residence features four spacious bedrooms and two and a half bathrooms, thoughtfully designed to accommodate both relaxation and entertaining. Step inside to discover a warm and inviting interior, where plush carpeting, luxury vinyl, tile flooring and tasteful window treatments create a cozy atmosphere. The kitchen boasts high-end appliances, including a built-in microwave, electric range, and dishwasher, ensuring culinary endeavors are met with ease. The adjoining dining area provides a perfect setting for intimate meals or festive celebrations. Retreat to the primary suite, a tranquil haven featuring an en-suite bath that exudes luxury. The additional bedrooms are generously sized, offering ample space for personalization and comfort. A charming fireplace in the living area adds a touch of warmth, making it the perfect spot to unwind after a long day. The exterior of the home is equally impressive, set on a 0.44-acre lot that backs to lush trees, providing a sense of privacy and tranquility. The property features a well-maintained front yard and a spacious rear yard, ideal for outdoor activities or simply enjoying nature's beauty. A deck and porch extend the living space outdoors, perfect for morning coffee while soaking in the serene views of the surrounding woods. Parking is a breeze with an attached two-car garage and a concrete driveway, ensuring convenience for you and your guests. The home is equipped with a PV solar array, promoting energy efficiency and sustainability, while the traditional architectural style adds timeless charm. Located in a peaceful cul-de-sac, this property offers a unique opportunity to embrace a lifestyle of comfort and elegance. With its blend of high-end features and inviting spaces, this home is not just a place to live, but a sanctuary to create lasting memories. Experience the perfect balance of luxury and warmth in this exceptional residence.

1610 Winters Ct, Cambridge

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

5207 Brooks Rd, Woolford
$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:

5230 Heron Rd, Cambridge
$699,000
4 Beds ⋅ 3 Baths
This custom-built 4 bedroom home on over 3.5 acres in Heron Harbor perfectly blends elegance and luxury with coastal charm and comfort! With a private community pier and dock on Fishing Creek, homes like this are seldom available but this 2019 Charles " Wiggs" Brohawn custom dream home can be yours for under $700K! The floor plan is designed for both sophistication and livability...access formal living and office space with crown molding and 9'+ ceilings from the foyer, relax with family and friends in the open kitchen and great room at the back of the main level with a gas fireplace and screened rear porch. The gourmet Kitchen features quartz countertops, a 5 burner gas cooktop, double wall oven, large island, and stainless appliances. A large Butler's Pantry with wet bar and wine storage provides additional storage beyond the extensive custom cabinetry. In addition to the island seating, enjoy meals in the bright and sunny dining space. Enjoy the rear screened porch with ceiling fan during three seasons and the inviting gas fireplace in the expansive great room during the winter months. At the top of the stairs, guests can enjoy a large flex-space to the right while the private bedrooms are accessed to the left. The spacious primary bedroom has 2 walk-in closets and a luxurious en-suite bathroom with an oversized tile walk-in shower with seat and multiple shower head as well as dual vanities. A large central atrium connects the primary to the 3 additional large bedrooms, laundry room, and bathroom with dual vanities and tub-shower along with pull-down attic access. In addition to the stunning interior, enjoy the charm of the welcoming front porch, the convenience of an oversized 2 car garage, and the beauty & privacy of the wooded 3.73 acres. Come see all that this property and community have to offer at our Open House on 9/12! Home is owner-occupied so please don't access property/driveway without an approved showing appointment; all buyers and their agents to complete due diligence regarding property taxes, zoning, measurements school, HOA, insurance, and other property information. Schedule your tour today!

5230 Heron Rd, Cambridge

Listing courtesy of EXP Realty, LLC. Contact:

5640 Thompsontown Rd, East New Market
$425,000
6 Beds ⋅ 3 Baths
Welcome to your own private slice of Maryland's Eastern Shore! Nestled on over 8 acres in picturesque East New Market, this one-of-a-kind country estate offers the perfect blend of space, functionality, and rural charm. Originally built in 1974, the home was thoughtfully expanded in 1999 with a spacious Colonial addition, creating an impressive residence featuring 6 generously sized bedrooms and 3 full bathrooms—ideal for large families, multigenerational living, or anyone who appreciates room to spread out. The heart of the home offers multiple living areas, a formal dining room, and abundant natural light, while the attached two-car garage provides everyday convenience. For hobbyists, mechanics, contractors, farmers, or entrepreneurs, the property truly shines with two massive detached workshop/garage buildings. These versatile structures provide exceptional storage, workspace, equipment housing, or the opportunity to operate a home-based business. Step outside and experience everything country living has to offer. More than 7 acres are currently utilized for crop production, making the property ideal for hobby farming, homesteading, horses, or continued agricultural use. Enjoy harvesting fresh peaches, pears, and grapes from your own fruit trees and vines, while the expansive grounds offer endless possibilities for a large vegetable garden, additional orchards, or recreational space. Relax on the welcoming front porch with your morning coffee or entertain family and friends on the rear patio while taking in peaceful views of the surrounding farmland and open skies. Located just minutes from the historic town of East New Market and a short drive to Cambridge, the property provides convenient access to shopping, dining, schools, healthcare, and outdoor recreation, including the Choptank River, Blackwater National Wildlife Refuge, boating, fishing, hunting, and numerous public parks. Commuters will also appreciate easy access to Maryland Routes 14, 16, and 50, connecting you to the Chesapeake Bay, Easton, Salisbury, and Delaware beaches. If you've been searching for acreage, privacy, workshop space, and a spacious home with unlimited potential, 5640 Thompsontown Road delivers a rare opportunity to enjoy the best of Eastern Shore living.

5640 Thompsontown Rd, East New Market

Listing courtesy of EXP Realty, LLC. Contact:

1619 Perseus Rd, Cambridge
$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:

5214 David Greene Rd, Cambridge
$599,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, comfort, and waterfront living with this exceptional move-in-ready Colonial, nestled on 6.01 scenic acres. Offering 4 bedrooms, 3 full baths, and an abundance of versatile living space, this property is ideal as a full-time residence, weekend retreat, or multigenerational home. Wake up to peaceful water views and enjoy your morning coffee on the expansive rear deck overlooking the tranquil setting. Inside, you'll find a spacious country kitchen, a flexible first-floor bedroom or home office, and inviting living areas designed for both everyday living and entertaining. The property is loaded with sought-after amenities, including a private floating dock for boating, fishing, or kayaking, a detached workshop with electricity, heating, and air conditioning perfect for hobbies or storage, and a separate in-law suite complete with its own sauna, providing an ideal space for guests, extended family, or potential rental opportunities. Additional features include a two-car attached garage, an attractive stone walkway with brick front steps, and the peace and privacy that only a rural waterfront setting can provide. Conveniently located just minutes from Cambridge's shopping, restaurants, and schools, while also offering easy access to nearby beaches and major metropolitan areas, this is a rare opportunity to own an affordable waterfront property with acreage, privacy, and exceptional versatility.

5214 David Greene Rd, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

2243 Wingate Bishops Head Rd, Wingate
$289,000
3 Beds ⋅ 2 Baths
Newly remodeled, fully furnished and low-maintenance - ready to call home! This 3-bedroom, 2-full-bath home offers a welcoming setting for everyday living or a weekend escape. Beautiful hardwood and luxury vinyl plank flooring complement the interior, while central heating and air, mini-splits and a pellet stove provide year-round comfort. A new detached one-car garage features a finished bonus room above, complete with electric, water and a mini-split for heating and cooling. Outside, relax around the fire pit and enjoy the established orchard with pin oak, apple and persimmon trees. A storage shed and deer feeder also convey. The property backs up to a 350+ acre managed Sika deer/farm property, providing a scenic backdrop for nature enthusiasts and hunters alike. A nearby public boat ramp and marina offer easy access to the Honga River for boating and fishing. Whether you’re seeking a full-time residence, getaway or hunting retreat, just bring your suitcase and settle in! The existing septic system is functioning and operational; however, replacement was recommended. A permit for a new septic system is in hand.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact:

2439 Asquith Island Rd, Crapo
$129,900
2 Beds ⋅ 1 Baths
Escape to your own private retreat with this 5.02-acre property located just minutes from the renowned Blackwater National Wildlife Refuge. Featuring a 2-bedroom, 1-bath home, this fixer-upper offers an excellent opportunity to renovate, invest, or create the hunting cabin or private retreat you’ve always wanted. Surrounded by some of Maryland’s premier outdoor recreation, the property is ideally situated for hunters and nature enthusiasts. Enjoy outstanding opportunities for sika deer, whitetail deer, and wild turkey hunting, with Blackwater National Wildlife Refuge and thousands of acres of nearby public lands helping make this a destination for wildlife and outdoor adventure. Nearby marinas and public boat ramps provide excellent opportunities for boating, fishing, and crabbing. Whether you����re looking for a weekend getaway, recreational property, or a project with ample potential, this property offers the perfect combination of privacy, acreage, and an exceptional location. Bring your vision and make this Eastern Shore property your own. Property sold as-is.

2439 Asquith Island Rd, Crapo

Listing courtesy of Iron Valley Real Estate Crossroads. Contact:

5229 Heron Rd, Cambridge
$50,000
Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up access. With easy access to downtown Cambridge, shopping, restaurants, and more, you’ll enjoy the perfect balance of convenience and seclusion. Embrace the best of Eastern Shore living in this quiet, water-oriented community.

5229 Heron Rd, Cambridge

Listing courtesy of Northrop Realty. Contact:

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