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 natural beauty of the Eastern Shore. Nestled in this idyllic setting is the highly regarded Dorchester County Public Schools district, known for its commitment to academic excellence and holistic student development. With a variety of educational programs, dedicated teachers, and a strong community focus, families can feel confident that their children are receiving a top-tier education while fostering lifelong friendships and connections.

Living in Dorchester County means more than just access to quality schools; it’s about embracing a lifestyle surrounded by nature. Imagine coming home to a beautiful residence with serene views of trees and woods, where the sounds of rustling leaves and chirping birds create a peaceful retreat. Homes with tree and woods views in this area offer a unique opportunity to connect with the great outdoors right from your backyard. Whether you enjoy morning coffee on the porch or evening strolls through the lush landscape, these properties provide a tranquil escape from the hustle and bustle of everyday life.

Dorchester County is rich in history, culture, and outdoor activities, making it the perfect place for families, retirees, and nature enthusiasts alike. With an array of parks, waterways, and scenic trails, there’s always something to explore. Combine this vibrant community with the excellent educational opportunities offered by Dorchester County Public Schools, and you have a recipe for a fulfilling and enriching lifestyle. Discover your dream home today, and experience all that this beautiful region has to offer!

Newest Dorchester County Public Schools Homes with Trees/Woods View

$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
$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: 8888607369
$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: 8888607369
$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
$424,900
3 Beds ⋅ 3 Baths
One of a kind 31+ acre farmette with established trails, open fields, ponds and Farm Creek water frontage, offering excellent Sika deer, goose and duck hunting and endless opportunities to enjoy the outdoors. The property includes a well-maintained 3 bedroom, 2 3/4 bath home with a conditioned crawl space, 3 stall barn, fenced pastures, pole barn and shop/shed. The perfect blend of recreation, hobby farming and peaceful country living for the hunter and nature enthusiast alike.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$624,000
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: 4103042011
$299,000
3 Beds ⋅ 2 Baths
Beautifully renovated and move-in ready, 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 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. *A new septic system is scheduled to be installed within the next 30-60 days. The existing system is functioning; however, replacement was recommended following a recent inspection, and the seller is moving forward with installation.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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: 2403979292
$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: (302) 539-0800
$82,000
3 Beds ⋅ 2 Baths
Welcome to an exceptional opportunity in Cambridge! Whether you’re a first-time homebuyer, downsizing, or looking to relocate to the area, this charming property offers affordability, comfort, and convenience in one package. Featuring 3 bedrooms and 2 full bathrooms, this well-maintained home offers a functional layout with comfortable living spaces and plenty of natural light. The spacious living area flows into the kitchen and dining space, creating an inviting atmosphere for everyday living or entertaining. Outside, you’ll enjoy a manageable yard with room to garden, relax, or personalize to your liking. Conveniently located just minutes from downtown Cambridge, you’ll have easy access to local restaurants, shopping, the waterfront, parks, and the vibrant Chesapeake Bay lifestyle. Commuters will appreciate the quick access to Route 50, making travel to Easton, Salisbury and the Maryland and Delaware beaches a breeze. Don’t miss your chance to own an affordable home on Maryland’s beautiful Eastern Shore—schedule your private showing today! * Buyer must receive approval through Southside Landing office.

2631 Rebecca Ln, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$8,950,000
24 Beds ⋅ 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$167,900
Great opportunity to own nearly 8 acres featuring some of the highest and driest ground in Toddville. Located in sought after Sika deer country, this property offers a peaceful rural setting with hunting opportunities, abundant wildlife, and a creek running through the property. The land features a great combination of woods, newly planted pines and natural habitat, creating an ideal setting for Sika deer, wildlife and outdoor recreation. Property features a brand new complete 4 chamber septic system (never used), adding value and future potential, existing well. Also conveying is a 27 ft camper with bump out, providing a great setup for a hunting retreat or weekend getaway. The older home on the property is in need of repairs, including a new roof and is being sold as-is, bring your vision to renovate and bring back to life or tear down and build your own home. Enjoy the privacy, open space and natural beauty of Dorchester County with fishing, boating, public boat ramps and marinas close by.

2551 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
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