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

$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
Coming Soon! 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. This home is in excellent condition, features include 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, an 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. Deer feeder conveys.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$95,000
Discover the possibilities at 5600 Federal Hill Rd, Federalsburg, MD! Tucked away at the end of a quiet cul-de-sac, this vacant parcel offers the perfect opportunity to build the home you've been dreaming of. Enjoy the freedom of no HOA, giving you the flexibility to create a property that fits your lifestyle without restrictive community regulations. No builder tie-in's and when combined the property is little over 2 acres of paradise! Whether you're planning a custom residence, a peaceful weekend retreat, or an investment for the future, this lot provides a tranquil setting with the privacy and low-traffic appeal of a cul-de-sac location. Conveniently situated near local amenities while still offering a relaxed, rural atmosphere, this property is ready for your vision to come to life. Don't miss your chance to own a piece of land with endless potential in charming Federalsburg. Bring your builder and start planning your future today! Being sold with 5602 Federal Hill Rd adjacent to this lot

5600 Federal Hill Rd, Federalsburg

Listing courtesy of Engel & Volkers Ocean City. Contact: (443) 292-6767
$149,900
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
$90,000
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
$275,000
3 Beds ⋅ 1 Baths
Escape to the peace and privacy of Maryland's Eastern Shore with this charming ranch-style home situated on 2 acres of land. Offering comfortable one-level living, this well-maintained property features 3 bedrooms, 1 full bath, and a spacious layout designed for everyday living. Inside, you'll find a thoughtfully updated interior with modern touches while maintaining the home's warmth and character. Recent improvements include a newer roof and siding, providing added value and peace of mind. Outside, the oversized detached 2-car garage offers endless possibilities for vehicle storage, hobbies, a workshop, or recreational equipment. The expansive lot provides plenty of room for gardening, outdoor entertaining, pets, and enjoying the surrounding countryside. With no HOA restrictions, ample parking, and room for boats, RVs, trailers, or additional outdoor toys, this property offers the freedom and flexibility many buyers are seeking. Conveniently located near Cambridge and Route 50, you'll enjoy easy access to shopping, dining, healthcare, and all the recreation the Chesapeake Bay region has to offer. Whether you're looking for a full-time residence, a weekend retreat, or a property with space to spread out and enjoy country living, this Eastern Shore gem is ready to welcome you home.

3714 Hicksburg Rd, East New Market

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
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