Dorchester County Public Schools Homes with Trees/Wooded Lot features

Dorchester County Public Schools Homes with Trees/Wooded Lot features

Welcome to Dorchester County, Maryland, where picturesque landscapes meet exceptional educational opportunities! Nestled in this charming region, the Dorchester County Public Schools district is dedicated to fostering academic excellence and personal growth. With a commitment to providing a well-rounded education, the district boasts a variety of programs tailored to meet the diverse needs of its students. From dedicated teachers to innovative learning environments, families can feel confident that their children are receiving a quality education that prepares them for a bright future.

Beyond its educational offerings, Dorchester County is renowned for its stunning natural beauty, particularly in neighborhoods featuring homes with trees and wooded lots. Imagine waking up to the gentle rustling of leaves and the sweet songs of birds as you sip your morning coffee on your deck. These serene, tree-lined properties not only provide a peaceful retreat from the hustle and bustle of daily life but also create an inviting atmosphere for family gatherings and outdoor activities.

Whether you’re exploring the local parks, embarking on nature trails, or simply enjoying the tranquility of your wooded backyard, life in Dorchester County offers a unique blend of community spirit and natural splendor. With the added benefit of top-notch schools just a stone’s throw away, you’ll find that this area is perfect for families looking to plant roots in a nurturing environment. Discover your dream home in Dorchester County, where education and nature come together to create a fulfilling lifestyle!

Newest Dorchester County Public Schools Homes with Trees/Wooded Lot features

$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
$95,000
Tucked away at the end of a quiet cul-de-sac, this wooded homesite at 5602 Federal Hill Rd offers the perfect opportunity to build your dream home in a peaceful Eastern Shore setting. With no HOA restrictions, you'll enjoy the freedom to create a property that suits your lifestyle, whether you envision a private retreat, custom residence, or weekend getaway. Surrounded by mature trees, the lot provides natural privacy and a serene backdrop while remaining conveniently located near Federalsburg's local amenities, parks, schools, and outdoor recreation. Bring your own builder and your vision—this is a rare chance to own a tranquil parcel where you can enjoy the beauty of nature without sacrificing convenience. No builder tie-in's and when combined with adjacent parcel being sold with it's over 2 acres of paradise! Don't miss the opportunity to secure your own slice of Maryland's Eastern Shore and build exactly what you've been dreaming of. Being sold with 5600 Federal Hill Rd

5602 Federal Hill, Federalsburg

Listing courtesy of Engel & Volkers Ocean City. Contact: (443) 292-6767
$189,500
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 offers a working well and newer 4 chamber septic system, adding value and future potential. 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
$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:

$585,600
91± Acres – Wooded Recreational Retreat with Residential Potential (2 parcels) - Sika-Whitetail-Turkey Discover the perfect escape with this expansive 91± acre wooded property, offering a rare blend of privacy, accessibility, and versatility. Featuring established logging roads running through both parcels, the land provides excellent internal access—ideal for navigating the property by ATV, truck, or on foot. Outdoor enthusiasts will appreciate the abundant recreational opportunities, including prime hunting for deer (Sika and Whitetail) and Turkey, ATV riding, hiking, and general nature exploration. The diverse wooded landscape creates a true sportsman’s haven while still offering peaceful seclusion. An active perc test is currently underway, presenting the potential for future residential use and adding long-term value to the property. Whether you’re envisioning a private homesite, hunting cabin, or weekend getaway, this tract offers flexibility to suit your needs. Access is convenient from both Taylors Island Road and Deep Point Road, making entry and use of the property straightforward. The land is also well-suited for immediate enjoyment, with ample space to accommodate a camper or temporary setup.

Taylors Island Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$399,500
3 Beds ⋅ 2 Baths
A unique opportunity to own waterfront property! This ranch-style log home situated on Galestown Pond features 225ft of pond frontage and a private dock. Add your personal touches and create a beautiful oasis...imagine the possibilities!!

5610 Galestown Newhart Mill Rd, Galestown

Listing courtesy of CALLAWAY FARNELL AND MOORE. Contact: 3026294514
$1,350,000
4 Beds ⋅ 4 Baths
Welcome to a rare waterfront retreat on Hudson Creek offering 30± acres of privacy, recreation, and breathtaking natural beauty with easy access to the Chesapeake Bay. With over 1,000± linear feet of shoreline and stunning water views throughout, this exceptional property is perfectly suited for boating, fishing, hunting, or simply relaxing and taking in the peaceful surroundings. The property features an extended private pier complete with boat lift, providing direct and convenient water access for all your waterfront activities. A significant bonus is the DU impoundment ideal for waterfowl habitat. The home offers 4 spacious bedrooms and 3 full baths and 1 half bath, designed to accommodate both comfortable everyday living and entertaining. A massive great room and dining area serve as the centerpiece of the home, highlighted by an open balcony that surrounds the space and creates a dramatic, airy feel. Dual stairways provide access to the upper level, adding both functionality and architectural appeal and water views. The eat-in kitchen includes a center island and stainless steel appliances, ideal for gatherings and casual dining. A bright and inviting sun porch offers the perfect place to enjoy morning coffee or unwind while overlooking the water. Additional features include a laundry/utility area, welcoming front porch, and a rear porch that further captures the serene water views. Outside, you’ll find a storage shed and a detached two-car garage, offering ample space for equipment, vehicles, and recreational gear. Whether you’re seeking a private waterfront residence, a weekend escape, or a recreational haven (boating, kayaking, fishing and hunting), this unique property delivers unmatched space, versatility, and waterfront living.

5704 Ross Neck Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$599,900
5 Beds ⋅ 3 Baths
Completely renovated from top to bottom, this exceptional property offers a rare opportunity to enjoy the Eastern Shore lifestyle with the privacy, acreage, and storage many waterfront buyers are seeking—without the waterfront maintenance. Situated on nearly 7 secluded acres in the highly sought-after Neck District of Dorchester County, this property is just minutes from both the public boat ramp in Cambridge and Ragged Point Marina, providing convenient access to some of the region's best boating, fishing, crabbing, and watersports opportunities. A brand-new architectural shingle roof and thoughtfully redesigned open floor plan create a stunning great room where the kitchen, living, and dining areas flow seamlessly together—ideal for everyday living and entertaining. The beautifully updated kitchen features new countertops, ceramic tile backsplash, and all-new appliances, while updated bathrooms, flooring, wiring, lighting fixtures, and fresh landscaping ensure a truly move-in ready experience. The first floor offers two bedrooms and one full bath. Upstairs, the spacious primary suite includes a private bath and walk-in closet, along with two additional bedrooms and another full bathroom. Outside, the property transforms into a private retreat. Enjoy peaceful views of the pond from the expansive rear deck, gather with friends and family under the stars, or simply relax and take in the sights and sounds of nature. Surrounded by mature woods and abundant wildlife, including deer and turkey, the setting offers exceptional privacy and tranquility. For boating enthusiasts, the impressive 45' x 30' metal outbuilding with concrete floor provides ample room for boats, jet skis, trailers, recreational equipment, workshop space, or a home-based business. Whether you're returning from a day on the water or enjoying the serenity of your own acreage, this property delivers the best of both worlds. Located less than 10 minutes from Cambridge, this is a rare opportunity to own a fully renovated home that combines modern comfort, exceptional privacy, abundant storage, and easy access to the waterways that make the Eastern Shore such a special place to call home.

5951 Ross Neck Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$179,900
Hunters Haven! The perfect blend of recreation and opportunity with this 16-acre hunting property. Featuring a versatile large agricultural field, a blank canvas to make it your own, strategically plant food plots or the back right corner is an ideal location for a future impoundment to attract and sustain wildlife. This property has a little bit of everything for outdoor enthusiasts, offering excellent hunting for sika deer, whitetail deer, waterfowl, and turkeys along with some pond fishing. The diverse habitat and open field create ideal conditions for both seasoned hunters and those looking to establish a private retreat. An older mobile home currently sits on the property and is considered a tear-down, but it provides a valuable head start with existing infrastructure. Electric service is active, and there is an existing septic system on site (condition unknown), offering potential for future building or campsite development. Whether you're looking to create your own hunting getaway, invest in recreational land, or develop a rural homestead, this property offers a unique opportunity with plenty of potential.

2839 Lakesville Crapo Rd, Church Creek

Listing courtesy of Taylor Properties. Contact:

$179,900
1 Beds ⋅ 1 Baths
Hunters Haven! The perfect blend of recreation and opportunity with this 16-acre hunting property with 2 ponds. Featuring a versatile large agricultural field, a blank canvas to make it your own, strategically plant food plots or the back right corner is an ideal location for a future impoundment to attract and sustain wildlife. This property has a little bit of everything for outdoor enthusiasts, offering excellent hunting for sika deer, whitetail deer, waterfowl, and turkeys along with some pond fishing. The diverse habitat and open field create ideal conditions for both seasoned hunters and those looking to establish a private retreat. An older mobile home currently sits on the property and is considered a tear-down, but it provides a valuable head start with existing infrastructure. Electric service is active, and there is an existing septic system on site (condition unknown), offering potential for future building or campsite development. Whether you're looking to create your own hunting getaway, invest in recreational land, or develop a rural homestead, this property offers a unique opportunity with plenty of potential.

2839 Lakesville Crapo Rd, Church Creek

Listing courtesy of Taylor Properties. Contact:

$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
$239,000
Birds-Birds-Birds... – This unique hunting property, along with an existing church, has the potential to be your dream hunting lodge. This remarkable estate offers a rare opportunity to own your hunting camp in the heart of nature's bounty, bordered on the southern property line by Fishing Bay Wildlife Sanctuary. The property's key feature is its ideal location, nestled in the serene surroundings of Crapo, MD, offering a tranquil escape from the hustle and bustle of modern life. While conveniently close to modern metro centers, it's ideally situated amid some of the best hunting and fishing grounds on the East Coast. The property boasts an existing church that opens up exciting possibilities. Transform it into your hunting lodge, creating a unique and atmospheric retreat for you and your friends. For hunting enthusiasts, this property is a haven for Sika deer and waterfowl. The property is expertly set up for duck hunting and features a long boardwalk that takes you to the duck pond and duck blind in the center of the marsh. And a convenient location in the pines with a deer stand and feeder. Immerse yourself in the natural beauty and abundance of wildlife that surrounds you, creating an unparalleled hunting experience. Take advantage of this rare opportunity to own an affordable piece of paradise. Whether you're a seasoned hunter or looking to establish a nature retreat, this property offers a cost-effective way to make your dreams a reality. This is more than just a property; it's an invitation to immerse yourself in the great outdoors, create lasting memories, and build a unique haven for hunting and relaxation. You can use the opportunity to make 3241 Robbins Rd your private retreat in the heart of nature's wonders. The property consists of two lots. Church: 0.519 acres (See the attached survey plat in documents). The more considerable lot: the tax map indicates 15 acres; however, the survey documents indicate 34.5 acres. (A survey performed by the former owner but not recorded is attached in the documents, indicating 34.5 acres are connected to the documents)

3241 Robbins Rd, Crapo

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
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