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

2249 Wingate Bishops Head Rd, Wingate
$95,000
3 Beds ⋅ 1 Baths
Create your own private weekend getaway, hunting retreat or full-time residence with this 3 bedroom, 1 bath rancher featuring a newer well and septic system. The home needs TLC and is ready for your personal touches. Enjoy a private setting just a short drive from two marinas, public boat ramps, public hunting areas and Elijah’s General Store. Spend your days fishing, crabbing and hunting, then head home to unwind after a day outdoors. The property across the street, featuring 5.71 acres with a pond and access to Wingate Creek, is also available for sale (Land Listing MLS# MDDO2013492). The properties are listed separately and may be purchased together with an acceptable offer for a combined 7+ acres. Purchase both properties to enjoy opportunities for waterfowl, Sika deer and turkey hunting along with crabbing from the recreational parcel.

2249 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact:

4548 Hoopers Neck Rd, Taylors Island
$599,000
Discover 39± acres of Chesapeake Bay waterfront land along Hoopers Neck Road on Taylors Island in Dorchester County, Maryland. Featuring approximately 450 feet of western-facing shoreline on scenic Oyster Cove and over 385 yards of road frontage, this diverse property offers an exceptional combination of waterfront, mature timber, productive farmland, and outstanding Sika deer and waterfowl habitat. A county-recorded septic reserve area (SRA) within the front 9± acre field provides an attractive potential homesite for a private Chesapeake Bay retreat. Mature stands of loblolly pines create a scenic and secluded setting, while two separate tillable fields of approximately 6 and 9 acres offer opportunities for agricultural use and potential passive income through a farming lease. A spring-fed pond adds another desirable natural feature and valuable water source for wildlife. Several acres of phragmites and marsh vegetation along Oyster Cove provide excellent cover for the area's healthy Sika deer population. The cove is also a well-known wintering area for a variety of waterfowl, offering excellent hunting and wildlife viewing opportunities. The combination of fields, timber, wetlands, and waterfront creates a diverse habitat for outdoor recreation. Recent engineering site work has been completed, and a recorded plat identifying the septic reserve area is available upon request. Buyers should conduct their own due diligence with Dorchester County and applicable regulatory agencies regarding residential building permits, septic approvals, and potential waterfront pier construction. Buyer-due dilligence required for AG conservation area, Nontidal / Critical areas. Recent sitework has been down with engineering frims. Survery Plat is available upon request. The property adjoins a separately listed waterfront residence on 23.23± acres, offering the opportunity to purchase either property individually or combine both for a private Chesapeake Bay estate totaling over 62 acres. An ultra-rare opportunity to own waterfront land with homesite potential along the western-facing Chesapeake Bay shoreline, offering exceptional wildlife viewing and breathtaking sunsets on Maryland's Eastern Shore.

4548 Hoopers Neck Rd, Taylors Island

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

Cambridge
$2,300,000
Located on Town Point Road near Cambridge in Dorchester County, Maryland, this 134.87± acre waterfront hunting property offers an outstanding combination of managed waterfowl habitat, productive farmland, wooded hunting acreage, and navigable waterfront access to the Little Choptank River. The property features approximately 19.5± acres of tillable ground, 15± acres of newly constructed waterfowl impoundments, and 95± acres of woods, marsh, and open ground, providing diverse habitat for whitetail deer, sika deer, wild turkeys, ducks, and geese. A gravel lane winds through agricultural fields with a history of corn and soybean production. Approximately 83% of the farm consists of Elkton silt loam, with an overall NCCPI soil productivity score of 47.5. Predominantly pine timber, mixed hardwoods, and thick understory connect to a larger wooded block in the northwest corner, creating excellent wildlife cover and natural travel corridors. An established box blind overlooks the fields and ponds, while additional duck and goose blinds provide multiple hunting locations throughout the property. A major highlight is the approximately 15± acres of waterfowl impoundments completed during the summer of 2026. Three impoundments are designed for planting corn, milo, or managing natural moist-soil vegetation, while a deeper holding pond offers potential waterfowl roosting habitat. Newly installed Agri Drains and culverts provide water management capabilities, and a new well near the shed offers the potential to supply additional water with appropriate connections. Two impoundments are currently planted in standing corn. The underlying Elkton silt loam helps retain water, while seasonal drawdowns can encourage natural moist-soil vegetation. The combination of agricultural fields, mature timber, thick cover, and marshland creates diverse hunting opportunities for whitetail deer, sika deer, and wild turkeys. The property's established hunting improvements and habitat features provide an excellent foundation for continued wildlife and recreational management. Near the agricultural fields, a former homesite includes an existing well and septic system, with condition and suitability subject to buyer verification. A newer shed equipped with HVAC and additional amenities offers a comfortable recreational gathering space. Electrical service is available throughout the property, providing flexibility for future improvements. Potential residential construction at the former homesite is subject to applicable county approvals. The gravel lane continues to the waterfront, where a dock and walkway provide access to a navigable cove connecting to the Little Choptank River for boating, fishing, and crabbing. Additional waterfront improvements include a camper hookup, utility building, and screened porch equipped with a refrigerator, ceiling fan, and electric service. With newly constructed waterfowl impoundments, established hunting blinds, diverse deer and turkey habitat, productive agricultural fields, and navigable waterfront access, this 134.87± acre property represents a rare opportunity to own a managed hunting and recreational retreat on Maryland's Eastern Shore.

Cambridge

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

Kirwans Neck Rd - Kirwans Neck Rd - Waterfowl & Sika Deer, Church Creek
$1,990,000
Welcome to Holly Marsh, an exceptional waterfront sporting estate spanning over 87 acres across three adjoining parcels on Maryland’s Eastern Shore. Established waterfowl impoundments with a well and newly updated piping and gates (2026) provide excellent duck and goose hunting, while the property also offers great sika deer and turkey hunting, along with great fishing in the Honga River and Chesapeake Bay. Expansive water views, spectacular sunrises and sunsets and a private setting capture the outdoor traditions and natural beauty of the Eastern Shore. Complementing the land is a 5 bedroom, 4 bath waterfront home with ample space to gather after a day outdoors. A pool, hot tub, private beach and pier with boat lift provide additional opportunities to enjoy this remarkable private setting. Recent improvements include a fully renovated kitchen and laundry room with new appliances, fresh paint throughout, a new dock and boat lift, shoreline riprap and a resurfaced parking area (2024), followed by a new retractable pool cover and rescreened porch and hot tub area (2025). From mornings in the waterfowl impoundments to evenings overlooking the water, Holly Marsh brings together exceptional hunting, waterfront recreation and the comforts of home in a private Eastern Shore retreat.

Kirwans Neck Rd - Kirwans Neck Rd - Waterfowl & Sika Deer, Church Creek

Listing courtesy of Meredith Fine Properties. Contact:

5430 Indiantown Rd, Rhodesdale
$929,000
3 Beds ⋅ 3 Baths
A rare offering in North Dorchester, this exceptional 58.96-acre property offers a unique combination of space, versatility, and endless possibilities! From the welcoming circular driveway to the impressive shop and pole building, there is so much to discover. The main residence features a traditional floor plan with both formal and informal living areas, perfect for entertaining and everyday living. Enjoy cozy winter evenings in the family room, where the fireplace currently features a gas insert, with the option to remove it and enjoy the timeless charm and crackle of a wood fire while preparing dinner. The abundance of additional accommodations and amenities truly sets this property apart, including a second two-bedroom, handicap-accessible home ideal for in-laws or extended family, an apartment above the detached garage, and an additional kitchen and bath in the attached garage. A whole-property generator system provides backup power to the main residence, second home, apartment, and shop, adding valuable peace of mind. Whether you're seeking a multigenerational retreat, room for hobbies and equipment, or simply the privacy and freedom that acreage provides, this remarkable property offers a rare opportunity to make your vision a reality! Bring your business with separate gated lane, accessable from the main house. Huge shop and pole building. Interior photos coming soon

5430 Indiantown Rd, Rhodesdale

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4928 Gregory Rd, Cambridge
$998,500
4 Beds ⋅ 3 Baths
Set along the shores of Church Creek, this property spans 3.395+/- acres, offering a private setting, sweeping water views, and direct boating access. With over 470 feet of protected shoreline, a private dock with four feet of water depth, and a boat lift, the property embraces the best of Eastern Shore living. The approximately 3,400+/- square-foot home features four bedrooms and thoughtfully arranged living spaces designed to take full advantage of the waterfront setting. The main level offers an updated kitchen, spacious living and dining areas with creek views, and a stunning screened porch ideal for waterfront entertaining and quiet evenings overlooking the water. Upstairs, the primary suite features walk-in closets, a clawfoot soaking tub, a walk-in shower, and a private deck with sweeping views of Church Creek. Two additional bedrooms and a full bath complete the second floor. The third floor offers two additional rooms, providing flexible space for a home office, media room, or guest retreat. A detached two-car garage, three-bay kennel, and separate storage building add versatility to the property. Located just minutes from downtown Cambridge with restaurants, marinas, and community activities.

4928 Gregory Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

3214 Kirwans Neck Rd, Church Creek
$1,990,000
5 Beds ⋅ 4 Baths
Welcome to Holly Marsh, this exceptional waterfront estate spans over 87 acres across three adjoining parcels on Maryland’s Eastern Shore. Expansive water views, spectacular sunrises and sunsets create a remarkable setting for this 5 bedroom, 4 bath waterfront home. A pool, hot tub, private beach and pier with boat lift offer endless opportunities to relax, entertain and enjoy life on the water. Recent improvements include a fully renovated kitchen and laundry room with new appliances, fresh paint throughout, a new dock and boat lift, shoreline riprap and a resurfaced parking area (2024), plus a new retractable pool cover, rescreened porch and hot tub area (2025). Established waterfowl impoundments with well, updated with new piping and gates (2026), provide excellent duck and goose hunting, while great sika deer & turkey hunting can be enjoyed throughout the property. Rooted in the outdoor traditions of the Eastern Shore, Holly Marsh offers privacy, natural beauty and a waterfront retreat to share with family and friends.

3214 Kirwans Neck Rd, Church Creek

Listing courtesy of Meredith Fine Properties. Contact:

007 Griffith Neck Rd, Cambridge
$2,199,000
LEGENDARY 289± ACRE SIKA DEER & DUCK HUNTING PROPERTY | GRIFFITH NECK ROAD | DORCHESTER COUNTY, MARYLAND AN EPIC EASTERN SHORE HUNTING LEGACY — TURNKEY, FULLY EQUIPPED, AND READY FOR YOUR NEXT ADVENTURE! Opportunities to own a property of this caliber rarely come along. Spanning an incredible 289± acres along Griffith Neck Road in Dorchester County, Maryland, this extraordinary hunting property is a true Eastern Shore sportsman’s paradise, offering an exceptional combination of legendary sika deer hunting, waterfowl hunting, and recreational opportunities. Completely turnkey and ready to hunt, this is a rare chance to step into an established hunting operation with the infrastructure, improvements, and habitat to make every season memorable. The property is exceptionally well equipped, featuring 15 custom-built box blinds, several feeders, and two strategically placed duck blinds overlooking beautiful Parrish Pond. An extensive internal road system stretches nearly two miles throughout the property, allowing you to access the many hunting locations and explore the acreage with ease. Grab your e-bike or buggy and be in your stand in minutes. Your hunting headquarters begins with a convenient trailer camp complete with an outhouse, providing a practical base for weekends in the field and extended hunting adventures. For equipment and gear, a thoughtfully constructed storage area features two shipping containers beneath a large protective roof, offering valuable space to organize and store your hunting gear. Inside the container you will find an argo that conveys with the property in fairly good condition. One of the property's most unique features is the Duck House, nestled right in the marsh and within a short walking distance of Parrish Pond. Adding even more versatility is a brand-new dock, providing a convenient launching point for your boat or canoe. From here, head out to access the duck blinds, sneak into the box blinds from the waters edge, explore the waterways, or simply enjoy the incredible natural surroundings. The hunting opportunities are what truly set this property apart. The acreage supports an abundant population of TROPHY-CLASS sika deer, along with whitetail deer, waterfowl, quail, and small game. With established blinds, feeders, duck-hunting setups, extensive access roads, and a diverse outdoor setting, this property offers an outstanding foundation for pursuing multiple species throughout the hunting seasons, providing epic adventures. Properties of this size, quality, and level of preparation are exceptionally rare. Hunting properties like this are often held within families for generations, making the opportunity to acquire an established sporting property of this magnitude especially meaningful. Whether you're looking to continue a proud hunting tradition, create unforgettable memories with family and friends, or establish your own private Eastern Shore hunting destination, this remarkable property is ready for its next chapter. 289± ACRES. 15 CUSTOM BOX BLINDS. TWO DUCK BLINDS. PARRISH POND. A MARSH-SIDE DUCK HOUSE. NEARLY TWO MILES OF INTERNAL ROADS. (Deeded acres being sold, property may be larger, see OnX pictures attached.) This is more than a hunting property — it is a Legendary Eastern Shore sporting legacy waiting for someone to carry on its traditions. Don't let this once-in-a-generation opportunity pass you by.

007 Griffith Neck Rd, Cambridge

Listing courtesy of Charis Realty Group. Contact:

3523 Chateau Dr, East New Market
$2,000,000
3 Beds ⋅ 2 Baths
Over 55 Acres. Active chicken and grain farm. Three 40 x 500 chicken houses, growing for Amick. Quite a bit of open/clear land so adding more chicken houses is probably an option. Two homes, three bedrooms each, one owner-occupied and the other tenant-occupied. Great location, just off Rt. 50 and tucked away on a small road, in a very private setting.

3523 Chateau Dr, East New Market

Listing courtesy of Sunset Properties. Contact:

5500 Ross Neck Rd, Cambridge
$365,000
Rare opportunity to own 31.458 acres of waterfront land in Cambridge’s coveted Neck District. Located at 5500 Ross Neck Road, this exceptional property combines privacy, abundant wildlife, and outstanding water access with the opportunity to create your own custom Eastern Shore retreat. The property features approximately 175 feet of water frontage with an impressive 4–5 feet of mean low water depth, offering excellent access for boating and other water activities. Build your private dock, keep your boat just steps from home, launch kayaks, or simply enjoy the peaceful waterfront setting. Much of the groundwork for a future homesite has already been completed. The property has an approved perc test, and a new plat prepared by Fink, Whitten & Associates identifies the building site, well location, and sewage disposal area—helping provide a clear path toward designing and building your dream home. For the outdoor enthusiast, the acreage offers a remarkable natural setting with abundant wildlife, including whitetail deer, Sika deer, and wild turkey. Whether you envision a private waterfront estate, an Eastern Shore hunting and recreational retreat, or a peaceful escape surrounded by nature, this property offers a rare combination of acreage, water access, and buildability. Enjoy over 31 acres of your own piece of Maryland’s Eastern Shore, with deep-water frontage and the freedom to create a property uniquely your own.

5500 Ross Neck Rd, Cambridge

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

6108 Delaware Line Reliance Rd, Rhodesdale
$660,000
3 Beds ⋅ 2 Baths
Motivated sellers! 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. Horse friendly! Great deer hunting! Subdivision potential. Hunting and tilling rights rented for added income.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:

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