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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:

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:

5610 Galestown Newhart Mill Rd, Galestown
$365,000
3 Beds ⋅ 2 Baths
Waterfront Retreat or Dream Homestead Overlooking a 40-Acre Pond! Nestled on a sprawling 1.13-acre lot, this unique property offers the perfect blend of peaceful country living, rustic charm, and water-oriented recreation. Enjoy scenic pond views, your own private pier/dock, and endless opportunities for fishing, boating, kayaking, or simply relaxing by the water. Imagine starting your day with coffee overlooking the pond and ending the evening enjoying the tranquility of your private outdoor oasis. Inside, you'll find 3 spacious bedrooms and 2 full baths, with knotty pine throughout, creating a warm and inviting atmosphere. Gather around the cozy fireplace on chilly evenings or enjoy additional living space in the separate sitting room/family room. The primary bedroom features a private ensuite bath, while the generously sized rooms provide plenty of space for family and guests. An additional studio/office off the garage offers flexibility for working from home, pursuing hobbies, or creating your own private creative space. Outdoor living is a highlight, with a rear screened deck offering the perfect setting for entertaining, alfresco dining, or simply taking in the beautiful surroundings. The fenced rear yard provides added privacy, while the 1.5-car garage offers convenient parking and storage. A generator adds extra peace of mind. Whether you're searching for a full-time homestead, a weekend escape, or a private waterfront retreat, this property offers a rare opportunity to embrace the beauty of nature while enjoying comfortable living. With room to relax, entertain, and make it your own, this special setting invites you to slow down, enjoy the water, and experience the lifestyle you've been dreaming of!

5610 Galestown Newhart Mill Rd, Galestown

Listing courtesy of Mabry Real Estate LLC. Contact:

6016 Blue Heron Dr, East New Market
$1,495,000
3 Beds ⋅ 4 Baths
Custom-built new construction on 3.73 acres along the Choptank River, offering a truly unique waterfront setting with views of the river, a peaceful backwater slough and a picturesque pond. With water and open landscape in nearly every direction, this property offers a sense of space and tranquility that is hard to duplicate. Step inside to an open, light-filled floor plan where thoughtful design and custom details are evident throughout. Wide-plank wood flooring flows through the main living areas, while vaulted ceilings and a striking fireplace create a dramatic focal point in the great room. Expansive glass doors open directly to a large patio, extending the living space outdoors and providing another place to enjoy the surrounding landscape and water views. The gourmet kitchen is a standout with custom cabinetry, an oversized island, stainless steel appliances, double wall ovens and a cleverly concealed butler’s pantry offering exceptional storage and prep space. Just off the eat-in kitchen area, a spacious screened porch takes full advantage of the peaceful setting and provides the perfect spot for outdoor dining, entertaining or simply relaxing and enjoying the view. Offering 3 spacious bedrooms and 3.5 baths, each bedroom has its own private ensuite bath, providing comfort and privacy for both owners and guests. The second-floor bedroom creates an especially inviting retreat with a private balcony overlooking the Choptank River and surrounding property. Distinctive tile selections, contemporary finishes and thoughtful architectural details throughout give this home a character all its own. Outdoor living is an integral part of this special property. Enjoy morning coffee on the screened porch, gather with friends on the patio, or retreat to the upstairs balcony to take in the river views. Nature lovers will appreciate the abundant birdlife, with eagles, osprey and other native birds frequently seen throughout the area. And as the day comes to a close, settle in for the spectacular sunsets that make the name “Sunset Cove” especially fitting. The waterfront lifestyle continues with a shared community pier on the Choptank River. Slips are planned, with one reserved for this property, providing future access for boating, fishing, crabbing and exploring the waterways of the Eastern Shore. An attached two-car garage, paved driveway and generous acreage complete this exceptional property. Custom new construction, 3.73 acres, remarkable waterfront, outdoor living spaces and future boat slip access come together in a setting that truly captures the beauty and lifestyle of Maryland’s Eastern Shore. Shown by appointment only.

6016 Blue Heron Dr, East New Market

Listing courtesy of TTR Sotheby's International Realty. 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:

1621 Terrapin Cir, Cambridge
$360,000
5 Beds ⋅ 3 Baths
Seller help with closing costs available! Five bedrooms, three full baths, and room for everyone in Blackwater Landing. 1621 Terrapin Circle delivers the space that’s hard to find at this stage: 2,610 square feet of nearly new Colonial living with nothing to fix, update, or wait on. The open main level is bright and easy to live in, with flow from kitchen to living areas that works just as well for a quiet weeknight as it does for a holiday crowd. Five bedrooms give you real flexibility: a guest suite, a home office, a hobby room, or simply room to spread out. The attached garage keeps daily life simple, and the rear patio is ready for morning coffee, evening grilling, and weekend get-togethers. Life in Blackwater Landing means stepping outside to four large fishing ponds, walking trails, and a waterside gazebo that’s a favorite spot to slow down at the end of the day. Downtown Cambridge’s historic district, restaurants, and shops are just minutes away, and Rt. 50 puts Easton, Annapolis, and the beaches within easy reach. Newer construction, generous space, and a community with genuine character. Sellers will help with closing costs with an acceptable offer, so come see it in person and schedule your private showing today.

1621 Terrapin Cir, Cambridge

Listing courtesy of Bayside Realty. Contact:

964 Taylors Island Rd, Madison
$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:

5253 Ragged Point Rd, Cambridge
$1,250,000
5 Beds ⋅ 4 Baths
🔥 Eastern Shore Waterfront Estate 🔥 Welcome to a true sportsman’s paradise tucked along the shores of the Chesapeake Bay—where space, privacy, and waterfront living come together in a BIG way. Built in 1988 and spanning nearly 5,000+/- square feet, this one checks boxes most properties can’t even reach… 🏡 5 Bedrooms | 3.5 Baths | 4,933+/- Sq Ft Step inside and you’ll find: • A massive eat-in country kitchen (with heated floors 👀) • Formal dining for hosting the big nights • TWO oversized family rooms for spreading out • Space for everyone… and then some But here’s where it gets wild 👇 🎯 Next-Level Extras: • Huge workshop + multiple garage spaces • Dedicated entertainment hall with FULL kitchen, bar & pool table • Built for hosting, holidays, and unforgettable weekends 🌅 Waterfront Lifestyle: • Private pier on Brooks Creek • TWO boat lifts + electric lift • Westerly sunset views over the Bay (the kind people chase 🌅) • Expansive deck for relaxing or entertaining • Private pond adding to the already unreal setting ⚙️ Major Upgrades: • Geothermal system (efficient + smart) • New roof (Oct 2024) • Expanded shop addition This isn’t just a home… it’s a compound. A retreat. A place people don’t want to leave once they get here. 💬 If you’ve been waiting for something special on the Eastern Shore… this is it.

5253 Ragged Point Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

964 Taylors Island Rd, Madison
$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:

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