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$299,000
3 Beds ⋅ 3 Baths
Welcome to this charming farmette featuring a 3 bedroom, 2 3/4 bath home that has been elevated and features a conditioned crawl space, includes a 3-stall barn, pole barn and shop/shed. Situated on over 8.5 acres, this property offers open fields, established pastures with fencing, a pond and wooded areas, creating the perfect blend of recreation, hobby farming and peaceful country living for the nature enthusiast and hunters alike. Enjoy Sika deer and waterfowl hunting right in your own backyard, with endless opportunities to enjoy the outdoors. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$199,000
One of a kind nearly 22+/- acre recreational property offering an exceptional setting for the outdoor enthusiast. Partially wooded with established trails, open fields and Farm Creek water frontage, the property offers excellent opportunities for Sika deer, goose and duck hunting. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing. Whether you're looking for a private hunting retreat or simply a place to enjoy the Eastern Shore outdoors, this unique property offers endless recreational opportunities. This property is accessible from Toddville Road, providing easy, private access.

Sika Deer & Waterfowl Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,690,000
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,690,000
7 Beds ⋅ 3 Baths
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron 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
$3,200,000
Looking for a business opportunity, want to expand your business? This exceptional property offers outstanding income and business potential, including opportunities for a private retreat, vacation rental, event or wedding venue, guided hunting and fishing, sporting clay, kayak, water sports experiences and other outdoor recreational offerings. Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
5 Beds ⋅ 6 Baths
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

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
$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
$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
$25,000
Attention hunters, anglers, and outdoor enthusiasts! Escape to Hoopers Island and claim your own private base camp in one of the Chesapeake Bay’s most sought-after fishing and hunting destinations. This water-view lot offers the perfect setting to unwind, recharge, and enjoy the best of Maryland’s Eastern Shore. The property includes two storage sheds—ideal for stowing boats, gear, decoys, and everything you need for your next adventure. Take in scenic views of the Chesapeake Bay and experience the peace and quiet that make island living so special. Conveniently located just minutes from Old Salty's Restaurant and a short drive to Blackwater National Wildlife Refuge, you’ll have easy access to some of the region’s premier hunting grounds and world-class fishing waters. Public boat ramps and marinas are nearby, making it simple to get out on the Bay whenever the mood strikes. Whether you're casting for rockfish at sunrise or setting up for waterfowl season, this property puts you right in the heart of it all.

2125 Hoopersville Rd, Fishing Creek

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

$650,000
4 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

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

$378,000
102.4 Acres of prime waterfowl hunting. Property is 2 parcels. Parcel 4 is 35 Acres and Parcel 5 is 67.4 Acres. Parcel 5 was subdivided in January of 2026 and was originally 131 Acres.

Griffith Neck Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$675,000
Do you dream of a serene waterfront escape with room for horses, privacy, and the opportunity to create something truly special? Recently PERC APPROVED for a 5-bedroom home, this 10-acre horse farm on Hudson Creek offers exciting new possibilities to renovate the existing residence or build the waterfront home you’ve envisioned. The property is already well equipped for equestrian use with two fenced pastures, a barn, run-in shed, storage shed, and fresh water systems for the horses. Surrounded by wide-open space and limited future development, the setting offers exceptional privacy and peaceful, protected views. Water lovers will appreciate the 100-foot T-shaped pier with over 4 feet of mean low water on protected Hudson Creek, providing easy access to the Chesapeake Bay and some of the area’s best fishing and crabbing. A charming old crab shack near the shoreline offers additional potential with some repairs. An oversized detached brick 4-car garage provides plenty of room for a workshop, hobby equipment, boats, or collectible vehicles. The existing all-brick home is being sold AS IS and features three bedrooms, two-and-a-half baths, a brick fireplace, and attached 2-car garage. With 10 waterfront acres, established equestrian amenities, deep-water access, and the recent 5-bedroom PERC approval, this property presents a rare opportunity to bring your vision to life on Maryland’s Eastern Shore.

5816 Indian Quarter Rd, Cambridge

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