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$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
$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
$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
$439,900
3 Beds ⋅ 2 Baths
Whether you're dreaming of a peaceful country lifestyle or ready to bring your horses home, this picturesque farmette on nearly 5.5 acres is ready for you. The property is already set up with established pastures, a barn featuring four stalls and a feed room and plenty of space for horses and other animals. The updated 3 bedroom, 2 full bath farmhouse blends modern updates with timeless charm and features newer mini-split heating and cooling systems, a cozy pellet stove and a convenient first-floor primary bedroom. A detached two car garage includes a 1 bedroom, 1 bath apartment above, ideal for guests, extended family, rental income, or a private home office.

5125 Rhodesdale Rd, Rhodesdale

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$159,900
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
$319,700
BACK ON THE MARKET WITH IMPROVED PRICE-THIS IS THE LOCATION!!!! ***********************PUBLIC SEWER IS ON THIS PROPERTY************************************* If you’ve been searching for the perfect canvas to build your Delmarva masterpiece, look no further. This rare offering features over 1.5 acres of low-maintenance waterfront land on the Little Choptank River, comprised of two cleared, level lots ready for your own personal dream. One of the most significant hurdles to waterfront building has already been cleared for you. This property comes with a current tidewater buffer setback variance (BOA Case #2109), allowing for the construction of a dwelling inside the typical 100-foot setback. Most importantly, this variance does not expire and transfers directly to the new owner, providing a unique "plug and play" opportunity that is nearly impossible to find. Call me today to learn more.

1609 Heliport Rd, Woolford

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400
$215,000
3 Beds ⋅ 1 Baths
Tucked away on a very private 2-acre wooded lot, this 3 bedroom, 1 bath rancher offers peaceful country living with room to spread out. Surrounded by mature trees, the property provides a serene setting with plenty of privacy. Includes a 24x24 detached garage with electric, spacious yard and convenient one-level living. The seller has significantly reduced the price to reflect repairs needed following a recent home inspection.

5260 Wilson Rd, Cambridge

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
$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
$475,000
3 Beds ⋅ 2 Baths
Updated 3-bedroom, 2-bath waterfront home on Hudson Creek offers breathtaking water views. Enjoy crabbing, fishing and boating from your very own Hudson Creek oasis. New 90 ft private pier with 10x20 sun deck and 2 boat slips. Enjoy the large yard, rear screened-in porch, waterside gazebo. Features include a 2-car garage, paved driveway, and ideal spaces for relaxation and entertaining. New well, septic, new kitchen and foyer luxury vinyl flooring. New kitchen countertop, new first floor full bathroom, new front door and fresh paint. Bring your boat and enjoy all pleasures this waterfront home has to offers.

5841 Hudson Wharf Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$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:

$99,900
3 Beds ⋅ 1 Baths
Affordable 3 Bedroom, 1 Bathroom home conveniently located in Toddville and includes the vacant land parcel across the street (Parcel 164). Previously rented as a hunting lodge, good for overnights, a casual retreat or full time living. Located across from Elijah’s General Store and near public boat ramps, Blackwater national wildlife refuge and marinas. Enjoy fishing, crabbing, hunting, biking, and boating.

2703 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$339,900
3 Beds ⋅ 2 Baths
*Sellers will need 30-90 days OR less to find their home of choice. Nestled on 1.89 acres of mostly cleared flat land, this move in ready 3 bed, 2 bath home offers a perfect blend of privacy, comfort and natural beauty. Surrounded by woods, the property provides a peaceful year around retreat but close enough to local restaurants, shops and activities. Spacious open concept living area with a cozy fireplace that flows into a large fully equipped kitchen. This home features 3 beds, 2 full baths and huge heated/air conditioned 12x36 sun room over looking the scenic back yard. A new roof, HVAC system, fresh new carpet and hardwood flooring makes this home a true gem. Outside you will find a 2 car carport along with a detached heated garage. Enjoy the outdoor life that Cambridge offers including fishing, boating, parks and playgrounds!

5622 Ross Neck Rd, Cambridge

Listing courtesy of Samson Properties. Contact: 4433437660
$134,900
Affordable 3-bedroom, 1-bath home situated on 13+ acres across four parcels in Sika deer country.. Property offers Sika deer hunting with some whitetail deer and pond offers possible waterfowl. Home has been rented as a hunting lodge, good for overnights, a casual retreat or full time living. Conveniently located across from Elijah's general store, near public boat ramps, Blackwater National Wildlife Refuge and marinas. Enjoy year-round hunting, crabbing, fishing, biking and boating. Property sold as is.

2707 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$134,900
3 Beds ⋅ 1 Baths
Affordable 3-bedroom, 1-bath home situated on 13+ acres across four parcels in prime Sika deer country. Property offers Sika deer hunting with some whitetail deer and pond offers possible waterfowl. Home has been used as a hunting lodge, good for overnights, a casual retreat or full time residence. Conveniently located across from Elijah's general store, near public boat ramps, Blackwater National Wildlife Refuge, marinas. Enjoy hunting, crabbing, fishing year round, biking & boating! Property sold as is.

2707 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$99,000
READY TO HUNT SIKA PROPERTY!!! This 25 acres of marsh with a few pines is ready to go with two handmade elevated box blinds with feeders on platforms. The box blinds have been custom crafted and are cemented into the ground for stability and security. This property is located off of Goose Creek Road, and runs out to Fishing Bay, where you will find it contains an offshore blind site for waterfowl hunting. Access to the property can be found off of Goose Creek Road, or by boat if you like. The entire property is marsh, but you'll find numerous trails and sign from sika deer use. Property is boardered by and across the street from other managed sika deer hunting farms. This is a great chance to get some acerage that won't break the bank. Schedule you private tour today!

Goose Creek Rd, Toddville

Listing courtesy of Charis Realty Group. Contact: 2409139339
$59,950
Price Improvement — Beautiful Homesite Near the Water in Ferry Farms Take advantage of a rare opportunity to own this 2.20± acre homesite in the sought-after Ferry Farms community. Located just a short walk from the water and the community pier, this property offers a peaceful, private setting bordered by wooded, community-owned open space. The natural surroundings create a tranquil retreat with a scenic, tree-lined backdrop perfect for relaxing and enjoying the outdoors. Whether you’re planning a full-time residence or a weekend escape, this property offers the ideal setting to build your custom home near the water while still enjoying privacy and the beauty of nature. Buyer Notice: Buyers are encouraged to contact the Maryland Department of the Environment (MDE) and Dorchester County Planning & Zoning to confirm all building requirements, including wetlands or Critical Area considerations, possible restrictions, and connection requirements for the community B.I.P. system. Plat, covenants, and restrictions are available in the document section.

814 Cody Dr Unit #LOT 17, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$125,000
Large lot in northern Dorchester County, well located with easy access to Cambridge and Easton for work and play. Delaware not far for tax free purchases. Wooded with mature pine and hardwood in a rural area of open farmland offering privacy. Lot size is 6.51 acres, of which 4.48 is in a forest conservation area, leaving more than ample room of 2.03 acres for your new home and other improvements. (see plat in Documents). Home site is partially cleared. There are deed restrictions for value protection which are not too burdensome. This is a finished lot ready for home construction, Contact Dorchester County Dept of Planning and zoning for permitting

Gravel Branch Rd, Hurlock

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