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$135,000
3 Beds 1 Baths
Step back in time while enjoying the comforts of home at 26399 Old State Road in Crisfield, Maryland! Built in 1875, this charming 3-bedroom home offers approximately 1,300 square feet of living space and is situated on a .32-acre lot. From the classic exterior to the unique details throughout, this home is filled with character you simply don’t find in newer construction. Inside, the spacious kitchen offers abundant cabinetry and counter space along with room for dining and gathering. The home’s farmhouse-inspired touches add warmth and personality while leaving plenty of opportunity for the next owner to make it their own. Outside, mature trees and established landscaping create a welcoming setting. The spacious backyard offers plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Multiple outdoor seating areas provide great spots for summer cookouts and relaxing in the shade, while the storage sheds offer additional space for tools, lawn equipment, and hobbies. With 3 bedrooms, approximately 1,300 sq. ft., a .32-acre lot, and more than 150 years of history, this Crisfield home offers an opportunity to own a property with true Eastern Shore character. If you're looking for a home that isn't cookie-cutter, this one deserves a look. Schedule your showing and see the possibilities for yourself! Sold as-is.

26399 Old State Rd, Crisfield

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200

$229,990
Investor Alert - 1/2-occupied duplex, a couple blocks from Historic Downtown Princess Anne, and less than a mile to University of Maryland Eastern Shore campus. Unit 1 is a 3BR/1BA unit with a welcoming front porch, nice-sized living room with a wide opening into the eat-in kitchen w/built-in microwave, stove, fridge. 3 bedrooms, full bath with stacked washer/dryer included. Unit 2 is a 2BR/1BA unit - cute living room, eat-in kitchen w/ stove, built-in microwave, fridge, and stacked washer/dryer included. 30704 Hampden was rented for $1,395/month - vacant as of 08/08/2026; 30706 Hampden rents for $800/mo, currently occupied. Water readers on lines separate each unit. Sizes, taxes approximate

30704 Hampden Ave, Princess Anne

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$450,000
3 Beds 3 Baths
Privacy abounds on this exceptional 8.7-acre property offering the perfect blend of peaceful country living and modern convenience. This well-maintained 2,125-square-foot home features 3 bedrooms, 2.5 baths, and an inviting open floor plan designed for comfortable everyday living and entertaining. Luxury vinyl plank flooring runs throughout the home, while the spacious kitchen is equipped with a large center island, walk-in pantry, and stainless steel appliances. Step outside to the deck and enjoy the serene surroundings and abundant outdoor space. Car enthusiasts, hobbyists, and those needing extra storage will appreciate the oversized 2,084-square-foot attached garage with additional storage space, along with ample parking for guests, recreational vehicles, or equipment. Conveniently located just around the corner from the charming Whitehaven Ferry, you’ll enjoy quick access across the Nanticoke River to Wicomico County while still savoring the privacy and tranquility this remarkable property provides.

13925 5 Farms Dr, Princess Anne

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$399,999
5 Beds 3 Baths
Tucked away on **5 private acres**, this spacious **5-bedroom, 3-bath** home offers the flexibility and space that's hard to find. With an existing layout that could easily accommodate a **6th bedroom**, the lower level features its own living area and kitchen, making it an excellent setup for multigenerational living, rental income, or a private guest suite. Enjoy the outdoors from the **large rear deck**, complete with a **wheelchair ramp** and **chair lift** providing easy access to the main level. Outside, you'll find a **large two-bay outbuilding**, perfect for running a business, storing equipment, or tackling your favorite hobbies. A **circular driveway** provides plenty of parking and makes getting in and out a breeze. Whether you're looking for room to grow, a property with income potential, or the privacy of country living with versatile space, this home checks all the boxes.

29523 Polks Rd, Princess Anne

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$439,500
4 Beds 3 Baths
Stunning Country Rancher with Endless Potential on Over 2 Acres! Welcome to 4565 Jacksonville Rd, a spacious and impeccably maintained 3,100+ sq. ft. rancher situated on a private 2.23-acre lot less than a mile from the scenic Janes Island State Park. Designed for comfort and effortless everyday living, this home features 4 generous bedrooms and 2 full and 1 half bathrooms. The expansive master suite serves as a true private retreat, accompanied by three additional oversized bedrooms boasting exceptional closet space. At the heart of the home, the inviting family room showcases a gorgeous brick fireplace framed by custom built-ins. An open-concept flow connects the family room to a formal dining room and a sprawling living room, making it ideal for hosting gatherings of any size. The well-appointed country kitchen offers abundant cabinet and counter space and seamlessly opens to a bright breakfast area. Additional highlights include a convenient home office tucked just off the oversized attached 2-car garage, central vacuum system, and classic touches throughout. Step outside to discover a private lot accented by beautiful mature trees, offering plenty of space to relax, play, or entertain. For hobbyists, entrepreneurs, or car enthusiasts, the property features a standout detached oversized 2-car garage, 2,400+ sq. ft. between the 2 levels, with a finished second level complete with drywall, electric, heat, a window-unit air conditioner, and its own convenient half bathroom. This bonus space is ready to serve as an incredible game room, or a home-based business setup (as it is currently used). Combining a peaceful, nature-rich setting—located just 3.0 miles from the Crisfield City Dock—with boundless versatility, this exceptional property is a must-see!

4565 Jacksonville Rd, Crisfield

Listing courtesy of RE/MAX Plus. Contact: 3018827567

$145,000
3 Beds 1 Baths
Welcome to this lovely island waterfront home cherished by the same family since 1940 and originally built by the owner's father. This unique home is full of character and carefully cared for throughout the decades. A welcoming front porch sets the tone perfect for relaxing before stepping inside to the inviting family room. The living area is complete with original moldings and a pair of lovely wall sconces that provide a warm tone in the space. The efficient eat - in kitchen features custom-made cabinetry, including original tall base cabinets designed for added comfort while cooking. A vintage gas stove remains in working condition, and you'll find plenty of cabinet space with clever storage areas and a convenient pantry. The main level includes two comfortable bedrooms, one with water views, and the second features a custom built-in wall cabinet. The full bath showcases beautifully preserved original tile and a tub set in an elegant alcove with a window perfectly placed to capture serene water views. The spacious laundry room has a utility closet, a washer and dryer and a separate walk in shower stall. There's also plenty of room for an additional refrigerator or freezer. Upstairs, a bonus room with extra storage tucked under the eaves plus a separate room for another bedroom or flex space. Dormer windows bring in natural light and frame picturesqe water views of the Chesapeake Bay and surrounding marshes. Outside the beautifully maintained yard with sidewalks and chain-link fencing also includes an 8' x 12' storage shed with electricity. A move-in ready home offering timeless charm and beautiful water views. Whether you're looking for a peaceful year-round residence or a relaxing waterfront retreat, this special property offers a rare chance to own at home where history and scenic beauty come together.

3287 Marsh Road, Ewell

Listing courtesy of Wilson Realty. Contact: (410) 968-1882

$94,250
8.7± acres in the heart of Maryland’s beautiful Eastern Shore, offering a peaceful, wooded setting with convenient access to local marinas, fishing, crabbing, boating, and the abundant wildlife that makes Somerset County so special. Currently used for hunting, this property offers exceptional recreational opportunities today while also presenting potential for future possibilities. Based on conversations with Somerset County and the Maryland Department of the Environment (MDE), the property contains non-tidal wetlands; however, that does not preclude development. MDE advised that limited impacts may qualify for a streamlined authorization process, while larger impacts would require additional review and permitting. As with any rural property, buyers are encouraged to consult with their engineer, surveyor, and the appropriate regulatory agencies to determine the best location and design for any future improvements. The property may be reached via a strip of land from Deal Island Road or by way of a semi-private drive from Pine Pole Road. For showing instructions, additional property information, and the contact information for the Somerset County officials and Maryland Department of the Environment representatives familiar with this property, please contact the listing agent directly.

0 Deal Island Rd, Princess Anne

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919

$210,000
1 Beds 1 Baths
Priced to sell!! This charming and tastefully updated 1-bedroom, 1-bath home situated on an impressive 14.15± total acres spanning two separate parcels. This unique offering provides an exceptional opportunity for those seeking space, flexibility, and the tranquility of country living. The existing home (priced accordingly and as-is) is nestled on the smaller parcel, which is improved with its own septic system, while the larger parcel also has an existing septic system, creating exciting potential for future use, expansion, or additional improvements (subject to applicable approvals). Inside, the home offers a cozy and functional layout filled with natural light. Step outside and enjoy the beauty of the surrounding acreage, where you'll find abundant room to garden, explore, hunt, enjoy wildlife, establish trails, or create the self-sufficient homestead you've always envisioned. Whether you're looking for a private retreat, recreational getaway, family homestead, or an investment with future possibilities, this property delivers tremendous versatility. Opportunities to own 14.15± acres across two parcels with existing improvements are increasingly rare. Don't miss your chance to own this peaceful slice of the countryside and make it your own. Buyer and Buyer's Agent are responsible for performing their own due diligence and independently verifying all information contained herein, including but not limited to acreage, parcel information, septic systems, zoning, permitted uses, and any future development potential.

6028 Cornstack Rd, Marion Station

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$100,000
OPPORTUNITY ZONE - 3.43 Acres Industrial lot for sale in the Princess Anne Industrial Park. Fully equipped with water, sewer, utilities and access roads. Fiber optic lines at the entrance to the park. The site is level, cleared and ready for immediate construction (subject to permits). The Industrial Park is accommodating to a wide range of light manufacturing, warehouse, service and office users. The Town of Princess Anne is committed to maintaining an attractive industrial park for all present and future businesses, and customers. All construction plans and timetables are subject to approval by the Princess Anne Town Commissioners. Located in the Princess Anne Industrial Park with Industrial Park Zoning. Located in a State of Maryland Enterprise Zone for new construction tax abatements and a HUB Zone which promotes job growth, capital investment and economic development to historically underutilized business zones. Princess Anne, Somerset County, is accessible to the east cost markets with north/south and east/west access by major US highways.

30380 Park Dr, Princess Anne

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440

$1,099,900
5 Beds 2 Baths
A truly one-of-a-kind waterfront estate offering 82+ acres across three parcels in historic Crisfield, Maryland. Known as the legendary "Home of the Terrapin King," this extraordinary property seamlessly blends Chesapeake Bay history with breathtaking waterfront living. Learn more about the property's fascinating story at www.TerrapinKing.org. Built in 1925, this beautifully updated residence offers approximately 2,921 square feet of living space with 5 bedrooms and 2 full bathrooms. Surrounded by water on three sides, nearly every room showcases spectacular panoramic views of the Chesapeake Bay, tidal marshes, and unforgettable sunsets. Extensive recent improvements make this historic home move-in ready while preserving its timeless coastal character. Updates include new luxury vinyl plank flooring throughout, updated lighting, new plumbing, a new water treatment system, new sump pumps and drainage systems with backflow valve preventers, and most mini-split HVAC units replaced within the past few months. The home is being offered fully furnished, making it ideal as a primary residence, vacation home, or turnkey investment property. The spacious primary suite features a pellet stove, double closets, and sweeping waterfront views. One of the home's most iconic spaces, the Captain's Room, features expansive bay windows that create the feeling of standing at the helm of a ship overlooking the Chesapeake. Two screened porches and a second-story balcony provide multiple spaces to relax and enjoy the peaceful waterfront setting. The estate encompasses over 82 acres, including approximately 20 acres of upland, with the balance consisting of pristine waterfront, marshlands, and natural habitat. Private trails offer opportunities for hiking, wildlife observation, hunting, and exploring, while the property's private beach and dock provide direct access to boating, fishing, kayaking, and all that the Chesapeake Bay has to offer. Additional exterior improvements include the removal of all former beach pilings, installation of additional riprap for shoreline stabilization, and backfilling of the yard, further enhancing the property's usability and protecting the shoreline. Beyond its exceptional waterfront lifestyle, this property presents exciting future possibilities. Any future development remains subject to all required governmental approvals, permitting, environmental review, and applicable regulations. One of the property's most valuable features is its existing connection to city sewer, an uncommon and highly desirable amenity for a waterfront estate of this size that can significantly reduce future infrastructure costs. Steeped in history as the former headquarters of Albert Tallmadge LaVallette Jr.'s renowned terrapin enterprise, this remarkable estate has become one of Maryland's most recognizable waterfront landmarks. The property currently operates as a successful short-term rental, and the seller reports annual gross short-term rental income approaching $100,000, offering exceptional income potential while serving as a truly unforgettable waterfront retreat. Whether you're searching for a private estate, an income-producing investment, a family compound, or a once-in-a-lifetime Chesapeake Bay property, 1 Lavallette Road delivers unmatched history, privacy, recreation, development potential, and panoramic waterfront beauty. Fireplaces convey As-Is. Total acreage is approximately 82+ acres, including approximately 20 acres of upland. Furnishings included with acceptable terms.

1 Lavallette, Crisfield

Listing courtesy of Worthington Realty Group, LLC. Contact: 8558494663

$120,000
3 Beds 2 Baths
Step back in time at 3188 Boone Rd, a charming two-story Craftsman home built in 1900 that showcases timeless character with spacious rooms, original moldings, and a beautiful original staircase. Blending historic appeal with thoughtful updates, the home features energy-efficient mini-split heating and air conditioning, double-pane windows, and a cozy gas fireplace for those cool evenings. The main level offers a spacious eat-in kitchen, a large living room, a comfortable den, and a full bathroom. Upstairs, you'll find three generously sized bedrooms along with a convenient half bath. Whether you're drawn to the craftsmanship of a bygone era or looking for a home you can make your own, this property offers endless potential. Enjoy peaceful country living with a large yard and a storage shed that's perfect for woodworking, gardening, or additional storage. Come add your personal touch and make this classic home your own.

3188 Boone Rd, Crisfield

Listing courtesy of Keller Williams Realty. Contact: 3028467839

$1,099,900
5 Beds 2 Baths
A truly one-of-a-kind waterfront estate offering 82+ acres across three parcels in historic Crisfield, Maryland. Known as the legendary "Home of the Terrapin King," this extraordinary property seamlessly blends Chesapeake Bay history with breathtaking waterfront living. Learn more about the property's fascinating story at www.TerrapinKing.org. Built in 1925, this beautifully updated residence offers approximately 2,921 square feet of living space with 5 bedrooms and 2 full bathrooms. Surrounded by water on three sides, nearly every room showcases spectacular panoramic views of the Chesapeake Bay, tidal marshes, and unforgettable sunsets. Extensive recent improvements make this historic home move-in ready while preserving its timeless coastal character. Updates include new luxury vinyl plank flooring throughout, updated lighting, new plumbing, a new water treatment system, new sump pumps and drainage systems with backflow valve preventers, and most mini-split HVAC units replaced within the past few months. The home is being offered fully furnished, making it ideal as a primary residence, vacation home, or turnkey investment property. The spacious primary suite features a pellet stove, double closets, and sweeping waterfront views. One of the home's most iconic spaces, the Captain's Room, features expansive bay windows that create the feeling of standing at the helm of a ship overlooking the Chesapeake. Two screened porches and a second-story balcony provide multiple spaces to relax and enjoy the peaceful waterfront setting. The estate encompasses over 82 acres, including approximately 20 acres of upland, with the balance consisting of pristine waterfront, marshlands, and natural habitat. Private trails offer opportunities for hiking, wildlife observation, hunting, and exploring, while the property's private beach and dock provide direct access to boating, fishing, kayaking, and all that the Chesapeake Bay has to offer. Additional exterior improvements include the removal of all former beach pilings, installation of additional riprap for shoreline stabilization, and backfilling of the yard, further enhancing the property's usability and protecting the shoreline. Beyond its exceptional waterfront lifestyle, this property presents exciting future possibilities.Any future development remains subject to all required governmental approvals, permitting, environmental review, and applicable regulations. One of the property's most valuable features is its existing connection to city sewer, an uncommon and highly desirable amenity for a waterfront estate of this size that can significantly reduce future infrastructure costs. Steeped in history as the former headquarters of Albert Tallmadge LaVallette Jr.'s renowned terrapin enterprise, this remarkable estate has become one of Maryland's most recognizable waterfront landmarks. The property currently operates as a successful short-term rental, and the seller reports annual gross short-term rental income approaching $100,000, offering exceptional income potential while serving as a truly unforgettable waterfront retreat. Whether you're searching for a private estate, an income-producing investment, a family compound, or a once-in-a-lifetime Chesapeake Bay property, 1 Lavallette Road delivers unmatched history, privacy, recreation, development potential, and panoramic waterfront beauty. Fireplaces convey As-Is. Total acreage is approximately 82+ acres, including approximately 20 acres of upland. Furnishings included with acceptable terms.

1 Lavallette, Crisfield

Listing courtesy of Worthington Realty Group, LLC. Contact: 8558494663

$367,999
3 Beds 2 Baths
Waterfront living at its finest! This 3-bedroom 2-bath A-frame home is perfectly situated on St. Peters Creek with direct access to the Manokin River, Tangier Sound and the Chesapeake Bay. Whether you enjoy boating, fishing, crabbing, or hunting, this property offers the ideal Eastern Shore lifestyle with a private dock and boat lift just steps from your door. Very close by, is The Deal Island Wildlife Management Area (13,000 plus public acres) that offers Whitetail deer, Sitka deer, turkey, duck and goose hunting. The interior features are highlighted by the floor-to-ceiling stone fireplace and expansive water views. The main level offers two bedrooms and a full bath, while the private upper-level primary suite includes a full bath and overlooks the spacious family room below. Relax on the deck while watching the water, spend the day exploring the Bay, or catch fresh fish and crabs for dinner right off your own dock. Whether you're looking for a full-time residence, a weekend getaway, or an investment opportunity, this waterfront retreat offers the perfect blend of comfort, charm, and coastal living.

27093 Point Rd, Princess Anne

Listing courtesy of Iron Valley Real Estate of Central MD. Contact: (410) 989-9896

$185,000
3 Beds 2 Baths
Start your next chapter at 11950 Drexwood Dr! This recently updated 3-bedroom, 2-bath ranch home has been freshly painted throughout with brand-new carpet in all three bedrooms, features a spacious living room, a functional kitchen and dining area with plenty of storage, and a private primary suite with its own bathroom! The sunroom/den provides the perfect spot to enjoy your morning coffee, unwind after work, or gather with family and friends. All appliances convey, including the washer, dryer, refrigerator, and stove, making your move even easier. Conveniently located near downtown Princess Anne, shopping, restaurants, and everyday amenities, this home offers the opportunity to put down roots and enjoy a place to truly call your own.

11950 Drexwood Dr, Princess Anne

Listing courtesy of Keller Williams Realty Central-Delaware. Contact: 3026770020

$318,900
3 Beds 2 Baths
Closing help with full price offer! Eastern Shore waterfront living awaits you at Harbour Light, offering stunning views of the Tangier Sound for a fraction of the cost of most waterfront locations. This beautifully maintained home features 3 spacious bedrooms, 2 full baths, beautiful wood floors, third‑floor water views, and a 40' private deeded boat slip (D‑1)—all available immediately so you can start enjoying those unforgettable sunsets right away. Step inside to a home that feels completely renovated, clean, and move‑in ready. The centrally located kitchen offers abundant cabinet space, pantry, pull‑out base trays—now enhanced with a new refrigerator, new stove, new sink, new dishwasher, and new backsplash. Additional upgrades include fresh paint, a renovated bathroom, new sliding glass doors, new ceiling fans, new washer and dryer, a new programmable thermostat, and remote‑controlled blinds for effortless comfort. Enjoy beautiful water views from the living room, kitchen, primary bedroom, balcony, and screened porch. A separate laundry/utility room provides extra storage for pool gear or fishing supplies, while the exterior storage closet is perfect for tools, toys, and tackle. Elevator access, a heated community pool, and a pool house with men’s and women’s changing areas and a full bath house add exceptional convenience and comfort. The location is exceptional—close to medical offices, with a new medical annex opening soon, plus nearby shopping and walkable restaurants and cafés that make everyday living easy and enjoyable. Outdoor lovers will appreciate being just minutes from Janes Island State Park, Somers Cove Marina, Wellington Beach, and easy access to boating, biking, crabbing, and seasonal duck hunting. Crisfield offers year‑round charm with beloved local events including the Soft‑Shell Festival, Freedom Fest, Tangier Sound Music Festival, and the Crab & Clam Bake. Whether you're seeking a full‑time residence, a weekend escape, or an investment opportunity—this is coastal Eastern Shore living at its finest. internet/cable, water, security and a Deeded dock all included.

101 Williams St Unit #303, Crisfield

Listing courtesy of RE/MAX Real Estate Connections. Contact: 7037544341

$379,900
3 Beds 2 Baths
Looking for a minimal maintenance home with all the bells and whistles? Brick rancher on 2.93 acres has been updated in all the best ways, completely remodeled kitchen, family room, dining room, primary bath and utility area. Encapsulated crawl space eliminates moisture related problems, limits allergens, and helps with heating and cooling bills. Roof, gutters and fascia were replaced in 2018 and 2017. Gorgeous kitchen with granite counters, wine bar, LVP flooring, stainless appliances. Primary bedroom has two walk in closets and another closet, double doors open to ensuite bathroom with deep soaking tub, walk in shower, quartz countertops. Large formal living room with fireplace for entertaining, family room also has wood burning fireplace, both have been cleaned, and are ready for a cozy fire! Single car garage has work bench and freezer. Landscaped and manicured lawn with patio overlooking back yard. Separate lot included in 2.93 acreage could be a building site. Don't forget the three season porch at the rear for your morning coffee! Air conditioning unit is just two months old!

26443 Asbury Ave, Crisfield

Listing courtesy of Wilson Realty. Contact: (410) 968-1882