Refine Search
Sort by
1 Dock St Unit 402, Crisfield
$499,000
3 Beds ⋅ 3 Baths
Rare waterfront penthouse living at Captains Quarters in Crisfield, Maryland. This 4th-floor, 3-bedroom, 3-bath condominium offers approximately 1,753 square feet of one-level living, elevator access, and a premier marina-front setting. The larger floor plan and three full baths provide comfort and flexibility for full-time living, a second home, or hosting family and guests, creating value rarely found in smaller waterfront condos. Expansive outdoor living areas include multiple balconies, wraparound deck space, and a rooftop patio with panoramic views of Tangier Sound, Somers Cove Marina, Daugherty Creek, the harbor, and the surrounding waterfront. From sunrise over Somers Cove to sunset over Tangier Sound, this property delivers more than a view — it offers a daily waterfront experience. Inside, the open living and dining area features cathedral ceilings, Brazilian cherry hardwood flooring, crown molding, a gas fireplace, and direct balcony access. The distinctive two-story turret adds architectural character and natural light, making the dining area a true focal point. The kitchen includes granite countertops, breakfast bar seating, recessed lighting, double sink, wall oven, convection oven, oversized refrigerator, dishwasher, disposal, microwave, stove, and trash compactor. The primary suite offers balcony access, water views, cathedral ceiling, hardwood flooring, attached bath, and large dual closets. Additional bedrooms are generously sized, with one offering attached bath access and balcony access, giving guests privacy and comfort. Interior features also include a slate foyer, built-ins, upgraded countertops, ceiling fans, recessed lighting, window treatments, sound system, and in-unit washer and dryer. Community amenities include common grounds, elevator, extra storage, pier/dock access, reserved parking, and assigned parking. The condo fee includes common area maintenance, exterior building maintenance, insurance, lawn maintenance, sewer, trash, and water. A new roof was installed in October 2025, and condo assessment fees have been paid. Located near Somers Cove Marina, public boat launch access, fishing, kayaking, local dining, ferry activity, Janes Island State Park, the Tawes Museum, and Crisfield’s waterfront district, Unit 402 offers space, views, lifestyle, and long-term coastal appeal. This is not simply another condo — it is a rare marina-front penthouse opportunity on Maryland’s Lower Eastern Shore. Schedule your private tour and experience the view for yourself.

1 Dock St Unit 402, Crisfield

Listing courtesy of ERA Martin Associates. Contact:

26813 Johnson Creek Rd, Crisfield
$69,000
3 Beds ⋅ 2 Baths
3 Bedroom 1.5 Bath farmhouse nestled amongst the Eastern Shore’s charm. Home is close to the Chesapeake Bay and its fishing, crabbing, and boating. Several renovations have been made including the exterior siding, roof, and windows. Inside porcelain floor in the downstairs master suite, laminate floors in the upstairs bedrooms, bathrooms have been replaced. Plumbing is working in both bathrooms and kitchen. There is no electric wiring done in the home. This property needs someone to put the finishing touches on it. This home has plenty of potential with its vaulted living room ceiling, large walk up attic, shed with lean-to, and spacious yard. Property has public water and sewer, but no city taxes. Cash or conventional financing ONLY. Sold AS-IS.

26813 Johnson Creek Rd, Crisfield

Listing courtesy of The Land Group. Contact:

2899 Byrdtown Rd, Crisfield
$164,900
FANTASTIC Investment Opportunity in Crisfield, MD! Don’t miss this income-producing duplex located at 2899 Byrdtown Rd in scenic Crisfield, Maryland — the “Crab Capital of the World” known for its waterfront charm, boating, fishing, and relaxed Eastern Shore lifestyle. This property features TWO spacious 3-bedroom, 1-bath units that have been recently freshened up and are ready for new tenants. Anticipated rental income is approximately $1,200/month per unit, making this an excellent addition to your investment portfolio or a great owner-occupant opportunity. Recent improvements include a metal roof installed in 2018, updates to the second-floor kitchen, some new flooring, and new heaters being installed in the downstairs unit, plus additional updates throughout. There are even washer/dryer hookups for added tenant convenience. Situated outside city limits, you’ll enjoy the benefit of county taxes only — no city taxes. The property has also been inspected and certified lead-free for peace of mind. Set on a spacious lot surrounded by natural beauty, this duplex offers strong rental potential in a peaceful setting just minutes from Crisfield’s marinas, waterfront dining, and ferry access to Smith Island. Great opportunity to secure an income-generating property or buy it and live in one unit while you rent the other out!! Schedule your appointment today!

2899 Byrdtown Rd, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact:

26835 & 26841 Roland Tyler Rd, Crisfield
$895,000
4 Beds ⋅ 2 Baths
Presenting 26835 Roland Tyler Road, a distinguished, gated estate encompassing approximately twenty acres with direct waterfront access to Johnson’s Creek, which opens to ape Hole and then Big water of the Sounds. A private asphalt drive, flanked by mature crape myrtles, four brick lighted pillars, and a professionally riprapped drainage swale, establishes a refined approach. The circular drive and dedicated hardscaped parking pad provide ample guest parking. The grounds comprise roughly twelve acres of mature timber with income potential and eight acres of marshland, creating a serene natural sanctuary with direct water access. This property supports a wide range of outdoor pursuits. Sportsmen will appreciate opportunities for deer, turkey, and waterfowl hunting, as well as crabbing, fishing, and boating from the creek. The tranquil setting is equally suited to nature observation, birdwatching, and peaceful walks with sweeping marsh views. Homestead amenities include a chicken coop, raised garden beds, a greenhouse, and extensive landscaping. A private road extends to the water for convenient shoreline access and small-craft launch, and a substantial outbuilding accommodates storage and large-scale outdoor entertaining, including traditional crab feasts. For equestrian interests, there is ample acreage for future pasture, and select existing structures are adaptable for stalls or weather shelter. Approached via a hardscaped walk, the brick-front country porch opens to interiors distinguished by quality construction, custom millwork, and handsome hardwoods. The formal dining room features picture-frame wall detailing, dental crown molding, extensive chair rail, and hardwood flooring. The family room offers a brick fireplace with a gas insert and a wood-beamed ceiling for inviting, four-season comfort. The chef’s kitchen is appointed with brick flooring, a generous seating island, granite countertops, a tiled backsplash, a farmhouse sink, stainless steel appliances including double ovens and a cooktop, a premium refrigerator, dual pantries, and a wood-beamed ceiling. Adjacent to the kitchen, a private four-season laundry suite presents a cathedral wood ceiling, bay and transom windows, LVP flooring, a sliding barn door, custom doors and shutters, abundant cabinetry, and an additional exterior entry, and it is equipped with a front-loading washer and dryer (gas). The primary suite is a restful retreat with hardwood floors, a cathedral wood-beam ceiling, wainscoting below the chair rail, a sliding door to a private deck, pocket and custom barn doors, a large walk-in closet, and an adjoining reading or study room, with the safe conveying. The en suite bath includes a tiled walk-in glass shower, tiled flooring, dual granite vanities, and a soaking tub. On the main level, an additional bedroom currently utilized as an office offers a walk-in closet, a bay window, LVP flooring, and access to a nearby full bath. The upper level provides two additional bedrooms—one with a walk-in closet—highlighted by knotty pine ceilings and floors and knee-wall storage, reached via a custom wood staircase with picture-framed wall detailing. Systems and enhancements include a private generator, an encapsulated crawl space with dehumidifier, recessed lighting throughout, public water service with reverse osmosis filtration, a Rinnai gas tankless water heater for on-demand hot water, an ADT security system, and Andersen and Pella windows. In summary, 26835 Roland Tyler Road offers a rare combination of privacy, recreational opportunity, and craftsmanship in a classic Eastern Shore setting. Private showings are available by appointment.

26835 & 26841 Roland Tyler Rd, Crisfield

Listing courtesy of ERA Martin Associates. Contact:

103 Williams St Unit 416, Crisfield
$299,999
3 Beds ⋅ 2 Baths
Waterfront Living on the Chesapeake Bay! Now offered at $299,999, this beautiful waterfront condo in Harbour Lights offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle you've been dreaming of. This well-maintained, one-owner condo features 3 bedrooms, 2 full baths, and has never been used as a rental. Wake up to breathtaking bay views from the large windows and enjoy spectacular sunrises and sunsets from your private balcony. Whether you're sipping your morning coffee or unwinding after a day on the water, the views are simply unforgettable. Included with the property is your own deeded boat slip in the private marina, making this a perfect home for boating enthusiasts and waterfront lovers alike. Residents enjoy: Waterfront pool Secure building access Elevator service Private marina Low-maintenance waterfront living Located in Crisfield, Maryland, the Seafood Capital of the World, you'll be just minutes from Jane's Island State Park and a short boat ride from Smith Island and Tangier Island. Whether you're looking for a year-round residence, a weekend getaway, or a summer retreat, this is your chance to own a piece of paradise on the Chesapeake Bay. Contact me today for your private showing before this waterfront gem is gone!

103 Williams St Unit 416, Crisfield

Listing courtesy of ERA Martin Associates. Contact:

20805 Severn Rd, Ewell
$129,000
2 Beds ⋅ 1 Baths
Welcome to your cozy little island cottage! This two bedroom, one bath, fully renovated bungalow is move-in ready and easily accessible. Tucked away at the end of the street on a quiet corner lot, the property is surrounded by beautiful shrubbery and shady trees. Featuring an open concept design and wood flooring throughout, this gem of a home is tastefully decorated with many desirable features. Each room has pocket doors and there’s an inviting feel to the space. All appliances and most furnishings are included in the sale. This property currently operates as a vacation rental and has some bookings already secured. Comfy, cozy, clean, neat and tidy best describe it. Come check out this storybook listing on Smith Island, Maryland.

20805 Severn Rd, Ewell

Listing courtesy of Wilson Realty. Contact:

4395 Crisfield Hwy, Crisfield
$900,000
Marshall’s Marine, LLC, a premier full-service marine facility, is now available in Crisfield, Maryland. Located on Crisfield Highway, Route 413, this expansive property spans three acres and features six meticulously designed buildings. Building #1 has a storefront, retail space, and a separate office. Building #2 is currently an occupied rental space, featuring a spacious layout with ample workspace and plenty of shelving. Building #3 offers a massive open air, general-purpose space, with 13 foot ceilings, and a separate 12x12 insulated garage door for forklift access to the loft/storage area above. Two workshops, side-by-side connect the general workspace to the two newly constructed bay areas. These large bay areas - buildings, #4 and #5 both have 16-foot ceilings, 14x14 insulated garage doors, insulation, LED lighting, and fans. Bay #4 features wooden wainscoting, heating and air conditioning. Bay #5 has metal walls, ventilation, and a plenty of workspace. Building #6 with 11 foot ceilings is another open-air general-purpose space equipped with ventilation and lighting, as well as a separate large office space. Outside the property, the parking lot features more than 100 parking and storage areas and a large open-ended metal storage which houses machinery used throughout the property. Other amenities include public water and sewer services and modern electric upgrades-200 amp service. This boat storage, expert business, with repair and maintenance, and retail storefront, all provide a comprehensive marine hub. With its strategic location and versatile design, this property is poised with limitless possibilities for the right entrepreneur.

4395 Crisfield Hwy, Crisfield

Listing courtesy of Wilson Realty. Contact:

40 W Chesapeake Ave, Crisfield
$55,000
2 Beds ⋅ 1 Baths
Classic 2-bedroom home with oversized yard space, solid bones, and room to make it your own near downtown Crisfield. Set on a generous lot with a wide front lawn and expansive backyard, this 2-bedroom, 1-bath home gives you the chance to create value while enjoying the character of a traditional Eastern Shore property. Inside, the living room and bedrooms are well-sized to provide flexibility for guests, hobbies, or work-from-home space. The kitchen and bathroom are functional and ready for everyday use, with plenty of opportunity for cosmetic updates and customization over time. Throughout the home, you’ll find a layout that offers a strong starting point for renovations without losing the original charm and structure that make older homes appealing. The seller has invested over $100K in renovations since purchasing the property, which is now being sold as-is. The hot water tank is approximately one year old, and the home is connected to city sewer. Currently, there is a tenant paying monthly rent. Outside, the large detached shed could be restored into a workshop, storage area, hobby space, or additional utility building. The backyard gives you plenty of open space for gardening, entertaining, pets, or future outdoor projects. You’ll be close to downtown Crisfield, Crisfield City Dock, Somers Cove Marina, Crisfield Municipal Park, local seafood restaurants, and waterfront attractions that make this Chesapeake Bay community so unique. If you’re searching for an investment opportunity, rental property, weekend getaway, or a home you can improve over time, this property offers plenty of upside in a quiet small-town setting. Contact us today!

40 W Chesapeake Ave, Crisfield

Listing courtesy of EXP Realty, LLC. Contact:

30555 Skipjack Cir Unit 83, Princess Anne
$297,500
3 Beds ⋅ 2 Baths
Be the first to own this brand-new 3-bedroom, 2-bath rancher, currently under construction in an up-and-coming community that continues to gain attention for its growth and convenience. Offering 1,351 square feet of thoughtfully designed living space, this home features an open layout that’s ideal for both everyday living and entertaining. Inside, you’ll find a spacious primary suite complete with a private en suite bath and walk-in closet. The home is finished with luxury plank flooring throughout the main living areas, cozy carpet in the bedrooms, and a modern kitchen featuring granite countertops and stainless steel appliances. A dedicated laundry room adds everyday convenience. Looking to expand your living space? An optional four-season room can be added—perfect for enjoying the home year-round. Connected to public water and sewer, this property offers the ease of modern utilities without the burden of city taxes. Enjoy all the perks of brand-new construction—modern layouts, updated finishes, energy efficiency, and minimal maintenance for years to come. As an added bonus, if you get in early enough, you can pick your own colors and finishes!

30555 Skipjack Cir Unit 83, Princess Anne

Listing courtesy of Keller Williams Realty Delmarva. Contact:

10821 Toddville Rd, Deal Island
$40,000
Come check out this half acre property near the water! There is an existing 3-bedroom, 1.5-bath home, with electric, septic & a well in the heart of Deal Island offering the opportunity to make the best of coastal country living! Tucked on a quiet street and not in a flood zone, this property is ideally located near Deal Island Beach, multiple marinas, public boat ramps, and abundant hunting grounds and wildlife management areas—perfect for outdoor enthusiasts. It includes several sheds for added storage. Whether you're looking for a weekend getaway or a year-round retreat, this home offers incredible potential at a price point that leaves room to customize and create your ideal coastal escape. No HOA. No Ground Rent.

10821 Toddville Rd, Deal Island

Listing courtesy of Northrop Realty. Contact:

2735 Lloyd Webb Rd, Crisfield
$1,499,000
3 Beds ⋅ 1 Baths
Presenting, Lawson Marsh, Crisfield, Maryland – 1119.42+- acres. The habitat value of Lawson Marsh is significant both today as it was in the mid-1900s when the Ward Brothers were perfecting their decoy carving craft along Jenkins Creek and Lawson Marsh. This property includes a 7.43+- acre parcel on Lloyd Webb Rd featuring a 1,250 sq ft lodge. On the opposite side of the property along the shoreline, the various recreational activities are enhanced through the use of the cabin with pier to access the vast amount of acreage and to extend your stay on the marsh and water, as well as the offshore blind. The salt marsh has miles of shoreline on Broad Creek, the Little Annemessex River, and through many guts including Landing Gut, Straight Gut, and Massey Creek providing numerous waterways to the interior. The estuarine marsh is characterized by the typical flora that being salt hay (Spartina patens) on the high marsh and cord grass (Spartina alterniflora) on the lower parts of the marsh. A complex of salt marsh ponds dominates the landscape of Lawson Marsh. The salt marsh ponds, together with the complex of creeks and high marsh habitats provide critical wintering habitat to wintering waterfowl throughout the migratory season. The entire shoreline is licensed with DNR for waterfowl hunting. the lodge, built in 2020, offers the opportunity for long stays on the property. There is a large, paved parking area to keep your vehicles, including trailers. The three-bedroom lodge provides plenty of sleeping quarters with the existing double beds and bunk beds. The lodge has a screened-in porch, heating and air conditioning, a water treatment system, and washer and drying for all-season use. The lodge is elevated with the garage at ground level. The lodge is being sold furnished including the Evans custom boat, built to navigate shallow water, and Argo From the shoreline, there is a large offshore blind, a 115’ perpendicular pier with fish cleaning station where you can tie up to access the cabin. The ground on which the permitted cabin was built was raised 22” and the cabin is elevated on over 6’ pilings and reinforced with hurricane braces. The pilings are enclosed with a single door on one end and a double door on the other end to secure and store equipment. Built approximately 15 years ago, the cabin has a 16’ x 22’ living area, 8’ x 6’ porch with storage closet, and bunk beds to sleep six. There is a permitted composting toilet, propane is brought in for lights, heat, stove, and refrigerator.

2735 Lloyd Webb Rd, Crisfield

Listing courtesy of The Land Group. Contact:

4974 Annemessex Rd, Crisfield
$474,900
3 Beds ⋅ 2 Baths
Beautifully maintained 3-bedroom, 2-full bath waterfront brick ranch home situated on a canal in the charming waterfront community of Annemessex Ridge. Nestled on a large corner double lot, this property offers the perfect blend of comfort, convenience, and coastal living. Inside, you’ll find a spacious open floor plan designed for easy entertaining and everyday living. Relax year-round in the inviting 3-season room overlooking the canal, or step outside to the rear deck and patio complete with a hot tub where you can unwind while listening to the peaceful sounds of the water along your private dock. Boating enthusiasts will love the newer boat lift, making it easy to keep your boat ready for a day on the water at a moment’s notice. The property is equipped with impressive 320-amp electric service, including electric at the dock and an RV hookup along the side of the home perfect for hosting friends and family traveling with a camper. Additional highlights include a large side-entry 2-car garage, generous outdoor space, and all the advantages of waterfront living. This exceptional home is the perfect retreat for anyone looking to enjoy life on the water. THE FOLLOWING ITEMS HAVE BEEN UPDATED: 1. NEW ROOF, 2. WASHER/DRYER, 3. KITCHEN COUNTERS AND APPLIANCES, 4. MAIN BATHROOM - 2025, 5. NEW BOAT LIFT - 2024, 6. HOT TUB 2024, 7. ELECTRIC SERVICE (320 AMP), 8. 50 AMP RV CIRCUIT AND SPOT TO PARK, 9. SHED 12X24, 10. HEAT PUMP, 11. BLOWN IN INSULATION IN ATTIC, 12. POWER AT THE DOCK

4974 Annemessex Rd, Crisfield

Listing courtesy of RE/MAX Eagle Realty. Contact:

26278 Peach St, Crisfield
$98,000
2 Beds ⋅ 2 Baths
Cute as a button, single wide mobile home located outside city limits of Crisfield with public water and sewer. Home was remodeled in 2015, with house type Thermopane windows and laminate floors throughout. Home is in excellent shape. Open floor plan makes it feel so much bigger. Large living room with wood look exposed beams. Off the living room is the master bedroom with large walk-in closet and master bath. The kitchen had plenty of room for your dining room table. Off the kitchen is the 2nd bedroom with its full bathroom. Nice size yard with small deck to sit on. There is a Large 12'x20' garage/storage building that is big enough to park a car. Convenient location for shopping and recreational facilities, within walking distance to public beach and fishing pier. Fireplace is "AS IS", it has never been hooked up by seller.

26278 Peach St, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact: