14 properties for sale in Wenona, Deal Island District 14 Deal Island Somerset County Maryland

Looking for peace, tranquility, and true Eastern Shore living? Welcome home. This unique 5-bedroom retreat on Deal Island is still in its teenage years and ready to meet its next chapter. Lovingly cared for by the original owner since completion in 2008, this 2,400-sq-ft home blends comfort, privacy, and value rarely found in this setting. Tucked into its own private pocket of mature trees and marsh, the property spans just over 2 acresperfectly balanced with usable yard space and low-maintenance natural beauty. Spend less time on upkeep and more time enjoying small beaches, boat launches, fishing, bird-watching, and peaceful scenic walks just moments away. Inside, the first floor offers three bedroomsincluding a primary suite with en-suite bath and walk-in closetplus a full hall bath and a bonus room for flexible use. A generous laundry/utility room provides side entry and flows into an efficient kitchen with heat-resistant Corian countertops and dining space. Off the dining area, a s

Incredible Investment Opportunity or Family Vacation Retreat! Single Family home of 1440 square feet. 1 Bedroom/1 Bath also features two 20' X 40' Garage/Sheds AND three efficiency apartments with covered back porches on waterfront! 1.47 Acre Lot Located on picturesque Deal Island, this charming and versatile property offers endless potential as a short-term rental, multi-family vacation compound, or full-time coastal residence. Featuring a spacious layout and situated just minutes from the Chesapeake Bay, this home provides easy access to boating, fishing, crabbing, and all the natural beauty the Eastern Shore has to offer. The home boasts multiple living areas, ample bedroom, with a huge bathroom and generous outdoor spaceideal for entertaining or relaxing with family and friends. With Deal Islands increasing popularity among vacationers, this property is perfectly positioned to generate strong Airbnb income or become a treasured family getaway. Property Highlights: Ideal for Airbnb

Looking for peace, tranquility, and true Eastern Shore living? Welcome home. This unique 5-bedroom retreat on Deal Island is still in its teenage years and ready to meet its next chapter. Lovingly cared for by the original owner since completion in 2008, this 2,400-sq-ft home blends comfort, privacy, and value rarely found in this setting. Tucked into its own private pocket of mature trees and marsh, the property spans just over 2 acres—perfectly balanced with usable yard space and low-maintenance natural beauty. Spend less time on upkeep and more time enjoying small beaches, boat launches, fishing, bird-watching, and peaceful scenic walks just moments away. Inside, the first floor offers three bedrooms—including a primary suite with en-suite bath and walk-in closet—plus a full hall bath and a bonus room for flexible use. A generous laundryu002Futility room provides side entry and flows into an efficient kitchen with heat-resistant Corian countertops and dining space. Off the dining ar

Waterfront 2 subdivided lots totaling 2+ acres. Main home and tenant house and duck blind on the water with small pier. Public water. Private septic. Open concept. Great room 44x16. 2 Balconies. 2 multi level decks. Gas cooking. Spiral stairs and dumb waiter to lower level. Brazilian hardwood, ceramic tile, porcelain tile floors. Custom kitchen with huge center island. Fantastic views for miles from every window. Goose Creek Marina, Pub and Free boat launch. Small house has 1 bath, 1 bedroom, kitchen and dining room combo, separate driveway. 20x 10 storage shed. Above ground pool. Main house is open concept, 3 bedrooms, 2.5 baths, huge open space on both levels. Not a drive by! Please view all pictures and descriptions. Call for additional info and appointment to view

Waterfront 2 subdivided lots totaling 2+ acres. Main home and tenant house and duck blind on the water with small pier. Public water. Private septic. Open concept. Great room 44x16. 2 Balconies. 2 multi level decks. Gas cooking. Spiral stairs and dumb waiter to lower level. Brazilian hardwood, ceramic tile, porcelain tile floors. Custom kitchen with huge center island. Fantastic views for miles from every window. Goose Creek Marina, Pub and Free boat launch. Small house has 1 bath, 1 bedroom, kitchen and dining room combo, separate driveway. 20x 10 storage shed. Above ground pool. Main house is open concept, 3 bedrooms, 2.5 baths, huge open space on both levels. Not a drive by! Please view all pictures and descriptions. Call for additional info and appointment to view

Welcome to 7940 Riverview. Located in the Waterside Village of Rumbley this beauty faces straight into the Tangier Sound/Chesapeake Bay! Pride of Ownership and attention to detail are evident both inside and out of this pristine property. This 3 Bedroom 2 Bath gem makes efficient use of every square inch of living space. The Primary Living Room is large enough for entertaining but isn't the only living space. Check out the Den which has Sliding Doors that face the Bay and has a propane fireplace for a cozy feel or to take the edge off on a cool day. Walkout from the family room to the spacious open deck or take cover in the screened in porch alongside. The Kitchen is ample enough to make meal prep a whiz and the breakfast nook is convenient for when the crowd is a little smaller. There is a dining area as well that can handle those larger get togethers. The Large Owners Suite is located on the opposite end of the home from the other two bedrooms giving all parties extra privacy! There

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Welcome to 11060 Roland Parks! Looking to get close to the Bay and all it has to offer without breaking the bank? Look no further! The bones are good on this home. Featuring Three Bedrooms, Large Sunroom and Two Car Garage! A little TLC will breathe new life into the adorable rancher! Sitting on a Double Lot measuring just over an acre. There is room to park all your toys or expand your foot-print if you so desire! The Bay is easily in reach from this property! Whether you take a two-mile drive to the Deal Island Marina to launch your boat or get the fresh catch of the day from local crabbers or want to put your toes in the sandy beach, the beach is located next to the Marina, you can enjoy it all! Take in the Skip jack races every Labor Day and all that festival offers! If a calmer pace is in order, take a trek to the end of Roland Parks Rd where you'll find a perfect place to launch your Kayak or john boat to enjoy a peaceful excursion! Don't let this one slip away! Enjoy your'Peace'

Let 'Home' be here! Your forever vacation in a quaint rural nautical town or make this cottage home a great 2nd home for seasonal getaways! Neighborly community with water access in every direction. This charming 2 Bedroom 1 Bathroom cottage home hosts all NEW stainless steel kitchen appliances and solid hardwood floors! Large unfinished attic space can be finished as a bonus room. All Furniture is included! Spend a day out fishing, crabbing kayaking or boating on the Tangier Sound on the west and south and the Wicomico River to the North. Buyer and Buyer's agent should do their due diligence and verify all taxes, schools and any and all information pertaining to this property

Beautiful Waterfront Retreat on Tangier Sound Welcome to the island life! This unique waterfront home offers a rare opportunity to own a property with 180 feet of bulkhead on the navigable Tangier Sound. Imagine spending your days crabbing and fishing right from your own backyard, and your mornings with a cup of coffee watching breathtaking sunrises. The evenings are just as magical, with romantic sunsets that are perfect for a quiet glass of wine. The home's main floor features an open floor plan with a combination living room and kitchen, complete with new granite countertops. The upstairs loft is a versatile space with two large rooms, both offering incredible water views of the Tangier Sound. From here, you can watch crab and oyster boats sail by from the nearby marina. The property also includes a separate laundry room and a double-car garage with high-bay doors, perfect for storing extra-large items. A public boat ramp is less than five minutes away, so you can easily launch your

Waterview! This charming rancher offers serene living on a 2-acre lot overlooking Haines Pond and the Tangier Sound, surrounded by the beauty of nature and breathtaking sunsets over the Chesapeake Bay. Enjoy daily sightings of eagles, osprey, herons, and other wildlife (plus the famous Skipjacks) right from your own property. Outdoor recreation is right at your doorstep. Kayak or paddle on the pond or Tangier Sound, take a short bike ride to nearby public beach, catch crabs from the small bridges just feet from the property, or walk to Scotts Cove Marina. A public boat ramp is also nearby, making it easy to enjoy everything the Chesapeake Bay has to offer. Inside, easy-care laminate flooring flows throughout the home, while the updated kitchen and replacement windows provide modern comfort and efficiency. This unique property perfectly blends the tranquility of waterfront living with convenient access to local coastal activities. Whether you're seeking a peaceful second home, an income

Tucked away in a peaceful neighborhood next to Deal Island and the shores of Tangier Sound, this ranch-style home offers comfort and opportunity. Set on a 1-acre, mostly cleared, corner lot, the property provides plenty of room for outdoor entertaining, gardening, or future expansion. Enjoy the best of both worlds—serene coastal living with the convenience of Salisbury just under 30 minutes away, giving you easy access to shopping, dining, and recreation. The surrounding community is warm and welcoming, making it an ideal setting for those seeking a quiet retreat near the water without sacrificing everyday essentials. This 2-bedroom, 1-bath home is being sold as-is and has been refreshed with new paint, offering a clean slate for your vision. With a bit of updating and remodeling, it’s a fantastic opportunity for investors or buyers ready to make it their own. Key updates include a BAT septic system installed in 2009, a new water pump in 2022, HVAC in 2024, and a Sentricon termite bait

Escape to the charm of coastal country living at 23483 Beckett Rd in Deal Island, where peace, space, and modern comfort meet. Nestled on 1.43 acres and not in a flood zone, this fully renovated 3-bedroom, 2-bath farmhouse blends timeless appeal with thoughtful upgrades, creating the perfect getaway or full-time residence. Inside, you’ll find brand-new luxury vinyl plank flooring, new stainless steel appliances, a new roof, and even a backup generator for peace of mind. The inviting primary suite features both a walk-in shower and a spacious walk-in closet. A finished attic offers flexible space ideal for a home office, playroom, or hobby area. Outside, enjoy easy-care landscaping, a gravel-filled driveway, a storage shed, garage, cozy firepit, and a charming new front walkway that sets the tone the moment you arrive. Soak up the Eastern Shore lifestyle—cast a line or go crabbing, explore nearby public hunting grounds, visit the local beach or launch your boat from one of three local m

Price improvement on this direct waterfront property —an ideal boating and fishing retreat with sweeping open-water views of the Tangier Sound. This charming coastal cottage is a classic Eastern Shore getaway where you can catch rockfish year-round, crab right from your backyard, or set out by boat or kayak from your private 60' pier. Open floor plan inside is designed for relaxed coastal living, with stunning water views from nearly every angle. Abundant natural light shows off the gleaming hardwood floors. Home features two spacious bedrooms plus a cozy sleeping alcove and two full bathrooms. Updated six-panel doors add warmth and character throughout. Large 20' x 12' shed currently serves as a workshop with built-in shelving, electric service and lighting. A second storage area on the side of the house is perfect for kayaks and other outdoor accessories. Recent upgrades and excellent maintenance history provide peace of mind and modern comfort. New HVAC, (2026), water heater (2025),

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Seller is motivated! Seller offering 5k toward closing! This spacious townhouse condo can be ready to GO and offers beautiful views with an attached garage located in a very convenient quaint waterfront community. This home has been updated with fresh paint, just choose your own new carpet or flooring! It is a 3 bedroom 3 full bath with a loft that can be an extra 4th bedroom, or a family hang out. Relax here with NO yard work, a pool out the front door, a community beach directly out the back and a community pier. Remarkable bayfront location with a very short walk to boat slips that are available for purchase. Just a few steps out the front door is the welcoming pool to enjoy. You must come and see it to appreciate the value, call for an appointment! The home comes with all stainless appliances and gas instant water heater and gas stove with an open concept kitchen/ dining/ living room. Upstairs is the huge master suite with a seating area, walk in closet and very large bathroom with

Refuced to sell! Totally renovated. 3-bedroom, 2-bathroom farmhouse WITH LARGE GARAGE! Located in the historic waterfront community of Crisfield. Everything is new. Stainless steel appliances, kitchen countertops, cabinets, pantry, roof, vinyl siding, insulation, electric, plumbing, septic connection, hot water heater, washer. Dryer, windows, HVAC mini-splits, electrical fixtures and ceiling fans, recessed lighting, LP and carpet flooring, paint, storm doors and baths. Everything! Downstairs boats a master bedroom/bath suite with a large walk. In closet and a recently finished 4 season room/private laundry. There are two bedrooms and one full bath upstairs. Outside, one will find a remodeled 28x40 foot 2 bay detached garage and a workshop with electric, cement floors, a work bench, upstairs storage and a new metal roof. Bring your boat, fishing poles and move right in. Garage would make an awesome man or she cave!

Experience waterfront living where the views invite you into serenity. Offering 1,624 square feet across two thoughtfully designed levels, this home provides plenty of room for family and guests to spread out and enjoy coastal living. Featuring three bedrooms, two and a half baths, a desirable first-floor primary suite, and a screened porch overlooking the water, the layout balances comfort, privacy, and convenience. The sellers have treasured the peaceful setting, breathtaking sunsets, family gatherings, and the simple joy of life on the water. Why pay high condo fees when you can own this direct-access waterfront home complete with Boat Slip #1 just steps from your door? Enjoy the freedom to do as much or as little as you want. Launch your paddle board and cruise to the library or Wellington Beach, spend the day fishing, crabbing, boating, or enjoying water sports, or take a scenic boat ride to Janes Island and the Nature Center. And with the quaint, charming town of Crisfield, also

Discover the potential of this flat lot located just minutes from the serene Nanticoke River, which flows directly into the Chesapeake Bay. This parcel comes equipped with an existing well (condition unknown). No septic system exists. Backed by woods for added privacy and natural beauty, the property is ideally situated less than 10 minutes from Nanticoke Harbor and a public beachcomplete with boat slip rentals for water enthusiasts. The conveniences of Salisbury, Maryland are just a short 30-minute drive away. Please note: The existing structure on the property is uninhabitable, and all visitors must sign a Hold Harmless Agreement prior to access. Buyer to perform all due diligence regarding utility connections, zoning, and property condition. Whether you're looking for a weekend escape or a future homesite near the water, this property offers a unique opportunity in a sought-after location

Seller is willing to do some owner financing to help with down payment as a second mortgage! Beautiful Waterfront Home in Annemessex Ridge! Home is over 2500 sq ft and sits on 3 lots. Home has had many upgrades and renovation done. New roof has been put on 2025, freshly painted inside and new flooring. The kitchen has beautiful cabinets and granite counter tops. Tons of cabinet and counter space. The large living room has a gas burning fireplace. There is a nice family room with water views. The oversized porch is a great party room looking out over canal. The master suite is LARGE, with his and hers closets and master bath. There are 2 more very large bedrooms and 2 baths. The patio off the back of house leads to the dock and pier for your boats or jet skis!