Maryland Waterfront Homes for Sale 21821

Find the best Maryland Waterfront Homes for Sale 21821. Get help from Frank Rosati, a top real estate professional with over 15 years proven track records.

Featured Maryland Waterfront Homes for Sale 21821

HISTORIC RENOVATED WATERVIEW  COMPOUND IN THE VILLAGE OF DEAL ISLAND! When the US was an English Colony, Deal Island was called Devil's Island because Pirates such as Bluebeard raided the coastline and took captured ships to the tributaries to loot them. The Queen of England appointed a Customs Officer, Lt. A. Price to build a home on the highest elevation in order to create law and order and collect taxes from the local residents. Price's land is now known as 23391 Custom House Rd. and it's on a high elevation in Deal Island. The property borders a Wildlife Preserve that is a Naturalist's Paradise. When you pass through the gate at the end of Custom House Road you are entering a private 2.9 acre Compound that has been thoughtfully updated . The 2,605 square feet home has been completely renovated with a new HVAC system, new vinyl siding, tilt-in windows, architectural shingle roof,  luxury vinyl plank floors and a Culligan Water Purification System that has a 20 year Warranty. The kitchen offers new granite countertops, custom cabinetry and a stainless steel appliance package. The original bathroom has been renovated and two additional bathrooms have been added. There is a first floor Master Bedroom, two large bedrooms on the second floor, one with a sitting room that is being used as an office, and a large bedroom on the third floor. All upstairs bedrooms offer water views of the Wildlife Preserve and it's large tributaries.  The focal point of family and guest entertainment is a 21'x30' Family Gathering Center that is located on the second floor of an outbuilding. This room has custom cabinetry, a granite countertop bar with a sink and sun decks that offers amazing water views of the tributaries and wildlife to the east and a large pond and the house to the west. The Compound offers storage galore with a 13'x46' building with a concrete floor and a new 11'x12' storage shed. Vehicles and heavy equipment can be stored in a 26'x26' pole barn that has new siding and an architectural shingle roof. There is a natural path that goes from the property to a beachhead where a kayak, canoe or paddleboard can be launched. Bring your larger boat and take advantage of the public double boat ramp or dock it at the protected marina in Wenona, which is less than a five minute drive from the property.  Also located five minutes away is a public boat ramp and marina in Deal Island that has a public beach where you can swim in the Chesapeake Bay, collect sea glass or watch the working boats bring in their freshly caught seafood. This marina takes center stage during the Labor Day weekend with a Skipjack boat race, watermen docking competition, live music and a variety of vendors. Skipjacks are sailboats that were prevalent in the late 1800s and early 1900s and were used by watermen to catch crabs and oysters. The Eastern end of the Compound is in an AE 100 year floodplain and the home and all outbuilding are on higher ground and are located in a 500 year floodplain. There was no standing water on the Compound during Hurricane Sandy, which was the worst storm in 100 years. ENJOY THE SOLITUDE, THE NATURAL BEAUTY AND THE RENOVATED HOME AND OUTBUILDINGS THAT THIS FAMILY COMPOUND HAS TO OFFER!
23391 Custom House Road
Deal Island, Maryland
  • 4 Beds
  • 3 Baths
  • 2,605 SqFt
  • 2.920 Acres
What a View! Fabulous 1600 sf+ 3 bedroom, 2 Bath  waterfront rancher in Chance Maryland. Very well built with 2 x 6 exterior walls, this home is in perfect condition and turn-key. Open concept kitchen dining and great room. 3 large bedrooms, 2 car attached garage, huge screened porch.  Very recent and extensive bulkheading and a boat lift!
11115 Lee Avenue
Deal Island, Maryland
  • 3 Beds
  • 2 Baths
  • 1,616 SqFt
  • 0.520 Acres
This exceptional waterfront property is sure to provide plenty of opportunities for rest and relaxation. With 3.35 acres of land encompassing 245 feet of bay frontage, you can enjoy the long views and peaceful serenity of nature that abounds here. From deer, fish, and herons, to turkeys, you will be mesmerized by the abundance of wildlife that inhabit the area. This three-bedroom, two-bathroom home has an owner suite and offers breathtaking views of the Chesapeake Bay. Three miles down from the Wicomico River. Recently added heating and air conditioning to the 12x24 Florida room make it a perfect place to relax any time of year. Per the owner, the 288sq ft is not reflected in the tax records sq ftg. Plus, the owner is replacing multiple decks with composite wood for added durability and beauty. Don't miss out on this incredible opportunity to own a piece of paradise. Buyers should confirm square footage, taxes, and school districts.
11015 Mahlon Price Road
Deal Island, Maryland
  • 3 Beds
  • 2 Baths
  • 2,184 SqFt
Peace, tranquility, serenity are words that can all be used when describing this beautiful waterfront home located in Deal Island. This 3 bedroom 3 full bathroom house could be a dream come true for anyone that loves boating, fishing, swimming, and amazing views! Enjoy the views the second you walk in the front door with an open kitchen and dining room overlooking the Tangier Sound. The home offers a split floor plan with the Primary Suite on one side and the other 2 bedrooms on the opposite end of the house. The Primary bedroom also has a four-season room attached with incredible views of the Sound. This house has so much more to offer than can be put in words. Book your showing today and see for yourself.
23165 Rolfe Lane
Deal Island, Maryland
  • 3 Beds
  • 3 Baths
  • 2,191 SqFt
  • 0.680 Acres
**Back on the market due to buyer default**Welcome to the Cottage on the Cove! Situated on 1.25 acres of direct waterfront on Scotts Cove, leading to the Tangier Sound, enjoy expansive views of Scott's Cove and Marina, a safe harbor for historic Skipjacks of the Chesapeake Bay. This 3BR/2.5BA home features water views from nearly every room.  New septic (2022) as well as new hot water heater and water treatment system (owned). The open floorplan with warm hardwood floors throughout the living and sleeping areas while  all 3 baths boast granite tile floors . Spacious living room opens into the dining room and waterfront sunroom. Designer kitchen with custom butcher block counter and stainless steel appliances. First floor owner's bedroom with walk-in closet and laundry center, full en-suite bath w/glass-enclosed step-in shower. A convenient half bath completes the first floor. Upstairs, 2 large bedrooms w/gorgeous hardwood floors, walk-in closets and charming built-in shelves.  Save some money on utilities with upgraded energy-efficient insulation and thermal windows. High-speed cable internet available as well.
23351 Cove Road
Deal Island, Maryland
  • 3 Beds
  • 3 Baths
  • 1,551 SqFt
  • 1.250 Acres
SPECIAL LIMITED TIME HOLIDAY PRICE REDUCTION! SELLERS WILL ALSO PAY ALL TRANSFER TAXES  AND 2023/24 PROPERTY TAXES AT CLOSING  FOR  ACCEPTABLE OFFER RECEIVED ON OR BEFORE 12/10/23 9 PM.  SPACIOUS UPDATED BAY VIEW HOME EQUAL DIStANCE b/w OCEAN CITY MD AND CHINCOTEAGUE VA with FISHING, BOATING AND CRABBING ACCESS across from its own .69 ACRE LOT with NO HOA FEES, NO WATER/SEWER BILLS with its own onsite well and recently cleaned/pumped septic and $60 ANNUAL TRASH PERMIT FEE. MAGNIFICENT SUNRISES stream through the windows of this 2,309 sq ft home which features OPEN LAYOUT LIVING ROOM with fireplace and dining area leading into spacious UPDATED KITCHEN with plenty of counter/cupboard space; NEW dual sink and faucet; NEW overhead lighting and window blinds and NEW hot/cold water Primo water cooler. THREE BEDROOMS, one being used as a second floor office, overlooks the harbor and leads to an OPEN AIR DECK WITH WATER VIEWS. NEWLY PAINTED BATHROOMS include NEW shower massage heads and a NEW faucet in the first floor facility. LARGE ENCLOSED FRONT PORCH NEWLY PAINTED features NEW blinds, NEW area carpet and dining area with its own harbor views. Outdoor area features PLENTY OF LAWN SPACE for pets, swing set, above ground pool and tomato garden. SPACIOUS TWO STORY WORKSHOP offers plenty of workbench space with tools and hardware, and a roomy second floor with enough space for fishing/boating equipment, carpentry and building materials, small business office or photography/art studio. DETACHED SINGLE VEHICLE GARAGE comes with mechanics' tool chests and lots of room for bicycles/kayaks/canoes/jet skis/small sailboat/riding mower.ADDITIONAL STORAGE available in DUAL STORAGE SHED as well as cavernous SOLID WOOD FLOORED ATTIC inside the home which leads to a UNIQUE NEW ENGLAND SEACOAST STYLE WIDOW'S WALK with panoramic views of single masted skipjacks and the bay. ADDITIONAL ROOMS include COMBINATION PANTRY/LAUNDRY with dual stainless steel sink; plenty of cabinetry and canning area; washer/dryer; upright freezer and hardwood floor. MUDROOM with exterior access also makes a pet friendly area. TILT-IN WINDOWS in the living room, kitchen, bedrooms and upstairs hall make for easier cleaning. CEILING FANS in three bedrooms, living room and enclosed porch accent cooling from WINDOW A/C UNITS with heat provided by GAS FIREPLACE (gas lines inspected May 2023) and electric baseboard heat. LOW TRAFFIC ROAD IDEAL FOR BICYCLES LEADS TO SANDY BEACH OFTEN WITH NO CROWDS for sunrise jogging, afternoon swimming, evening pet walks and spectacular sunset views. In addition to rockfish and world famous blue crabs,THE AREA IS A HAVEN FOR WILDLIFE INCLUDING BALD EAGLES; a variety of gulls, herons and egrets; seasonal pelicans; turtles and vibrantly colored frogs and WHITE-TAILED DEER WHICH VISIT THE BACKYARD. ITEMS TO CONVEY include refrigerator; upright freezer; Primo water cooler; washer; dryer; dishwasher; Smart TV style wall mounted TV; picnic table and patio chairs; furnishings and decor; crabbing/fishing equipment; garden tools and electric mower; window a/c units; tools/tool chests. Purchase for use as a primary residence, retirement home, seasonal or weekend getaway or a possible weekly/long term rental/Bed and Breakfast.. Sellers have enjoyed the home and completing many improvements and updates, but due to family situation, need to sell and WILL SERIOUSLY CONSIDER ALL REASONABLE OFFERS WITH QUICK SETTLEMENT POSSIBLE. ACTUAL ANNUAL AMOUNTS PAID BY SELLERS 2023: Property Taxes $1,481; NO WATER OR SEWER BILLS (Onsite well, septic):. Home Owners $1,757*; Flood Insurance $1,184* (*Amounts based upon seller coverage.)
8960 Deal Island Road
Deal Island, Maryland
  • 3 Beds
  • 2 Baths
  • 2,309 SqFt
  • 0.690 Acres
Welcome to your sanctuary of serenity on Deal Island! Nestled in a picturesque setting, this charming residence offers a haven of peace and tranquility. Immerse yourself in the breathtaking 360-degree views of the bay, where you can relish both the sunrise and sunsets, all from the comfort of your expansive wrap-around deck.

This home is a water lover's dream, just mere steps away from the bay, providing direct access to nature's beauty. Additionally, a short stroll will take you to the marina, offering convenient options to dock your boat or lease a boat slip, ensuring that every marine adventure is within easy reach.


A newly constructed large shed stands ready to accommodate all your storage needs. All three bedrooms have new flooring, paint and furniture.

All you need to do is just bring yourself and start living the good life today in this fully furnished home.
Don't miss the opportunity to make this idyllic retreat your own. Schedule a visit to experience firsthand the unmatched beauty and tranquility that this Deal Island home has to offer. Your slice of paradise awaits!
23146 Manokin Court
Deal Island, Maryland
  • 3 Beds
  • 2 Baths
  • 1,026 SqFt
  • 0.550 Acres
Wonderful family home or investment opportunity in a historic Deal Island neighborhood. Blue Ribbon elementary school and fire department are within walking distance. Recently operated as an Airbnb. Located close to public boat ramps in Chance and Wenona, both on Deal Island. This home provides a large yard for outdoor entertainment and open fires. An outdoor shower offers hot/cold water for sand and salt rinse to keep the home clean. Inside you will find updated flooring, plumbing, ceiling fans, and a modern kitchen that boasts an Italian 36" range and convection oven, and a large hot water heater. Four nice bedrooms and 2 full baths. Enjoy both the savings and ambiance of a glass front wood-burning stove (new stainless liner) as well as new propane and new electric baseboard heaters. This home is historic with all the modern conveniences. Don't wait! Book your showing today!
23180 Harrison Road
Deal Island, Maryland
  • 4 Beds
  • 2 Baths
  • 1,408 SqFt
  • 0.810 Acres
Come see the amazing views in this ready to move in condo in Wenona Harbor which includes a boat slip! This quiet community of 10 units is located on a picturesque peninsula at the end of the world. Come find peaceful tranquility on the rear screened in porch where all you hear is the occasional work boat passing by! This two bedroom, one and a half bath 2 story condo  has recent upgrades in bathrooms like paint and lighting throughout, and the entire home has new flooring. You will also LOVE that this home includes a deeded boat slip in this price as well. Come and relax with no stress and no work because all outside maintenance is done by association, just show up and enjoy. All the current assessment upgrades are paid for. The units are receiving new screened porches, and new boardwalks, and has received upgrades to septic and plumbing. Condo association is run by owners; and  the association is responsible for entire outside of unit which includes insurance and maintenance. The owner is also flexible so if the buyer likes any of the furnishings, the buyer is welcome to them. Make your appointment today before its gone at this affordable price.
8857 Deal Island Road 4
Deal Island, Maryland
  • 2 Beds
  • 2 Baths
  • 1,072 SqFt
Nice rancher that sits on 1.91 acres of land and is located only 3 miles from the public boat ramp.  Nice land that you could build up and catch some of the beautiful island settings.  Property is being sold As Is, Where is.
 Buyers should do their own due diligence to measure property and confirm all information to their satisfaction including but not limited to schools, sizes, tax information.
22980 Parkinson Road
Deal Island, Maryland
  • 4 Beds
  • 2 Baths
  • 1,848 SqFt
  • 1.910 Acres
Come check out this beautiful updated farmhouse located in the heart of deal island.  Has a nice sized yard, along with a shed and garage which is a year old. Spacious porch with a custom built swing. As you walk in you will come to bedroom number one as well as your main living space and bathroom. Through the living room you'll find your small dining room along with your kitchen and washer and dryer. Upstairs you will find 2 more bedrooms as well as an entrance to the attic. A lovely getaway home come check it out today !
(Seller is aware of tight space to bathroom willing to negotiate)
23310 H Milbourne Rd
Deal Island, Maryland
  • 3 Beds
  • 1 Baths
  • 1,024 SqFt
  • 1 Acres
Looking for a great and cozy 2 bedroom bungalow for full year living or weekend getaways; nestled off the road surrounded by mature trees as a summer get away or year round living, then look no further!  This home had the roof replaced 2 years ago, and the septic replaced just 5 years ago and maintained ever since.  What an opportunity to enjoy the peace and tranquility of Deal Island!
9756 Deal Island Road
Deal Island, Maryland
  • 2 Beds
  • 1 Baths
  • 884 SqFt
  • 0.750 Acres
Very clean and bright ranch style home with 3 bdr. 1 large bath, eat in kitchen and open living room. New HVAC in 2017, new sump pump in crawl space.  Additional parcel has a bungalow style home with much potential for mother in law home or rental property.  Must be sold together.  Please check financing to see if this would be allowed, no FHA/VA.  Hunters, fishermen, this location is adjacent to State hunting lands, public boat ramp, and just 15 minutes to Princess Anne.  Great price on this property!
10781 Riley Roberts Road
Deal Island, Maryland
  • 3 Beds
  • 1 Baths
  • 912 SqFt
  • 0.470 Acres
Escape to this charming bungalow in the idyllic community of Deal Island, this cute bungalow offers the perfect blend of cozy comfort and tranquil retreat.  Imagine waking up and sipping your morning coffee or reading a good book on the front porch.  This home has hardwood floors and a large kitchen, 2 bedrooms and a large living room.  Whether you’re a fan of fishing, kayaking or crabbing you can unwind and relax in this home. Come experience the beauty and peacefulness that this charming bungalow has to offer.
9172 Deal Island Road
Deal Island, Maryland
  • 3 Beds
  • 1 Baths
  • 1,221 SqFt
  • 1 Acres
ACRE !!! Excellent rehab opportunity to add your touch to this single-family home sitting on 1 acre of land, backed to trees and open space. A Dame Quarters/Maritime Residential Community  Boating, Crabbing, Fishing, Public Parks, A paradise for nature lovers, hunters, fishermen, and more. Turn this Eastern Shore home into your own. Either a place to live or escape. Surrounding features include tidal bays, Rivers, Woodland, and close to the Bay...AS-IS! Schedule a showing today!

“This property has been placed in an upcoming event. All bids should be submitted at Xome.com. Please submit any pre-auction offer received through the property details page on Xome.com. Any post-auction offers will need to be submitted directly to the listing agent. All offers will be reviewed and responded to within 3 business days. All properties are subject to a 5% buyer’s premium pursuant to the Auction Participation Agreement and Terms & Conditions (minimums will apply). Please contact listing agent for details and commission paid on this property.
24719 Deal Island Road
Deal Island, Maryland
  • 2 Beds
  • 1 Baths
  • 1,284 SqFt
  • 1 Acres

Maryland Waterfront ZIP Code List