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Deal Island, MD Homes for Sale with AC

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  • /51

    $249,900

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    23232 Lola Wheatley Rd, Deal Island, MD 21821

    **Restored 1900 Traditional Farmhouse in Historic Deal Island, Maryland** Discover the charm of this beautifully restored 1900 traditional farmhouse, nestled in the picturesque setting of historic Deal Island. This stunning home perfectly balances timeless character with modern amenities, offering a unique opportunity to own a piece of history. As you enter, you'll be greeted by the warm ambiance

    Agent Photo

    Justin Yon

    Century 21 Home Team Realty

    (667) 297-6589

    23232 Lola Wheatley Rd, Deal Island, MD 21821
  • /58

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft

    23212 Haines Point Rd, Deal Island, MD 21821

    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

    Rebecca Lewis Century 21 Harbor Realty

    23212 Haines Point Rd, Deal Island, MD 21821
  • /30

    $225,000

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    10116 Deal Island Rd, Deal Island, MD 21821

    This charming cottage style home is located in the heart of Deal Island, Maryland. Make this two bedroom, one bath home your permanent oasis away from the hustle and bustle of everyday life or make it your weekend getaway or a vacation rental. All furniture is included and the home has updated appliances. The extra large attic has been framed for additional rooms or organized storage. The home is

    Chrystianna Wilkins-Gosnell Keller Williams Realty

    10116 Deal Island Rd, Deal Island, MD 21821
  • /56

    $298,000 Open House 4/10

    • 2 Beds
    • 2 Baths
    • 2,130 Sq Ft

    23258 Hastings Dr, Deal Island, MD 21821

    A Corner lot with great water views at Scott's Cove! Life here is surely going to bring you the relaxation and luxury at this waterfront community! This treasure of a rancher has all the bells and whistles. Fully Furnished (flatscreens and mounts included), 2 Bedroom 2 Bath with flex space for a workout room or hobby room, etc. The house details will amaze you! New Kraftmaid kitchen cabinets with

    Caroline Reed Century 21 Harbor Realty

    23258 Hastings Dr, Deal Island, MD 21821
  • /40

    $255,900

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft

    23550 Deal Island Rd, Deal Island, MD 21821

    Welcome to Deal Island and this beautifully renovated home, where peaceful coastal living meets modern comfort. Located less than one mile from the public beach and boat ramp, and near the well-known Deal Island Labor Day Skipjack Race, this property offers a relaxed island lifestyle with a strong sense of community. Several nearby State Wildlife Management Areas add to the natural beauty and

    Sharon Fisher RE/MAX Advantage Realty

    23550 Deal Island Rd, Deal Island, MD 21821
  • /58

    $299,000

    • 3 Beds
    • 3.5 Baths
    • 1,550 Sq Ft

    11161 Roland Parks Rd, Deal Island, MD 21821

    Welcome to your island escape in Chance, Maryland—a serene coastal retreat for true nature lovers, just steps from the Tangier Sound and a short boat ride to the Chesapeake Bay. This beautifully updated three-bedroom, three-bath home offers a sought-after first-floor primary suite, with two generously sized upstairs bedrooms featuring ample closet space.Designed for indoor-outdoor living, the

    Casey Neves The Parker Group

    11161 Roland Parks Rd, Deal Island, MD 21821
  • /64

    $319,900

    • 5 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    23290 Custom House Rd, Deal Island, MD 21821

    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

    William Brown EXP Realty, LLC

    23290 Custom House Rd, Deal Island, MD 21821
  • /34

    $415,000

    • 6 Beds
    • 2.5 Baths
    • 2,401 Sq Ft

    10515 Cassandra Dr, Deal Island, MD 21821

    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

    Jennifer Whittington EXP Realty, LLC

    10515 Cassandra Dr, Deal Island, MD 21821
  • /77

    $550,000

    • 4 Beds
    • 4 Baths
    • 2,168 Sq Ft

    10273 Deal Island Rd, Deal Island, MD 21821

    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

    Maureen Bryant Keller Williams Flagship

    10273 Deal Island Rd, Deal Island, MD 21821
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