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9000 Deal Island Rd, Deal Island
$725,000
5 Beds ⋅ 3 Baths
PRICE ADJUSTMENT!!!! Waterfront Estate on 5.56 Acres | Private Dock & Expansive Shoreline Welcome to 9000 Deal Island Road — a rare waterfront estate offering privacy, beauty, and limitless opportunity on Maryland’s Eastern Shore. Set at the end of a private, pine-lined drive, this five-bedroom, three-bath home rests on 5.56 acres with over 400 feet of protected shoreline. The property is zoned Residential, Agricultural, and Commercial, offering extraordinary flexibility for living, recreation, or enterprise. Every space has been thoughtfully refreshed. The main level features new flooring, recessed lighting, and freshly painted interiors in soft, modern tones. The primary suite has been fully remodeled with quartz and tile finishes, a spacious shower, and a soaking tub. A new roof (2025), new water treatment system, new LG stainless appliances, and electric hot water heater ensure modern comfort and peace of mind. Step outside to a private waterfront world of your own — with a pier, party deck, benches, and panoramic views across open water. Eagles, osprey, and dolphins complete the view, while the sunsets speak for themselves. Located just steps from a small marina and minutes to a larger inshore harbor, the property is ideal for boating, fishing, and crabbing. With two 200-amp electrical panels (one exterior for future expansion), a completed survey (Dec 2024), and room to build a barn, workshop, or business structure, this property is ready to become whatever you envision. 9000 Deal Island Road is more than a home — it’s a chance to create something lasting, surrounded by the peace and natural beauty of Maryland’s Eastern Shore.

9000 Deal Island Rd, Deal Island

Listing courtesy of Coldwell Banker Premier - Rehoboth. Contact:

Selling Office: Unrepresented.

11152 Roland Parks Rd, Deal Island
$330,000
3 Beds ⋅ 1 Baths
If you’ve ever dreamed of living in a little cottage by the sea, this is it! Tucked away in the historic and sought-after Deal Island area of Chance, Maryland, this charming waterfront retreat is the definition of a hidden gem. Though cozy in size, the home lives large with breathtaking panoramic water views that steal the show from nearly every angle. This direct waterfront cottage offers three bedrooms, giving everyone the ability to enjoy privacy and comfort while embracing the simplicity of coastal living. The living room and kitchen are perfectly positioned to soak in the endless water vistas, while the screened porch invites you to relax with your morning coffee, unwind with evening sunsets, and enjoy the peaceful sounds of the shoreline. Outside, the generously sized lot provides plenty of room for outdoor entertaining, games, gardening, or simply enjoying life by the water. Whether you are searching for a weekend escape, a peaceful retreat, or your own best-kept-secret getaway, this special property captures the timeless charm and tranquility of Maryland’s Eastern Shore.

11152 Roland Parks Rd, Deal Island

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Weese Properties, LLC.

23392 Custom House Rd, Deal Island
$162,000
3 Beds ⋅ 1 Baths
Are you looking for a secluded home at the end of a lane? Tranquility and peace are what is offered here in the quaint town of Deal Island. Close to water, boat ramps and room for a good size garden. Whether this is your getaway vacation home or your primary home, it is a little slice of heaven! This lovely Victorian home is rich with historic character and is a beautiful setting on 2.06 acres. ( there is an adjacent - 5 + acres available for separate purchase if you wish to expand ). With its large screen porch, it's the perfect spot for summertime crab feasts! With 1760 square feet of living space, first floor bedroom, 3 large bedrooms and 1 full bath. This is one of the higher pieces of land in the area and according to the owners, has never flooded. The home does need some repairs and the owner has attached the inspection report. Features include a new roof, large detached garage with cement floor and electric, an additional shed, bald eagles often seen soaring above, a ton of deer and other wildlife too! Here is your opportunity to get out of the rat race and get to enjoying peacefulness. And after all....You Deserve It!

23392 Custom House Rd, Deal Island

Listing courtesy of Keller Williams Realty Delmarva. Contact:

Selling Office: Keller Williams Realty Delmarva.

8920 Deal Island Rd, Deal Island
$61,250
1.06 Acres – Parcels 0039, 0038, and 0436A This sale includes parcels 0039, 0038, and 0436A, totaling approximately 1.056 acres of prime land combined with 8920 Deal Island Road – a rare opportunity to own 0.82 acres of waterfront property overlooking Wenona Marina and the breathtaking Tangier Sound. Welcome to a once-in-a-lifetime chance to own both space and scenery in one of Maryland’s most picturesque waterfront settings. This exceptional property offers water access, panoramic views, and versatile Maritime Residential/Commercial (MRC) zoning, opening the door to countless possibilities—build your dream coastal retreat, launch a business, or hold as an investment in an area rich with charm and growth potential. Located at the dead end of Route 363, this property provides privacy while remaining steps from the marina, pier, and public boat ramp. Boating and fishing enthusiasts will love the navigable waters, giving direct access to the Chesapeake Bay. With a 3.5-foot right-of-way to the water, you’ll enjoy direct river access and all the recreation that comes with waterfront living. No well or septic permits have been applied for, allowing full flexibility for future design and development. Surrounded by quality homes and a proud waterman’s community, this property delivers the perfect blend of tranquil coastal living and everyday convenience. Don’t miss your chance to secure this rare slice of Maryland’s Eastern Shore—where sunsets over Tangier Sound and the promise of true waterfront living await.

8920 Deal Island Rd, Deal Island

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Keller Williams Realty.

9121 Deal Island Rd, Deal Island
$16,200
3 Beds ⋅ 2 Baths
Discover the potential at 9121 Deal Island Rd, a 0.25-acre property located in the quiet, coastal community of Deal Island, MD. The 924 sq. ft. manufactured home currently that has little life left, offering a rare opportunity to start fresh and design your ideal Eastern Shore getaway, full-time residence, or investment property. Being sold as-is, this property is ready for your vision — whether you choose to rebuild, replace the home, or create a peaceful retreat surrounded by nature. Enjoy the laid-back lifestyle of Deal Island, just minutes from the Chesapeake Bay, local marinas, and scenic fishing spots. Bring your plans and imagination — this is your chance to make something truly special on Maryland’s Eastern Shore! **Utilities are unknown besides well and septic. Located in a X flood zone.

9121 Deal Island Rd, Deal Island

Listing courtesy of Whitehead Real Estate Exec.. Contact:

Selling Office: Whitehead Real Estate Exec..