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$799,000
4 Beds ⋅ 3 Baths
Two Homes, One price! Imagine waking up each morning to breathtaking, unobstructed views of the Chesapeake Bay. Here, the water isn’t just something you see—it’s part of your everyday life. Relax on your private pier, launch your kayak, cast a fishing line, or simply watch the sun dance across the Bay. A sandy beach has been thoughtfully created, allowing you to enjoy carefree days by the water regardless of the tide. Nature lovers will appreciate watching the resident ospreys return each year to build their nests, hatch their young, and soar above the shoreline—a front-row seat to one of the Chesapeake’s greatest treasures. The charming waterfront A-frame has been enhanced with a beautifully enclosed porch, creating the perfect space to gather with family and friends for steamed crabs, oysters, and unforgettable waterfront dinners in every season. Expansive decking on the front, rear, and second level provides multiple outdoor living spaces where panoramic bay views become the backdrop to everyday life. Inside, you’ll find a warm and inviting atmosphere highlighted by a cozy fireplace for crisp winter evenings. Recent improvements include updated bathrooms, a renovated kitchen, new kitchen appliances, fresh interior and exterior paint, new pier boards, and updated fencing, making this home move-in ready. A detached carport with an attached storage shed offers covered parking and plenty of room for all your beach gear, boating equipment, and tools. Just across the driveway sits an equally charming one-bedroom, one-bath guest cottage. Whether you use it for visiting family and friends, a private home office, or continue its success as a short-term vacation rental, it offers exceptional flexibility and income potential. Rarely does an opportunity like this come along. Own not one, but two highly sought-after vacation rental homes in the picturesque waterfront community of Scotland, Maryland. Whether you’re looking for a personal waterfront retreat, a family compound, or an income-producing investment, this exceptional Chesapeake Bay property delivers the best of coastal living.

14940 Chesapeake Bay Dr, Scotland

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$925,000
3 Beds ⋅ 3 Baths
This well-maintained, three-story Waterfront home on Tanners Creek offers a spacious and versatile layout. Three levels of living space including 3 bedroom 3 bath. The main level features 2 bedrooms, 1 full bathroom, a living room, a kitchen, and a dining area. The upper level includes a primary bedroom with a full bath, while the lower level offers a kitchenette with a large pantry, a family room, and 1 full bath. Both the main and lower levels have been freshly painted. All three levels have exterior access to each level of the home with large deck areas for maximum water views. A spiral staircase connects all three levels, adding charm and character. The home and detached garage have recently been power washed, and the pier was rebuilt in 1993. Situated across the street on a separate lot, the impressive garage spans over 2,500 sq ft across two climate-controlled levels and provides ample parking. Garage door openers were installed in 2007. A shed in the backyard conveys with the property, and French doors were added to the lower level in 2008. The generator, purchased in 2009, is also included. Square footage is based on tax records and may not be accurate. The home sits on a 0.20-acre lot and features large decks on both the main and upper levels, as well as a screened-in porch ideal for summer gatherings. A new oil tank was installed in 2019, and the heating/AC system was replaced in September 2018. The septic system was pumped in March 2025. This sale includes four separate lots with separate tax id #'s which will be provided in disclosures. Please note: the property is located in a flood zone, and two TDRs (Transferable Development Rights) do not convey with the sale but may be negotiable. Less than 1/2 mile to Point Lookout State Park; Check out video tour

14623 C Way Dr, Scotland

Listing courtesy of NOVA Brokers, LLC.. Contact:

$780,000
5 Beds ⋅ 4 Baths
Updated photos coming soon! Wake to the soft glow of sunrise spilling across the Chesapeake Bay and end your evenings watching the sky melt into watercolor reflections over the water. Nestled in the heart of Scotland, this exceptional Bayfront retreat captures sweeping, unobstructed views and the quiet serenity only true waterfront living can provide — all secured by a brand-new seawall for lasting peace of mind. Walls of windows invite the outside in, filling the home with natural light and endless horizon views from multiple vantage points. The living spaces feel open, airy, and effortlessly connected — designed for both intimate mornings and memorable gatherings by the water. Step onto the expansive Trex and vinyl balcony and breathe in the salt air as boats drift by in the distance. Slip into the hot tub on the enclosed porch and let the day melt away beneath a painted evening sky. With direct beachfront access, spontaneous sunset strolls and days spent out on the Bay become part of everyday life. A spacious two-car garage adds comfort and convenience to this peaceful coastal escape. 15370 Holly Drive is more than a home — it’s a private waterfront sanctuary where time slows, views stretch endlessly, and every day feels like a getaway. Chesapeake Bay living at its most magical.

15370 Holly Dr, Scotland

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$250,000
Beautiful waterfront property on the Chesapeake Bay with 250FT of sandy beach. Another 400FT of water frontage on Deep Creek. Lot 15A plus additional acreage on the northern half of the Deep Creek inlet. The total acreage is approx. 4.69 acres. Come tour this beautiful beach and property. The perfect spot for crabbing, fishing, sun & sand, camping and relaxation.

15399 Holly Dr, Scotland

Listing courtesy of Pax River Realty LLC. Contact: