14940 CHESAPEAKE BAY DR, Scotland, MD 20687

• 4 beds |
• 3 baths |
• 1,644 sqft

Property Description

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.

Listing Status:

Coming Soon

Date Added:

July 26, 2026

Data Last Updated:

July 7, 2026 at 1:17AM

Listing Office:

CENTURY 21 New Millennium : 3018622169

Listing Agent:

Jessica D Raley : 3019041781

MLS ID:

MDSM2032020

Interior

• General: Kitchen - Table SpaceEntry Level BedroomWindow TreatmentsWood FloorsFloor Plan - Open2nd KitchenFamily Room Off Kitchen
• Rooms: Living RoomPrimary BedroomBedroom 3KitchenBedroom 1OtherBathroom 2Screened Porch
• Appliances: DishwasherExhaust FanRefrigeratorStoveWaterHeater
• Laundry: Main Floor
• Flooring: Ceramic tileHardwood
• A/C: Ceiling Fan(s)Central A/C
• Heating: Forced AirHeat Pump(s)ElectricOil
• Fireplace: EquipmentWoodFireplaceFireplaces: 1
• Disability Feature: Other

Exterior

• General: Outbuilding(s)Above GradeBelow Grade
• Style: A-Frame
• Other Structures: PorchBalconies- MultipleDeck
• Parking: Gravel Driveway

Construction

• Roofing: Shingle
• General: Frame2Crawl Space

Location

• Originating MLS: BRIGHT_MAIN
• School District: ST. MARY'S COUNTY PUBLIC SCHOOLS
• County: SAINT MARYS-MD

Lot

• Zoning: RPD1901016288
• View: WaterBay
• Waterfront: 76

Utilities

• Utilities: Cable tv availablePhone available
• Water: Well-Shared
• Sewer: Septic Exists

Financial

• Source: BRIGHT_MAIN