14940 Chesapeake Bay Dr, SCOTLAND, MD

$799,000

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4

Beds

3

Baths

1,644

Square feet

1.08

Acres

About 14940 Chesapeake Bay Dr

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.

Features of 14940 Chesapeake Bay Dr

MLS® # MDSM2032020
Price $799,000
Bedrooms 4
Bathrooms 3.00
Full Baths 3
Square Footage 1,644
Acres 1.08
Year Built 1996
Type Residential
Sub-Type Detached
Style A-Frame
Status Active

Community Information

Address 14940 Chesapeake Bay Dr
Subdivision RODO BEACH
City SCOTLAND
County SAINT MARYS-MD
State MD
Zip Code 20687

Amenities

Amenities Entry Level Bedroom, Window Treatments, Wood Floors
Utilities Cable TV Available, Phone Available
Parking Gravel Driveway
View Water, Bay
Is Waterfront Yes
Waterfront Bay

Interior

Interior Features Floor Plan - Open
Appliances Dishwasher, Exhaust Fan, Refrigerator, Stove, Water Heater
Heating Forced Air, Heat Pump(s)
Cooling Ceiling Fan(s), Central A/C
Has Basement No
Fireplace Yes
# of Fireplaces 1
Fireplaces Equipment, Wood
Stories 2

Exterior

Exterior Frame
Exterior Features Outbuilding(s),Deck(s),Balconies- Multiple,Porch(es)
Lot Description No Thru Street
Roof Shingle
Construction Frame
Foundation Crawl Space

School Information

District ST. MARY'S COUNTY PUBLIC SCHOOLS

Additional Information

Date Listed September 1st, 2026
Days on Market 9
Zoning RPD
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeCENTURY 21 New Millennium

Listing Map

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