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14940 Chesapeake Bay Dr , Scotland, MD 20687
$799,000
Est. Payment: $4,252.61/mo
4 Bed
3 Bath
1644 Sqft
1.08 Acres
Status: active | Days on site: 60
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CENT2010 - 63906
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House 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.

Highlights

Listed by Jessica D Raley , 3019041781 CENTURY 21 New Millennium , 3018622169. Bright MLS

Property Type

Residential

Lot/Acreage
1.08

Year Built

1996

County

Saint Marys

Neighborhood

Rodo Beach

School District

St. Mary's County Public Schools

Listing ID

MDSM2032020

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:4
  • ▪ Bathrooms:3
  • ▪ Full Bathrooms:3
Appliances:Dishwasher, Exhaust Fan, Refrigerator, Stove, Water Heater
Air Cond:Ceiling Fan(s),Central A/C
Fireplaces:Equipment,Wood,1 Fireplace
Floor:Ceramic Tile,Hardwood
Above Ground Sq Ft:1644
Other:
  • ▪ Main Floor Bedrooms:2
  • ▪ Additional:Kitchen - Table Space, Entry Level Bedroom, Window Treatments, Wood Floors, Floor Plan - Open, 2nd Kitchen, Family Room Off Kitchen
Water:Well-Shared

Exterior Features

Lot:No Thru Street,Not New Construction,Horse Property: No,Waterfront
Garage Capacity:6
Zoning:RPD
Roof:Shingle
Others:
  • ▪ Additional:Outbuilding(s), Excellent
Sewer:Septic Exists
Parking Features:Gravel Driveway,Off Street,Driveway,Detached Carport,4+ Spaces,3+ Spaces,2+ Spaces,1+ Spaces
Principal Interest
$4,253
Taxes
$358

Home Price

$799,000

Loan Details

30 yrs
7%

Down Payment

20%
$159,800
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$4,252.61

Principal

Taxes

Principal Taxes HOA Total
Monthly $4,252.61 $357.75 $0.00 $4,610.36
Yearly $51,031.36 $4,293.00 $0.00 $55,324.36
Total $1,530,940.88 $128,790.00 $0.00 $1,659,730.88
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Chico Gordy
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Market insight data is pulled from the same city as the listing being viewed (Scotland, MD).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Information provided by Bright MLS, and is deemed reliable but not guaranteed accurate.

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Data last updated: 2026-11-13T23:12:42.000Z

© 2026 Bright MLS