# 14940 CHESAPEAKE BAY Drive, Scotland, MD 20687 > **TL;DR:** 4bd/3ba single family, $799,000 ($486/sqft), built 1996, 1,644 sqft. > Fireplace, Waterfront, A/C. Est. $4,273/mo. Listed 61 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $799,000 | | Price/sqft | $486 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 1,644 | | Year Built | 1996 | | Lot Size | 47,045 sqft (1.08 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 61 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,040 | | Estimated Insurance | $233 | | **Total** | **$4,273** | ## Key Amenities - Fireplace - Waterfront - A/C ## Property Highlights - Built in 1996 - 1.08 acre lot - 2 stories - 6 parking spaces - Fireplace - Waterfront ## Description ### Agent 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. ## Location - **Address:** 14940 CHESAPEAKE BAY Drive, Scotland, MD 20687 - **County:** SAINT MARYS - **Neighborhood:** RODO BEACH - **Coordinates:** 38.07704, -76.3306 - **Google Maps:** https://www.google.com/maps?q=38.07704,-76.3306 ## Virtual Tour & Media - **Video Tour:** http://tour.c21nm.com/home2/AGYX4U/14940-CHESAPEAKE-BAY-DR-SCOTLAND-MD-MDSM164378 ## Listing Agent - **Name:** Jessica D Raley · **License:** 524473 - **Brokerage:** Century 21 New Millennium - **Broker Phone:** (703) 753-7910 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/14940-Chesapeake-Bay-Dr_Scotland_MD_20687_M69803-50985?f=listhub&s=TRENDPA&m=MDSM2032020&c=propsimple) ## Photos ![14940 CHESAPEAKE BAY Drive - Photo 1](http://lh.rdcpix.com/3e02da6316b3df9517b1e99788e10be4l-f1443922399r.jpg) ![14940 CHESAPEAKE BAY Drive - 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Photo 83](http://lh.rdcpix.com/3e02da6316b3df9517b1e99788e10be4l-f4013652094r.jpg) ![14940 CHESAPEAKE BAY Drive - Photo 84](http://lh.rdcpix.com/3e02da6316b3df9517b1e99788e10be4l-f590597595r.jpg) ![14940 CHESAPEAKE BAY Drive - Photo 85](http://lh.rdcpix.com/3e02da6316b3df9517b1e99788e10be4l-f3565709986r.jpg) --- **MLS#:** MDSM2032020 | **Updated:** 2026-10-27 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/14940-chesapeake-bay-drive-scotland-md-20687-e065e9ac4b93402586bfc4f997940e15) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/14940-chesapeake-bay-drive-scotland-md-20687-e065e9ac4b93402586bfc4f997940e15#listing", "url": "https://www.propertysimple.ai/listing/14940-chesapeake-bay-drive-scotland-md-20687-e065e9ac4b93402586bfc4f997940e15", "name": "14940 CHESAPEAKE BAY Drive, Scotland, MD 20687", "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. 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