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Single family home for sale at 14940 Chesapeake Bay Dr, Scotland, MD 20687 | MLS# MDSM2032020 | Listing updated on 2026-09-22
Photo 1 of Single family home for sale at 14940 Chesapeake Bay Dr, Scotland, MD 20687 | MLS# MDSM2032020 | Listing updated on 2026-09-22
Photo 2 of Single family home for sale at 14940 Chesapeake Bay Dr, Scotland, MD 20687 | MLS# MDSM2032020 | Listing updated on 2026-09-22
Photo 3 of Single family home for sale at 14940 Chesapeake Bay Dr, Scotland, MD 20687 | MLS# MDSM2032020 | Listing updated on 2026-09-22
Photo 4 of Single family home for sale at 14940 Chesapeake Bay Dr, Scotland, MD 20687 | MLS# MDSM2032020 | Listing updated on 2026-09-22
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$799,000

Monthly Est:$3,977

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,644sqft

14940 Chesapeake Bay Dr, Scotland, MD 20687

$3,977/moEst:

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  • Single Family Residence

  • Built in 1996

  • $-- HOA

  • 1.08 acres lot

  • $486/sq.ft

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 enh
anced 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.

  • Houzeo last checked: 0 minutes ago
  • Listing updated: September 22, 2026 at 7:35 pm
  • Listing Provided by: Jessica D Raley (301) 904-1781 | CENTURY 21 New Millennium (301) 862-2169
  • Source: Bright MLS-NJ | MLS#: MDSM2032020 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Saint Marys Md County

  • City

    Scotland

  • Neighborhood

    --

  • Year Built

    1996

  • HOA Fees

    -

  • Finished Area

    1,644 sqft

  • Lot Size

    1.08 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDSM2032020

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    22

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Flooring

    Ceramic Tile, Hardwood

  • Interior Features

    Kitchen Table Space, Entry Level Bedroom, Window Treatments, Wood Floors, Floor Plan Open, 2nd Kitchen, Family Room Off Kitchen

  • Sewer

    Septic Exists

  • Appliances

    Dishwasher, Exhaust Fan, Refrigerator, Stove, Water Heater

  • Exterior Features

    Outbuilding(s)

  • Heating

    Forced Air, Heat Pump(s)

  • Cooling

    Ceiling Fan(s), Central A/c

Construction

  • Year Built

    Year Built: 1996

  • Home type

    Single Family Residence

  • Property Condition

    Excellent

  • Architectural Style

    A Frame

  • Roof

    Shingle

  • Construction Materials

    Frame

  • Foundation Details

    Crawl Space

Utilities & Energy

  • Fireplace Features

    Equipment, Wood

  • Parking Features

    Gravel Driveway

  • Utilities

    Cable Tv Available, Phone Available

  • Water Source

    Well Shared

Other Features

  • Patio And Porch Features

    Deck, Balconies Multiple, Porch

  • Lot Features

    No Thru Street

  • Subdivision Name

    Rodo Beach

Price History

DateEventPrice

09/01/2026

Source: mls_logoBright MLS-NJ #MDSM2032020

Listed for Sale

$799,000 +82.00%

$486/sqft

07/21/2020

Source: mls_logoBright MLS-NJ #MDSM168940

Price Increased

$439,000 +46.82%

$267/sqft

05/06/2013

Source: mls_logoBright MLS-NJ #1003429576

Price Increased

$299,000 +19833.33%

$182/sqft

10/19/2010

Source: mls_logoBright MLS-NJ #1005016752

Sold

$1,500

$1/sqft

Nearby Homes

Based on information from Bright MLS through Oct 09, 2026, 11:00AM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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