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$799,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1,644 Sq. Ft.
  • Updated 4 days ago
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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.

Full Property Details for 14940 Chesapeake Bay Dr

General

  • Price: $799,000
  • Taxes: $4,293 (2025)
  • Status: Coming Soon
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2032020
  • Updated: 6/27/2026
  • Added to Site: 5 day(s) ago
  • Expected Market Date: 7/26/2026

Interior

  • Rooms/Areas: Living Room, Primary Bedroom, Bedroom 3, Kitchen, Bedroom 1, Other, Bathroom 2, Screened Porch
  • Interior Features: Kitchen - Table Space, Entry Level Bedroom, Window Treatments, Wood Floors, Floor Plan - Open, 2nd Kitchen, Family Room Off Kitchen
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Equipment, Wood
  • Appliances: Dishwasher, Exhaust Fan, Refrigerator, Stove, Water Heater
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 2
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Main Floor

Exterior

  • Exterior Features: Outbuilding(s)
  • Porch/Patio/Deck: Deck(s), Balconies- Multiple, Porch(es)

Parking

  • Carport Spaces: 2
  • Total Spaces: 6
  • Parking Features: Gravel Driveway
  • Parking Type: Off Street, Driveway, Detached Carport

Location

  • County: SAINT MARYS
  • Subdivision: RODO BEACH
  • Driving Directions: Rt 5 South to Scotland, Continue straight past monument, Left on Rodo Beach Rd to T Right at T onto Chesapeake Bay Dr, home near end on left, cottage on the right.
  • Location Details: Bayfront

School Information

  • School District: St. Mary's County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Heat Pump(s)
  • Heating Fuel: Electric, Oil
  • Water Heater: Electric

Utilities

  • Sewer: Septic Exists
  • Water: Well-Shared
  • Dist. to Water: 0 Feet
  • Utility Description: Cable TV Available, Phone Available

Structural Information

  • Architectural Style: A-Frame
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Crawl Space
  • Roof: Shingle
  • Walls/Ceilings: 9'+ Ceilings, High, Cathedral Ceilings
  • Doors: Six Panel, Sliding Glass
  • Stories Description: Main, Upper 1
  • Square Feet: 1,644
  • Sq. Ft. Source: Estimated
  • Living Area: 1,644 Sq. Ft.
  • Finished Above Grnd: 1,644 Sq. Ft.
  • Year Built: 1996
  • Year Built Source: Assessor
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Shed, 2nd House

Lot Features

  • Property View: Water, Bay
  • Lot Size (Acres): 1.08
  • Lot Size (Sq. Ft.): 47,044
  • Lot Size Source: Estimated
  • Zoning: RPD
  • Lot Description: No Thru Street

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Swimming Allowed, Waterski/Wakeboard
  • Water Front Type: Bay
  • Water Front Name: Chesapeake Bay
  • Docks: 1
  • Power Boats: 2
  • Non-Power Boats: 3-5

Financial Considerations

  • Price Per Sq. Ft.: $486.01
  • Assessment Year: 2026
  • County Tax: $4,293
  • County Tax Freq: Annually
  • Tax w/Assessment: $479,100
  • Tax Amount: $4,293
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1484

Disclosures and Reports

  • Ownership: Fee Simple
  • Multiple Parcels: Yes
  • Inclusions: 14945 Chesapeake Bay Drive

Listed by CENTURY 21 New Millennium, Jessica D Raley

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Listing agent

— 14940 Chesapeake Bay Dr —

  • Jessica D Raley

    CENTURY 21 New Millennium

Listing Office Email: tommy.higgins@c21nm.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14940 Chesapeake Bay Dr

School District:St. Marys County Public Schools
NameGradesDistance
Ridge Elementary School, Ridge, MD
49430 Airedale Rd, Ridge, MD 20680
PK-53 mi
Spring Ridge Middle School
19856 Three Notch Road, Lexington Park, MD 20653
6-810.1 mi
Great Mills High School
21130 Great Mills Road, Great Mills, MD 20634
9-1214.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14940 Chesapeake Bay Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/27/2026
Listed
$799,000
82%
MLS
7/20/2020
Sold
$439,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14940 Chesapeake Bay Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$4,116
—
$447,300
8%
2023
$4,116
—
$415,500
8%
2023
$4,116
13%
$383,700
1%
2022
$3,656
-1%
$380,933
1%
2019
$3,693
-8%
$378,167
1%
2020
$4,022
—
$375,400
—
2019
$4,021
—
$375,400
-1%
2018
$4,021
—
$377,300
—
2017
$4,038
1%
$377,300
—
2016
$3,996
-4%
$377,300
-6%
2015
$4,148
-3%
$401,900
—
2014
$4,267
—
$401,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 14940 Chesapeake Bay Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by CENTURY 21 New Millennium, Jessica D Raley

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14940 Chesapeake Bay Drive, Scotland, MD 20687 (MLS# MDSM2032020) is a Single Family property with 4 bedrooms and 3 full bathrooms. 14940 Chesapeake Bay Drive is currently listed for $799,000 and was received on June 27, 2026. Want to learn more about 14940 Chesapeake Bay Drive? Do you have questions about finding other Single Family real estate for sale in Scotland? You can browse all Scotland real estate or contact a Coldwell Banker agent to request more information.

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