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.
For sale
$799,000
14940 Chesapeake Bay Dr, Scotland, MD 20687
4beds
1,644sqft
Single Family Residence
Built in 1996
1.08 Acres Lot
$605,100 Zestimate®
$486/sqft
$-- HOA
What's special
Charming waterfront a-frameCozy fireplaceSandy beachRenovated kitchenCovered parkingNew kitchen appliancesWarm and inviting atmosphere
- 9 days
- 845
- 66
Zillow last checked:
Listing updated:
Listed by:
Jessica Raley 301-904-1781,
CENTURY 21 New Millennium 3018622169
Source: Bright MLS,MLS#: MDSM2032020
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 2
- Main level bedrooms: 2
Rooms
- Room types: Living Room, Primary Bedroom, Bedroom 3, Kitchen, Bedroom 1, Other, Bathroom 2
Primary bedroom
- Features: Flooring - HardWood
- Level: Upper
- Area: 192 Square Feet
- Dimensions: 12 X 16
Bedroom 1
- Level: Main
Bedroom 3
- Features: Flooring - HardWood
- Level: Upper
- Area: 143 Square Feet
- Dimensions: 11 X 13
Bathroom 2
- Level: Upper
Kitchen
- Features: Flooring - Tile/Brick
- Level: Main
- Area: 247 Square Feet
- Dimensions: 13 X 19
Living room
- Features: Flooring - HardWood
- Level: Main
- Area: 228 Square Feet
- Dimensions: 12 X 19
Other
- Level: Unspecified
Screened porch
- Level: Main
- Area: 288 Square Feet
- Dimensions: 12 X 24
Heating
- Forced Air, Heat Pump, Electric, Oil
Cooling
- Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Dishwasher, Exhaust Fan, Refrigerator, Cooktop, Water Heater, Electric Water Heater
- Laundry: Main Level
Features
- Kitchen - Table Space, Entry Level Bedroom, Open Floorplan, 2nd Kitchen, Family Room Off Kitchen, 9'+ Ceilings, High Ceilings, Cathedral Ceiling(s)
- Flooring: Ceramic Tile, Hardwood, Wood
- Doors: Six Panel, Sliding Glass
- Windows: Window Treatments
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Equipment, Wood Burning
Interior area
- Total structure area: 1,644
- Total interior livable area: 1,644 sqft
- Finished area above ground: 1,644
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Gravel, Off Street, Driveway, Detached Carport
- Carport spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Other
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch, Screened Porch
- Exterior features: Balcony
- Pool features: None
- Has view: Yes
- View description: Water, Bay
- Has water view: Yes
- Water view: Water,Bay
- Waterfront features: Sandy Beach, Bayfront, Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Swimming Allowed, Waterski/Wakeboard, Bay
- Body of water: Chesapeake Bay
- Frontage length: Water Frontage Ft: 76
Lot
- Size: 1.08 Acres
- Features: No Thru Street
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Additional parcels included: 14945 Chesapeake Bay Drive
- Parcel number: 1901016288
- Zoning: RPD
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: A-Frame
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Crawl Space
- Roof: Shingle
Condition
- Excellent
- New construction: No
- Year built: 1996
Utilities & green energy
- Sewer: Septic Exists
- Water: Well-Shared
- Utilities for property: Cable Available, Phone Available
Community & HOA
Community
- Subdivision: Rodo Beach
HOA
- Has HOA: No
Location
- Region: Scotland
Financial & listing details
- Price per square foot: $486/sqft
- Tax assessed value: $479,100
- Annual tax amount: $4,293
- Date on market: 9/1/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,VA Loan
- Inclusions: 14945 Chesapeake Bay Drive
- Ownership: Fee Simple
Estimated market value
$605,100
$569,000 - $641,000
$2,729/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/1/2026 | Listed for sale | $799,000+82%$486/sqft |
Source:  Bright MLS #MDSM2032020 Report a problem | ||
| 8/12/2020 | Sold | $439,000-1.3%$267/sqft |
Source: Public Record Report a problem | ||
| 4/21/2020 | Listed for sale | $445,000-3.1%$271/sqft |
Source: Century 21 New Millennium #MDSM168940 Report a problem | ||
| 3/1/2020 | Listing removed | $459,000$279/sqft |
Source: CENTURY 21 New Millennium #MDSM164378 Report a problem | ||
| 12/2/2019 | Price change | $459,000-8%$279/sqft |
Source: CENTURY 21 New Millennium #MDSM164378 Report a problem | ||
| 8/23/2019 | Listed for sale | $499,000+0.8%$304/sqft |
Source: CENTURY 21 New Millennium #MDSM164378 Report a problem | ||
| 6/22/2018 | Listing removed | $495,000$301/sqft |
Source: CENTURY 21 New Millennium #1004273681 Report a problem | ||
| 1/16/2018 | Listed for sale | $495,000-17.5%$301/sqft |
Source: CENTURY 21 New Millennium #1004273681 Report a problem | ||
| 12/13/2017 | Listing removed | $599,900$365/sqft |
Source: Century 21 New Millennium #1001774647 Report a problem | ||
| 11/14/2017 | Price change | $599,900+26.3%$365/sqft |
Source: Century 21 New Millennium #1001774647 Report a problem | ||
| 3/13/2017 | Pending sale | $475,000$289/sqft |
Source: CENTURY 21 New Millennium #SM9874281 Report a problem | ||
| 3/3/2017 | Listed for sale | $475,000$289/sqft |
Source: Century 21 New Millennium #SM9874281 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,865 +22% | $447,300 +7.7% |
| 2024 | $3,988 +8.3% | $415,500 +8.3% |
| 2023 | $3,683 +0.7% | $383,700 |
| 2022 | $3,656 +0.7% | $383,700 +1.5% |
| 2021 | $3,630 +0.7% | $378,167 +0.7% |
| 2020 | $3,603 | $375,400 |
| 2019 | $3,603 | $375,400 |
| 2018 | $3,603 -1.4% | $375,400 -0.5% |
| 2017 | $3,656 -25.4% | $377,300 |
| 2016 | $4,902 | $377,300 |
| 2015 | $4,902 | $377,300 -6.1% |
| 2014 | $4,902 | $401,900 |
| 2013 | -- | $401,900 |
| 2012 | -- | $401,900 -14.1% |
| 2011 | -- | $467,630 +2.1% |
| 2010 | -- | $458,230 +2.1% |
| 2009 | -- | $448,830 +2.1% |
| 2008 | -- | $439,430 +20.3% |
| 2007 | -- | $365,236 +25.4% |
| 2006 | -- | $291,316 +34.2% |
| 2005 | -- | $217,050 +0.1% |
| 2004 | -- | $216,906 -1.7% |
| 2003 | -- | $220,693 +1.9% |
| 2002 | -- | $216,620 +1.8% |
| 2001 | -- | $212,882 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 20687
Nearby schools
Schools provided by the listing agent
- District: St. Mary's County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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