Date
Details
Price
Change
Source
1/24/2026
Listed
$359,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/65
$359,900 Just Listed
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Property Description
Situated on an unusually large 1.8+ acre lot on charming Cobb Island, this adorable cottage-style home offers the perfect blend of comfort, character, and island living. Designed for easy main-level living, with primary bedroom, full bath and washer & dryer all on the main level. The spacious family room invites you to relax, while the galley kitchen flows into a cozy dining area-ideal for everyday living or weekend getaways. A generous foyer and second bedroom complete the main level. Upstairs, you'll find a true retreat: an additional bedroom, another full bath, and extra living space that's perfect for guests, a home office, or a quiet escape. Outside, the expansive lot provides endless possibilities, complemented by one large garage/shed plus two additional oversized sheds-plenty of room for storage, hobbies, or island toys. Whether you're looking for a full-time residence or a peaceful getaway, this home delivers. Located in a water-oriented community, you'll enjoy nearby water access, marinas, waterfront restaurants, and a local market, all while benefiting from a highly sought-after school district. This is Cobb Island living at its best-laid-back, welcoming, and full of charm.
Full Property Details
Full Property Details for 18323 Oakland Dr
General
- Price: $359,900
- Taxes: $3,645 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDCH2050900
- Updated: 1/24/2026
- Added to Site: 5 day(s) ago
Interior
- Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Foyer, Bonus Room
- Appliances: Dishwasher, Disposal, Dryer - Front Loading, Exhaust Fan, Microwave, Refrigerator, Stove, Washer - Front Loading
- Flooring: Luxury Vinyl Plank
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Upper Floor Baths: 1
- Upper - Full Baths: 1
- Main Floor Baths: 1
- Main - Full Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 1
- Bedrooms Main & Up: 2
Other Rooms
- Laundry: Main Floor
Exterior
- Exterior Features: Exterior Lighting, Outbuilding(s), Secure Storage
Parking
- Total Spaces: 3
- Parking Type: Driveway
Location
- County: CHARLES
- Subdivision: COBB ISLAND
- Driving Directions: 301 to RT257(Rock Point Rd), right on Cobb Island Rd, left on Neale Sound Dr, continue left on Neale Sound Dr, , right on Oakland Dr to house on the right.
School Information
- School District: Charles County Public Schools
- Elementary School: Dr. Thomas L. Higdon
- Middle School: Piccowaxen
- High School: La Plata
Heating & Cooling
- Cooling Type: Programmable Thermostat, Multi Units
- Cooling Fuel: Electric
- Heating Type: Baseboard - Hot Water, Wall Unit
- Heating Fuel: Electric, Oil
- Water Heater: Oil
Utilities
- Sewer: Public Sewer
- Water: Well
Structural Information
- Architectural Style: Cottage, Colonial
- Structure Type: Detached
- Construction: Vinyl Siding
- Foundation: Crawl Space
- Walls/Ceilings: Dry Wall
- Stories Description: Main, Upper 1
- Square Feet: 1,590
- Sq. Ft. Source: Assessor
- Living Area: 1,590 Sq. Ft.
- Finished Above Grnd: 1,590 Sq. Ft.
- Year Built: 1953
- Year Built Source: Assessor
- Property Condition: Very Good
Additional Structures
- Other Structures: Shed, Storage Barn/Shed
Lot Features
- Lot Size (Acres): 1.82
- Lot Size (Sq. Ft.): 79,279
- Lot Size Source: Estimated
- Zoning: RV
- Lot Description: Front Yard, Level, Partly Wooded, Rear Yard, SideYard(s)
Financial Considerations
- Price Per Sq. Ft.: $226.35
- Assessment Year: 2025
- County Tax: $3,318
- County Tax Freq: Annually
- Tax w/Assessment: $258,000
- Tax Amount: $3,645
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1590
Disclosures and Reports
- Ownership: Fee Simple
- Multiple Parcels: Yes
- Section: A
- Lot Number: 152-155 & 187-188
Listed by CENTURY 21 New Millennium, Christy M Gartland
We Value Your Privacy
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Listing agent
— 18323 Oakland Dr —
Christy M Gartland
CENTURY 21 New Millennium
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 18323 Oakland Dr
School District:Charles County Public Schools
| Name | Grades | Distance |
|---|---|---|
Dr. Thomas L. Higdon Elementary School 12872 Rock Point Road, Newburg, MD 20664 | PK-5 | 8.6 mi |
Piccowaxen Middle School 12834 Rock Point Road, Newburg, MD 20664 | 6-8 | 8.8 mi |
La Plata High School 6035 Radio Station Road, La Plata, MD 20646 | 9-12 | 20.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 18323 Oakland Dr
Tax History
Tax History for 18323 Oakland Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,520
15%
$258,000
11%
2023
$3,049
—
$232,800
12%
2023
$3,049
21%
$207,600
3%
2022
$2,518
7%
$200,933
3%
2018
$2,344
-13%
$194,267
4%
2021
$2,692
3%
$187,600
3%
2020
$2,612
4%
$182,800
3%
2019
$2,510
3%
$178,000
3%
2018
$2,440
1%
$173,200
—
2017
$2,420
1%
$173,200
—
2016
$2,404
—
$173,200
—
2015
$2,404
—
$174,000
—
2014
$2,404
—
$174,000
—
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
Estimate the Cost for 18323 Oakland Dr
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- Active
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- Single Family
- Active
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- Updated 1 day ago
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- 1,296Sq. Ft.
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- Single Family
- Closed
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,410Sq. Ft.
18323 Oakland Drive, Cobb Island, MD 20625 (MLS# MDCH2050900) is a Single Family property with 3 bedrooms and 2 full bathrooms. 18323 Oakland Drive is currently listed for $359,900 and was received on January 24, 2026. Want to learn more about 18323 Oakland Drive? Do you have questions about finding other Single Family real estate for sale in Cobb Island? You can browse all Cobb Island real estate or contact a Coldwell Banker agent to request more information.