Get new listings emailed daily! JOIN SIGN IN
The Jesse Hersh Team
REALTORS®
(717) 475-0378
Facebook Icon LinkedIn Icon Instagram Icon 
Refine Search

18323 Oakland Drive, Cobb Island, MD 20625

$359,900
  • 18323 Oakland Drive, Cobb Island, MD 20625 Main Photo

65 Total Photos [Click to View All]

BEDS3 BATHS2 full SQUARE FEET1,590 MLS#MDCH2050900
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONCOBB ISLAND SCHOOLCHARLES COUNTY PUBLIC SCHOOLS

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.

18323 Oakland Drive | MLS# MDCH2050900

This single family home located at 18323 Oakland Drive, Cobb Island, MD 20625 is currently listed for sale with an asking price of $359,900. This property was built in 1953 and has 3 bedrooms and 2 full baths with 1590 sq. ft. Oakland Drive is located in the COBB ISLAND subdivision within the CHARLES COUNTY PUBLIC SCHOOLS school district. Search COBB ISLAND real estate on www.jessehershteam.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Programmable Thermostat, Multi Units
Fuel Type: Electric, Oil
Heating: Baseboard - Hot Water, Wall Unit
Home Style: Cottage, Colonial
Lot Size: 1.82 Acres
Stories: 1.5
Taxes: $3,645
Year Built: 1953

Feature Descriptions

Accessibility: Level Entry - Main
Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer - Front Loading, Exhaust Fan, Microwave, Refrigerator, Stove, Washer - Front Loading
Exterior: Vinyl Siding
Exterior: Exterior Lighting, Outbuilding(s), Secure Storage
Flooring: Luxury Vinyl Plank
Lot: Front Yard, Level, Partly Wooded, Rear Yard, SideYard(s)
Lot Dimensions: 1.82 Acre(S)
Parking Notes: 3 Total Parking Spaces
Rooms: Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Kitchen, Family Room, Foyer, Bonus Room
Sewer: Public Sewer
SQFT Above Finished: 1590
SQFT Total Finished: 1590
Structure Type: Detached
Total Garage/Parking Spaces: 3
Water: Well
Wooded: Yes

Local Schools

High School: LA PLATA
Middle School: PICCOWAXEN
Elementary School: DR. THOMAS L. HIGDON
School District: CHARLES COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: CENTURY 21 New Millennium
Agency Phone: 3016099000

IDX logo

Estimate Your Payment

Estimated Payment

$ 1,209.70 per month $800.98 Principal & Interest $303.75 Property Tax $104.97 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Monthly PMI fees could increase payment if above 80% LTV)
Getting pre-qualified is the first step to buying a home! GET PREQUALIFIED NOW Home Mortgage Logo
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers 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 on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:00:05 AM EST) or Bright MLS (last updated Tue 03/03/2026 11:50:12 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.


Agent License Information: 
Licensed in Pennsylvania
The Jesse Hersh Team
Jesse Hersh, Aimee Brossman, Tyler Mow 

215 S. Centerville Road, Lancaster, PA 17603
717-393-0100

Login to Saved Search

Pixel