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10931 Piney Island Drive, Bishopville, MD 21813

$1,829,000
  • 10931 Piney Island Drive, Bishopville, MD 21813 Main Photo

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New to the Market
BEDS3 BATHS3 full SQUARE FEET4,443 MLS#MDWO2036564
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONPINEY ISLAND II SCHOOLWORCESTER COUNTY PUBLIC SCHOOLS

Property Description

A One-of-a-Kind Waterfront Sanctuary on the Peninsula of Piney Island Truly one of a kind, this remarkable custom residence is gracefully tucked away on the secluded peninsula of Piney Island. Welcome to 10931 Piney Island Drive, redesigned and rebuilt in 2012, where architecture, nature, and water converge to create an extraordinary coastal sanctuary. From the moment it comes into view, the home feels as though it has always belonged to this peaceful landscape. Cloaked in natural cedar shake siding and thoughtfully designed to blend with its wooded surroundings, the residence reflects a harmonious fusion of Craftsman, Asian, and classic Shingle-style architecture, elevated with clean modern lines and expansive glass. Perched in a regal position above the surrounding waterways, the home captures breathtaking panoramic views of Shingle Landing Prong and Perkins Creek. Here, the ever-changing light dances across the water, and the scenic waterways invite endless exploration, leading adventurous boaters all the way to the Atlantic Ocean. Inside, architectural artistry and refined craftsmanship take center stage. Walls of glass frame the spectacular natural surroundings, filling the home with light while blurring the boundary between indoors and out. Thoughtfully designed spaces, rich architectural details, and carefully curated finishes create interiors that rival the beauty of the landscape beyond. The kitchen has been beautifully refreshed in 2025 with new appliances including a refrigerator/freezer, dishwasher, wine cooler, and refrigerated drawers, creating a well-appointed culinary hub perfect for entertaining. Throughout the home, tray ceilings with ambient lighting add elegance to the bedrooms, dining room, and foyer, while unique features such as a dedicated humidor and a striking 75-gallon aquarium reflect the home’s custom character. Outdoor living here is nothing short of exceptional. Multiple decks, including three on the second level, offer private vantage points for soaking in the sweeping water views. Gather around the gas fire pit, enjoy the warmth of the outdoor fireplace while watching the game on the patio television, or relax on the welcoming front porch. The porch off the kitchen is perfect for grilling, making alfresco dining effortless. The grounds themselves feel like a private retreat, enhanced by two serene ponds, a gentle stream, and elegant rain chains that guide water into tranquil garden features. A waterfall and fountain create a peaceful backdrop to the rear patio, while perennial gardens cascade naturally along the waterfront bank. Boating and waterfront recreation are easily enjoyed from the private dock, which features a 12,000 pound boat lift, fish cutting station, and illuminated post for evening returns from the water. Recent improvements further enhance the home’s comfort and efficiency, including a new geothermal HVAC system in 2024, a renovated primary bath with updated flooring, tile, and fixtures, refreshed interior paint, updated flooring in the primary bedroom, and an upgraded hall bath. A whole-house generator, water treatment system, alarm system, and thoughtfully integrated multi-zone audio system provide modern convenience and peace of mind. The lower-level Utility/Storage room offers abundant space for all of your outdoor gear. There is a oversized 2-car garage with a walk-up to an additional room, perfect for an office and offers more storage options. Private, refined, and surrounded by breathtaking natural beauty, 10931 Piney Island Drive is more than a home, it is a waterfront retreat designed for living, gathering, and experiencing the very best of coastal life.

10931 Piney Island Drive | MLS# MDWO2036564

This single family home located at 10931 Piney Island Drive, Bishopville, MD 21813 is currently listed for sale with an asking price of $1,829,000. This property was built in 1986 and has 3 bedrooms and 3 full baths with 4443 sq. ft. Piney Island Drive is located in the PINEY ISLAND II subdivision within the WORCESTER COUNTY PUBLIC SCHOOLS school district. Search PINEY ISLAND II real estate on www.sandraleiby.com today.

Property Features

Property Type: Residential - Single Family
Basement: Outside Entrance, Poured Concrete
Basement: Yes
Cooling: Central A/C, Geothermal
Fireplaces: 2
Fuel Type: Geo-thermal, Propane - Leased
Garage: 2
Heating: Heat Pump(s), Other
Home Style: Contemporary, Craftsman
Lot Size: 0.56 Acres
Roof Type: Architectural Shingle, Pitched
Stories: 2.0
Taxes: $8,997
Year Built: 1986

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Refrigerator, Icemaker, Stove, Built-In Microwave, Built-In Range, Cooktop, Energy Efficient Appliances, Freezer, Oven - Double, Oven - Self Cleaning, Oven/Range - Gas, Range Hood, Stainless Steel Appliances, Water Dispenser
Building Name: NONE AVAILABLE
Exterior: Cedar, Stick Built, Brick, Cement Siding, Frame, Stone,
Exterior: Extensive Hardscape, Exterior Lighting, Stone Retaining Walls, Water Fountains, Bump-outs, Flood Lights
Fireplace: Mantel(s)
Flooring: Ceramic Tile, Hardwood, Luxury Vinyl Plank, Partially Carpeted, Slate
Interior: Bar, Breakfast Area, Built-Ins, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Dining Area, Entry Level Bedroom, Exposed Beams, Floor Plan - Open, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Recessed Lighting, Sound System, Upgraded Countertops, Walk-in Closet(s), Water Treat System, Window Treatments, Wood Floors, Wine Storage
Lot: Backs to Trees, Fishing Available, Front Yard, Landscaping, Partly Wooded, Rear Yard, SideYard(s)
Lot Dimensions: 0.56 Acre(S)
Parking Features: Brick Driveway
Parking Notes: 2 Total Parking Spaces
Rooms: Living Room, Primary Bedroom, Sitting Room, Kitchen, Family Room, Foyer, Great Room, Additional Bedroom
Sewer: Septic Pump
Special View Info: Bay, River
SQFT Above Finished: 4443
SQFT Total Finished: 4443
Structure Type: Detached
Total Garage/Parking Spaces: 2
Water: Well
Water Access: Boat - Powered
Waterfront: Rip-Rap
Windows: Casement, Double Pane, Insulated, Screens, Vinyl Clad, Wood Frame
Wooded: Yes

Room Sizes

Sitting Room: 11 x 10 Level - Main

Local Schools

High School: STEPHEN DECATUR
Middle School: STEPHEN DECATUR
Elementary School: SHOWELL
School District: WORCESTER COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Northrop Realty
Agency Phone: 3025390800

Shown By

Agent Name: Sandy Leiby
Agent Phone: (717) 659-9488
Agency Title: Berkshire Hathaway HomeServices Homesale Realty

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Estimated Payment

$ 5,353.77 per month $4,070.56 Principal & Interest $749.75 Property Tax $533.46 Homeowner's Insurance

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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 03/17/2026. The listing information on this page last changed on 03/17/2026. 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 Tue 03/17/2026 12:27:51 AM EST) or Bright MLS (last updated Tue 03/17/2026 12:21:56 AM 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.
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Agent License Information: 
Licensed in Pennsylvania
Sandra Bare Leiby 

1680 Kenneth Road, York, PA 17408
717-757-7811

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