$2,795,000

12355 Southhampton Dr, Bishopville, MD, 21813

5

Beds

Baths

4,867

Square feet

1.14

Acres

Welcome to 12355 Southampton Drive, the crown jewel of Lighthouse Sound, one of the Eastern Shore's most prestigious waterfront golf communities. This is a rare opportunity to own arguably the finest homesite in the neighborhood, where this extraordinary custom residence captures sweeping panoramic views of Assawoman Bay and the sparkling Ocean City skyline from nearly every rear-facing room. A dramatic two-story foyer with a graceful curved staircase sets the tone, drawing your eye straight through the soaring great room to the breathtaking water beyond. The two-story family room is anchored by a stunning natural stone fireplace with gas insert, creating an unforgettable gathering space framed by walls of glass. Designed for both everyday living and effortless entertaining, the chef's kitchen features gas cooking, granite countertops, a large center island, breakfast bar, sunny dining nook, walk-in pantry, and a fully equipped butler's pantry complete with wet bar and sink. Every space is thoughtfully connected to the expansive rear decks, ensuring the spectacular views are always part of the experience. The luxurious first-floor primary suite is a true private retreat, offering direct deck access, uninterrupted bay views, two professionally organized walk-in closets, and a spa-inspired bath with dual vanities, soaking tub, and oversized walk-in shower. A private study, spacious dining room, and main-level laundry complete the first floor. Upstairs, an impressive open landing overlooks the great room below and leads to four generously sized guest suites, each with private vanity and dressing areas and convenient en-suite bath access, providing exceptional comfort for family and guests alike. The outdoor living is every bit as remarkable as the interior. Nearly 1,700 square feet of wraparound Trex decking spans the rear of the home across two levels, creating an unparalleled setting for morning coffee, sunset cocktails, entertaining under the stars, or relaxing around the fire pit while watching boats drift across the bay and the Ocean City skyline come alive each evening. During the summer, enjoy a front-row seat to the free fireworks display every Sunday evening, launched from Northside Park just across the bay, a spectacular tradition that can be enjoyed from the comfort of your own deck. Additional highlights include Brazilian cherry hardwood flooring throughout, an oversized three-bay garage with abundant storage for vehicles and water toys, recessed lighting, ceiling fans, and quality craftsmanship throughout. Residents of Lighthouse Sound enjoy championship golf, an elegant clubhouse, dining, and one of the most spectacular waterfront settings on Maryland's Eastern Shore. Luxury. Views. Lifestyle. Rare opportunity. This isn't simply a home, it's a front-row seat to one of the most breathtaking waterfront panoramas on the East Coast. Once you experience the views from 12355 Southampton Drive, everywhere else feels ordinary.

Listing Details

OfficeNorthrop Realty
Buyer Broker Compensation 1.5% All offers of buyer broker compensation or seller concessions are negotiable and must be memorialized in a written agreement between the parties. Please consult with your real estate agent for more information.

Facts & Features

MLS® # MDWO2039008
Price $2,795,000
Bedrooms 5
Bathrooms 5.50
Full Baths 5
Half Baths 1
Square Footage 4,867
Acres 1.14
Year Built 2002
Type Residential
Sub-Type Detached
Style Coastal
Status Active

Community Information

Address 12355 Southhampton Dr
Area Worcester East of Rt-113
Subdivision LIGHTHOUSE SOUND
City Bishopville
County WORCESTER-MD
State MD
Zip Code 21813
Senior Community No

Amenities

Amenities Bathroom - Jetted Tub, Bathroom - Tub Shower, Bathroom - Stall Shower, Bathroom - Walk-In Shower, Built-Ins, Butlers Pantry, Ceiling Fan(s), Crown Moldings, Entry Level Bedroom, Pantry, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Window Treatments, Wood Floors
Parking Brick Driveway
# of Garages 3
Garages Garage - Front Entry, Oversized, Garage Door Opener
View Bay, Panoramic, City
Is Waterfront Yes
Waterfront Bay
HOA Amenities Club House, Golf Course

Interior

Interior Features Floor Plan - Traditional
Appliances Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Cooktop, Oven - Wall, Oven - Double
Heating Heat Pump(s)
Cooling Central A/C
Fireplace Yes
# of Fireplaces 2
Fireplaces Gas/Propane
Stories 2

Exterior

Exterior Stone
Exterior Features Extensive Hardscape,Exterior Lighting,Deck(s),Wrap Around
Windows Double Hung, Double Pane, Screens, Sliding, Transom, Vinyl Clad
Roof Shingle
Construction Stone
Foundation Crawl Space
Other Structures 10000001172,10000001174

School Information

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

Additional Information

Date Listed June 25th, 2026
Days on Market 69
Zoning R-1
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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