12355 Southhampton Drive Bishopville, MD $ 2,795,000
12355 Southhampton Drive
$ 2,795,000
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12355 Southhampton Drive

Bishopville, MD, 21813
$ 2,795,000
Bedrooms5 Baths5.1 Sq 4,867

Monthly Estimate*

$ 17,648

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Single Family Home for sale in Bishopville, MD

for $2,795,000 with 5 bedrooms and 5 full baths, 1 half bath. This 4,867 square foot home was built in 2002 on a lot size of 1.14.

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.

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Single Family Active

Price

$ 2,795,000

Bedrooms

5

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 9,868

Style

Coastal

Lot Size

1.14

Year Built

2002

Town/City

Bishopville

County/Region

Worcester

MLS | Web ID

MDWO2039008

Features
General
Living Area 4867
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C
Possession Settlement
Roof Shingle
Appliances Dryer Washer Dishwasher Exhaust Fan Disposal Microwave Refrigerator Cooktop Oven - Wall Oven - Double
Zoning R-1
HOA Fee 1017.00
Garage Spaces 3.00
Association Fee Includes Snow Removal
Patio/Porch Features Deck(s) Wrap Around
Architectural Style Coastal
Security Features Main Entrance Lock Smoke Detector
Construction Materials Stone
School District WORCESTER COUNTY PUBLIC SCHOOLS
Year Built 2002
View Bay Panoramic City
Levels 2
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Waterfront Features None
Building Name NONE AVAILABLE
Accessibility Other
Assoc Fee Paid Per Annually
County WORCESTER
New Construction N
Property Type Residential
Association Amenities Club House Golf Course
HOA Y
Subdivision Name LIGHTHOUSE SOUND
Garage Y/N Y
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 5
Status ACTIVE
Directions From Ocean City Expy/MD-90 Ttrn right onto Saint Martins Neck Rd. Turn right onto Southhampton Dr.
City BISHOPVILLE
Body of Water Assawoman Bay
Senior Community Y/N N
MLS Area Worcester East of Rt-113
Lot Size Units Square Feet
Lot Size Square Feet 49658.00
Tax Annual Amount 9868.0
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 1
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 574.28
Vacation Rental Y/N N
Virtual Tour https://unbranded.youriguide.com/12355_southhampton_dr_bishopville_md
Standard Status Active
Year Built Source Assessor
Legal Subdivision Lighthouse Sound
Tax Lot 29
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Interior
Interior Amenities Bathroom - Jetted Tub Bathroom - Tub Shower Bathroom - Stall Shower Bathroom - Walk-In Shower Breakfast Area Built-Ins Butlers Pantry Ceiling Fan(s) Crown Moldings Dining Area Entry Level Bedroom Flo
Heating Fuel Electric
Flooring Ceramic Tile Hardwood
Total Fireplaces 2
Fireplace Features Gas/Propane
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Window Features Double Hung Double Pane Screens Sliding Transom Vinyl Clad
Fireplace Y/N Y
Above Grade Finished Area 4867
Half Baths 1
Central Air Y/N Y
Total Bedrooms 5
Below Grade Finished Area 0
Room Type Living Room Dining Room Primary Bedroom Bedroom 2 Bedroom 3 Bedroom 4 Bedroom 5 Kitchen Breakfast Room Laundry Other Office
Main Level Bedrooms 1
Below Grade Finished Area Unit Type Square Feet
Laundry Type Has Laundry Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 6
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Exterior
Exterior Amenities Extensive Hardscape Exterior Lighting
Pool No Pool
Parking Features Brick Driveway
Water Source Well
Garage Features Garage - Front Entry Oversized Garage Door Opener
Type of Parking Attached Garage
Foundation Details Crawl Space
Water View Y/N Y
Lot Dimensions 0.00 x 0.00
Lot Size Acres 1.14
Water Body Type Bay
Lot Size Source Assessor
Waterfront Y/N Y
Door Features Six Panel Double Entry Sliding Glass
Land Assessed Value 0.00
Navigable Water Y/N Y
Water Oriented Y/N Y
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Internal Only
Street Number 1 12355
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* Excluded Features
List By
Northrop Realty

Broker

anniebuxbaum1@gmail.com

Email

Affordability Calculator

$18,470
Per Month
96%
4%
0%
Monthly Principal & Interest
$17,648
Monthly Property Taxes
$822
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3533548 Elementary School
3533416 Middle School
Stephen Decatur High School High School
Pricing History
DatePricePrice ChangeDescription
6/26/2026$2,795,000 Listed Price

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12355 Southhampton Drive, Bishopville, MD, 21813 is a Single Family Home for sale at $2,795,000 with 4,867 sqft and a lot size of 1.14. 12355 Southhampton Drive has 5 bedrooms, 5.1 baths, and was built in 2002. The property's zip code is 21813 which is in Bishopville, MD