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12355 Southhampton Dr , Bishopville, MD 21813
$2,795,000
Est. Payment: $14,876.16/mo
5 Bed
6 Bath
4867 Sqft
1.14 Acres
Status: active | Days on site: 128
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NRP9 - 3255910
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House Description

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.

Highlights

Listed by Ann Buxbaum , 4432350878 Northrop Realty , 3025390800. Bright MLS

Property Type

Residential

Lot/Acreage
1.14

HOA Fee

1017 Annually

Year Built

2002

County

Worcester

Area

Worcester East of Rt-113

Neighborhood

Lighthouse Sound

School District

Worcester County Public Schools

Listing ID

MDWO2039008

Questions about this listing?

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:5
  • ▪ Bathrooms:6
  • ▪ Full Bathrooms:5
  • ▪ 1/2 Bathrooms:1
Appliances:Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Cooktop, Oven - Wall, Oven - Double
Air Cond:Central A/C
Fireplaces:Gas/Propane,2 Fireplaces
Floor:Ceramic Tile,Hardwood
Above Ground Sq Ft:4867
Other:
  • ▪ Main Floor Bedrooms:1
  • ▪ Additional: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, Floor Plan - Traditional, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Window Treatments, Wood Floors
Water:Well

Exterior Features

Lot:Not New Construction,Horse Property: No,Waterfront
Lot Dimensions:0.00 x 0.00
Garage Capacity:3
Zoning:R-1
Roof:Shingle
Others:
  • ▪ Additional:Extensive Hardscape, Exterior Lighting, Club House, Golf Course, Snow Removal
Sewer:Public Sewer
Parking Features:Brick Driveway,Garage - Front Entry,Oversized,Garage Door Opener,Attached Garage,3+ Spaces,2+ Spaces,1+ Spaces
Principal Interest
$14,876
Taxes
$822
HOA
$1,017

Home Price

$2,795,000

Loan Details

30 yrs
7%

Down Payment

20%
$559,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$14,876.16

Principal

Taxes

HOA

Principal Taxes HOA Total
Monthly $14,876.16 $822.33 $1,017.00 $16,715.50
Yearly $178,513.97 $9,868.00 $12,204.00 $200,585.97
Total $5,355,418.97 $296,040.00 $366,120.00 $6,017,578.97
Lender profile image
Chico Gordy
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Market insight data is pulled from the same city as the listing being viewed (Bishopville, MD).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Information provided by Bright MLS, and is deemed reliable but not guaranteed accurate.

IDX service by Blueroof 360

Data last updated: 2026-11-14T01:13:51.000Z

© 2026 Bright MLS