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12355 Southhampton DriveBishopville, MD 21813Price: $2,795,000

  • Price: $2,795,000
  • Est. Mortgage of $/month
  • 20 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jul 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $2,795,000List Price
  • 5Bedrooms
  • 6Bathrooms
  • 4,867Square Feet
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.
Listed by Ann Buxbaum of Northrop Realty

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • Date Listed06/25/2026
  • ZoningR-1
  • MLS Area MajorWorcester East of Rt-113
  • UsmAreaBishopville - Worcester East of Rt-113

School Information

  • Junior HighStephen Decatur
  • High SchoolStephen Decatur
  • Elementary SchoolShowell

Basic Information

Building

  • ViewBay, Panoramic, City
  • Water Oriented YNYes
  • Rooms
    • Bedroom 2
    • Bedroom 3
    • Bedroom 4
    • Bedroom 5
    • Breakfast Room
    • Dining Room
    • Kitchen
    • Laundry
    • Living Room
    • Office
    • Other
    • Primary Bedroom
  • Door FeaturesSix Panel, Double Entry, Sliding Glass
  • Walls CeilingsHigh,2 Story Ceilings,9'+ Ceilings, Dry Wall
  • Interior FeaturesBathroom - 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
  • Association Fee$1,017
  • Association Fee FrequencyAnnually
  • Association Fee IncludesSnow Removal
  • Security FeaturesMain Entrance Lock, Smoke Detector
  • Association YNYes
  • High School DistrictWorcester County Public Schools
  • Broker NameNorthrop Realty
  • Building Number12355
  • Distance To Body Of Water50
  • DirectionsFrom Ocean City Expy/MD-90, Ttrn right onto Saint Martins Neck Rd. Turn right onto Southhampton Dr.
  • Distance To Body Of Water UnitsFeet
  • Num Attached Garage Spaces3
  • Main Level Total Baths2
  • Main Level Bedrooms1
  • Main Level Half Baths1
  • Main Level Full Baths1
  • Upper Levels Total Full Baths4
  • Upper Levels Total Bedrooms4
  • Upper Levels Total Baths4
  • Upper Level1 Bedrooms4
  • Upper Level1 Full Baths4
  • Upper Level1 Total Baths4
  • Story ListMain, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsStone
  • Property StyleCoastal
  • Bedrooms5
  • Full Bath5
  • Bathroom6
  • Half Baths1
  • Laundry TypeHas Laundry, Main Floor
  • Levels2
  • Fireplace FeaturesGas/Propane
  • Fireplace YNYes
  • Fireplace2
  • Garage TypeGarage - Front Entry, Oversized, Garage Door Opener
  • Garage Spaces3
  • GarageYes
  • Patio And Porch FeaturesDeck(s), Wrap Around
  • Garage SQFT960

Basic Information

  • MLS NumberMDWO2039008
  • Ownership InterestFee Simple
  • List Price$2,795,000
  • Square Feet4,867
  • Acreage1.14
  • Year Built2002
  • MLS Property TypeResidential
  • StatusACT
  • HOA Fee1017.00 / Annually

Parking

  • Parking FeaturesBrick Driveway
  • Parking TypesAttached Garage
  • Total Garage And Parking Spaces3

Property

  • Lot Size Dimensions0.00 x 0.00
  • New Construction YNN

Exterior

  • RoofShingle
  • FoundationCrawl Space
  • Window FeaturesDouble Hung, Double Pane, Screens, Sliding, Transom, Vinyl Clad
  • Exterior FeaturesExtensive Hardscape, Exterior Lighting

Utilities

  • Water SourceWell
  • SewerPublic Sewer
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterElectric
  • Heating FuelElectric
  • Heat SystemHeat Pump(s)

Water Body

  • Water View YNYes
  • Waterfront FeaturesNone, Navigable Water
  • WaterfrontYes
  • Water Body TypeBay
  • Water Body NameAssawoman Bay
  • Water AccessYes

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Total Finished Sq Ft4,867
  • Tax Assessment Amount1219800
  • Tax Year2025
  • Taxes$9,868
  • County Tax$8,676
  • County Tax Payment FrequencyAnnually
  • Assessment Year2026

Location

  • Address12355 Southhampton Drive
  • Area Total4,867
  • SubdivisionLighthouse Sound
  • TownBishopville
  • StateMD
  • Zip21813
  • CountyWorcester

Interior

  • FlooringCeramic Tile, Hardwood
  • Appliances Included
    • Cooktop
    • Dishwasher
    • Disposal
    • Dryer
    • Exhaust Fan
    • Microwave
    • Oven - Double
    • Oven - Wall
    • Refrigerator
    • Washer
  • Heating YNYes
  • CoolingCentral A/C

Property Information

  • Lot Size Square Feet49,658
  • Above Grade Finished Area4867

Amenities

  • PoolNo Pool
  • AmenitiesClub House, Golf Course
  • Accessibility AmenitiesOther
  • PricePerSqFt574
  • Other AmenitiesFireplace, Golf, Waterfront, Water View

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated July 14, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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