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Single family home for sale at 12355 Southhampton Dr, Bishopville, MD 21813 | MLS# MDWO2039008 | Listing updated on 2026-07-23
Photo 1 of Single family home for sale at 12355 Southhampton Dr, Bishopville, MD 21813 | MLS# MDWO2039008 | Listing updated on 2026-07-23
Photo 2 of Single family home for sale at 12355 Southhampton Dr, Bishopville, MD 21813 | MLS# MDWO2039008 | Listing updated on 2026-07-23
Photo 3 of Single family home for sale at 12355 Southhampton Dr, Bishopville, MD 21813 | MLS# MDWO2039008 | Listing updated on 2026-07-23
Photo 4 of Single family home for sale at 12355 Southhampton Dr, Bishopville, MD 21813 | MLS# MDWO2039008 | Listing updated on 2026-07-23
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$2,795,000

Monthly Est:$13,912

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon4,867sqft

12355 Southhampton Dr, Bishopville, MD 21813

$13,912/moEst:

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  • Single Family Residence

  • Built in 2002

  • $84.75/mo HOA

  • 1.14 acres lot

  • $574/sq.ft

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.

  • Houzeo last checked: 5 minutes ago
  • Listing updated: July 23, 2026 at 2:46 pm
  • Listing Provided by: Ann Buxbaum (443) 235-0878 | Northrop Realty (302) 539-0800
  • Source: Bright MLS-NJ | MLS#: MDWO2039008 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Worcester Md County

  • City

    Bishopville

  • Neighborhood

    --

  • Year Built

    2002

  • HOA Fees

    $84.75/mo

  • Finished Area

    4,867 sqft

  • Lot Size

    1.14 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDWO2039008

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    29

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Location

HOA Management

N/A

HOA Fees

$1,017/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Club House Club House

Snow Removal Snow Removal

Golf Golf

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 6

Interior

  • Appliances

    Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Cooktop, Oven Wall, Oven Double

  • Exterior Features

    Extensive Hardscape, Exterior Lighting

  • Interior Features

    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

  • Flooring

    Ceramic Tile, Hardwood

  • Heating

    Heat Pump(s)

  • Window Features

    Double Hung, Double Pane Windows, Screens, Sliding, Transom, Vinyl Clad

  • Sewer

    Public Sewer

  • Cooling

    Central A/c

Construction

  • Year Built

    Year Built: 2002

  • Home type

    Single Family Residence

  • Roof

    Shingle

  • Construction Materials

    Stone

  • Architectural Style

    Coastal

  • Foundation Details

    Crawl Space

Utilities & Energy

  • Parking Features

    Brick Driveway

  • Fireplace Features

    Gas/propane

  • Water Source

    Well

  • Security Features

    Main Entrance Lock, Smoke Detector

  • Association Amenities

    Club House, Golf Course

Other Features

  • Subdivision Name

    Lighthouse Sound

  • Patio And Porch Features

    Deck, Wrap Around

Price History

DateEventPrice

06/25/2026

Source: mls_logoBright MLS-NJ #MDWO2039008

Listed for Sale

$2,795,000 +305.95%

$574/sqft

07/24/2002

Source: mls_logoBright MLS-NJ #1000615612

Sold

$688,510

$141/sqft

Nearby Homes

Based on information from Bright MLS through Nov 04, 2026, 12:15AM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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