Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 4,867 Sq. Ft.
  • 3 Car Garage
  • Updated 2 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Sunday 6/28 11:00 AM - 1:00 PM

12355 Southhampton Drive,Bishopville, MD 21813

12355 Southhampton DriveBishopvilleMD21813

Get directions
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 12355 Southhampton Dr

General

  • Price: $2,795,000
  • HOA FEE: $85/month
  • HOA FEE FREQ.: Annually
  • Taxes: $9,868 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDWO2039008
  • Updated: 6/25/2026
  • Added to Site: 3 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Breakfast Room, Laundry, Other, Office
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Gas/Propane
  • Appliances: Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Cooktop, Oven - Wall, Oven - Double
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1
  • Upper Floor Baths: 4
  • Upper - Full Baths: 4
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Has Laundry, Main Floor

Additional Information

  • Shared Amenities: Club House, Golf Course
  • Security/Safety: Main Entrance Lock, Smoke Detector

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting
  • Porch/Patio/Deck: Deck(s), Wrap Around

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 3
  • Parking Features: Brick Driveway
  • Parking Type: Attached Garage
  • Garage Description: Garage - Front Entry, Oversized, Garage Door Opener

Location

  • Area: Worcester East of Rt-113
  • County: WORCESTER
  • Subdivision: LIGHTHOUSE SOUND
  • Driving Directions: From Ocean City Expy/MD-90, Ttrn right onto Saint Martins Neck Rd. Turn right onto Southhampton Dr.

School Information

  • School District: Worcester County Public Schools
  • Elementary School: Showell
  • Middle School: Stephen Decatur
  • High School: Stephen Decatur

Community

  • Association: Yes
  • Assoc. Fees Include: Snow Removal

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Well
  • Dist. to Water: 50 Feet

Structural Information

  • Architectural Style: Coastal
  • Structure Type: Detached
  • Construction: Stone
  • Foundation: Crawl Space
  • Roof: Shingle
  • Walls/Ceilings: High, 2 Story Ceilings, 9'+ Ceilings, Dry Wall
  • Windows: Double Hung, Double Pane, Screens, Sliding, Transom, Vinyl Clad
  • Doors: Six Panel, Double Entry, Sliding Glass
  • Stories Description: Main, Upper 1
  • Square Feet: 4,867
  • Sq. Ft. Source: Assessor
  • Living Area: 4,867 Sq. Ft.
  • Finished Above Grnd: 4,867 Sq. Ft.
  • Year Built: 2002
  • Year Built Source: Assessor

Lot Features

  • Property View: Bay, Panoramic, City
  • Lot Size (Acres): 1.14
  • Lot Size (Sq. Ft.): 49,658
  • Lot Size Source: Assessor
  • Zoning: R-1

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Front Type: Bay
  • Water Front Name: Assawoman Bay

Financial Considerations

  • Price Per Sq. Ft.: $574.28
  • Association Fee: $1,017
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2026
  • County Tax: $8,676
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,219,800
  • Tax Amount: $9,868
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 4867

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 29

Listed by Northrop Realty, Ann Buxbaum

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 12355 Southhampton Dr —

  • Ann Buxbaum

    Northrop Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 12355 Southhampton Dr

School District:Worcester County Public Schools
NameGradesDistance
Showell Elementary School
11318 Showell School Road, Berlin, MD 21811
PK-35.1 mi
Berlin Intermediate School
309 Franklin Avenue, Berlin, MD 21811
4-67.9 mi
Stephen Decatur Middle School, Berlin, MD
9815 Seahawk Road, Berlin, MD 21811
7-86.7 mi
Stephen Decatur High School
9913 Seahawk Road, Berlin, MD 21811
9-126.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 12355 Southhampton Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/25/2026
Listed
$2,795,000
186.67%
MLS
6/04/2021
Sold
$975,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 12355 Southhampton Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$8,468
—
$1,064,500
17%
2023
$8,468
—
$909,200
3%
2023
$8,468
6%
$884,900
3%
2021
$8,003
—
$860,600
3%
2021
$8,003
—
$836,300
—
2020
$8,003
-5%
$836,300
-6%
2019
$8,432
—
$890,400
—
2018
$8,407
—
$887,800
—
2017
$8,383
—
$885,200
—
2016
$8,358
7%
$882,600
—
2015
$7,785
—
$882,600
—
2014
$7,785
—
$882,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 12355 Southhampton Dr

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Northrop Realty, Ann Buxbaum

Similar Properties near 12355 Southhampton Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

36 Leigh Dr, Ocean Pines, MD 21811 - Photo 1 Price Reduced
-$100,000 (-4.18%)
$2,295,000

36 Leigh Dr  Ocean Pines, MD 21811

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,400
    Sq. Ft.
Listed by Dylan Markward (443) 373-8993
10542 Egret Ct, Bishopville, MD 21813 - Photo 1
$2,950,000

10542 Egret Ct  Bishopville, MD 21813

  • Single Family
  • Active
  • 7
    Beds
  • 8
    Total Baths
  • 7,467
    Sq. Ft.
Listed by Keller Williams Realty, R. Erik Windrow

Just Listed near 12355 Southhampton Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

31880 Two Ponds Rd, Selbyville, DE 19975 - Photo 1 Just Listed
$595,000
Open House

31880 Two Ponds Rd  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,056
    Sq. Ft.
Listed by Glenn Bechtold (443) 878-3472
37745 Teaberry Cir, Selbyville, DE 19975 - Photo 1 Just Listed
$669,000

37745 Teaberry Cir  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,794
    Sq. Ft.
Listed by The Real McCoy Group (302) 500-0503
36358 Sea Grass Way, Selbyville, DE 19975 - Photo 1 Just Listed
$710,000

36358 Sea Grass Way  Selbyville, DE 19975

  • Townhouse
  • Active
  • Updated 22 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,400
    Sq. Ft.
Listed by Monument Sotheby's International Realty, Kelly A Johnston
36727 Roxana Rd, Selbyville, DE 19975 - Photo 1 Just Listed
$975,000

36727 Roxana Rd  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,104
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices PenFed Realty, Pamela Price

Price Reduced near 12355 Southhampton Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

32434 Killdeer Dr, Selbyville, DE 19975 - Photo 1 Price Reduced
-$10,100 (-1.89%)
$524,900

32434 Killdeer Dr  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,830
    Sq. Ft.
Listed by Kelley Bjorkland (443) 880-1032
36267 Waterleaf Way, Selbyville, DE 19975 - Photo 1 Price Reduced
-$14,500 (-2%)
$709,900

36267 Waterleaf Way  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,800
    Sq. Ft.
Listed by Denise D'Adamo (443) 243-4410
9337 Greenway Trl, Selbyville, DE 19975 - Photo 1 Price Reduced
-$4,500 (-1.2%)
$369,990

9337 Greenway Trl  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,676
    Sq. Ft.
Listed by D.R. Horton Realty of Delaware, LLC, Conrad J Heilman III
32143 Lynch Rd, Selbyville, DE 19975 - Photo 1 Price Reduced
-$24,999 (-2.5%)
$975,000

32143 Lynch Rd  Selbyville, DE 19975

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,941
    Sq. Ft.
Listed by Century 21 Gold Key-Dover, Margaret Poisson

Recent Sales near 12355 Southhampton Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

30536 Lightkeepers Wy, Selbyville, DE 19975 - Photo 1 Sold
$2,543,813

30536 Lightkeepers Wy  Selbyville, DE 19975

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
Listed by Monument Sotheby's International Realty, Audrey P Serio and Monument Sotheby's International Realty, Franklin T. Serio
Sold by Monument Sotheby's International Realty, Kelly A Johnston
30765 Keepers Walk, Selbyville, DE 19975 - Photo 1 Sold
$2,430,369

30765 Keepers Walk  Selbyville, DE 19975

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 5,320
    Sq. Ft.
Listed by Monument Sotheby's International Realty, Audrey P Serio and Monument Sotheby's International Realty, Franklin T. Serio
Sold by Non Subscribing Office, NON MEMBER
36992 Dupont Blvd, Selbyville, DE 19975 - Photo 1 Sold
$2,500,000

36992 Dupont Blvd  Selbyville, DE 19975

  • Lots/Land
  • Closed
  • 4.6
    Acres
Listed by Rinnier Development Co, William Rinnier
Sold by Unrepresented, Unrepresented

12355 Southhampton Drive, Bishopville, MD 21813 (MLS# MDWO2039008) is a Single Family property with 5 bedrooms, 5 full bathrooms and 1 partial bathroom. 12355 Southhampton Drive is currently listed for $2,795,000 and was received on June 25, 2026. Want to learn more about 12355 Southhampton Drive? Do you have questions about finding other Single Family real estate for sale in Bishopville? You can browse all Bishopville real estate or contact a Coldwell Banker agent to request more information.

Tour this property