Single Family for Sale: 4 Middleton, Hilton Head Island, SC 29928

3 beds
2 full, 1 half baths
2,733 sqft
mls #511980
$4,250,000
$4,250,000
4 Middleton, Hilton Head Island, SC 29928
3 beds
2 full, 1 half baths
2,733 sqft
mls #511980
$4,250,000
Price:
$4,250,000

Type Single Family
Style Two Story
Beds 3
Baths 2 full, 1 half baths
Square Footage 2,733 sqft
Year Built 1979

City Hilton Head Island
County Beaufort
Subdivision OVERLOOK PLACE
Area Port Royal

MLS 511980
Status Active
This exceptional Oceanfront home Designed by internationally acclaimed architect Dean Winesett, whose work has been featured in *Architectural Digest* and *Southern Living*, is a remarkable expression of timeless Lowcountry architecture. Also featured in *Southern Living*, the home showcases Winesett's signature style and craftsmanship, exemplified in several of his most celebrated residences throughout Hilton Head Island and Bluffton. Nestled beneath magnificent live oaks and surrounded by mature, natural landscaping, this private oceanfront retreat offers sweeping beach views and an unparalleled sense of serenity. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining just minutes from Hilton Head's renowned dining, golf, shopping, and amenities. The thoughtfully designed residence features 3 bedrooms and 2.5 baths, with the existing half bath easily converted back to its original full bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that seamlessly connect to the surrounding landscape. An expansive rear deck provides the perfect setting for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. Offering ample room for expansion, this property presents a rare opportunity to personalize and enhance an already extraordinary oceanfront estate. As one of Hilton Head Island's most exclusive residential communities, Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that make this oceanfront enclave one of the island's most desirable addresses. Exclusive to Port Royal property owners and their guests, the community's exceptional private amenities further elevate the lifestyle. Residents enjoy an oceanfront Beach House with a swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and a host of recreational and social amenities that make Port Royal one of the island's premier private communities.A rare architectural legacy, an irreplaceable beachfront setting, world-class private amenities, and endless possibilities combine to create one of the finest opportunities currently available on Hilton Head Island.

Room Features

Den Yes
Dining Room Yes
Eat In Kitchen Yes
Kitchen Yes
Laundry Yes
Library Yes
Living Room Yes
Primary Bedroom Second Level

Virtual Tours for 4 Middleton Hilton Head Island, SC

Lot & Building Features

Appliances Warming Drawer, Double Oven, Convection Oven, Stove, Self Cleaning Oven, Dryer, Washer, Disposal, Microwave
Association Amenities Beach Access, Beach Rights, Basketball Court, Garden Area, Picnic Area, Fire Pit, Playground, Pickleball, Clubhouse, Tennis Courts, Trails, Fitness Center, Guard, Pool
Style Two Story
Construction Materials Stucco
Cooling Central Air
Heating Central
Parking Features Driveway
Water Source Public

Price History of 4 Middleton, Hilton Head Island, SC

Date Name Price Difference
08/05/2026 Listing Price $4,250,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Map of 4 Middleton, Hilton Head Island, SC

Location Map Street View
Photo of Bill True
Bill True
CEO
Direct: 843-384-9088
Office
23C Shelter Cove Ln., #100A
Hilton Head Island, SC 29928
843-785-9500

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Listed by COAST PROFESSIONALS III brokered eXp Realty, COAST Professionals III
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4 Middleton (MLS #511980) is a twostory single family home located in Hilton Head Island, SC. This single family home is 2,733 sqft and on a lot of 25,700 sqft (or 0.59 acres) with 3 bedrooms, 3 baths and is 47 years old. This property was listed on 08/05/2026 and has been priced for sale at $4,250,000.

Nearby zip codes are 29026, 29920 and 29926. This property neighbors other cities such as St Helena Island.

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Listing information courtesy of: COAST PROFESSIONALS III brokered eXp Realty