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For sale
  • $4,250,000

    4 Middleton Pl, Hilton Head Island, SC 29928

    3beds
    2,733sqft
    : 
    $24,973/mo
    Get pre-qualified
    Single Family Residence
    Built in 1979
    0.59 Acres Lot
    $-- Zestimate®
    $1,555/sqft
    $-- HOA

    What's special

    Oceanfront homeSweeping beach viewsExpansive rear deckBreathtaking coastal viewsPrivate oceanfront retreatWide-plank pine floors
    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.
    15 days
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    1,471
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    40
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    Zillow last checked:

    Listing updated:

    Listed by:

    COAST Professionals III 843-310-4998,

    COAST PROFESSIONALS III brokered eXp Realty

    Source: REsides, Inc.,MLS#: 511980MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Second
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Convection Oven, Double Oven, Dryer, Disposal, Microwave, Self Cleaning Oven, Stove, Warming Drawer, Washer
      Features
      • Attic, Bookcases, Built-in Features, Ceiling Fan(s), Fireplace, Multiple Closets, Smooth Ceilings, Upper Level Primary, Window Treatments, Eat-in Kitchen
      • Flooring: Tile, Wood
      • Windows: Other, Window Treatments
      Interior area
      • Total interior livable area: 2,733 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Driveway
      Features
      • Stories: 2
      • Patio & porch: Rear Porch, Deck, Front Porch
      • Exterior features: Deck, Propane Tank - Owned, Porch, Propane Tank - Leased, Storage
      • Pool features: Community
      • Has view: Yes
      • View description: Ocean
      • Has water view: Yes
      • Water view: Ocean
      Lot
      • Size: 0.59 Acres
      • Features: 1/2 to 1 Acre Lot
      Details
      • Parcel number: R51000500001900000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Two Story
      • Property subtype: Single Family Residence
      Materials
      • Stucco
      • Roof: Shake,Wood
      Condition
      • Year built: 1979
      Details
      • Builder model: Custom

      Utilities & green energy

      • Water: Public

      Community & HOA

      Community
      • Subdivision: Overlook Place
      HOA
      • Amenities included: Beach Rights, Basketball Court, Beach Access, Clubhouse, Fitness Center, Fire Pit, Garden Area, Picnic Area, Playground, Pickleball, Pool, Guard, Tennis Court(s), Trail(s)
      Location
      • Region: Hilton Head Island

      Financial & listing details

      • Price per square foot: $1,555/sqft
      • Tax assessed value: $2,315,400
      • Annual tax amount: $8,577
      • Date on market: 8/5/2026
      • Listing terms: Cash,Conventional

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/5/2026Listed for sale$4,250,000$1,555/sqft
        Source: REsides, Inc. #511980 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,577 -0.9%$67,090
        2024$8,653 +0.3%$67,090
        2023$8,631 +8.7%$67,090 +15%
        2022$7,940 -3.4%$58,340
        2021$8,216 $58,340
        2020-- $58,340
        2019$7,600 +2.2%$58,340
        2018$7,439 -10%$58,340 +15%
        2017$8,270 $50,730
        2016$8,270 $50,730
        2015$8,270 $50,730
        2014$8,270 $50,730
        2013$8,270 $50,730
        2010$8,270 +4.4%--
        2009$7,921 +4.3%--
        2008$7,598 +6.5%$65,508
        2007$7,136 -22.5%$65,508 +26%
        2005$9,210 -22.2%$52,006 -23%
        2004$11,834 +49.4%$67,508 +107.1%
        2003$7,921 $32,600
        2001-- --
        2000-- $815,000
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: Port Royal

        Getting around

        0 / 100
        Car-Dependent
        36 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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