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For sale
  • $1,325,000

    109A Chocolate Hole Rd, Saint John, VI 00830

    5beds
    3,498sqft
    Single Family Residence
    Built in 1984
    0.52 Acres Lot
    $-- Zestimate®
    $379/sqft
    $44/mo HOA

    What's special

    Exceptional sunset viewsGentle tradewindsRooftop terrace
    Perched gracefully into the hillside of coveted Chocolate Hole, 109A is a refined multi-unit estate offering exceptional sunset views, strong rental performance, and an extraordinary level of mechanical modernization -- a rarity in the St. John market.Framed by one of the island's most expansive and nearly level lawns, this property captures the essence of Caribbean luxury living. From the rooftop terrace, watch golden sunsets melt into the horizon while ducks drift peacefully across the pond below. Gentle tradewinds and the serene location provide both privacy and a peaceful atmosphere -- all less than five minutes from the vibrant heart of Cruz Bay. Recently re-launched on VRBO and Airbnb, the property has seen immediate demand, securing multiple new reservations and filling the calendar through late spring, with strong bookings extending into summer and the upcoming high season. Its multi-unit configuration offers flexible use -- continue as a high-performing income property, enjoy as a private compound, or combine both for an ideal owner-occupied investment strategy.
    1 day
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    Zillow last checked:

    Listing updated:

    Listed by:

    Katie Zachary,

    Holiday Homes of St. John

    Source: St John BOR,MLS#: 26-60

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • 1/2 bathrooms: 1
      Cooling
      • Central Air
      Appliances
      • Included: Dryer, Refrigerator, Stove, Washer
      Features
      • Furnished: Yes
      Interior area
      • Total structure area: 3,498
      • Total interior livable area: 3,498 sqft

      Property

      Features
      • Pool features: None
      • Has spa: Yes
      • Spa features: Hot Tub/Spa
      • Has view: Yes
      • View description: East/sunrise, South Shore, Valley
      • Has water view: Yes
      • Water view: South Shore
      Lot
      • Size: 0.52 Acres
      • Features: Natural Landscaped
      • Topography: Moderate
      Details
      • Parcel number: 109A
      • Zoning: W-1WaterfrontPl

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Masonry, Stone
      • Foundation: Masonry
      • Roof: Concrete
      Condition
      • Year built: 1984
      Details
      • Builder name: Monsanto

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Masonry Cistern

      Community & HOA

      Community
      • Subdivision: Chocolate Hole
      HOA
      • Has HOA: Yes
      • HOA fee: $531 annually
      Location
      • Region: Saint John

      Financial & listing details

      • Price per square foot: $379/sqft
      • Date on market: 9/9/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        9/9/2026Listed for sale$1,325,000$379/sqft
        Source: St John BOR #26-60 Report a problem

        Public tax history

        Tax history is unavailable.

        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 00830

        Getting around

        24 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating

        No schools nearby

        We couldn't find any schools near this home.