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.
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
- 1 day
- 57
- 12
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
| Date | Event | Price |
|---|---|---|
| 9/9/2026 | Listed 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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Neighborhood: 00830
Nearby schools
GreatSchools rating
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