Description
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.
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5BEDS
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0.52ACRES
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4BATHS
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11/2 BATHS
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3,498SQFT
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$407$/SQFT
School Ratings & Info
Description
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.
© 2026 St. John Board of Realtors. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Hanley Team | Farchette & Hanley Real Estate. Data last updated: 2026-06-12T23:55:37.077.