A rare walled historic estate with harbor views located in the heart of Christiansted. Anchored by a five bedroom 4 bathroom main residence showcasing classic Danish West Indian architecture, the estate also includes a separate 1 bedroom 1 bathroom 18th-century guest cottage and multiple parcels that offer exceptional flexibility and development potential. Enclosed by tall masonry walls and centered around a lush tropical courtyard and pool, the property provides an uncommon level of privacy and tranquility for an in town historic offering. This grand historic main residence reflects classic Caribbean craftsmanship dating to the early 1800s. Distinctive features include reclaimed ship timbers used as structural floor joists, ballast-brick staircases, five French doors encircling the living room, a signature Captain's Watch, a tiled front porch entry with classic rocking chairs, and an expansive veranda overlooking the harbor. Recently refinished living room floors and split-system air conditioning enhance everyday comfort while preserving the home's historic character. A poolside tool/workroom with plumbing offers the opportunity to create an additional guest suite. Rare for in-town Christiansted properties, the estate also includes two garages and valuable off-street parking. Set across multiple parcels, this rare in-town landholding includes a separate 18th-century guest cottage of approximately 1,000 square feet, along with an additional large walled and gated lot currently utilized for parking. The lot features historic ruins, an 18th-century foundation and cistern, and architectural plans available for further development, while currently providing additional off-street parking. In total, the property offers more than 6,000 square feet of flexible space, allowing for a wide range of residential, hospitality, or commercial configurations. Located within an Enterprise Development Zone, the property may qualify for meaningful tax incentives, positioning it as both a lifestyle investment and a strategic business opportunity. Zoned B-2, the property lends itself to numerous commercial or mixed-use options. Possibilities include a boutique hotel, bed-and-breakfast, spa, medical or professional offices, gallery, retail space, or restaurant. The guest cottage has operated successfully as an Airbnb for many years and offers excellent potential for hospitality or dining use while maintaining the main residence for private living, or vice versa. Its proven short-term rental history further underscores the income potential. Modern upgrades complement the historic character throughout the property. Substantial structural and cosmetic improvements have been completed, along with nearly all-new appliances and air-conditioning systems. The kitchen features a Smeg gas range with pot filler, ventilation hood, and adjoining walk-in pantry. The spacious primary suite includes double walk-in closets and a large open primary bath with skylight and a spa soaking tub with new pump. Outdoor spaces are equally compelling. Between the main residence and guest cottage lies an exceptional private tropical courtyard centered around the pool, with the two residences gracefully framing the space while maintaining privacy from one another. Extensive Trex decking surrounds the pool and extends along the walkway to the cottage, enhancing the courtyard setting and creating a seamless indoor-outdoor living experience. The courtyard also features a separate street entrance, providing convenient access and additional flexibility for guests or boutique hospitality use. The entire compound is enclosed by tall masonry walls, reinforcing the privacy and seclusion rarely found in an in-town property. Energy and infrastructure upgrades add further value and resilience. Solar panels with dual Power walls supply a substantial portion of the main home's power, supported by separate generators for each residence. Independent cisterns, UV filtration systems, tankless water heaters with electric backup, separate meters, and a wireless cistern monitoring system provide efficiency and reliability.