OLD SAN JUAN - PR9120208 - 364 CALLE SOL #2B, OLD SAN JUAN, FL 00901
19 Days on yellowkey

$490,000 | Condo | 1 beds | 1.0 baths

*** Tax Free Historical Property *** Located in the oldest city in the United States, Old San Juan, this well-appointed apartment at 364 Calle Sol offers an exceptional opportunity to live within the cobblestone charm of a 500 year old city. Spanning 736 sqft of thoughtfully configured living space, the residence is presented in great condition, offering a move-in-ready experience. The generous living room serves as the undisputed centerpiece of the home — an open, airy space bathed in soft, consistent lighting throughout the day thanks to its coveted north-facing orientation. A large private balcony extends directly from the living area, providing excellent cross ventilation throughout the whole apartment. Whether enjoyed as a morning retreat with coffee or an evening perch overlooking the city, this balcony adds a desired dimension of natural light that few Old San Juan apartments can provide.

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Listing is courtesy of: JORGE J ORTIZ LONGO REAL ESTATE

OLD SAN JUAN - PR9118776 - 17 CALETA DE LAS MONJAS #1B, OLD SAN JUAN, FL 00901
79 Days on yellowkey

$865,000 | Condo | 2 beds | 2.0 baths

One or more photo(s) has been virtually staged. Set along Caleta de las Monjas—known to locals simply as La Caleta—this residence is anchored in one of Old San Juan’s most enchanting enclaves, where the city’s romance feels almost cinematic. The street is a narrow ribbon of smooth blue cobblestone, framed by beautifully painted Spanish Colonial façades and classic balconies that instantly evoke the sensation of stepping into a centuries-old coastal town. Just steps away, Plazuela de la Rogativa—widely considered the most breathtaking viewpoint in Old San Juan—unfolds above the bay with its canopy of trees, the historic city walls below, and the shimmering water beyond, in a scene so extraordinary it’s often chosen as a wedding setting. With only a limited number of residences along this exclusive stretch, opportunities here are exceptionally rare—making this not only a home, but a true Old San Juan acquisition. Set quietly in the interior of the building, the home enjoys a sense of privacy and calm—an unexpected retreat from the vibrant energy of the streets just beyond. At its center, a charming open-air courtyard brings natural sunlight into both levels, with the residence thoughtfully arranged around three sides of this private interior oasis. The result is bright, inviting, and refreshingly serene, with an effortless “townhouse” feel from the moment you arrive. Inside, the space has been tastefully updated with modern flooring, a sleek open kitchen that flows into the dining area, and two contemporary bathrooms featuring clean, polished finishes. Fully air-conditioned throughout, the home is elevated by curated lighting and an eclectic, worldly design aesthetic—layered, colorful, and sophisticated, offering a welcome alternative to the predictable all-white minimalism seen everywhere today. The open-air courtyard is a charming centerpiece—an intimate pocket of sky and light that invites effortless personalization, whether through curated greenery, a subtle water element, or ambient evening lighting. Ideal as a primary residence, a refined pied-à-terre, or an exceptional income-producing property, this home delivers what few Old San Juan addresses can: privacy, character, and the rare privilege of living just steps from the city’s most iconic and breathtaking setting—La Caleta and the unforgettable Plazuela de la Rogativa. NOTE: Interior courtyard photograph has been virtually staged.

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Listing is courtesy of: BOURET REAL ESTATE

CAPITOLIO PLAZA - PR9119418 - 100 CALLE DEL MUELLE #21007, OLD SAN JUAN, FL 00901

$1,495,000 | Condo | 3 beds | 2.5 baths

Enjoy elevated coastal living in this spacious two-level penthouse in Old San Juan offering 2,589 SqFt of total area, including 1,799 SqFt of interior space and a 790 SqFt private rooftop terrace ideal for entertaining. The residence features three bedrooms — highlighted by a primary suite with walk-in closet and en-suite bath — and comes fully furnished with a kitchen nook, powder room, and laundry room. Panoramic views overlook the Atlantic Ocean and the historic Castillo San Cristóbal. Residents enjoy resort-style amenities including pools, fitness center, jogging trail, tennis and basketball courts, playground, event room, 24/7 security, full backup generator, water cistern, visitor parking, two covered parking spaces, and two storage units. Ideally located near dining, culture, the Port of San Juan, this move-in-ready penthouse blends historic charm with modern convenience.

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Listing is courtesy of: LUXURY COLLECTION REAL ESTATE