Old San Juan Homes for Sale in Old San Juan - 5 homes

Remarks: In the heart of Old San Juan, where centuries of architecture frame the city’s most storied streets, 205 Luna rises as one of the district’s most remarkable commercial offerings: a fully restored, 21,899-square-foot historic building anchored by a 1913 theater. Originally home to Cine Luna—one of Puerto Rico’s earliest movie houses—the property has lived many lives, and today stands renewed after an extensive restoration by Universidad Carlos Albizu. This rare, mid-scale structure blends institutional quality with architectural heritage, offering a flexible canvas for cultural, educational, corporate, and creative uses. The building’s centerpiece is its meticulously rebuilt theater: an intimate performance and screening hall ideal for lectures, premieres, conferences, and private events. A gracious reception foyer and large interior patio establish an elegant arrival sequence suitable for gatherings, exhibitions, and hospitality activations. Through a central stair and elevator, the second and third floors reveal expansive office suites, private offices, conference rooms, and large open work areas—easily adaptable for a single anchor tenant, a hybrid innovation hub, or a multi-tenant professional environment. With its restored façade, modern infrastructure, and elevator access, 205 Luna offers the scale, history, and architectural presence rarely found in Old San Juan. Its zoning and configuration support an extraordinary range of possibilities: a cultural and innovation campus, creative industry headquarters, satellite university center, boutique event venue, or corporate flagship with a public-facing theater. Offered at $6,500,000, this is a singular opportunity to steward a revitalized landmark and define its next chapter in one of the Caribbean’s most iconic urban settings. EXECUTIVE SUMMARY: A Historic Theater and 21,899 SF Commercial Building Positioned for Institutional, Cultural, and Creative Re-Use. 205 Luna Street is a 21,899 SF, three-level historic building in Old San Juan featuring a fully restored 1913 theater at its core. After decades of disrepair, the property underwent a comprehensive rehabilitation completed in 2018 by Universidad Carlos Albizu, transforming it into a modern institutional-grade facility while preserving its architectural character. Today, the building offers exceptional flexibility for cultural, educational, office, and creative uses.

Listing is courtesy of: BOURET REAL ESTATE (787-642-9293)

Listing Agent: Coral Bouret (787-642-9293)

Remarks: HERITAGE COMMERCIAL PROPERTY ON FORTALEZA STREET. Just steps from Plaza Colón, at the gateway to Old San Juan, this heritage commercial property embodies the city’s historic pulse and cultural vitality. Positioned on the Eastern end of the iconic Fortaleza Street, one of the city’s most bustling thoroughfares, this historic mixed-use building is surrounded by eateries, boutiques and specialty shops, with the city’s main parking garages less than a block away. This stretch of Fortaleza runs adjacent to Plaza Colón, which remains one of San Juan’s most emblematic squares. Historic landmarks like Teatro Tapia and the Antiguo Casino Español form the plaza’s perimeter, while a marble statue of Christopher Columbus rises at its center. This storied setting situates the property within the cultural and civic heart of the old city, where heritage and daily life converge. Floor-to-ceiling glass windows decorate the building’s façade and reveal over 3,000 square feet of open-plan space. Currently curated as an art gallery, the first level of the building features soaring beamed ceilings, modern lighting, and central air conditioning. Sweeping arches lead to a dramatic interior patio and a central atrium that extends vertically through the height of the building. Enclosed in glass, this imposing architectural feature bathes every floor with natural light, while shielding the interiors from direct exposure to the elements. The main stairwell runs parallel to the central atrium, while a secondary stairwell provides direct access to the second and third levels from the street. A contemporary office space awaits on the second level with five main offices and a generous reception area, as well as a spacious executive suite that doubles as a conference room and opens to an enchanting balcony with views of Fortaleza Street. The third level, which has been brought to shell condition, is a blank canvas awaiting transformation into a private residence, creative studio or additional commercial space. Natural light pours in from the central atrium, while a generous terrace provides additional outdoor space. Above it all, a sweeping rooftop crowns the property, offering privileged city views and the opportunity to develop additional space for entertaining guests or hosting private events. Offering a rare combination of historic character and functional design, this building stands out as one of Old San Juan’s most versatile mixed-use properties and provides a singular opportunity for investors, entrepreneurs, and visionaries, to steward one of Fortaleza’s defining addresses into its next era.

Listing is courtesy of: BOURET REAL ESTATE (787-642-9293)

Listing Agent: Coral Bouret (787-642-9293)

Remarks: This offering features two historic mixed-use buildings in the heart of Old San Juan, Puerto Rico. With a combined area of approximately 29,753square feet and passenger elevator in each property. These properties are located at the intersection of 251 Recinto Sur Street and 301 San Justo Street, a prime spot in one of the Caribbean's most vibrant districts. 251 Recinto Sur Street comprises 12,769 square feet over four floors plus a cellar. The ground floor is leased on a month-to-month basis to a restaurant, creating a lively dining space. The upper floors include professional of spaces, and the top floor features a luxury apartment with stunning views of San Juan Bay. The rooftop provides an additional outdoor space with panoramic city and ocean views expanding the possibilities for redevelopment with unique amenities. 301 San Justo Street offers approximately16,984 square feet across four floors. The ground floor is currently occupied by a pizza restaurant on a month-to-month basis. The upper floors are shell condition, ready for redevelopment into boutique hotel rooms, upscale apartments, or other commercial uses. Both buildings are located in ahigh-traffic area, making them attractive for businesses and residents alike. This is a rare opportunity to own a piece of history in Old San Juan, combining cultural significance with redevelopment commercial potential.

Listing is courtesy of: DIEGO SAMPSON (787-503-9288)

Listing Agent: Diego Sampson (787-503-9288)

Remarks: 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.

Listing is courtesy of: BOURET REAL ESTATE (787-642-9293)

Listing Agent: Coral Bouret (787-642-9293)

Remarks: *** 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.

Listing is courtesy of: JORGE J ORTIZ LONGO REAL ESTATE (743-351-1019)

Listing Agent: Jorge Ortiz Longo (787-368-6407)