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00901 - PR9120368 - 253 LUNA ST, OLD SAN JUAN, FL 00901 11 Days on yellowkey
$1,700 | Apartment | 1 beds | 1.0 baths
Experience the allure of Old San Juan with this stunning apartment at 253 Luna St. Situated in the heart of Puerto Rico’s most historic and vibrant district, this residence is perfect for investors and tourists. This elegant apartment offers a spacious lofted bedroom and one full bathroom. The building includes modern amenities like an elevator, water cistern, and power generator, providing comfort and security. Fully furnished with air conditioning and appliances, it’s move-in ready. Old San Juan’s rich history, art, dining, and entertainment make it a prime location. Seize the opportunity to own a piece of Puerto Rican heritage combined with modern luxury.
Listing is courtesy of: LIBE REAL ESTATE (786-321-0364)Listing Agent: Ricardo Torres Gonzalez (786-321-0364)
00901 - 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.
Listing is courtesy of: JORGE J ORTIZ LONGO REAL ESTATE (743-351-1019)Listing Agent: Jorge Ortiz Longo (787-368-6407)
00901 - 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.
Listing is courtesy of: BOURET REAL ESTATE (787-642-9293)Listing Agent: Coral Bouret (787-642-9293)
00901 - PR9118739 - 205 LUNA, OLD SAN JUAN, FL 00901 81 Days on yellowkey
$6,500,000 | Apartment
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.
00901 - PR9116790 - 354 FORTALEZA, OLD SAN JUAN, FL 00901 177 Days on yellowkey
$2,495,000 | Apartment
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.
00901 - PR9116613 - 301 GALLARDO OFFICE BLDG. #Suite M, OLD SAN JUAN, FL 00901 186 Days on yellowkey
$6,000 | Condo | 2.0 baths
PREMIUM CORPORATE OFFICE SUITE | Prime Commercial Location in Old San Juan. A exceptional opportunity to lease a private, full-floor office suite in one of the few commercial-only buildings in Old San Juan. Prominently located opposite the US Federal Courthouse, and directly across from Doña Fela parking garage, plus a cargo/drop-off zone at building entrance, this address offers unparalleled accessibility for staff and clients—a favorable advantage in the historic zone. This fully remodeled, turn-key office occupies the entire mezzanine level of the building. Access to this floor is key-controlled via elevator, ensuring exclusive entry for authorized personnel only. Inside, the space has been thoughtfully renovated with contemporary finishes: elegant glass partitions defining private conference rooms and meeting areas; recessed lighting and sleek tile flooring throughout; central A/C (5-ton unit); fully furnished and move-in ready with a corporate aesthetic. Ideal for corporate tenants seeking a private, professional environment in the heart of Old San Juan - particularly law firms, consulting offices, or financial services firms. Located just steps from the U.S. Federal Courthouse, major banks, and government institutions, this office combines privacy, security, and accessibility in one of Puerto Rico’s most distinguished business addresses. Layout includes: reception, clerk station, 4 offices, 2 conference rooms, filing area, lounge/kitchen, 2 bathrooms, and utility room. Rent includes: water, high-speed internet, CAM, property taxes, and condo insurance. Not included: electricity & A/C maintenance.
00901 - PR9110120 - 251 & 301 RECINTO SUR & SAN JUSTO, OLD SAN JUAN, FL 00901 511 Days on yellowkey
$6,800,000 | Multi-Family 5+
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)
00901 - 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.
Listing is courtesy of: LUXURY COLLECTION REAL ESTATE (787-420-6303)Listing Agent: Charmaine Llauger Ramirez (787-458-4141)
00901 - PR9119804 - 65 CALLE SAN FRANCISCO, OLD SAN JUAN, FL 00901
$14,000 | Townhouse | 4 beds | 5.0 baths
Charming three-story historic residence at 65 Calle San Francisco in Old San Juan, blending timeless colonial character with modern comforts. Originally built in 1850 and renovated in 2010, this home offers 4 bedrooms and 5 bathrooms thoughtfully distributed across three floors, providing both privacy and inviting gathering spaces. At the heart of the residence is a serene interior patio, complemented by a spacious terrace and private rooftop, ideal for relaxing or entertaining while enjoying Caribbean breezes and historic surroundings. Located just steps from plazas, galleries, restaurants, and the waterfront, this property captures the unique rhythm of Old San Juan living while offering rare space and comfort.
Listing is courtesy of: THE COLECTIVO GROUP LLC (787-979-0149)Listing Agent: Monica Gotay (787-529-0716)
00901 - PR9119811 - 354 FORTALEZA #2, OLD SAN JUAN, FL 00901
$8,000 | Apartment | 1.0 baths
Just steps from Plaza Colón, at the gateway to Old San Juan, this heritage corporate office captures the city’s vibrant spirit. Situated on the eastern end of Fortaleza Street—one of Old San Juan’s most dynamic corridors—this full-floor corporate office is strategically well located, with key parking garages less than a block away. Occupying the entire second level, a contemporary office suite unfolds with five private offices, a reception area, and an elegant executive room opening to a balcony overlooking Fortaleza Street. Blending historic architecture with modern versatility, this is one of Old San Juan’s rarest opportunities—a completely remodeled, fully outfitted office, ideal for professional offices, corporate headquarters, or the creative entrepreneur.
00901 - PR9119826 - 301 GALLARDO OFFICE BUILDING #204, OLD SAN JUAN, FL 00901
$2,850 | Condo
PROFESSIONAL OFFICE SUITE | Modern, Turn-Key Workspace in Prime Recinto Sur Location. Well-appointed office suite available for lease in a professional office building on Recinto Sur Street, directly across from the U.S. Federal Courthouse and steps from the Doña Fela parking garage. Ideally suited for attorneys, consultants, or boutique professional firms seeking a refined, efficient workspace in Old San Juan. This 733-square-foot suite has been thoughtfully remodeled with a clean, contemporary aesthetic, featuring white paneled walls, light wood finishes, recessed lighting, and central air conditioning, creating a bright and polished work environment ready for immediate occupancy. The well-designed layout includes a welcoming reception area with a separate glass-enclosed secretary or administrative station, two private offices with windows providing natural light, and a conference room with elegant wood paneling, ideal for client meetings or collaborative work. Located on the building’s second floor alongside other professional offices, the suite offers easy accessibility and a collegial professional environment, with shared hallway restrooms serving the floor. A rare opportunity for professionals seeking a refined, move-in-ready office in one of Old San Juan’s most strategic business locations. Rent includes: water, high-speed internet, CAM, property taxes, and condo insurance. Not included: electricity & A/C maintenance. Additional perks: Cargo/drop-off zone at entrance. Ideal for attorneys or corporate firms.