Old San Juan Homes for Sale in Old San Juan - 6 homes

Remarks: Masterfully Designed Penthouse | Reina de Castilla, Old San Juan Experience the pinnacle of historic luxury in this impeccably renovated penthouse at Reina de Castilla Condominium. Offering a rare single-level layout in the heart of Old San Juan, this residence blends timeless elegance with modern sophistication, featuring panoramic views of San Cristóbal Fort, San Juan Harbor, and the Atlantic Ocean. The home is designed with an intentional, fluid floor plan where every room enjoys seamless access to an east-facing balcony, bathing the interior in natural light. The expansive living and dining area is anchored by expertly laid travertine floors and adorned with bespoke artwork. An enclosed balcony with counter-height seating serves as the perfect vantage point for watching ships glide through the harbor. Chef’s Culinary Suite The designer kitchen is a masterpiece of form and function, featuring: • Cabinetry: Sleek NEFF luxury systems. • Appliances: Brand-new Sub-Zero refrigeration and a ducted downdraft cooktop. • Surfaces: Striking granite countertops. • Versatility: An open-concept layout flows into an inviting family room—easily convertible into a third bedroom—which opens onto a private terrace. The Primary Retreat The grand primary suite is a sanctuary of comfort, boasting custom walk-in closets and a spa-inspired ensuite bathroom. Indulge in the freestanding soaking tub, a full-sized glass shower, and a double vanity, all finished to the highest standards. Unmatched Infrastructure & Amenities A true rarity for the Historic District, this residence provides total peace of mind and convenience: • Parking: Three (3) deeded, covered parking spaces. • Climate & Safety: Double-paned stormproof windows/doors, individual mini-split A/C units for efficiency, and a central A/C system for main areas. • Building Features: Full-power backup generator, cistern water reserves, 24-hour security, and high-speed fiber optic accessibility. From the custom Poliform furniture to the breathtaking sunsets over the fort, every inch of this penthouse has been curated for the discerning buyer seeking culture, convenience, and a "luxury level of trust" in their next home.

Listing is courtesy of: MICORREDOR.COM (787-717-0187)

Listing Agent: Javi Rodriguez (787-717-0187)

Remarks: This charming 1-bedroom, 1-bathroom apartment in Old San Juan, PR, boasts 823 square feet of living space, blending historic charm with modern convenience. With two lovely balconies and proximity to vibrant restaurants, bars, and tourist attractions, it’s perfect for experiencing the local culture. Whether you're searching for a permanent residence, a vacation home, or a lucrative rental investment, this property offers unparalleled charm and convenience in one of Puerto Rico's most beloved neighborhoods. Don't miss your chance to own a piece of paradise in Old San Juan! Features Fully Furnished: Move right in with all furniture included, offering both style and comfort. Prime Location: Experience the best of Old San Juan with everything you need. Seller Financing Available: Flexible purchasing options make this gem more accessible than ever.

Listing is courtesy of: LIBE REAL ESTATE (786-321-0364)

Listing Agent: Ricardo Torres Gonzalez (786-321-0364)

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: *** 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)