Old San Juan Single Family Homes For Sale in San Juan - 8 homes

Remarks: Step into a piece of history with this exquisitely renovated 2,716 SF Spanish Colonial masterpiece, nestled next to the Governor’s Mansion and steps to La Princesa Boardwalk in Old San Juan. Thoughtfully restored to preserve its timeless elegance, this two-story residence seamlessly blends historic charm with modern comforts. From the moment you enter, you are welcomed by an air-conditioned grand room with soaring 20-foot ceilings, where a full-wall library invites both quiet reflection and sophisticated entertaining. Every step through this home tells a story, with intricate tilework sourced from the historic San José Church (circa 1810), adding an unparalleled touch of authenticity and character. Original "soles truncos" archways stand as a testament to the home’s Spanish heritage, casting beautiful patterns of light throughout the space. Designed for both elegance and ease, the living room, dining area, and kitchen flow seamlessly through graceful arched openings to an indoor covered terrance and interior patio where natural light and fresh air create an inviting atmosphere for relaxation or entertaining. A conveniently located half bath is available for guests. The newly crafted wooden kitchen, equipped with brand-new appliances and a washer/dryer, is enhanced by traditional arches and stained-glass “vitrales,” adding both beauty and functionality to the space. Upstairs, you’ll find three spacious air conditioned bedrooms, three full bathrooms, and a laundry room. The two primary bedrooms feature custom closets, restored original wood floors, and double doors that open onto Old San Juan’s iconic balconies, offering picturesque views of the historic streetscape. An additional open balcony overlooks the indoor garden, providing the perfect spot to unwind. The property includes a full-power generator and a water cistern for added convenience and reliability. Ideally located on San Francisco Street, this exceptional home offers both security, with a police station directly across the street, and convenience, just a short walk from the San Juan Cathedral, Plaza de Armas, and an array of fine dining restaurants. A rare opportunity to own a true Old San Juan treasure, this residence is a perfect blend of history, charm, and refined living.

Listing is courtesy of: ALMA MARTINEZ QUIÑONES (787-367-8507)

Listing Agent: Alma Martinez Quiñones (787-367-8507)

Remarks: Welcome to Casa Lila, an extraordinary oceanfront villa in the heart of Old San Juan, where 500 years of history, Caribbean beauty, and modern luxury come together in one irreplaceable property. Beautifully restored and rich with character, Casa Lila offers the rare opportunity to own a piece of Puerto Rico history. Set along the iconic cobblestone streets of Old San Juan, this historic villa captures the essence of the city’s charm while offering breathtaking views of the Atlantic Ocean and the legendary Castillo San Cristóbal. Designed for both refined living and unforgettable hospitality, Casa Lila features two spacious bedrooms, three full bathrooms, multiple outdoor living areas, and a spectacular rooftop wood deck ideal for entertaining, sunset cocktails, or al fresco dining with ocean breezes as the backdrop. The primary suite is a private retreat, complete with a luxurious full bathroom, walk-in closet, and private balcony showcasing sweeping ocean and fort views. The guest bedroom offers its own sense of romance and elegance with two Juliet balconies and an antique wardrobe that complements the villa’s historic ambiance. Upon entry, an interior patio welcomes you with a hammock and comfortable lounge furnishings, creating a peaceful escape within the home. The first level features air-conditioned living and dining areas, a fully equipped kitchen, and a full bathroom, blending everyday convenience with timeless architectural charm. A spiral staircase leads to the second level, where the bedrooms offer privacy and comfort. Above, the third-level rooftop deck becomes one of the home’s most memorable spaces, with room for dining, sunbathing, and taking in the magic of Old San Juan from above. Casa Lila is equipped with modern comforts including Wi-Fi, air conditioning, washer and dryer, BBQ grill, linens, towels, and essential amenities, making it well-suited as a private residence, vacation home, or luxury short-term rental investment. Currently positioned as a desirable short-term rental, Casa Lila offers exceptional appeal for buyers seeking a property with both emotional and income-producing value. Its oceanfront setting, historic architecture, rooftop entertaining space, and walkable Old San Juan location create a truly unique ownership opportunity. Whether envisioned as a personal Caribbean retreat, a legacy residence, or a boutique hospitality asset, Casa Lila is more than a home — it is a story, a destination, and a rare chance to own part of Puerto Rico’s living history.

Listing is courtesy of: MARICELLE RIVERA RIVERA (787-822-8888)

Listing Agent: Maricelle Rivera Rivera (787-525-8189)

Remarks: 255 San Justo is an exceptional historic property located in the heart of Old San Juan. This restoration project presents an incredible opportunity for those with a vision. Spanning approximately 9,530 square feet, the space is evenly distributed over two expansive floors, offering limitless potential for customization. The property boasts the possibility of developing a large rooftop area, perfect for enjoying the picturesque views of Old San Juan and the San Juan Bay. Whether you dream of transforming it into a luxurious residence or a vibrant commercial space, 255 San Justo provides a blank canvas for your creativity. Situated on the desirable street of San Justo, this property offers excellent walkability and is conveniently close to parking lots, making it accessible for both residents and visitors. Embrace the charm and history of Old San Juan while crafting a unique space that meets your needs.

Listing is courtesy of: PUERTO RICO SOTHEBY'S INTL. REALTY (787-523-6500)

Listing Agent: Paula Lapciuc (305-989-0748)

Remarks: Experience the Old San Juan lifestyle. This spacious and cool residence is located in one of the most quiet but central streets of the old town center. It has 2 bedrooms, 2.5 bathrooms, a space for a family room or office, kitchen with quartz countertops, dining room, living/family room, interior terrace with a mini pool and a spiral staircase that leads to a large rooftop with views of the San Juan Bay. Sold with or without furniture. One parking space at Cochera Parking Garage included.

Listing is courtesy of: ALBERTO HERNANDEZ REAL ESTATE (787-728-6124)

Listing Agent: Natalia Rivero Fernandez (787-428-4838)

Remarks: This is a fourth floor roof top studio that has it all. A full size kitchen, large closet, and a breathtaking ocean view not only from the living quarters but from the Rain shower as well. It has all new appliances as well as AC unit and updated plumbing and electrical. The highlight of this unit is your ability to walk out on to the largest private terrace in Old San Juan. As you walk out, to your right you have clear water views. towards the front of the building, you have an unobstructed view of the Castillo San Felipe del Morro as well as the Catedral de San Juan Bautista which is the second oldest in the Western hemisphere and the oldest on US soil. And to the left, you can watch cruise ships dock at the Marina. The rooftop is large enough to hold private events such as weddings and birthdays. This unit is great for long term or short term rentals and would be a great stream of revenue if you were to purchase one of the other units listed.

Listing is courtesy of: CHRISTIE'S INTERNATIONAL REAL ESTATE PUERTO RICO (787-400-0699)

Listing Agent: Lana Slobodskaya (847-553-1238)

Remarks: This is a two-bedroom + two full-bath condo with a private office and laundry. It has been meticulously remodeled over the past two years without sparing any expenses and currently generating an 11.9 cap rate at the asking price. We kept as many original features as possible such as the original tile in the living room and beautiful ornate hand-carved wood doors separating the guest bedroom. Every room has been updated with new AC units and ceiling fans, as well as updated plumbing and electrical. All tiles and fixtures were imported from Spain to keep with the original Spanish feel. Every exterior door has been upgraded for sound and stormproofing. All the cabinets have been custom-made and imported from the US. All new appliances have allowed us to keep the original features but with an upgraded feel. There is not one detail that has been overlooked!

Listing is courtesy of: CHRISTIE'S INTERNATIONAL REAL ESTATE PUERTO RICO (787-400-0699)

Listing Agent: Lana Slobodskaya (847-553-1238)

Remarks: Located on the third floor, this is a three-bedroom + two full-bath condo with a jetted bathtub and private terrace over looking San Sebastian, the largest unit in the building, and currently generating an 11.9 cap rate at the asking price. This unit also has its own private laundry room with a brand new stack-able washer and dryer. Through the remodel process we were able to find two original windows that are in the original blue prints that had been sealed up for over 100 years! Now the new windows add natural sunlight to the master bedroom and guest bathroom. Every room has been updated with new AC units and ceiling fans, as well as updated plumbing and electrical. All tiles and fixtures were imported from Spain to keep with the original Spanish feel. Every exterior door has been upgraded for sound and storm-proofing. All the cabinets have been custom-made and imported from the US. All new appliances have allowed us to keep the original features but with an upgraded feel. There is not one detail that has been overlooked!

Listing is courtesy of: CHRISTIE'S INTERNATIONAL REAL ESTATE PUERTO RICO (787-400-0699)

Listing Agent: Lana Slobodskaya (847-553-1238)

Remarks: Here’s your chance to own a slice of history! Own your very own century-old gem, nestled in the 500-year-old heart of Old San Juan. No other property compares, and the location is unparalleled. Positioned on a serene side street, it’s mere steps from the renowned Calle San Sebastián and the Catedral Basilica de San Juan Bautista. From the largest private rooftop in the area, savor unobstructed views of Castillo San Felipe del Morro, the fortress that shielded Puerto Rico for centuries, with sunsets to marvel at year-round, this incredible property is producing an 11.9 cap rate at the current asking price. To the north, behold the waves crashing against the colorful, historic shanty town of La Perla. To the east, watch cruise ships dock and depart daily, gliding past you. The building consists of 3 total units allowing you to live in one and rent out the others, or rent all three. This exquisite masterpiece, restored to its original magnificence, is truly one of a kind.

Listing is courtesy of: CHRISTIE'S INTERNATIONAL REAL ESTATE PUERTO RICO (787-400-0699)

Listing Agent: Lana Slobodskaya (847-553-1238)