Old San Juan Homes for Sale in San Juan - 21 homes

Remarks: 251 Recinto Sur presents a rare opportunity to acquire a property in the heart of Old San Juan, one of Puerto Rico’s most iconic and supply-constrained markets. Located along a highly walkable corridor with consistent pedestrian activity, the property benefits from strong surrounding demand driven by tourism, local commerce, and long-term urban relevance. The asset offers a compelling value-add opportunity with the ability to reposition and enhance income through strategic improvements and leasing. Its location and layout support a variety of uses aligned with the character and demand of Old San Juan. Commercial / mixed-use potential with flexibility for retail, office, or integrated uses, subject to zoning and applicable regulations. Buyer to perform all due diligence regarding zoning, permitted uses, and property condition.

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

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

Remarks: Discover the charm of Old San Juan in this beautiful 2-bedroom, 1-bathroom apartment with cozy living room and dining area. Completely furnished. On the second floor of the building. Perfectly located near the beach, this gem offers delightful walks with ocean views and is just steps away from the iconic El Morro and San Cristobal Castles. Stroll to countless restaurants serving delicious Puerto Rico cuisine, explore unique shops, and soak up the vibrant history that surrounds you. The San Juan Bay is just around the corner-ready for you to hop on a cruise ship and set sail! This is more than a home, it's a daily adventure in one of the most enchanting cities in the Caribbean. Currently operating as an Airbnb, this property generates excellent income - a perfect blend of history, lifestyle, and investment opportunity.

Listing is courtesy of: WISE CHOICE REAL ESTATE (787-607-0711)

Listing Agent: Ruth Wise (787-607-0711)

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: Under contract-accepting backup offers. Colonial Property for Sale - San Sebastián Street, Old San Juan Unique opportunity to own an authentic colonial residence located on one of the most iconic streets in Old San Juan. This single-story home with a balcony, a rare and highly desirable feature for this type of property, preserves the charm and character of Puerto Rico's historic architecture. The property features one bedroom, one bathroom, a living area, an interior courtyard, traditional Spanish tile floors, and high ceilings. Its layout offers an excellent potential for a thoughtful restoration. Located in a non-flood zone, the property sits on a lot of 86 square meters 925.70 square feet with a Gross Living Area (GLA) of 734 square feet, making it an excellent investment opportunity for restoration and preservation. The property requires repairs and/or restoration, to be completed in accordance with the regulations of the Puerto Rico Institute of Culture, ensuring the preservation of its historical and architectural integrity. Ideal for those who appreciate Old San Juan's history, culture, and the unique opportunity to restore a truly special heritage property. $435K (appraised value).

Listing is courtesy of: MAYRA RODRIGUEZ (310-745-2680)

Listing Agent: Mayra Rodriguez (310-745-2680)

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: 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)

Remarks: Live an enchanting lifestyle highlighted by the captivating allure of the Old City within this two-level residence. Located on the second floor of the building with entry via stairwell, Apt. 4 in 203 Fortaleza St. showcases a unique open layout and two charming patios with lovely assorted greenery. Two bedrooms, two bathrooms and one powder room are harmoniously featured within the approx. 1,353 Sq. Ft. interior footprint, as well as a dedicated laundry space. The home's U-shaped kitchen affords a modern design, seamlessly connecting to the living area and dining room. The primary suite is sizable and includes accommodating closet space. Tasteful exposed wood-beam ceilings enhance and brighten the home’s second floor. Old San Juan is the epicenter of Puerto Rican culture and is dotted with several UNESCO World Heritage Sites. It serves as one of the leading tourist destinations in the Caribbean and its celebrated buildings are renowned for their elegance and historic significance. The area is known for its numerous dining, shopping and nightlife options. Minutes away from Condado Beach and the Miramar Arts District. Stroll along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan.

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

Listing Agent: Monica Alvarez (787-523-6500)

Remarks: One or more photo(s) has been virtually staged. Perfectly positioned within two of Old San Juan's most iconic streets, this historic jewel with approx. 6,042 total Sq. Ft. presents a rare and versatile investment opportunity. The multi-level property is uniquely designed with dual-street access and joint interior courtyard, offering a grand private home on 418 Norzagaray St. and income-generating potential on 419 Sol St. 418 Norzagaray's expansive six-bedroom, four-bathroom floor plan is accented by highly coveted features within OSJ, such as a one-car garage and a rooftop terrace overlooking the ocean. 419 Sol is divided into six independent apartments, each with its own dedicated kitchen and appliances. Two of the units feature a two-bed, one-bath layout with mezzanines and four of the units feature a one-bed, one-bath layout. Old San Juan is the epicenter of Puerto Rican culture and is dotted with several UNESCO World Heritage Sites. It serves as one of the leading tourist destinations in the Caribbean and its celebrated buildings are renowned for their elegance and historic significance. The area is known for its numerous dining, shopping and nightlife options. Minutes away from Condado Beach and the Miramar Arts District. Stroll along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan. Photos 3, 4, 5 and 9 are virtually staged and do not reflect the current state of the property. Photos 6 and 7 are virtually staged and feature a conceptual kitchen remodel - The aforementioned images do not reflect the current state of the property.

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

Listing Agent: Monica Alvarez (787-523-6500)

Remarks: 01 San Justo presents a rare opportunity to acquire a property in the core of Old San Juan, one of Puerto Rico’s most established and supply-constrained urban markets. Situated along a highly walkable corridor with consistent pedestrian traffic, the property benefits from strong surrounding demand driven by tourism, local commerce, and long-term historical significance. The asset offers a value-add opportunity with the ability to reposition and enhance income through renovation, lease-up, or redevelopment. Its location supports a range of uses aligned with the character and demand of Old San Juan. Commercial / mixed-use potential including retail, office, or integrated uses, subject to zoning and applicable regulations. Buyer to perform all due diligence regarding zoning, permitted uses, and property condition.

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

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

Remarks: Unique Opportunity on 201 Tetuan Street, Old San Juan! Located directly across from the iconic Banco Popular and just steps from the vibrant Old San Juan waterfront, this impressive property, spanning 32,900 sqft over 8 floors, offers endless possibilities. Currently, 26 apartments are being built for sale, along with 2 commercial spaces. Featuring an elevator that connects all levels and ocean views, this historic building, once the headquarters of Chase Manhattan Bank, is ideal for conversion into condominiums, a boutique hotel, or a mixed-use development. In one of the most sought-after areas in the Caribbean, surrounded by cobblestone streets, recreational plazas, and Caribbean fusion restaurants, this is the perfect opportunity to invest in the heart of Old San Juan. Don’t miss out on this property, rich in history and full of potential!

Listing is courtesy of: IBROKERS LISTINGS, LLC (786-304-2979)

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

Remarks: Unique Opportunity in Old San Juan! Prime commercial and residential space is available at 209 Calle San Francisco, Old San Juan, one of Puerto Rico’s most iconic and tourist-friendly locations. This 2,500 SqFt property features five apartments, one retail space, and eight bathrooms, offering an exceptional opportunity to start or expand your business in a high-traffic area rich in history, culture, and commerce. Don’t miss the chance to grow your business and enjoy residential space in one of the most sought-after addresses on the island! Immediate availability. Contact us today for more details!

Listing is courtesy of: IBROKERS LISTINGS, LLC (786-304-2979)

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

Remarks: Welcome to 254-256 Calle San Francisco. The Old San Juan offers you this spacious 2-bedroom, 2-bathroom apartment with 1, 200 sqft of beautifully furnished living space. Featuring a modern, fully-equipped kitchen perfect for culinary enthusiasts, this home combines comfort and style in one of Puerto Rico's most desirable neighborhoods. Enjoy living just steps away from the vibrant culture, history, and breathtaking views that make Old San Juan unique. Don't miss the opportunity to own a piece of Puerto Rico paradise!

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

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

Remarks: Discover the perfect blend of modern living and historic charm with this stunning 2-bedroom, 2-bathroom apartment at 254-256 Calle San Francisco. Offering 1,189 sqft of thoughtfully designed space, this fully furnished home features an open-concept living area and a spacious kitchen, as well as breathtaking views of the vibrant streets of Old San Juan. This apartment is in an unbeatable location, steps away from cultural landmarks, dining, and entertainment. Experience the best of the Puerto Rico lifestyle today!

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

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

Remarks: Located at 254-256 Calle San Francisco, this beautifully furnished 2-bedroom, 2-bathroom and a beautiful balcony. This apartment offers 986 sqft of spacious living in one of the most iconic neighborhoods of Puerto Rico. Ideal for a couple or small family, the property combines comfort, style, and a prime location. Enjoy vibrant city life with historic charm, steps from cafes, restaurants, and stunning views of the San Juan Bay. Experience the unique culture of Old San Juan, while having a peaceful retreat in your modern home. Don’t miss out on the opportunity to own a piece of paradise!

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

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

Remarks: This fully-furnished 2-bedroom, 2-bathroom apartment offers 983 sqft of spacious living. Located at 254-256 Calle San Francisco, enjoy stunning views of the picturesque streets of Old San Juan from your private balcony. Ideal for a couple or small family, this home combines modern comfort with a prime location in one of Puerto Rico’s most iconic neighborhoods. Step outside and immerse yourself in the vibrant culture, historic landmarks, and breathtaking scenery that make Old San Juan unique. Don’t miss out on this perfect opportunity to live where history meets luxury!

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

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

Remarks: Experience a unique commercial opportunity in the heart of Old San Juan with the former Old Harbor Brewery space, a striking two-level property offering approximately 10,975 SF of versatile interiors. The ground floor spans 6,720 SF and features an open layout with two full bar areas, a spacious kitchen, and soaring 18-foot double-height ceilings that make a dramatic first impression. Upstairs, the 4,255 SF mezzanine level overlooks the main floor, making it ideal for events, dining, or lounge areas, and includes private office spaces in the rear. With its iconic location, historic charm, and flexible layout, this property is perfectly suited for a brewery, restaurant, event venue, or creative commercial concept. Situated on the bustling corner of Recinto Sur and Tizol Street, this location offers exceptional visibility and steady pedestrian traffic. Just moments away from the cruise ship port, it captures the attention of thousands of tourists entering Old San Juan daily, making it a high-impact spot for any customer-facing business. Additionally, it’s only one block away from three major public parking garages such as Dona Fela, Paseo Portuario and La Puntilla, providing convenience for both locals and visitors alike. This is a prime location for a dynamic commercial venture in one of the most visited and beloved areas of Puerto Rico.

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

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

Remarks: Located on the historic financial district of Old San Juan, 205 Calle Tetuan represents a rare and highly compelling investment opportunity in one of Puerto Rico’s most supply-constrained markets. This 8-unit multi-family property is comprised of two 2-bedroom units, four 1-bedroom units, and two studio apartments, offering a versatile unit mix ideally suited for short-term rentals, long-term leasing, or a hybrid strategy. The property enjoys charming city views throughout, with notable views of the San Juan Bay, particularly from the top floors and rooftop. A key highlight of this offering is its value-add and customization potential. The property can be finished and designed to a buyer’s specific vision, making it especially attractive for investors seeking to elevate the asset into a boutique short-term rental concept. The rooftop level offers additional upside, with the potential to be reimagined as a lounge or entertainment terrace and the possibility of creating additional units, subject to permits, maximizing both views and revenue potential. Surrounded by Old San Juan’s iconic architecture, waterfront promenades, dining, galleries, and cultural landmarks, 205 Calle Tetuan stands at the intersection of history, lifestyle, and income potential, an exceptional opportunity to create a high-performing asset in one of the Caribbean’s most enduring destinations.

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

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