Old San Juan Homes with Two Story Style

Old San Juan Homes with Two Story Style

Welcome to Old San Juan, a historic subdivision located in San Juan, Puerto Rico. Known for its charming cobblestone streets, colorful buildings, and rich cultural heritage, Old San Juan offers a unique living experience for those seeking a blend of old-world charm and modern convenience.

If you're looking for homes with a two-story style, Old San Juan has plenty to offer. From traditional Spanish colonial architecture to more contemporary designs, you'll find a variety of options to suit your taste and lifestyle. Imagine waking up to panoramic views of the ocean or enjoying a leisurely stroll through the vibrant streets lined with cafes, boutiques, and art galleries.

Living in Old San Juan means being part of a tight-knit community where neighbors become friends, and every corner tells a story. Whether you're interested in exploring the historic forts, sampling local cuisine, or simply soaking in the laid-back island vibe, there's something for everyone in this enchanting neighborhood.

Don't miss the opportunity to own a piece of history in Old San Juan. With its picturesque setting, rich cultural scene, and unique architectural styles, this subdivision is the perfect place to call home. Discover the beauty and charm of Old San Juan and experience the magic of living in one of Puerto Rico's most iconic neighborhoods.

Newest Old San Juan Homes with Two Story Style

$2,695,000
4 Beds ⋅ 4 Baths ⋅ PR9123266 MLS
An authentic colonial jewel at Callejón del Hospital, Old San Juan, PR. Positioned within one of the most historically significant settings, this light-filled two-story residence belongs to a very limited collection of private homes surrounding Casa Blanca, placing its future owner within an environment where history is not recreated, but preserved & lived every day. Offering approximately 3,000 sf of thoughtfully restored living space, this remarkable home embodies the perfect balance between authentic colonial character, comfort, & modern systems. It is a residence where original architectural elements, peaceful surroundings, & modern functionality coexist. The home welcomes you through a gracious foyer into inviting interiors designed for intimate living. The first level features a formal living room, a family room, a versatile flex room, and a charming interior patio that introduces natural light and a sense of serenity throughout the residence. The north wall of this private interior patio is formed by a portion of the historic walls of Casa Blanca, creating an architectural connection to the origins of San Juan itself. This first level also offers two bedrooms with two full bathrooms, along with a private guest bedroom featuring its own en-suite bathroom, providing flexibility for family living, visiting guests, or multigenerational living. The entire second floor is dedicated to the private owner's retreat, creating a secluded sanctuary within this historic residence. This level features a spacious primary bedroom with ample closet space, a generous spa-inspired bathroom complete with both an antique soaking tub and a separate shower, a dedicated office area, and an adjoining flex room ideally suited as a private lounge, library, creative studio, or wellness space. The primary suite is further enhanced by direct access to a classic colonial balcony overlooking the lush gardens of Casa Blanca. Framed by centuries-old greenery, both the bedroom and bathroom enjoy tranquil views of this landmark, creating an atmosphere of serenity and offering a level of peace rarely found in the center of a historic city. Crowning this property, the rooftop terrace reveals one of the residence's most captivating treasures: sweeping views of San Juan Bay and the enchanting gardens of Casa Blanca. Beyond its architectural and historical significance, the residence offers modern infrastructure that further distinguishes it from virtually every other historic home. Among its most highly valued features is its original restored underground Spanish colonial cistern, with a capacity of approximately 5,000 gallons. Designed centuries ago, as an ingenious rainwater harvesting system, the home's original stone channels continue to capture and naturally direct rainwater into the underground cistern, where it is collected, filtered, and stored, preserving an extraordinary example of colonial engineering that remains functional today. Complementing this piece of history is a full power generator connected directly to the city's natural gas system, eliminating the need for fuel refills and providing comfort and peace of mind during power interruptions. Buying this residence is not simply acquiring real estate. It is becoming the steward of a meaningful piece of Old San Juan's heritage. A place to live fully, gather with loved ones, create memories, and preserve its story for generations to come. A colonial treasure. A rare setting. A legacy to inherit.

52 Callejon Del Hospital, San Juan
$3,980,000
3 Beds ⋅ 3 Baths ⋅ PR9120467 MLS ⋅ La Victoria BLDG.
Pre-Construction. To be built. A true rarity, La Victoria at 425 Sol St. is a premier new development in the historic heart of Old San Juan. Modern elements and old-world charm intertwine to create a timeless sanctuary overlooking the Atlantic Ocean and San Cristobal Castle, an iconic landmark that defines the island’s majestic skyline. This 3-bedroom, 3-bathroom penthouse spans approx. 2,110 Sq. Ft. across two thoughtfully designed levels showcasing 9’ ceiling heights, Terrazzo flooring and curated design features. Two enclosed balconies, one on each floor, invite you to enjoy the essence of elevated Caribbean living with constant sea breezes and scenic panoramic vistas of the Old City. Upon entry, the first level immediately impresses with an exquisitely crafted open-concept living/dining area and designer kitchen bathed in natural light. A guest bedroom is discreetly tucked away on this floor, featuring its own walk-in closet and bathroom. A spiral staircase leads to the second level, which serves as a private retreat. This floor hosts an expansive secondary living area, as well as the beautifully-appointed primary suite with walk-in closet and an additional guest bedroom, both of which are ensuite. A boutique condominium, La Victoria, encompasses an exclusive collection of only three residential apartments and a commercial space, crowned by a shared rooftop with pool and BBQ area. The building is equipped with a full-power backup generator, water cistern and elevator access to each 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. Perfectly positioned, minutes away from Condado Beach and the Miramar Arts Districts. Stroll along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan. * All images of the property are renderings and do not reflect the current state of the development. The view from the residence may vary based on the chosen unit. Perspective rendering is an artist’s interpretation only. Architectural elements may vary from rendering. Renderings may show options not included in base price. The developer reserves the right to substitute any materials for others similar in quality if these are not available when required for construction and to modify places when considered necessary.

425 Sol Street Unit Penthouse, San Juan
$2,395,000
2 Beds ⋅ 3 Baths ⋅ PR9121059 MLS
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.

422 Norzagaray, San Juan
$926,000
1 Beds ⋅ 2 Baths ⋅ PR9119014 MLS
Your ideal retreat is at 203 Calle Recinto Sur in the heart of Old San Juan, Puerto Rico. This inviting 1547 SqFt loft style apartment offers a harmonious blend of comfort and elegance, perfect for singles or couples ready to embrace island living. Featuring 1 spacious bedroom, a full bathroom, and a convenient half bathroom, this fully furnished sanctuary is filled with natural light and boasts stunning bay views. With ample space and proximity to parking, it's designed for ease and relaxation. Where? in vibrant Old San Juan, immerse yourself in a city where history meets modernity, with cobblestone streets, lively local eateries, and a welcoming community. Experience the unparalleled beauty and adventure Puerto Rico offers, from pristine beaches to lush landscapes. Make this apartment your new home and discover the unique charm of island life.

203 Recinto Sur Unit 5, San Juan
$1,620,000
3 Beds ⋅ 3 Baths ⋅ PR9118962 MLS
Located at 203 Calle Recinto Sur in the heart of Old San Juan, this spacious loft-style apartment offers 1,912 SqFt of well-designed living space. The property features 3 bedrooms and 3 full bathrooms, providing a functional layout ideal for comfortable living or investment use. The apartment is fully furnished and filled with natural light, with open living areas and bay views that enhance its appeal. Generous interior spaces allow for both everyday living and entertaining. Convenient proximity to parking adds to the practicality of this Old San Juan residence. Situated in one of San Juan’s most iconic neighborhoods, the property is surrounded by historic architecture, cobblestone streets, dining, shopping, and cultural attractions. Easy access to beaches and major roadways offers the perfect balance between urban living and island lifestyle.

203 Recinto Sur Street Unit 2, San Juan
$1,800,000
2 Beds ⋅ 3 Baths ⋅ PR9116631 MLS
Experience timeless elegance and authentic Old San Juan charm in this exceptional single-family home, ideally located on one of the most desirable and tranquil streets in the historic district. This beautifully preserved residence offers 2 bedrooms and 2.5 bathrooms, with approximately 2,050 square feet plus an impressive 750-square-foot rooftop terrace that captures the essence of Caribbean living. The home showcases classic Spanish Colonial architecture, featuring high ceilings with exposed wooden beams, arched passageways, warm stone floors, and solid wood doors that reflect its historic character while blending seamlessly with modern comforts. Natural light floods the interiors through large windows and French doors, highlighting the texture and craftsmanship throughout. The master bedroom offers captivating ocean views, allowing you to wake up to the serene beauty of San Juan Bay. The property offers not one but two terraces, providing multiple spaces to relax or entertain, including a rooftop terrace that is truly a rare gem—offering breathtaking panoramic views of San Juan Bay, the daily arrival and departure of cruise ships, and the magnificent Casa Blanca, the home of Juan Ponce de León and his family. It’s the perfect setting to enjoy unforgettable sunsets over the water and the twinkling city lights at night. Additionally, the residence offers space and structural potential to accommodate an elevator, adding modern convenience to this timeless home. Nestled just a few doors from La Fortaleza, the Governor’s Mansion, this residence enjoys one of the most secure and prestigious locations in all of Old San Juan, only steps away from a peaceful park, a charming plaza, fine dining, and vibrant cultural attractions. This remarkable property presents a rare opportunity to own a piece of Puerto Rico’s rich history, offering a lifestyle defined by beauty, authenticity, and unmatched views.

10 Calle Sol, San Juan
$760,000
2 Beds ⋅ 3 Baths ⋅ PR9113377 MLS ⋅ Fortaleza 203 BLDG.
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.

203 Fortaleza Street Unit 4, San Juan
$2,900,000
3 Beds ⋅ 4 Baths ⋅ PR9112439 MLS
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.

50 San Francisco St, San Juan
$849,000
4 Beds ⋅ 4 Baths ⋅ PR9107368 MLS
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.

255 San Justo Street, San Juan
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