Old San Juan Homes with Three+ Story Style

Old San Juan Homes with Three+ Story Style

Welcome to the historic and vibrant subdivision of Old San Juan, located in the heart of San Juan, Puerto Rico. Known for its charming cobblestone streets, colorful colonial buildings, and rich cultural heritage, Old San Juan is a unique and enchanting neighborhood that offers a truly one-of-a-kind living experience.

If you're looking for homes with true character and charm, the Homes with Three+ Story Style in Old San Juan are sure to captivate you. These properties boast traditional architecture with multiple levels, offering plenty of space for you to live, work, and entertain in style. From cozy townhouses to grand colonial mansions, there is a diverse range of options to suit every taste and lifestyle.

Living in Old San Juan means immersing yourself in a vibrant community with a rich history and a lively atmosphere. Explore the narrow streets lined with boutiques, art galleries, and restaurants, or take a leisurely stroll along the historic city walls for breathtaking views of the ocean. With its perfect blend of old-world charm and modern conveniences, Old San Juan is the ideal place to call home for those who appreciate the beauty of the past and the excitement of the present.

Discover the magic of Old San Juan and find your dream home in this timeless neighborhood where history, culture, and luxury come together to create a truly special living experience.

Newest Old San Juan Homes with Three+ Story Style

$9,175,000
28 Beds ⋅ 29 Baths ⋅ PR9119415 MLS
Prime Investment Opportunity in Old San Juan Located on 153 San Justo St, this impressive property features 16 independent units, each with spacious bedrooms, modern bathrooms, and fully equipped kitchens with high-end finishes. Some units include private balconies or patios, adding to the property's charm and appeal. Perfectly situated in the heart of historic Old San Juan, this is an ideal opportunity for short-term rentals, boutique hotel development, or long-term income property. A rare find in one of Puerto Rico’s most sought-after locations.

153 San Justo, San Juan
$6,500,000
PR9118739 MLS
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.

205 Luna, San Juan
$5,000,000
10 Beds ⋅ 10 Baths ⋅ PR9118274 MLS
Located in the vibrant historic district of Old San Juan, this 10-unit residential building blends colonial charm with modern functionality. Featuring spacious units and 10800 sq ft of total building area, this property represents a true real estate gem in one of Puerto Rico’s most sought-after locations. Surrounded by historic architecture, cafés, museums, and rich cultural life, this building is ideal for an investment portfolio focused on high-value urban rentals.

152 San Justo Street, San Juan
$5,950,000
4 Beds ⋅ 5 Baths ⋅ PR9116025 MLS
A landmark of architectural and historical significance, 152 Calle de Tetuan once housed the prestigious Spanish Bank, inaugurated in 1894 as a cornerstone of Puerto Rico’s financial past. Set along Tetuan Street, once the island’s bustling financial district, this property with approved plans and construction permits carries with it the legacy of culture of Old San Juan’s golden era. Today, the building stands as a rare opportunity to reimagine a piece of history. Spanning three expansive floors, the interiors feature an open floor plan with soaring 19-foot ceilings, inviting abundant natural light and endless design possibilities. The property also boasts a usable rooftop, which can be enclosed into a signature amenity space or transformed into an outdoor terrace with panoramic views of the bay and San Juan’s port to the south, an ideal setting for entertaining or enjoying the city’s maritime landscape. Whether envisioned as a grand private residence or a distinguished legacy estate, 152 Calle de Tetuan offers the perfect canvas. Its location at the heart of Old San Juan, coupled with its rich heritage and architectural character, makes it one of the most unique and versatile properties available in Puerto Rico’s historic capital. * Images 1 and 3 through 12 are renderings and do not reflect the current state of the property.

152 Tetuan Street, San Juan
$9,500,000
4 Baths ⋅ PR9112748 MLS ⋅ 201 Tetuan St BLDG.
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!

201 Tetuan Street, San Juan
$5,200,000
5 Beds ⋅ 8 Baths ⋅ PR9112696 MLS ⋅ 209 San Francisco BLDG.
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!

209 San Francisco Street, San Juan
$3,812,000
6 Beds ⋅ 5 Baths ⋅ PR9108453 MLS
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.

9 Calle Del Mercado, San Juan
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