Meet the Upside Realty Team

The founding partners at Upside Realty, LLC are real estate attorneys and demonstrated entrepreneurs with a deep respect for their clients’ long-term objectives and budget considerations. The Upside Realty team is led by corporate and transactional attorney MR. Juan Carlos Stolberg, who has represented clients working in a variety of fields, including real estate developers, fund advisers, tech startup founders, beverage distributors, restaurant owners, and more. Since 2003, Mr. Stolberg has been a Director at the Stolberg Group, a commercial and residential real estate holding company based in Old San Juan, Puerto Rico, responsible for overseeing and managing over 25 units in the old city alone.

Ms. Sashira Cortés joins Upside Realty as Operations Director, where she oversees all the firm’s management processes and client accounts. Before joining the team at Upside Realty, Sashira spent more than three years working in the financial space managing accounts and performing auditing and quality control. The Upside Realty team is pleased to move our clients closer toward their real estate purchasing, selling, and investment goals with efficiency and professionalism.

Lcda. María Cristina Falcón Font, is a Real State Broker and Attorney.  At Upside, she is leading project management, contracts, client service, negotiations, property and business administration.

At Upside Realty, we understand all aspects of commercial and residential real estate as well as the legal aspects of the real estate industry in Puerto Rico. Get started on your real estate journey with a team of reliable, reputable professionals. Invest. Add Value. Profit. 

Juan Carlos Stolberg

Sashira Cortés

Giancarlo Gonzalez

Lcda. María Cristina Falcón

Situated in the heart of Old San Juan, 204 Tetuan stands as a testament to the city's rich history and architectural grandeur. Originally constructed in 1912 as a distinguished bank building, this property exudes timeless elegance with its magnificent stone facade and imposing 16-foot ceilings in the entrance hall. Upon stepping inside, one is greeted by the impeccably preserved original marble columns and flooring, a captivating reminder of the building's prestigious past. Descending to the lower floor unveils a fascinating feature—a former bank vault, presenting an exciting opportunity for conversion into a wine cellar or a captivating focal point within the home. The third floor, with its expansive open space, offers versatility and potential, ideal for crafting bedrooms that boast enchanting views overlooking Tetuan Street, with each floor boasting its own separate entrance. Moreover, the property's commercial zoning adds to its appeal, allowing for various possibilities to suit the discerning buyer's preferences and needs. For those seeking to weave their own narrative into the tapestry of Old San Juan's storied past, 204 Tetuan presents an unparalleled opportunity to transform a piece of history into a cherished residential sanctuary. 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 top tourist destinations in the Caribbean and its celebrated buildings are renowned for their elegance and cultural significance. The area is known for its numerous dining, shopping and nightlife options. Minutes away from Condado Beach and the Miramar Arts Districts. Walk along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan. $5,995,000 Active

204 Tetuan Street San Juan, Puerto Rico

1 Beds 4 Baths 12,535 SqFt 0.34 Acres

Enjoy an enchanting lifestyle in Old San Juan within this unique historical jewel overlooking the ocean. Beautifully constructed in the 1800’s, this exceptional two-level residence with four bedrooms and three bathrooms is without equal and evokes a timeless charm. The property is a rare find, spanning two interconnected buildings with dual entrances, one located on 254 Norzagaray and the other on 255 San Sebastian. An alluring aesthetic and captivating ambiance is showcased throughout the approx. 3,864 interior Sq. Ft. and approx. 1,111 Sq. Ft. of outdoor space. The home’s exceedingly striking design is exquisitely accented by partial original flooring, exposed brick walls and wood beam ceilings. The first floor features a courtyard for alfresco entertainment, fully-equipped kitchen with pantry, dining area, flex room, multiple living areas, two of the bedrooms and a bathroom. A lower level beneath the first floor offers a dedicated laundry room and storage options for added convenience. The second floor houses the primary suite, one additional bedroom and bathroom, as well as a rooftop space. The primary suite affords exclusive access to an expansive North-facing terrace with ocean views and a bespoke private bathroom with dual vanities and standalone tub. 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 Districts. Walk along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan. $5,470,000 Active

254 Norzagaray Street San Juan, Puerto Rico

4 Beds 3 Baths 4,975 SqFt 0.08 Acres

257 San Justo Street is situated in the heart of Old San Juan, a historic district renowned for its Spanish colonial architecture and vibrant cultural scene. The area is characterized by its cobblestone streets lined with pastel-colored buildings, bustling with tourists and locals alike. The property boasting 5,254 sf of air conditioned space and 82 sf of exterior space is beautifully maintained with a traditional façade, complete with wrought-iron balconies and street views of San Juan Bay, capturing the essence of Old San Juan’s architectural charm. The first floor showcases an elegant open-concept space with exposed wooden beams, which currently serves as an art gallery. It features refined marble floors and recently renovated powder rooms, providing modern comfort. As one walks further into the space, a stunning interior courtyard is revealed, protected by a skylight roof. The courtyard boasts a captivating fountain, living plant wall, and a full wet bar, making it ideal for a café or an entertaining area. There is also a full commercial kitchen in the back that connects to the upstairs, providing the perfect setup for events. The second floor offers a warm, residential feel with the utmost privacy. A foyer leads to the great room, which features wide planked wood floors and a generously-sized layout. Its large windows flood the space with natural light and open up to a balcony that faces San Justo Street and provides partial views of the bay, enhancing the allure of this one of a kind offering. There is also potential to create a rooftop area, adding even more versatility to this unique property. The neighboring property, 255 San Justo Street, is also available for purchase at $935,000. $3,700,000 Active

257 San Justo Street San Juan, Puerto Rico

1 Beds 4 Baths 5,337 SqFt 0.07 Acres

Situated in the heart of Old San Juan, this remarkable 6-bedroom, 6.5-bathroom residence seamlessly combines 18th-century charm with timeless elegance and modern comforts. Spanning approximately 4,074 Sq. Ft. of interior air conditioned space and an additional 1,914 Sq. Ft. of outdoor living, this palatial home with a private elevator offers an expansive 3-level layout designed for grand entertaining and a refined way of life. 275 Sol showcases tasteful living areas with an abundance of natural light throughout, in addition to a 83' 6'' x 22' 9'' rooftop terrace overlooking the old city with partial views of the bay and an indoor swimming pool on the ground floor. The first level also includes a guest bedroom with its own kitchen/living room and bath, allowing it to serve as a separate rental property to generate income as a rare investment opportunity. The main kitchen is located on the second floor, featuring top of the line appliances ready for your culinary endeavors. All of the bedrooms are ensuite and the primary includes a unique 2-level closet. This Spanish Colonial jewel with full tax exemption was recently restored to embody an enchanting lifestyle enriched by its storied history and architectural beauty. 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 Districts. Walk along the cobblestone streets and experience the mesmerizing vibrancy of what we call El Viejo San Juan. $3,500,000 Active

275 Sol Street San Juan, Puerto Rico

6 Beds 7 Baths 5,988 SqFt 0.04 Acres

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, the oldest Church in the Americas. 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. 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. $3,050,000 Active

9 Calle Del Mercado San Juan, Puerto Rico

6 Beds 5 Baths 3,420 SqFt 0.04 Acres

Now with a new price! Located on the first street ever built in Old San Juan, 66 Caleta de San Juan is a stunning 5-bedroom, 3-bathroom Spanish Colonial gem that offers an exquisite tapestry of historical grace and modern comforts. Situated on a beautiful, tree-lined street, this historic home benefits from its location on Caleta de San Juan, which begins at the iconic Puerta de San Juan and culminates at the majestic Cathedral of San Juan Bautista. Immerse yourself in a vibrant tapestry of history, culture, and cuisine, all within steps of your front door. Originally built in 1610 and meticulously renovated by Architect W. Ramirez, this home is steeped in history while thoughtfully expanded and updated over the years. A rare find in Old San Juan, this majestic residence welcomes you with its elegant facade and high-ceilinged interiors that speak of its rich heritage. Upon entering, the heart of the home unfolds with gracious living spaces where marble and traditional hydraulic tiles (losas criollas) flooring narrate the stories of bygone eras. The living area transitions into a formal dining space, leading to a well-appointed kitchen. This two-level residence thoughtfully separates the living quarters with the main social areas, including a wet bar, breakfast nook, one guest bedroom, one full bathroom, and a family/media room on the ground floor. Upstairs, the privacy of 4 additional bedrooms, 2 full bathrooms, and a laundry /kitchenette area await. A spiraled staircase ascends to a rooftop, offering an aerial embrace of the city's charm. (1st floor 1,332 Sq. Ft. | 2nd Floor 1,350 Sq. Ft. | Internal Patio 608 Sq. Ft. approx.) Step outside to the expansive internal patio space with an outdoor kitchen, where dining under the open sky becomes an everyday indulgence, providing a perfect backdrop for gatherings or moments of solitude. This furnished and equipped home also offers additional amenities, including a water softening system, backup power generator, 150-gallon water cistern, and a solar heater, ensuring uninterrupted comfort. 66 Caleta de San Juan is surrounded by historical, cultural, and culinary landmarks. Steps from iconic sites such as Hotel El Convento, Catedral de San Juan, Plaza de la Catedral, and Puerta de San Juan, this residence is more than a home—it's a legacy awaiting its next curator. $2,775,000 Active

66 Caleta De San Juan San Juan, Puerto Rico

5 Beds 3 Baths 3,290 SqFt 0.03 Acres

Under contract-accepting backup offers. Historic Gem in the Heart of Old San Juan - Lucrative Investment Opportunity! Welcome to the epitome of luxury living in Old San Juan! This meticulously maintained historic home, with a rich cultural heritage, is now available for sale. Boasting an impressive 4000 sqft of interior space, complemented by 2000 sqft of enchanting outdoor areas, this property is a haven for both residents and visitors alike. Key Features: Revenue Generation: A proven track record with a staggering $350,000 annual income from short-term rentals. Size & Layout: Sprawling across 7 bedrooms and 4.5 baths, this 4000 sqft home offers spacious and versatile living spaces, ideal for hosting guests or accommodating a large family. Outdoor Oasis: Enjoy the enchanting outdoor spaces, including a delightful patio and a panoramic roof deck, perfect for soaking in the charm of Old San Juan. Relaxation Retreat: Unwind in style with a private pool and a heated grotto jacuzzi in the basement, providing a luxurious escape right at home. Modern Amenities: No expense spared with luxury finishes and fully equipped interiors. The property has been thoughtfully remodeled to blend historic charm with contemporary comfort. Climate Control: Stay comfortable year-round with split AC units in every interior room and space, ensuring a cool and inviting atmosphere. . Private residence: You can also make this your own private residence if you wish. Many of the bedrooms and can be ocmbined to create more living space like adding a gym and/or office. Discover the allure of Old San Juan in the lap of luxury - seize this opportunity to make this historic home yours today! $2,450,000 Pending

356 Calle Luna Old San Juan, Puerto Rico

7 Beds 5 Baths 4,000 SqFt 0.07 Acres

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 and is the largest unit in the building. This unit also has its own private laundry room with a brand new stackable 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! $1,400,000 Active

9 Del Mercado 3 San Juan, Puerto Rico

3 Beds 2 Baths 1,600 SqFt 0.04 Acres

Exceptionally Charming and Fully-Furnished Home with Ocean Views! Majestically located for easy access in-and-out of Old San Juan, this 3BR/2.5BA residence captivates with stunning Spanish architecture, an open layout, soaring 13’7” ceilings (main-level), durable tile flooring, painted wood beam ceilings, welcoming dining room, exposed brick accent walls, and a sizeable living room. Comfortable and stylish furnishings offer universal appeal, while the soft natural light fills the interior with seemingly endless luminosity. Emanating a modern vibe, the brandnew gourmet kitchen features stainless-steel appliances, quartz countertops, sleek custom cabinetry, farmhouse sink, contemporary tile backsplash, open shelving, dishwasher, built-in microwave, electric stove, refrigerator, and a chic waterfall peninsula with a breakfast bar. Explore further to find an enclosed courtyard for alfresco dining or peaceful morning coffee. Each bedroom is wonderfully sized with cozy furnishings, while the primary bedroom also has an attached en suite. Enjoy the unsurpassed beauty of Puerto Rico from the rooftop with picturesque views of the dazzling ocean. Entertain on the rooftop with post-dinner drinks, or bask in the lovely private terrace. For those who value convenience, the home is close to amazing attractions, such as the fortress of Castillo San Cristobal (120-m), highly-rated restaurants (87+m), excellent schools (57+m), and terrific shopping (170+m). Call now for your private showing! $1,400,000 Active

405 Calle Sol Old San Juan, Puerto Rico

3 Beds 3 Baths 2,200 SqFt 0.03 Acres

"Historic 3-Level Gem in Old San Juan with High Ceilings – Perfect for living in or rent on Airbnb!" Description: "Step into history with this stunning 3-level house located in Luna Street in Old San Juan with an area provides approx. 1.893 Sq.. With original architecture, preserved colonial features, and its spanish cultural significance. Boasting high ceilings create a spacious and airy atmosphere and a perfect blend of colonial charm and modern comfort. Enjoy the vibrant culture, stunning architecture, and unbeatable location. Walk along the cobblestone streets and experience the enchanted Viejo San Juan. This house offers a unique experience you won't forget. The house is set up with all necessary supplies and comforts. • Levels: in the first level with living, dining room, updated fully equipped kitchen with washer/dryer one bath skylight; second level with the two separate bedrooms, one full bathrooms, skylight and exit to roof terrace. Lower level – family area with one separate bedroom, air conditioning in all the house. Comfortable bedding and linens- Completely Furnished. In the sales almost everything is include. $1,295,000 Active

402 Luna 402 San Juan, Puerto Rico

3 Beds 2 Baths 1,893 SqFt

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. 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! $1,250,000 Active

9 Del Mercado 2 San Juan, Puerto Rico

2 Beds 2 Baths 1,500 SqFt 0.04 Acres

Do you imagine having a property in a neighborhood recognized for its architecture, beautiful beaches, and excellent food? This situation could be possible, and you can make it happen, but how? The answer is straightforward: invest in a single home for sale. iBroker Listings has the perfect single house for sale: 152 Sol Street, San Juan PR 00901. It features two bedrooms, two bathrooms, and 2,000 Ft². We know this property is fantastic! Don’t miss this opportunity to increase your earnings. $985,000 Active

152 Sol Street San Juan, Puerto Rico

2 Beds 2 Baths 2,000 SqFt 0.01 Acres

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. $935,000 Active

255 San Justo Street San Juan, Puerto Rico

4 Beds 4 Baths 9,530 SqFt 0.11 Acres

Beautiful apartment on the 3rd floor with ocean view in the luxurious Condado Lagoon Villas at Paseo Caribe building. Located in the tourist area of ??San Juan next to the Caribe Hilton, steps from the beach, near the T-Mobile District, Convention Center, among other places of great interest. It consists of a studio with a bathroom, a private balcony where you will enjoy a beautiful view of the bay. Perfect opportunity to generate good income and rent in the short term. Do not miss this excellent investment opportunity and start generating income. The complex offers water and electricity for all apartments and has a generator. HOA $523.18 includes light and wather. $559,900 Active

25R Paseo Caribe San Juan, Puerto Rico

1 Beds 1 Baths 451 SqFt 451 Acres

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. $400,000 Active

9 Del Mercado 4 San Juan, Puerto Rico

1 Beds 1 Baths 320 SqFt 0.04 Acres

This two-story property offers the perfect blend of commercial and residential spaces. On the first level, there is a commercial space of approximately 2,000 square feet. The second level features two residential units: one with two bedrooms and one bathroom, and another with four bedrooms and one bathroom. The property is equipped with separate meters for commercial and residential electricity, along with a single water meter. This is an excellent investment opportunity, ideal for generating both commercial and residential income. $395,000 Active

303 Calle San Agustin San Juan, Puerto Rico

6 Beds 4 Baths 2,561 SqFt 0.06 Acres

4-White (1)

151 San Francisco St. Suite 201
San Juan, Puerto Rico 00901
(787) 725-3191