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

This Spanish colonial treasure is the epitome of city living with old world charm. Exquisitely constructed in the 19th century, 208 Luna has been beautifully restored and modernized over the years to create the perfect balance of romantic historic architecture and contemporary design elements. The 3-level layout features 7 bedrooms and 6 bathrooms tastefully distributed throughout the approx. 8,310 Sq. Ft. interior floor plan. Arched entryways, wooden beam ceilings, exposed brick walls and an abundance of natural light accent the home's timeless elegance and captivating allure. The first floor features an open-concept living area with kitchen and dining space, in addition to two ensuite bedrooms, wine cellar and courtyard with lush greenery. The second floor showcases a sizable family room and gym with basketball hoop, as well as an additional kitchen with custom-made shelving and 4 bedrooms, 2 of which are within portable "pods" that have a unique bi-level apartment layout. The third floor houses the primary suite and den which seamlessly connect to the outdoor space. Enjoy breathtaking views of the old city from any of the property's multiple balconies and terraces. An eco-sustainable haven, the residence is solar powered by 48 photovoltaic panels and two Tesla batteries. Two roof-top gardens serve as one of the home's many highlights. The garden on the North-facing terrace can be used to cultivate herbs, fruits and other diverse tropical flora. The garden on the East-facing terrace is the ideal space for entertaining, featuring a spacious BBQ area. This property is tax exempt due to its historic landmark recognition and includes a 1-car garage, a rare and highly coveted find within the community. 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. $6,200,000 Active

208 Luna Street San Juan, Puerto Rico

7 Beds 6 Baths 8,310 SqFt 0.080 Acres

Great location. Quiet Street. Beautifully restored luxury residence featuring an original layout and woodwork dating back to the late 1800's. 2 story home, featuring an open space with high ceilings, fans everywhere and an impressive exposed brick interior patio and exquisite underground wine cellar as well as a water cistern. Completely Renovated in 2012 and more upgrades 2021. This 2 level residence has 5 bedrooms and 4.5 Bths. each bedroom has an attached bathroom making it a excellent lay out for families. The home has been wired to function as an intelligent home, and boasts a theatre room with a full movie-going experience with Bose surround sound. Bathrooms remodeled, providing sleek modern design accents. Located on the precipice of the famous steps at Plaza de la Barandilla. Seller financing for a qualified Buyer with 25% down payment and a short term loan. Buyer Agent fee 3%. For showing instructions, please see MLS notes. $5,150,000 Active

305 Calle De La Luna San Juan, Puerto Rico

5 Beds 5 Baths 5,150 SqFt 0.060 Acres

259 Calle Fortaleza, San Juan PR 00901. Mixed use property residential & commerial. Approx.. 11,300 sq ft on 2 floors with a total of 3 units. +/- 2500 sq ft of prime commercial retail space on first floor street level, +/- 2500 sq ft of another adjacent prime commercial retail space on first floor street level, +/- 5,000 sq ft of office space in the second floor, +/- 1,300 sq ft of entrance and hallway leading to the second floor. Great location, in excellent condition, priced to sell. Space upstairs for offices or a gym Can easily be converted to 10 or 15 rooms hotel upstairs to benefit from busy demand for hotel room with a 40% tax credit towards purchase and rehab. Buyer Agent fee 3%. For showing instructions, please see MLS notes. $3,650,000 Active

259 Calle Fortaleza San Juan, Puerto Rico

10 Beds 10 Baths 11,300 SqFt 0.120 Acres

OLD SAN JUAN, step back in time and immerse yourself in the rich history and culture of Old San Juan, with this stunning colonial house for sale! This beautiful property, built in the late 1780s, has been carefully restored and preserved to retain its original charm and character. Located in the heart of the old city, this property offers the perfect blend of old-world charm and modern convenience. The house is a three-level home, having 3,500 square feet, featuring three bedrooms, three bathrooms, powder room, two living areas, dining, kitchen, family, office room, storage, patio, two terrace spaces at the second level and roof terrace. The lot has an area of 151 square meters. As you enter, you'll be greeted by a grand foyer that leads to a spacious living room with high ceilings and traditional Spanish marble tile floors. As you step into the zaguan of this stunning colonial home, you'll feel like you're being transported back in time to a bygone era of grandeur and elegance. The zaguan, with its soaring arches serves as a dramatic entryway, leading you from the bustling street outside to the serene and private living area within. Making your way through the zaguan, you'll notice the intricate details and craftsmanship that are hallmarks of colonial architecture. The tiled floors, meticulously laid by skilled artisans, create a sense of flow and continuity, leading you deeper into the heart of the home. The high ceilings, adorned with decorative moldings and carvings, lend a sense of greatness and importance to the space. The formal dining room is perfect for hosting dinner parties, with plenty of space for family and friends to gather around the table. The fully equipped kitchen has been updated with modern appliances, while still retaining the traditional style of the home. The second level has three spacious bedrooms, each with its own unique character and charm, and full bathrooms in addition to two terrace spaces at each end of this level. Gazing upon the historical masonry wall located in the lower level of the patio area, you will be mesmerized by the texture and color of the wall, along with the elaborate patterns of the bricks, telling the story of colonial times and cultural heritage. The warm sun and gentle breeze from the mango tree add to the peaceful ambiance, allowing you to fully appreciate the beauty of the architecture and the natural surroundings. Step outside to the expansive rooftop terrace, where you can enjoy stunning views of the city and the ocean beyond. The terrace is the perfect place to relax and unwind, with ample space for outdoor dining and entertainment. Located at the most desirable area of Sol Street, in the heart of Old San Juan, this property is just steps away from world-class restaurants, boutique shops, and historical landmarks. Whether you're looking for a vacation home or a permanent residence, this colonial house offers the perfect opportunity to immerse yourself in the vibrant culture and rich history of Puerto Rico. Don't miss this once-in-a-lifetime opportunity to own a piece of history in Old San Juan, one of the most sought-after neighborhoods in Puerto Rico. Contact us today to schedule a showing and experience the magic of this stunning colonial house for yourself! $2,985,000 Active

14 Calle Sol San Juan, Puerto Rico

3 Beds 4 Baths 3,500 SqFt 0.040 Acres

252 Calle de la Tanca, San Juan PR 00901. Mixed use Residential & Commercial. Building consists of approx. 5500 sq ft on 2 floors with a total of 2 units, located on the corner of Tanca Street and Tetuan Street. High traffic street as most cruise ship passengers and locals pass through Tanca to enter the Old City. The 1st floor commercial retail street level has high ceilings, a great layout with several display windows and street entrance doors. New floors, top of the line display cabinets with special lighting, air conditioning units. The 2nd fl large office/residential apartment (4B/2B Apt) with high ceilings, new floors, several office rooms that could also be used as bedrooms, an open kitchen with commercial size extractor, a living room, a beautiful skylight area and several balconies overlooking Tanca Street and Tetuan Street. Cash Only. Land 261.18m2, GPS 18.464696, -66.114276 Buyer Agent fee 3%. For showing instructions, please see MLS notes. $2,750,000 Active

252 Calle De La Tanca San Juan, Puerto Rico

5 Beds 3 Baths 5,500 SqFt 0.060 Acres

Welcome to your enchanting Old San Juan dream home! Tucked away on a tranquil residential street in the Historic District, this turnkey property stands out as one of the very few with a front porch and multiple outdoor oases. Meticulously remodeled, it seamlessly blends the historic charm of the Old City with modern comfort and convenience. Currently configured as a 2-bedroom and an office, it effortlessly converts to a 3-bedroom with three ensuite bathrooms. Spanning approximately a total of 2,600 square feet including terraces, this thoughtfully designed property offers ample space for comfortable living and outdoor entertainment. As you enter, the main level welcomes you with a grand room featuring a spacious living area, adjoining dining room, a well-appointed kitchen with a cozy breakfast nook, two bedrooms (one currently used as an office), and two full bathrooms. A stainless-steel wide staircase leads to the upper level, where you'll find a serene interior courtyard with an intimate seating area, perfect for moments of meditation. The large master bedroom boasts a walk-in closet and a luxurious bathroom. Beyond, there's an expansive rooftop terrace complete with a convenient wet bar and casual seating, providing an ideal setting for hosting gatherings or simply unwinding in the fresh air. This remarkable property also boasts double-height ceilings with recessed lighting, elegant marble floors, all ensuite baths, and air conditioning throughout. Immerse yourself in the captivating history and vibrant culture of Old San Juan, a UNESCO World Heritage Site, by exploring cobblestone streets, savoring world-class dining, and embracing the lively energy of the neighborhood. With all its unique features, this exquisite property is fully equipped and ready for you to make it your own. Don't miss the opportunity to experience the magic of Old San Juan living! $2,400,000 Active

267 San Sebastian San Juan, Puerto Rico

3 Beds 3 Baths 2,600 SqFt 0.040 Acres

Stunning multi-level colonial property located at the corner of Sol and Callejón del Toro in the historic Old San Juan. Its prime location grants it a main frontage along Sol Street, one of the most sought-after addresses in the area. The building, situated on a 177 square meter corner lot, stands tall with three stories, encompassing approximately 4,795 square feet, 5 bedrooms and 5 baths. This exceptional property offers you the versatility and unique opportunity of residing on the two upper floors and utilizing the lower floor as guest accommodations, home offices or apartments for short-term rentals. The first floor comprises two independent apartments. One features two bedrooms, one bath, a comfortable living/dining, and an inviting inner courtyard. The second unit offers a one-bedroom suite with a great room, ensuring ample space for residents or guests. Both units are fully equipped with independent kitchens and laundry rooms. Access to the upper floors is convenient and effortless via a staircase or an elevator. The second level of this turnkey property serves as its main floor, featuring an open floor plan with a grand room with high ceilings, exposed wood beams and marble floors, a gourmet fully equipped kitchen, two ensuite bedrooms, and home office. The grand room boasts six double doors that open to a large balcony that provides excellent cross ventilation, allows the flow of natural light, and enhances the living experience offering the perfect spot to relax and enjoy the neighborhood's charming ambiance. Ascending to the third floor, you'll discover a marvelous entertainment room, equipped with a kitchenette and a full bath. This multipurpose room extends onto a spacious rooftop terrace with North and East exposures. From here, the lovely ocean and city views provide a serene backdrop for outdoor gatherings or moments of personal tranquility. 350 Sol Street presents a unique opportunity to own a luxurious residential condominium in the heart of Old San Juan. Whether you choose to make it your home or capitalize on the rental potential, this unique property embodies convenience, versatility, and undeniable colonial charm. Don't miss the chance to make this elegant and functional residence your own and experience the captivating beauty of Puerto Rico's historic gem. $2,375,000 Active

350 Sol San Juan, Puerto Rico

5 Beds 5 Baths 4,795 SqFt 0.040 Acres

***UNDER CONTRACT*** Perfect for a resi conversion, this exceptional 3-level plus rooftop building in the highly coveted area of Old San Juan. Remodeled to Fortune 500 Corporation standards. Showcasing an exquisite Spanish Colonial design that appeals to all and an approx. 600 Sq. Ft. terrace with city views, rarely are one of a kind properties such as this available on the market. Two separate entrances are provided for added accessibility, as well as a bathroom and five powder rooms that are evenly distributed throughout the sizable approx. 8,513 Sq. Ft. interior layout. Equipped with a top electrical system and a versatile floorplan that can be customized to your taste. The unique opportunity of using the third floor as an apartment for short-term rentals or as a main residence above the two lower stories is also conveniently available. The location enjoys heavy foot traffic and is situated near many popular venues, such as multiple acclaimed restaurants and La Fortaleza, the governor's mansion. 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. $2,300,000 Pending

354 Fortaleza Street San Juan, Puerto Rico

1 Beds 6 Baths 8,513 SqFt 0.070 Acres

201 Calle de la Tanca, San Juan, Puerto Rico. (Corner with San Francisco St) This mixed use residential & Commercial property features a 3 bedroom/ 2 bath Apartment on the 2nd floor and a studio/terrace on the 3rd floor. The property also offers a ground level retail space with 2000+sq ft. Land 2002.09 sq ft, Cash Only. GPS 18.465904, -66.114224 Buyer Agent fee 3%. For showing instructions, please see MLS notes. $2,250,000 Active

201 Calle De La Tanca San Juan, Puerto Rico

3 Beds 3 Baths 4,400 SqFt 0.040 Acres

4 C. de San Justo, San Juan PR 00901. Residential historic home in prime location with ocean view on each level in Old San Juan.  3BR/ 2.5 bths built over 4 levels. Property is adjacent to the famous Gallery Inn Hotel in Old San Juan. Fully set up as a residential property with 3 floors and a 4th floor access to a beautiful open terrace that has an unobstructed view of the ocean. Property boats a 2400 sq ft comprised of 1850 sq ft plus terrace of 550 sq ft. Maybe be sold furnished. Currently generating income on AirBnB (sleeps 14 comfortably) The master bedroom has a huge balcony with views. Built 1893 and remodeled in 2022. CRIM(Property Tax) 1,528.84 p/yr, GPS 18.467961, -66.116013 Buyer Agent fee 3%. For showing instructions, please see MLS notes. $2,000,000 Active

4 Calle San Justo Old San Juan, Puerto Rico

3 Beds 3 Baths 2,400 SqFt 0.050 Acres

Beautiful colonial ocean view home in Old San Juan! Three story house with the option of renting the 1st and 2nd floor as 1 apt and the 3rd floor as another. The 1st and 2nd floor consists of living, dining, kitchen and 1 and 1/2 baths and a beautiful entrance terrace and the master bedroom with bath and balcony with an ocean view and a second area with another bed and a washer/dryer. The 3rd floor has a separate entrance with spiral staircase leading up to the 3rd floor apartment of a 1 bedroom, bath kitchen and roofed terrace used as a living and dining area with amazing ocean view. The roof can also be used as another terrace. CRIM (Property tax) $832.60 p/yr, property total is 2030 sq ft 1,730 sq ft Construction, plus terrace 300 sq ft on a 816 sqft lot. You can easily convert the roof top to an additional 700+ sq ft GPS 18.468003,-66.114884 Buyer Agent fee 3%. For showing instructions, please see MLS notes. $2,000,000 Active

268 Calle Norzagaray San Juan, Puerto Rico

3 Beds 3 Baths 2,300 SqFt 0.010 Acres

205 Calle de San Justo, San Juan PR 00901. Mized use property, one is a studio and another currently used as commercial. The property is in a busy street for food and beverage business, between Fortaleza Street and San Francisco Street. This historic building consists of 2 condo apartment units on 2nd and 3rd floors that are owned separately and a first-floor retail unit that are deeded also separately as 4 units consisting of approximately 3,600 sq ft. GPS 18.465379, -66.115332 Flexible terms with 20% cash down & 6.25% int. only payments for 3yrs. Buyer Agent fee 3%. For showing instructions, please see MLS notes. $1,450,000 Active

205 San Justo Street San Juan, Puerto Rico

1 Beds 2 Baths 3,800 SqFt 0.010 Acres

OLD SAN JUAN - Ready to renovate! Rarely does such an exciting property to be revived comes available in Old San Juan. This historic 18th Century property, full of patina as a true reflection of a by gone era, has all the traits and details of Spanish Colonial Architecture including, layout, 18’ high ceilings, “soles truncos”, “zaguán”, interior patio, “ausubo” wood beams and masonry walls. The memories of the past have been engraved in these masonry walls. For the past years, the property has been in use as 3 residential units, one main unit and 2 smaller units, nevertheless it could be easily returned to its original single-family layout and remodeled it into an exquisite 2 level house or continue its use as a 3-unit property. The lower-level layout consists of 12 historic rooms, 4 bedrooms, 2 bathrooms, interior patio and “zaguán”. The second level was added many years later, therefore having more recent finishes. This unit has 4 rooms, 2 bedrooms, 1 bathroom and an open roof area space. Total house area is 3,400 square feet with a lot size of 227 square meters. Property Taxes $1083. If you like history and architecture Old San Juan is the place to live. Enjoy living in this magical colonial neighborhood, surrounded by history and architecture and at walking distance to all historical sites, museums, galleries, shops, and fine dining. $1,300,000 Pending

54 Calle Cruz San Juan, Puerto Rico

6 Beds 3 Baths 3,400 SqFt 0.050 Acres

OLD SAN JUAN, In the heart of Old San Juan, Puerto Rico, awaits a unique remodeled colonial gem, overflowing with charm! This one-bedroom home, steeped in history, seamlessly blends old-world charm with modern comforts. This beautiful property was originally built in the late 1800s and has been carefully restored and preserved to retain its original character. As you step inside, you'll be greeted by the warm embrace of colonial architecture and details with high ceilings, exposed wooden beams, masonry walls, Old San Juan doors, arches, and interior patio. Every corner of this meticulously renovated residence tells the story of Puerto Rico’s rich heritage. The house is a one-level home, having about 940 square feet, featuring one bedroom, one bath, living area, kitchen, dining/family, and interior patio. Lot has an area of 89 square meters. As you step into the living area you are greeted by colonial elegance where history meets Sol Street views, adding to the timeless appeal. The remodeled kitchen boasts modern appliances and conveniences while retaining the character of the era. The charming dining area follows the inviting pathway to the interior patio space, the centerpiece of this unique property, a tranquil oasis bathed in natural light. It's the perfect spot for morning coffee or evening relaxation. The bedroom offers a peaceful retreat, with ample space and a glimpse into the rich history of Old San Juan. This home is not just a dwelling; it's a piece of living history, a testament to Puerto Rico's colonial past, and a haven for those who appreciate the melding of old-world charm and contemporary luxury. Don't miss the opportunity to own a piece of this enchanting neighborhood." Embrace the allure of Old San Juan and make this colonial remodeled house your own. Experience the perfect blend of history and modern luxury. Discover your new home in the heart of Puerto Rico’s Old city just steps away from world-class restaurants, boutique shops, and historical landmarks. Turn your historic dream into reality and make this colonial gem your home! Contact us for more information and to arrange a private showing. $895,000 Active

306 Calle Sol San Juan, Puerto Rico

1 Beds 1 Baths 940 SqFt 0.020 Acres

204 Calle San Jose, San Juan PR 00901. Ground commercial retail space. The first-floor street level is a commercial retail space with new floor, air conditioning and a flexible layout. 1700 sq feet of space. Buyer Agent fee 3%. For showing instructions, please see MLS notes. GPS 18.464817, -66.117043 $850,000 Active

204 Calle San Jose San Juan, Puerto Rico

1 Beds 1 Baths 1,700 SqFt 0.040 Acres

Excellent opportunity to buy. $107,000 Active

1333 CALLE 8 SO Urb Caparta Terrace San Juan, Puerto Rico

3 Beds 2 Baths 1,000 SqFt 238 Acres

4-White (1)

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