Meet Our Team

Our philosophy is simple: clients come first. We pledge to be in constant communication with our clients, keeping them fully informed throughout the entire buying or selling process. 

We believe that if you’re not left with an amazing experience, we haven’t done our job. We don’t measure success through achievements or awards, but through the satisfaction of our clients. 

Our code of conduct: Honesty and integrity.

Jackie O Real Estate is a team that is engaged, realistic, resourceful, proactive and professional. 


jackie o’connor
Principal, Realtor


As a top-producing agent in Greater Boston, Jackie is a Real Estate Consultant focusing on seller and buyer clients. She has sold at record-breaking prices for multiple sellers. Also, she is a Luxury Agent and holds an accreditation from the National Association of Realtors as Buyer Specialist.  

With a background in sales and customer service, Jackie understands her clients’ needs whether buying or selling. She can help you make the most educated and strategic decisions on keeping or selling your home and reaching your highest financial goals. If you want to own real estate that will deliver cash to complement your portfolio, Jackie will guide you on ways to use money from your equity to purchase another home, while maximizing your IRA/401k investments.  

Jackie is an Atlanta native, lived in Ann Arbor and now resides in Boston. Having relocated several times in her life, she understands firsthand the stresses of moving and aims to make the process as painless as possible. She consistently receive high praises, as well as referrals from past clients, on her negotiation skills, market knowledge, and relationships with the brokerage community. She holds a Bachelors of Science in Psychology from Georgia Southern University. 

Jackie’s full-service team will save you time, money, and heartache in this very unique market.


kyoko yamamoto
Direction of Operations and Business Development/Licensed Agent


A Massachusetts native and a longtime Boston resident, Kyoko has a passion and a deep understanding of Boston and its surrounding neighborhoods’ unique characteristics and history. Kyoko brings her broad experience in marketing, operations, finance, project management, real estate, and data analytics to enhance Jackie O Real Estate’s clients’ experiences and outcomes.

Prior to joining Jackie O Real Estate, Kyoko boasts a career working at companies such as Deloitte, Brigham and Women’s hospital, and Massachusetts General Hospital as well as a marketing consultant for Hitachi. At Deloitte, Kyoko’s clients included some of the largest Real Estate Investment Trusts (REITS) and investment management companies in Boston.

Kyoko holds a B.A. from Bryn Mawr College and a Masters from Boston University Graduate School of Medicine. She is fluent in Japanese and conversational in French and Nepali. An avid athlete, Kyoko was the captain of her college Rowing Team and continues to enjoy competitive running, outdoor activities and triathlons.


sydney o’keefe
Sales Agent


Sydney joined the Jackie O Real Estate Team after graduating from Fairfield University, where she majored in Marketing and Communication. During her college years, she interned within the marketing staff of a real estate firm. Her real estate internship has given her additional insights into the real estate market and how a real estate company operates. Sydney was also an avid soccer player in college and holds a black belt in Taekwondo; with her athletic background she has brought a competitive edge, teamwork, and hardworking ethics to the Jackie O Real Estate.

Her past experiences, coupled with her time at Jackie O Real Estate, have allowed her to understand the details and nuances involved in making sure her clients receive the very best service.

Outside of her busy life at Jackie O Real Estate, Sydney enjoys spending time with friends and family at the beach or boating with them on the weekend. She is also a strong supporter and advocate of pancreatic cancer awareness. Sydney regularly volunteers and helps organize events to raise money to support pancreatic cancer education and research.  

When Sydney is not hanging out with friends or volunteering, you will most likely see her in a Southie café sipping coffee.  Her obsession and search for great coffee has created a mission to try all the cafés in Boston!


aleksia bulku
Sales Assistant/Licensed Agent


Aleksia is a student at the Sawyer Business School at Suffolk University majoring in Finance and Marketing. The past three years, Aleksia has been a sales professional at Ralph Lauren in Boston. Her strong background in customer service and sales experience from Ralph Lauren is one of Aleksia’s strong assets.  

At a young age, Aleksia moved from Thessaloniki, Greece to the U.S. and recognizes the difficulties that can come with moving and buying a home. Her first experience with real estate was when she undertook the purchase of her parents’ first home. This personal experience brought a vast interest in real estate.

She wants to provide a smooth transition and enjoyable experience for her clients; whether they are starting a new chapter in their lives or are interested in real estate investment opportunities. Her customer service and sales experience coupled with her passion for real estate and desire to help clients find their perfect home is evident the moment you meet her.

In her free time, Aleksia loves exploring Boston and all the new trends the city has to offer. She is fluent in three languages: English, Greek and Albanian.


john ruggieri
Creative Director 


Based in Boston, John is an award-winning creative director, artist and entrepreneur. He designs and creates graphics and branding for Jackie O Real Estate on multiple platforms, including print collateral, social media, online and website. His expertise is in design, photography, social media, and content creation for realtors specializing in the high-end market.

Ever collaborative, he is a designer with an international sales and marketing background, a curator’s vision, and expertise in luxury branding, migrating a brand’s essence across multiple channels. Fluent in the world of commercial and fine art photography, he has worked in-house on creative at companies such as tech giant IBM and the fast-paced e-commerce company Rue La La.

His photography and painting can be found in private collections around the world and has been exhibited widely, rincluding at the Newspace Center for Photography, Art Now Fair/Art Basel Miami Beach, LFL Gallery and many others. He has created community-based public art, including ART@NIGHT project and documentary, supported by a $30,000 grant from the Fund for the Arts, a restricted fund of the New England Foundation for the Arts. He is an alumnus of both Rhode Island School of Design and Hampshire College.