SPOTLIGHT ON: Regina Winslow, Back Bay in Boston, MA

We’re so proud to welcome Regina Winslow of Boston, MA to this week’s Agent Spotlight! As a few of her client testimonials read, “Regina was a great buyer’s agent for us. She helped us pick the right home at the right price and the level of service was exceedingly high. We recommend her for anyone who is looking to buy or sell a property.” She is an absolute delight! Read on to discover more about Regina Winslow and contact her for any of your Boston real estate needs at

At the Nantucket Wine Festival

What drew you to the real estate industry?
I have been in the Real Estate business in Boston for 13 years. My father is a developer so it’s in my DNA. Growing up in San Diego at a time when it was transforming, I loved touring the model homes in the various planned communities. I think my negotiating skills and ability to spot a deal made me perfect for this industry.  William Raveis is a large company and yet offers luxury and boutique services to both the agents and our clients. I genuinely like the people in our company. They are honest and good people. Those characteristics can be hard to come by in a competitive and cut throat industry. Every successful agent also needs a solid company behind them.

Regina Winslow & her husband at the Mondance Gala for the Esplanade Association

Where did you grow up and where do you live now?
I grew up in San Diego. I moved to Boston after graduation from the University of Vermont and I have lived in the city ever since. I currently live in Charlestown with my husband and young son and daughter.
Without naming names, tell us the funniest/craziest story from a real estate transaction that you’ve experienced!
I had a listing once where the seller called me when someone injured themselves on the property. I asked her if she called 911 and suggested that she do so. She told me she called me FIRST!

With her Dad at the Padres game in Petco Park, San Diego

Name 5 things that most people don’t know about you.
-I am 100% Irish
-I was chased by a grizzly bear while hiking in the Yellowstone backcountry.
– I sing loudly and surprisingly on key while alone in the car.
– Baseball is my favorite sport. I root for the Padres and Red Sox. When they (rarely) play each other I have to root for my home team (padres), let’s be honest they need more support anyway.
-I chose my middle name in 6th grade, I picked my grandmother’s name, who I was very close with.

At Kilkea Castle in Ireland

You are stranded on a deserted island for one year, you get to bring 3 things.
My husband, my children, and champagne.
Your day cannot begin without…?
Checking my email.

Party in the Park – Supporting the Emerald Necklace Conservatory

Most used feature on Raveis365?  
Zipforms. Zipforms really allows you to work anywhere. I have written/ submitted offers from my car, the beach, or on an airplane. I could not function without it.
What is the best advice you received from your parents or loved ones?
Always follow the golden rule. Always be generous. My parents did an amazing job teaching us (my younger brothers and me) gratitude and encouraging us to be charitable with our time and through worthy donations.

At the La Jolla Beach & Tennis Club in California

If you weren’t in real estate, what would be your dream job?
I would start a charity or form an advocacy group for children in need. Recently, I was having a conversation with a dear friend who had been going through the process of trying to adopt a child. I was amazed about how many countries are closed for adoption. You have children that need homes and loving families who want to provide them. Yet, somehow there is red tape keeping this from happening. It is a truly tragic situation.
Name one celebrity, dead or alive, who you would like to sell a home.
When I was growing up Steve Garvey (former Padres player) owned an amazing house in La Jolla, CA. His home was one block from the beach and each window had a purple awning. It has always been one of my favorite pieces of real estate. He no longer owns that home, however, I would love to sell it after admiring it for so many years. And, I still love Steve Garvey!

Skiing in Beaver Creek, Colorado

What are your favorite local activities that you participate in? How do you engage with your community?

Being a Bostonian by way of California I have been involved with several organizations to help me meet people and establish roots in a city I have now called home for 13 years. I have served on the Board of the Ellie Fund, a local breast cancer organization. I have been a member of the Boston Junior league. I have worked on committees for the Esplanade Association, Community servings, and the Charlestown Mother’s Association. I also try to do as much as I can at my children’s school anytime there is an opportunity to be in their class and volunteer I jump at the chance. It is a privilege to raise my children and work in Downtown Boston.


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