Leading your way in Real Estate
Gregory Cumings

About Gregory Cumings


Picture of Gregory Cumings

-Born and raised in Winchester Massachusetts.
-Graduated from Winchester Highs School.
-Graduated from Boston University with a degree in Business Administration.
-Lived in Tokyo Japan for four years teaching English and training in Shotokan Karate.
-2002 became a member of Greater Boston Real Estate Board and Massachusetts Association of Realtors.
-2004 Founded Flagship Homes; assisting home buyers, sellers, and investors.
-2006 Established a short sale and foreclosure division in MA and RI assisting buyers avoiding foreclosure as well as representing National banks liquidating properties.
-2014 Founded Flagship Estate Services; representing Bankruptcy Attorneys,Trustees, and Ad-litems in the evalutation, management and sale of real properties.
-2015 established Belmont Karate; an after school program for kids of all ages learning the fundamentals of traditional karate.

I have lived in the Greater Boston Area for most of my life. I know intimately the pros and cons of these communities and am happy to share my knowledge with you. Please do not hesitate to reach out if you have even the simplest questions. I look forward to meeting you and appreciate your taking the time to learn more about me.


Gregory Cumings
Flagship Homes
Flagship Estate Services

Contact Me

address185 Trapelo Road
Belmont, MA 02478
state license #9061396

Company Info

Flagship Homes
185 Trapelo Road Belmont MA 02478



Greg found me the perfect investment property. He understood my financial and timing requirements and only showed me properties that met my criteria. We discussed all the pros and cons on various markets as I was not deeply knowledgeable of the different… (more)


Greg is a high energy, immensely likable person. He is professional and thorough, and makes an arduous process fun. He grew up in the greater Boston area, and is very knowledgeable about the region and the real estate business.
I would use Greg again for… (more)


I’ve used Greg Cumings and his associate Ed Mullowney for three major real estate transactions – including one of the most important deals of my lifetime.
Their professionalism is top notch. Their responsiveness and attention to detail is unmatched. And their… (more)

Ask a Question