Helping Clients Secure Mortgages for 20 Years And Counting

I’ve been working as a Massachusetts mortgage broker since the turn of the century. Since then, I’ve helped hundreds of clients buy or refinance residential property in Massachusetts. Each situation is different, yet every single one is so rewarding when we get to the closing table.

That’s the short story about me.

For a deeper dive into my background and how I became a mortgage broker, keep reading. Or if you simply want the basics, you can jump down to my no-nonsense bio below.

Professional Bio

Helping Clients Secure Mortgages for 20 Years And Counting

That’s the short story about me.

For a deeper dive into my background and how I became a mortgage broker, keep reading. Or if you simply want the basics, you can jump down to my no-nonsense bio below.

Professional Bio

The road to my own mortgage brokerage firm was a winding one.

I never planned on becoming a mortgage broker.

When I graduated from Skidmore College in 1995 with a business degree, I was accepted into the Transamerica training program—at the time, one of the country’s largest financial service companies. I learned a lot over the next couple of years, and, because I was living at home, I was able to save a lot of money as well.

One Thanksgiving, I got to talking with my aunt (she was a financial planner) about moving out and finding a place to rent on my own. She explained to me that rather than renting, if I were to purchase a multi-family home, I could rent out the unit and use the rental income to help cover the mortgage and begin building some equity. It was scary doing it on my own (I always assumed I’d wait until I got married to buy a home), but it made sense.

And so the following week, I walked into a local bank and applied for preapproval on a mortgage. I was a young woman and didn’t have much credit (although it was good), but the local bank took a gamble on me (thanks in part to the long-standing relationship it had with my dad). I was approved! Six months later, I bought a two-family home in Newton (I still own it).

Female woman hands holding small miniature white toy house

Seeing other people’s approach to mortgages inspired me to do better.

Over the next few years working for various financial companies, I became disillusioned with the way most mortgages were sold. Each company had a handful of products. The objective was to push one of those products onto the customer, regardless of how well it fit.

I began to realize that didn’t work for me, and I kept thinking back to the local bank that had the relationship with my dad—and how the bank considered my WHOLE financial history when deciding to give me a mortgage. Like that local bank, I wanted to help solve people’s problems in a way that made sense for their unique situation. And so in 2000, I left to start Westchester Mortgage (named after the street I lived on).

Portrait Of Hispanic Family Holding Keys To New Home On Moving In Day

Why I work with who I work with…

Over the years, I’ve worked with a wide variety of clientele, including the “traditional” first-time home buyers as well as those buying second homes or investment properties. But I also found myself drawn to people with what some lenders consider “complicated” financial situations—newly divorced women, couples who live together but aren’t married, and self-employed individuals (just to name a few demographics).

I discovered I loved finding mortgage solutions for these clients. Yes, it takes a bit more work and thinking outside the box, but that’s what I love about it: the challenge as well as the reward.

And so today, I help all sorts of people understand their mortgage or refinancing options so they can make the best financial decision for their particular situation.

Learn more about my approach to securing a mortgage and refinancing.

My Approach

Meet Debbie Siegel

Below is my formal bio, also known as the bit where I talk about myself in the third person.

Debbie Siegel

Massachusetts Mortgage Broker Extraordinaire

Debbie Siegel founded her mortgage brokerage firm Westchester Mortgage in 2000. Since then, she has helped hundreds of clients buy or refinance their homes. In addition, she’s cultivated an extensive professional network of real estate attorneys, insurance agents, contractors, mediators, business coaches, and financial planners, all of whom work with her, as needed, to support her clients.

Over the last twenty years, Debbie has contributed to a variety of print and online media outlets, including Boston Women’s Business, Home Business Magazine, Fox-25 News, New England Cable News, and Money Matters Radio. She’s been publishing her popular free monthly newsletter, “Raising the Roof,” since 2006.

Debbie is an active member in Business Networking International (BNI) and National Association of Divorce Professionals. She has volunteered with various organizations over the years, including several committed to helping women succeed in business and in life.

Debbie holds a Bachelor of Science in Business from Skidmore College in New York and currently lives in Newton with her husband and two daughters.

Need a mortgage?
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Helping Clients Secure Mortgages for 20 Years And Counting

Helping Clients Secure Mortgages for 20 Years And Counting

The road to my own mortgage brokerage firm was a winding one.

Seeing other people’s approach to mortgages inspired me to do better.

Why I work with who I work with…

Meet Debbie Siegel

Debbie Siegel

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