Tom Landry: Entrepreneur, Investor, Contractor, Agent In Portland, Maine

Young Tom and Family

Tom with his mom, Anna, and seven of his nine siblings.

Growing Up in Maine

Tom grew up on a small farm in Steep Falls, Maine. The youngest of ten kids, he routinely sold vegetables at their farm stand on the weekends, shoveled manure and fed the cows before school, and helped his father work on their rural farmhouse. Ask him about his childhood and he’s quick to tell you that growing up this way instilled in him the work ethic and resourcefulness foundational to his success today.

Read More

Always the entrepreneur, he bought his first property at 19, restoring much of it himself during his first year of college. This started a serious hobby that would later turn into a career in real estate sales and building.

While a student at USM, he took a job working the second shift at Barber Foods to pay his way through school and support his home remodels. After college, he remained at Barber, climbing the ladder from the production line to director of food service marketing. He stayed there for 11 years. Working a corporate job from 9-5 and on his latest remodel during nights and weekends, he spent much of his 20s burning the candle at both ends. Coming from a large family with little means, he saw real estate as his path to get ahead.

In 2003, Tom left a stable career to pursue a full-time real estate career. He founded Benchmark Real Estate in 2005, and the company quickly became a leading force in the Portland area. Tom’s marketing experience and innovative approach to “launching, not listing” properties helped him become one of Maine’s top-producing agents and Portland’s #1 Listing/Selling Realtor over the past two decades.

In addition to his work at Benchmark, Tom also founded CornerStone Building and Restoration, a full-service design, building, restoration and renovation company. This company allows Tom to use his extensive building and renovation experience to bring his clients’ visions to life. Whether working on new construction projects, renovations, remodeling or additions, Tom and his team at CornerStone are known for their high-quality workmanship and excellent client service.

Tom is deeply committed to supporting the local community, and this philosophy is at the core of both Benchmark Real Estate and CornerStone Building and Restoration. When he is not working, Tom enjoys spending time with his family and giving back to the community through various charitable efforts. He is a true local success story, and his dedication to his clients, community and craft is evident in everything he does.

Becoming a Real Estate Agent

Following a decade of buying, remodeling, and selling several homes, he met his wife, Amy, in 2001. He took a risk by showing her his latest project on their first date. It was an old run-down Victorian, which at that time was gutted to the studs. Amy wasn’t scared off and was soon helping him pull horsehair plaster from the ceiling and old linoleum from the floor. The couple moved into the home in 2002. They still live there today and have done several renovations since.

After a decade at Barber, Tom knew he hit the ceiling and began to think about what to do next. It was clear that real estate was his passion, and it was his wife that convinced him it was time to stop hiring a real estate agent and become one himself. He got his real estate license and left his corporate job less than a year later.

Read More

After only a few years in the industry, he founded Benchmark Real Estate in 2005. His business did well until the fall of 2008, when the stock market crashed, and real estate sales were hard to come by. It was a sobering experience. Working long days in his basement, Tom turned to what he knew best, marketing.

When other agents pulled back, he invested heavily in promoting himself and Benchmark. At the same time, he started a construction company, CornerStone Building & Restoration, and began marketing that as well. At one point, he had zero employees but kept the marketing flowing. It paid off. When the home market returned, both Benchmark and CornerStone had an influx of clients.


Building a Real Estate Legacy

Since then, both companies have continued to grow. In addition to real estate sales and construction, he continued to buy, restore, and sell homes. He doesn’t call it a flip, which he says has a bad connotation. He creates homes that he would want to live in and that he can be proud of

Read More

A natural progression, he applied his building and sales skills to developing condominiums. As a developer, he’s focused on creating high-quality and eco-friendly buildings on Portland’s peninsula, introducing many new housing units to the city. 

As a small business owner, he believes in giving back. From the beginning, Benchmark Real Estate has donated 10% of company profits to local charitable causes. He and his wife have volunteered for many organizations over the years and run their own charitable events. The longest-running of these is the Portland Kids Duathlon, which raises money for the Foundation for Portland Public Schools. 

When he’s not working, which isn’t a lot of time, he’s traveling to interesting places, playing with his daughter, on his road bike, or enjoying one of Portland’s exceptional restaurants. He’s always up for a coffee to talk about all things real estate, so shoot him a message sometime.

Benchmark & CornerStone

Tom has left a lasting mark on Portland by enlisting the help of his many team members in turning his visions into a reality.

Tom’s construction firm, has completed many projects in and around Portland, Maine. His extensive hands-on experience with construction, ability to see what a building or site could be, and leadership in tackling environmental concerns have helped the firm to become a reliable and significant part of Portland’s booming development. Learn more about CornerStone and Tom’s background in construction on the Building page.


Tom’s real estate firm, is a major player in the Greater Portland residential real estate market and a powerful homegrown Portland, Maine brand. Learn more about Benchmark and Tom’s expertise in real estate on the Real Estate page.

Bring Tom Landry’s Leadership and Experience to Your Conference, Training, or Event

With over 30 years of experience in real estate, Tom can speak on a myriad of topics and issues related to property sales, development, and building. He’s routinely tapped to speak about Maine’s real estate market by the news media and has been a speaker at educational events and conferences.

Topics Include (but are not limited to):


  • Residential and mixed-use real estate sales
  • Home market statistics and outlook
  • Home renovations
  • Historic restorations
  • New development
  • Portland zoning and property tax
  • Condo conversions
  • Multi-families
  • Real estate investing
DSC02494 (2)

Tom in the News


How to widen your network and sell more real estate

DSC04349 (1)

Tom's take on this unprecedented real estate market