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About

Meet Tom McKenna

Real Estate Salesperson·SERHANT.

Tom McKenna, Boston and North Shore real estate broker
Boston, Massachusetts

The Long Version

Built On Brute Force, Applied To Luxury

Most brokers will tell you they provide white glove service. I built my career through brute force, cold calling and door knocking ten hours a day. That contrast is deliberate. Over $100 million in career sales, I have learned that the agents who consistently win for their clients are not always the most polished, they are the most relentless.

Today I advise clients across Massachusetts and Southern New Hampshire on estate settlements, luxury residential sales and new construction opportunities, often in high stakes or highly sensitive situations. A significant portion of what I represent is sourced off market, directly from owners or through trusted relationships with wealth managers, private bankers, and estate and probate attorneys.

My business runs differently than the solo agent model. Systems, staff and a structured process ensure every transaction moves with discipline and clarity, from valuation strategy through negotiation and closing. My clients get direct communication, strong advocacy and no unnecessary noise.

Whether you are navigating a complex estate, seeking off market access to the $2 million and up market, or looking for a broker who thinks like an operator, I am open to the conversation.

By The Numbers

Track Record

$100M+

Career Sales

Built through direct outreach before it was ever built through referrals.

$4.6M

Highest Published Sale

A 7,962 square foot, five bedroom estate with six full baths.

MA + NH

Markets Advised

Boston, Greater Boston, the North Shore and Southern New Hampshire.

How I Help

Specialties

Three ways to begin, each handled personally from the first call to the closing table.

Recent Representation

Selected Sales

Published closings, from a 7,962 square foot estate to a six bedroom family home. A significant share of the rest of the business is off market and never appears on a portal.

Sold
$4,600,000
9 Tuttle Lane
Massachusetts
5 bd · 6 full, 1 half ba · 7,962 sqft
Published closing
Sold
$1,435,000
25 Towpath Drive
Massachusetts
6 bd · 3 full, 2 half ba · 4,784 sqft
Published closing

Thinking About A Move

Find out what your home is worth in today’s market

A private valuation, prepared personally, with a ranked list of what would lift the number before it goes to market.

Request A Valuation

Sales as published on the agent’s SERHANT. profile.

Client Reviews

What Clients Say

Buyers, sellers and families on both sides of a closing.

★★★★★
He told us what the house was worth, not what we wanted to hear, and then he went out and got the number.
Seller, North Shore
★★★★★
We were settling an estate from out of state. Every deadline, every document and every showing was handled without us flying in.
Estate representation, Greater Boston
★★★★★
He found the property before it listed. That is the entire reason we own it.
Buyer, Boston
★★★★★
Direct, available and completely unbothered by pressure. Exactly what you want when a deal gets complicated.
Seller, Marblehead
★★★★★
New construction has a hundred decisions. He kept the list short and the timeline honest.
Buyer, Southern New Hampshire
★★★★★
He told us what the house was worth, not what we wanted to hear, and then he went out and got the number.
Seller, North Shore
★★★★★
We were settling an estate from out of state. Every deadline, every document and every showing was handled without us flying in.
Estate representation, Greater Boston
★★★★★
He found the property before it listed. That is the entire reason we own it.
Buyer, Boston
★★★★★
Direct, available and completely unbothered by pressure. Exactly what you want when a deal gets complicated.
Seller, Marblehead
★★★★★
New construction has a hundred decisions. He kept the list short and the timeline honest.
Buyer, Southern New Hampshire

Areas Served

Neighborhoods

Six markets between Boston and the New Hampshire line. Each one prices on its own logic.

Back Bay & Beacon Hill

Back Bay & Beacon Hill

Brownstone floor plates, full service buildings and the tightest supply in the city.

Ask About Back Bay →
South End

South End

Bow fronts, parlour levels and Boston’s strongest renovation market.

Ask About South End →
Marblehead

Marblehead

Harbor frontage, Old Town lanes and the Neck.

Ask About Marblehead →
Manchester-by-the-Sea

Manchester-by-the-Sea

Coastal estates and family compounds, thirty five minutes north.

Ask About Manchester →
Newton & Brookline

Newton & Brookline

Schools, land and new construction for buyers leaving the city.

Ask About Newton & Brookline →
Southern New Hampshire

Southern New Hampshire

Land, acreage and new construction within commuting distance.

Ask About Southern New Hampshire →

By Appointment

Access Creates Leverage

Buying, selling or settling an estate. Start with a private conversation, no obligation.

Request A Consultation