Best Places to Live 2015: Who’s Buying What?

You know you’re going up against some tough competition. Here, five couples share their buying stories and why they ended up where they did. —Megan Johnson

Photograph by Dana Smith

Photograph by Dana Smith


John and Cara Mayfield


Occupations: John, 36, works for a cancer diagnostics company. Cara, 31, is in corporate communications.

Previous Digs: A Revere rental.

Found: A $395,000 Medford A-frame that needed updating.

Square Feet: 2,038

The Hunt: The newlyweds wanted something permanent for themselves and their dogs.

The Deal: “The seller had the house on the market earlier, and the deal fell through due to financing. We went into detail in a letter about how much we wanted the house, how we’re real people and not contractors, how we want to have a family there. The seller had been there 20 years and was touched by it,” John says.

Photograph by Dana Smith


Jesse and Luisa Lyons


Occupations: Jesse, 31, works for Boston Pedicab. Luisa, 31, a former Governor Patrick staffer, works for a nonprofit.

Previous Digs: A 600-square-foot apartment in East Boston.

Found: A five-bedroom, two-bath multi-family in Milton Village for $525,000.

Square Feet: 2,315

The Hunt: The couple searched for two and a half years throughout Boston.

The Deal: Jesse credits MassHousing financing, which only required a down payment of 5 percent.

The Negotiation: Another buyer couldn’t agree with the seller on fixing something that was broken, so the deal fell through. The Lyons family jumped right in.

Photograph by Dana Smith

Photograph by Dana Smith


Conrad and Kathy Feininger


Occupations: Conrad, 55, is an actor. Kathy (pictured), 56, is a playwright and director.

Previous Digs: The couple relocated from Washington, DC.

Found: A 3.5-acre home in Westport with water views for $795,000.

Square Feet: 4,500

The Hunt: The home was on the market for three years at $1.8 million with no bites.

The Negotiation: Kathy received email alerts every time the price dropped, and she jumped when it fell to 50 percent. They were told another family was interested, but Kathy sensed that it was an attempt to up the ante—she’d been told a Saudi prince was sniffing around a previous property she was interested in.

Photograph by Dana Smith

Photograph by Dana Smith


Brian and Liz Hess


Occupations: Brian, 39, is a mathematician. Liz, 38, is a homemaker.

Previous Digs: A Bolton home on a busy road.

Found: A contemporary in Bolton’s leafy Northwoods area, known as Drumlin Hill, for $890,000.

Square Feet: 3,900

The Hunt: The couple’s Realtor sent out postcards to homeowners in the neighborhood asking whether they would consider selling. Someone bit.

The Negotiation: The family put down more than 20 percent and faced zero competition, because the house was never on the open market.

Photograph by Dana Smith

Photograph by Dana Smith


Matthew and Michelle Benfer


Occupations: Matthew, 36, is an analyst at Longfellow Investment Management. Michelle, 35, is VP of sales at LogMeIn.

Previous Digs: A Milton condo.

Found: A home in Wellesley Fells for $1.64 million.

Square Feet: 4,600

The Hunt: The family wanted Wellesley’s neighborhood atmosphere for their two daughters. “Here, you could find a 2,800-square-foot house for $1.2 million,” Michelle says, “but it would need $200,000 to $300,000 worth of work.”

The Negotiation: The couple had lost a bid before. “People were paying over asking price or paying cash deals. We knew we had to be decisive,” Michelle says. They increased their budget and moved fast.


Check out all of our Best Places to Live 2015 coverage.

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