Spring House Hunt

Why writing a letter to win a home can be creepy AND backfire

Writing a letter to a seller can open you up to discrimination and the sellers to liability. Continue reading at realestate.boston.com.

. Ally Rzesa/Globe staff; Adobe Stock

When my husband and I were house-hunting in 2014 — such innocent, cheaper times — we toured kitchens without ceilings, yards that backed into highways, and one peculiar home decorated only with a large kneeling scarecrow dressed in a tattered plaid shirt. And after two years of searching with a toddler in tow, we desperately wanted them all. What was an anxious buyer to do? Write a love letter.

I turned into Columbo, sleuthing sellers on www.masslandrecords.com. This is the dirty little secret of the real estate world, where spies like me can browse public deeds and mortgage documents for any homeowner in the state. I’d type in the address, find the owner, Google their background, and contrive a way to charm. Croquet lover? Pigeon breeder? Oh, I’d make friends in a letter.


Fortunately, the charade didn’t last long. A neighbor tipped me off to a home owned by a writer looking to sell to a kindred spirit. With that twist of fate — and an offer over asking — we finally landed an abode.

But so it goes in the fickle world of Boston real estate, where inventory is at an all-time low. Buyers will do almost anything to snag a coveted home, including penning sentimental notes straight out of “Fatal Attraction.’’ This tactic can sometimes sweeten a deal, but it can also backfire. One creeped-out woman interviewed for this story received a letter from a prospective buyer who memorized children’s names on her personal effects and used them in the missive. It hit too close to home; she rejected the offer.

Another overeager buyer confessed that she sent homemade bread-and-butter pickles to a seller along with a note — an unsuccessful effort that still makes her cringe.

“I cried over a bushel of cucumbers,’’ she said. (She has since found a home.)

In a perfect world, the best offer should win based on purely objective criteria, such as purchase price, contingencies, and financing. Take Greg Martin, who fielded many offers for his Inman Square condominium in 2019. One wooer, the scion of a prominent Boston family, discovered boating gear in Martin’s closet during the tour and seized on it in a letter.


“He knew we were sailors and told us he was also a mariner. Someone who has been to prep school and Harvard can write a good letter,’’ he said.

Martin recognized the last name and appreciated the effort. However, the articulate sailor wasn’t moved to up his price during a final round of negotiations.

“The letter was entertaining but not enough to motivate us to sell for $20,000 less,’’ Martin said. He went with the better offer.

As it should be. Real estate agents say writing letters can actually subject sellers to liability and fair-housing concerns. Though hard to prove, shunned buyers could claim discrimination should they pen an unsuccessful letter that mentions protected-class identifiers such as race, religion, or sex.

When Jarrod Cohen was house-hunting with his husband, Timothy Sanford, things looked bleak. They’d put in five offers in the Reading area, without traction despite thoughtful letters promising to take care of each property and praising the neighborhood. His agent suggested that perhaps the notes weren’t a good idea.

“It could have opened us up to discrimination that otherwise we wouldn’t have,’’ Cohen said. “We were husbands looking to start a family. You just never know what that does to people. It was a concern we had as we were writing offers: Will we be discriminated against based on who we are?’’


In an extreme scenario, a buyer could file a complaint with the Massachusetts Commission Against Discrimination, and a real estate agent could be sanctioned. A seller might also pay a fine.

“[Letters] aren’t illegal, per se, but the issue you run into is how the information in the letter could open you up to liability. Often these ‘love letters’ contain information that identifies people in protected classes: family status, national origin, religion. Sellers could use that information, even with unconscious bias,’’ cautioned Catherine Taylor, associate counsel for the Massachusetts Association of Realtors. “Our bottom-line recommendation is: Do not engage in the passing or receiving of love letters. It could open you up to a fair-housing complaint.’’

As such, many listings now specify that the seller refuses to entertain letters.

Still, sometimes they do pay off. Recently, animal-lover Joanna Stepka put in a winning offer on a farm in Sutton with a heartfelt note about her rescue mares, including Betty, a therapy horse.

“We visit nursing homes and hospitals (well, pre-COVID) to spread smiles on a volunteer basis, and she is also part of an international anti-bullying campaign called ‘Just Say Whoa to Bullying,’ ” Stepka shared. “With the money we would save by not boarding our horses and having them in our backyard, we could do even more volunteer visits with the horses. … When I visit your farm, I envision our three mares grazing in the beautiful grass paddocks and living the dream life they deserve, while our kids run around making memories.’’


The seller was charmed by the story even though Stepka’s offer wasn’t the highest. She also appreciated that Stepka had small children, because her neighbors had kids around the same age and would enjoy having a family nearby.

More and more, though, this could become the exception to the rule in a seller’s market where all-cash offers are common.

After seeing 30 homes, Cohen and Sanford finally found a four-bedroom Cape in Reading six months ago. They wrote a letter. They couldn’t help it.

“At some point, you get invested personally,’’ Cohen said.

It didn’t matter, though. Cohen later discovered that the seller didn’t bother reading any notes. He won out the old-fashioned way.

“We just overpaid significantly,’’ he said.

Kara Baskin can be reached at [email protected]. Follow her on Twitter @kcbaskin. Subscribe to the Globe’s free real estate newsletter — our weekly digest on buying, selling, and design — at pages.email.bostonglobe.com/AddressSignUp. Follow us on FacebookLinkedInInstagram, and Twitter @globehomes.


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