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The advertising executive in her late 50s was in a quandary. She’d been divorced for four years. But it was only after the youngest of her three children packed off to college that she started weighing the pros and cons of selling the stately English Tudor house she owned in Wilmette.

“She was caught in a conundrum — going round and round about whether to sell that big family house with the beautiful diamond-shaped leaded windows,” recalls Mark Nash, a Coldwell Banker broker and author of “1,001 Tips for Buying and Selling a Home.”

Over the course of a year, the two had several heart-to-heart talks.

Gradually she realized that selling her 7,000-square-foot house would free her to start a new chapter in life. After Nash sold the property for her, she bought a low-maintenance luxury condo in downtown Chicago.

Though selling the family home is the best choice for many single women who become empty nesters, it’s not right for all, says Nash, who’s worked with many clients grappling with this decision.

“For a woman whose main focus has always been home and family, selling her house can be a huge psychological setback,” he says. “She feels like she’s lost her identity and sense of place.”

Here are several pointers for female homeowners confronted by this major housing choice:

*Address the financial realities.

The advertising executive owned her property free and clear. Her salary was substantial. And she could easily have afforded the taxes, insurance costs and maintenance fees on the five-bedroom house, with its manicured three- acre yard.

But many women in her position aren’t so well-fixed financially. For them, the decision to keep the house could mean they’d have to postpone a comfortable retirement, including the dream of traveling abroad. Or perhaps their children would have to finance college with substantial student loans, rather than graduating debt-free.

If you think that holding onto the family home could require tough monetary trade-offs, Nash suggests you consult a trusted financial planner or tax accountant before making any decision.

In preparation for a visit to see your financial adviser, Nash suggests you spend some time with your checkbook and credit card statements to determine exactly how much your house is costing you.

“Until they add it up, many people don’t realize how a house and yard can nickel-and-dime them into oblivion,” Nash says.

*Make your housing decision within the context of your life plan.

All too often, people isolate their real estate choices from the broader issues of their lives, says Michael Knight, a financial planner affiliated with the Garrett Planning Network (garrettplanningnetwork.com).

“All your money decisions — including whether to buy or sell a house — should be made with the big picture in mind,” Knight says.

Suppose you’re one of the lucky single women with financial choices. Whom should you turn to help chart your plans?

Sometimes a real estate agent who’s willing to listen to your story (and won’t push you to sell) is a better bet than a close friend or family member, according to Nash.

“The people in your inner circle often have biases or preconceptions about how you should conduct your life,” he says.

*Consider your level of emotional attachment to the house.

Some women aren’t as open to the idea of recasting their lifestyles as was the advertising executive from Chicago. Some are so attached to the home where they raised their children that they feel unanchored if they let go of the place.

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To contact Ellen James Martin, e-mail her at ellenjamesmartin gmail.com.