Couple standing in front of their Connecticut home with a for sale sign, husband looking confident while wife appears uncertain about selling

Ready to Sell Your CT Home? Answer These 6 Questions First

February 02, 20265 min read

A house in Hamden, CT—Paradise Preserve. Listed and ready to go.

Husband's ready to sell the house. Wife's not so sure.

He thinks she'll fold when the money shows up. She thinks the offers won't come.

The market does what it does. Within days, competitive offers stack up.

The wife refuses to sign. Wants the house off the market.

The deal's dead. Buyers are angry. Time and money wasted.

The problem: Not clear on question 1.

Six Questions Control Your Sale

Six questions control your CT home sale. Answer them in order or lose your mind.

  1. Why are you selling?

  2. Who is on your real estate team?

  3. Where are you going once you sell?

  4. What repairs, staging and prep do you need to do?

  5. How much are you going to list for?

  6. When are you going to list?

The answers to these questions build on each other and can change depending on market conditions. Your agent should be able to guide you through this. Click here to learn more about The 3 People Who Decide If Your Connecticut Real Estate Deal Closes or Dies

The first 3 questions form the foundation of your strategy. Screw these up and the process gets a lot harder.

Why Are You Selling?

Your "Why" isn't philosophy. It's what keeps you from folding when things get hard.

Kids don't want to leave their friends. You don't want to leave yours. The house you thought you hated suddenly doesn't seem so bad when offers hit the table and moving becomes real.

Without a strong "Why," you waffle.

Paradise Preserve is what waffling looks like. Competitive offers on the table. Deal dies because the "Why" wasn't aligned between husband and wife.

Write your "Why" down. Discuss it with everyone who has to sign the contract—spouse, kids old enough to have a real vote, anyone whose buy-in you need.

Share it with your agent. They should use it to guide every decision from pricing to negotiation strategy.

Who Is on Your Real Estate Team?

A couple came to see one of my rental properties a couple weeks ago.

They'd sold their $1 million home. Closing in three weeks. Five kids. No plan for where they were going.

The rental was too small for their needs, so they kept looking. But the conversation stuck with me.

They had their "Why" figured out. They picked an agent. They sold the house.

They didn't know their "Where."

How does an agent let that happen? How do you sell a million-dollar asset and end up staring at the possibility of homelessness with five kids?

When you interview agents, that's what you're looking for—someone who asks about your "Why" and "Where" upfront, not someone who waits until you're three weeks from closing to figure out you have nowhere to go.

Someone with strategies they adapt to your situation. Not a script they run the same way for everyone.

You'll hear agents pitch their brokerage's brand. Doesn't matter. Heroes and zeros work at every company in Connecticut. The brand on the yard sign means nothing. The person holding that sign means everything.

You'll hear about MLS access. Everyone has it. Every licensed agent in the state. It's baseline, not special.

You'll see social media posts—Instagram reels, professional photos, flashy content. According to the 2024 NAR Member Profile, only 3% of real estate business is directly generated from social networking websites. Over 90% find them on the MLS.

You need someone who wins where buyers actually search.

You make the decisions. The agent presents options with enough data to make them. That's the job you're paying for.

Where Are You Going?

Seven years ago, I almost let a client settle for an apartment she didn't want.

Not because the house didn't sell—it sold fast, $5K over asking. Because I didn't ask the right questions early enough.

Mary came to me wanting to sell her condo in Hamden. During our initial meeting, I asked where she was going after the sale. She said she planned to rent and stay in CT.

I asked if she had a place picked out.

She said "Yes."

Three weeks before closing—after inspection and appraisal were done—I asked when she was moving into her new apartment.

"I'm going to apply today."

I almost fell out of my seat.

The apartment she'd been watching? Rented to someone else a week earlier while she was "planning to apply."

We found one backup option. Not as nice. She wasn't happy but had no choice with three weeks to closing.

For two weeks, she waited. Checked listings daily. Nothing comparable opened up.

Eight days before closing, the original tenant backed out. Mary got the apartment she wanted.

Eight days. That's how close she came to settling for second choice because she assumed the apartment would still be available when she got around to applying.

Connecticut's real estate market moves. Your house will sell.

If you don't know where you're going before you list, you're setting yourself up to be a victim of your own success.

This is where your agent earns their commission. They should help you think through your options based on your "Why," your budget, and current market conditions.

Options exist:

  • Buy your new house first

  • Rent temporarily

  • Stay with family

  • Negotiate a lease-back with the buyer so you can stay in the house after closing

  • Already own another property you're moving into

Your agent should walk you through the pros and cons of each option for your specific situation. Market conditions matter here. Seller's market versus buyer's market changes which option makes sense.

The point is simple: Answer this question BEFORE you list. With your agent's help.

Mary got lucky. The couple with five kids? They're still looking.

Start Here

Your "Why" keeps you from backing out when the pressure's on and moving day becomes real.

Your "Who" determines whether you have a guide who helps you think through your "Why" and "Where"—or an order-taker who lists your house and hopes for the best.

Your "Where" keeps you from ending up homeless when your house sells faster than you expected.

The decisions about repairs, staging, pricing, and when to list all flow from these three questions.

Start here. Everything else follows.


Call 203-464-1479 or email [email protected] with questions about selling your CT home.

Broker / Owner of Bolduc Realty Group. Local real estate investor.  Call or text me at 203-464-1479

Dave Bolduc

Broker / Owner of Bolduc Realty Group. Local real estate investor. Call or text me at 203-464-1479

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