Don't 'Time' Your CT Move—Plan It: Two Real-World Outcomes
Jeff & Bridget tried to predict the perfect time to sell—and failed
In 2021, Jeff and Bridget realized their current house was too big.
The plan: sell their Middletown, CT house and buy smaller near the water.
But they hesitated after listening to media, friends and family warn of the impending real estate collapse.
“What if we buy at the peak?” they asked. And time passed.
June 2022: rates doubled. Their existing mortgage: ~3%. A new mortgage was 6%+.
Beach house prices kept climbing the whole time. Since 2021: up 60% per SMARTMLS.
Monthly payments were now thousands more than 2021.
Even with the Middletown house worth more, they couldn't afford the move.
They’re still in Middletown.
Priced out of their own plan.
And Middletown just rolled out a 10% property tax increase for 2026.
Waiting for the perfect time cost them in more ways than one.
Timing is guessing. Planning is deciding.
Nobody knows what happens next in real estate.
Not economists.
Not your neighbor who called 2008.
Make a plan around your actual situation.
Six Questions Control Your Sale
Six questions control your CT home sale. Answer them in order or lose your mind.
Who is on your real estate team?
Where are you going once you sell?
When are you going to list?
The answers to these questions build on each other and can change depending on market conditions.
Local market conditions matter more than the calendar
The “Spring Market” brings more buyers. Also brings more sellers. Net result depends on local conditions, not the calendar.
Buyer's market in April? Tough for sellers.
Seller's market in December? Tough for buyers.
The month doesn't change the fundamentals.
What actually matters:
How many homes are for sale in your area?
Where are mortgage rates?
How's the job market?
New construction activity?
Foreclosures?
These questions—except rates—are local. Your town. Your market. Not some national trend.
SMARTMLS proves seasonality exists:
3,900-4,200 homes sold in CT each July from 2023-2025.
3,200-3,400 each December.
When inventory was higher in 2021, July hit 5,900 and December hit 3,800.
Seasonality is real but it’s only one factor.
Sometimes the smart play is ignoring conventional wisdom.
Your personal situation is the deciding factor
Market conditions tell you how to sell.
Your situation tells you when.
Nobody knows what the market does next. From April to November 2022, rates rocketed up from 3% to over 7%. Market shifts happen—sometimes fast, sometimes slow, always unpredictable.
You can't control the market but you can control how you respond to your “Why”.
Your HOA jumps 20% while maintenance falls apart? Eat the cost and wait for the special assessment or move.
Your job relocates you in 60 days? Lose your job, live with burden of commuting or move.
Your parent needs 24-7 care? Hire someone you can trust, put them in a nursing home or move to a house with an in-law.
Define your “Why”. Build a team and strategy around it considering current market conditions.
When the market shifts—and it will—you adjust tactics. You don't abandon the plan.
Your situation drives the decision to act. Market conditions inform how you execute.
Moving on your schedule beats waiting for some calendar date that has nothing to do with your life.
Ann didn't wait—her costs were climbing too fast
Same town as Jeff and Bridget. Different outcome.
Ann's HOA jumped 20% while services and quality dropped. Middletown property taxes were heading up another 10%.
It was October 2025. Headed into winter. She listed anyway.
Tight inventory and high demand meant if she sold first, she might not have a place to live. So she found the condo she wanted before listing.
Sold the old condo. Bought the new one.
Her old complex? Prices are flat since she sold. The HOA increase and deteriorating property conditions killed buyer demand.
Her new place? Up 4.5% since she bought per MLS comps as of February 2026.
She avoided the tax increase by moving when her situation required it. Not when some expert said the market was "right."
Jeff and Bridget are still in Middletown waiting for certainty.
Your schedule. Not the market's.
Answer the six questions in order. Factor in current market conditions with your agent's help. Build a strategy that fits your situation.
Action beats waiting when your situation demands movement.
Call 203-464-1479 or email [email protected] with questions about selling your CT home.
This is blog 4 of 4 for CT homeowners preparing to sell. Check out the other three blogs in this series for the full framework on preparing your home for sale.
Blog 1 - Questions 1-3
Blog 2 - Question 4
Blog 3 - Question 5
