Downsizing on Long Island: How to Clear Out and Sell a House You've Lived In for Decades
Selling the house you've lived in for 30 or 40 years isn't like any other sale. The house is usually in decent shape. The hard part is everything in it: the basement, the attic, the garage, and the decisions about what comes with you and what doesn't.
I've walked a lot of Long Island homeowners through this, and the ones who get through it with the least stress follow roughly the same order. Here's that order, who to call at each step, and what to watch out for.
The short version
- Decide where you're going first. Every other decision gets easier once that's settled.
- Know your number early. What the house will sell for shapes your budget, your timing and your next move.
- Move what you're keeping before anything gets sold. Then estate sale, donations, cleanout, cleaning and photos, in that order.
- Expect to pay for help, and expect it to be worth it. Organizers, movers, estate sale companies and cleanout crews each handle one piece.
- Pull your property records early. Permit and record problems can hold up a closing for weeks.
Jump to: Where You're Going | The Order That Works | Who Does What | Estate Sales | Donating | Taxes | A Real Example | FAQ
Start With Where You're Going
Before you touch a single box, settle the destination: a smaller place on the Island, an apartment in the city, a 55-and-over community, or a move closer to family out of state. The size of the next place decides how much comes with you, and the timing decides how fast everything else has to happen.
Two questions to answer early:
- Buy first or sell first? Selling first gives you a clear budget and no double carrying costs, but you need somewhere to go. Buying first means a smoother move, but you may be carrying two homes for a while. There's no universal right answer. It depends on your finances and your next home.
- What's the house actually worth today? Start with a free home value estimate, then let me tighten it against recent sales on your street. If you bought decades ago, the number may surprise you.
The Order That Works
- Set the plan and the timeline. Where you're going, roughly when, and who's helping. Family, an organizer, or both.
- Get a value and talk to your advisors. Know your likely proceeds before you commit to a new place. Loop in your accountant and attorney.
- Pull your property records. Request your file from the town or village building department and check for open permits or missing Certificates of Occupancy. My prep guide covers what to look for.
- Handle the big items. Cars, boats, trailers, pianos and large collections take the longest to sell or rehome. Start with them.
- Sort and move what you're keeping. Decide what fits the new place, pack it and move it, or put it in storage. Get it out before the estate sale so nothing you want ends up with a price tag on it.
- Run the estate or tag sale. A good company prices, stages, advertises and staffs the sale.
- Donate and clean out the rest. Charities for usable furniture and goods, then a cleanout crew for whatever's left.
- Deep clean, fix the small stuff and take photos. Then list.
Who Does What
| Who | What they handle |
|---|---|
| Professional organizer or move manager | Sorting, deciding what fits the new place, packing, and often coordinating the other trades. "Senior Move Manager" is a registered service mark of the National Association of Senior Move Managers, so only NASMM members can use that title. |
| Movers and storage | Moving what you're keeping, and storing it if the new place isn't ready. |
| Estate or tag sale company | Pricing, staging, advertising and running the sale. Usually paid by commission on what sells. |
| Cleanout crew | Hauling away everything left after the sale and donations. |
| Cleaning service | A deep clean once the house is empty, before photos and showings. |
| Your agent | Pricing, timing, paperwork, photos, marketing, negotiating, and keeping the whole team on schedule. |
Estate Sales: What to Know Before You Sign
Estate sale companies on Long Island generally work on commission. Industry guides put typical Long Island commissions somewhere around 35 to 50 percent of total sales, depending on the company and the size and value of the sale. That sounds steep until you see how much work goes into pricing, staging and staffing a sale.
Before you hire one, get answers in writing:
- What's the commission, and are there any extra fees for setup, advertising, staffing or cleanout?
- Are you insured, and do you have references from recent Long Island sales?
- What happens to items that don't sell: donation, a second sale, or a cleanout?
- When do I get paid, and will I get an itemized accounting?
- Will you handle anything valuable, like jewelry, art or vehicles, separately?
One more thing: take what you're keeping out of the house first. Once the sale starts, everything in the house is fair game.
Donating What's Left
Usable furniture, appliances and building materials can do some good after the sale. Habitat for Humanity of Long Island runs a ReStore in Ronkonkoma that resells donated furniture, appliances and building materials to fund its housing work. Plenty of other local charities take clothing and household goods. Ask your estate sale company or cleanout crew which ones they work with. Many already have a routine.
For bulky trash and electronics, check your town's rules first. Pickup and drop-off rules vary across Long Island's towns and villages.
A Quick Word on Taxes
If you've owned the house a long time, the gain can be big. Under federal tax rules, if you owned and lived in the home as your main home for at least two of the five years before the sale, you may be able to exclude up to $250,000 of the gain from your income, or up to $500,000 if you're married filing jointly. The details matter, so talk to your accountant before you sign anything. The IRS explains the basics in Topic 701, Sale of Your Home.
Property taxes on your next place matter too. If you're staying on Long Island, look at the tax bill as closely as the price.
A Real Example: A Hicksville House Full of Decades
One of my sellers had a house and two garages full of decades of belongings, including three cars and a vintage motorcycle, and he wanted to move back to his apartment in the city. We sold the cars first, an organizer helped him decide what he wanted in the apartment, movers handled the move and storage, and he was back in the city by summer. On the Long Island end, an estate sale team, a cleanout crew, cleaners and a photographer got the house ready. The first open-house weekend brought four qualified offers.
Read the full story, with contact info for everyone who helped: How We Sold a Hicksville House for a Seller Moving Back to the City.
People I've Worked With
- Downsizing and organizing: Stow & Behold
- Moving and storage: Relocators
- Estate and tag sales: It's Simply Done
- House and garage cleanouts: Nicky's Property Management Corp.
- Deep cleaning: Cyclone Cleaning Corp.
- Listing photos: EPM Real Estate Photography
Phone numbers and emails are in the Hicksville story. Tell them John Cordeira sent you.
Clearing out a parent's house after they've passed? The cleanout order is the same, but the legal side is different. See my guide to selling an inherited home on Long Island.
Downsizing on Long Island FAQ
Where do I start when downsizing a house I've lived in for decades?
Decide where you're going and roughly when, then find out what your house is worth. Once you know those two things, you can plan what comes with you, what gets sold or donated, and how much help you need.
Should I clear out the house before I list it?
Usually yes. An empty, clean house photographs better and shows better, and buyers can see the space. In some cases, like an estate or a house that needs major work, selling with some contents left can make sense. Talk it through with your agent first.
How much do estate sale companies charge on Long Island?
Most work on commission, and industry guides put typical Long Island rates around 35 to 50 percent of total sales. Get the commission, any extra fees and the payout timeline in writing before you sign.
What's a Senior Move Manager?
A professional who helps older adults and families with downsizing and moving: sorting, planning the new space, packing and coordinating the move. The title is a registered service mark of the National Association of Senior Move Managers, and only its members can use it.
Will I owe taxes when I sell my Long Island house?
Maybe not on all of the gain. If you meet the IRS ownership and use tests, you may be able to exclude up to $250,000 of gain, or $500,000 if married filing jointly. Talk to your accountant about your situation.
Do I have to be on Long Island while the house is sold?
No. Plenty of sellers move first and let their agent handle the Long Island end. In my Hicksville sale, the seller was back in the city well before closing.
Ready to Start? Let's Walk the House Together.
I'll give you a straight number on what your house will sell for, a realistic timeline, and the right people in the right order, so you're not managing six contractors on your own. I'm John Cordeira, Broker/Owner of Cordeira Homes, with more than 20 years selling Long Island homes.
What Should I Add to My Downsizing Guide?
If you've downsized from a Long Island house, or helped a parent do it, you know what nobody warned you about. Organizers, movers, estate sale pros and cleanout crews: you've seen it all. Tell me what belongs here.
More guides for Long Island homeowners: Homeowner & Seller Resources
This guide is general information, not legal, tax or financial advice. Talk to your accountant and attorney about your situation.
John Cordeira
Broker/Owner, Cordeira Homes
#RippedRealtor