The Massachusetts Downsizing Checklist

A Step-by-Step Guide to Selling Your Home, Buying Your Next Home & Making the Transition Easier

Downsizing isn’t simply about moving into a smaller home.

For many homeowners, it means deciding what the next chapter of life should look like, deciding what to do with years of belongings, preparing a longtime home for sale, finding the right new home, and coordinating everything without becoming overwhelmed.

The key is to plan the move before listing the house.

PHASE 1: Decide What You Want Your Next Chapter to Look Like

Before thinking about selling, think about where you’re going.

  • Why do I want to downsize?
  • Do I want a smaller single-family home, condo, 55+ community, apartment, or another option?
  • Do I want one-level living?
  • Do I want fewer stairs?
  • How many bedrooms do I actually need?
  • Do I still want a yard?
  • Would I prefer maintenance-free exterior living?
  • Do I need a garage?
  • Do I want to remain in my current community?
  • Would I like to be closer to family, friends, shopping, healthcare, recreation, or other services?
  • Will this home still work for me in 5, 10, or 15 years?
  • Do I need space for visiting children or grandchildren?
  • Do I want to travel more and maintain a home less?
  • What monthly housing expenses would make me comfortable?

Think Beyond Square Footage

A smaller home isn’t automatically a better home.

The goal should be to find a property that better supports the way you want to live.

PHASE 2: Understand Your Financial Picture BEFORE Selling

One of the biggest downsizing mistakes is assuming:

“My house is worth a lot, so I’ll have plenty of money to buy the next one.”

Maybe—but let’s calculate it first.

  • Determine your home’s approximate current market value.
  • Determine your remaining mortgage balance, if any.
  • Estimate selling expenses.
  • Discuss potential tax consequences with your tax professional.
  • Estimate your likely net proceeds from the sale.
  • Determine how much cash you want to keep after purchasing your next home.
  • Establish a comfortable purchase price for your next property.
  • Compare current property taxes with potential taxes on the new property.
  • Compare condominium/HOA fees when applicable.
  • Estimate homeowners insurance.
  • Consider utilities and maintenance.
  • Budget for moving expenses.
  • Budget for new furniture, repairs, painting, or modifications to the new home.
  • Maintain an emergency reserve after the move.

The Important Number Isn’t Your Selling Price

It’s your estimated net proceeds.

Before making major decisions, have your real estate professional prepare a realistic estimated seller net sheet.

PHASE 3: Decide Whether to Sell First or Buy First

This is often the biggest downsizing question.

There isn’t one correct answer.

Your financial situation, housing needs, local market conditions, mortgage qualification, risk tolerance, and available properties all matter.

OPTION A: Sell First, Then Buy

Advantages

You know exactly how much money you have available.

You don’t have to carry two homes.

You may be able to make a stronger offer on your next property because your existing home is already sold.

Potential Problem

Where will you live between transactions if you don’t find your next home immediately?

Before choosing this strategy, consider temporary housing, family, a short-term rental, storage, or other arrangements.

OPTION B: Buy First, Then Sell

Advantages

You can move into the new home before preparing the old home for its final move-out.

You avoid worrying about finding a property before your current home closes.

The physical move can be much easier.

Potential Problems

You may temporarily own two homes.

You need to determine whether you can financially qualify and comfortably carry both properties.

Speak with a qualified lender and financial/tax professionals before choosing this strategy.

OPTION C: Coordinate the Sale and Purchase

This is often attractive but requires careful planning.

The goal may be:

Sell Current Home → Receive Sale Proceeds → Purchase New Home

Sometimes the closings can occur on the same day or within a short period.

However, closely coordinated transactions create additional risk because a delay in one transaction can affect the other.

Discuss the timing, contractual protections, financing, moving arrangements, and backup plan with your real estate agent, lender, and Massachusetts real estate attorney.

OPTION D: Make Your Purchase Dependent Upon Selling Your Current Home

In some transactions, a buyer may try to negotiate an offer contingent on selling an existing property.

Whether a seller will accept such an offer depends on the property, market conditions, competition, and specific terms.

Discuss the advantages, disadvantages, and risks before relying on this strategy.

PHASE 4: Develop a Backup Plan

Every downsizing move should have a Plan B.

Ask:

What happens if my home sells before I find another one?

Possible options might include:

  • Short-term rental
  • Extended-stay accommodation
  • Staying temporarily with family
  • Storage facility
  • Negotiated closing timing
  • Other temporary housing

What happens if I buy before my home sells?

  • Can I comfortably carry both properties?
  • How long could I afford to do so?
  • What happens if my current home sells for less than expected?
  • What expenses would I have on both properties?
  • Have I discussed financing options with my lender?

A backup plan reduces the pressure to make a poor real estate decision simply because the calendar is working against you.

PHASE 5: Start Downsizing Your Belongings EARLY

Do not wait until you receive an offer on your house.

Start before the home is listed.

Use Five Categories

Label items:

KEEP

GIVE TO FAMILY

DONATE

SELL

DISCARD

Then work through the house one area at a time.

  • Attic
  • Basement
  • Garage
  • Storage areas
  • Closets
  • Kitchen cabinets
  • Bedrooms
  • Home office
  • Living areas
  • Outdoor storage

Start With the Easy Things

Don’t begin with wedding photographs or your children’s baby clothes.

Start with:

Expired items.

Duplicate kitchen utensils.

Old paperwork.

Clothes you haven’t worn.

Broken items.

Unused household goods.

Emotional decisions get easier once you’ve built momentum.

PHASE 6: Measure the New Life, Not the Old One

Before deciding what furniture to keep, determine what will actually fit in the next home.

  • Obtain room measurements.
  • Measure important furniture.
  • Measure doorways and stairways.
  • Create a simple floor plan.
  • Determine where major furniture will go.
  • Decide how much storage the new home provides.
  • Measure closets.
  • Check garage dimensions.
  • Determine whether large pieces will physically fit through entrances.

Don’t Pay Movers to Move Things You Will Immediately Get Rid Of

Decide before moving day whenever possible.

PHASE 7: Handle Important Documents & Valuables Separately

Do not put essential documents in an ordinary moving box.

Create a secure file for:

  • Identification
  • Passports
  • Deeds and property records
  • Estate-planning documents
  • Insurance documents
  • Tax records
  • Financial records
  • Medication information
  • Important contact information
  • Jewelry and valuables
  • Sentimental photographs and irreplaceable items

Keep these personally accessible during the move.

PHASE 8: Prepare Your Current Home for Sale

You don’t necessarily need to renovate your house before selling it.

You need to decide which improvements will matter to buyers.

Before spending money:

  • Get a professional market analysis.
  • Walk through the property with your real estate agent.
  • Identify deferred maintenance.
  • Separate necessary repairs from cosmetic improvements.
  • Discuss which improvements could affect marketability.
  • Declutter.
  • Deep clean.
  • Remove excessive furniture.
  • Improve lighting where appropriate.
  • Address obvious exterior maintenance.
  • Gather permits, warranties, receipts, and records for major improvements when available.
  • Gather information about major systems.
  • Prepare for photography and marketing.

A Common Downsizing Mistake

Spending $30,000 improving a home when perhaps only a fraction of those improvements were necessary to successfully market it.

Talk with your real estate professional before undertaking major renovations solely for resale.

PHASE 9: Search for Your Next Home Differently

When downsizing, don’t evaluate the next property only on how it works today.

Consider how it may work later.

Look at:

  • Number of stairs
  • First-floor bedroom
  • First-floor full bathroom
  • Laundry location
  • Entry steps
  • Doorway widths
  • Shower/tub configuration
  • Exterior maintenance
  • Snow removal responsibilities
  • Lawn maintenance
  • Condominium services
  • Parking
  • Garage access
  • Storage
  • Distance to frequently used services
  • Overall monthly carrying costs

Massachusetts also provides housing resources for older adults, including tools for finding properties with accessibility features such as ground-floor units, elevators and roll-in showers.

PHASE 10: If Buying a Condominium, Look Beyond the Unit

A beautiful condo isn’t enough.

You are also buying into the condominium organization.

Review appropriate condominium documents with your attorney and other professionals.

Questions may include:

  • What is the monthly condominium fee?
  • What does it include?
  • Are special assessments pending?
  • Are major capital projects planned?
  • What maintenance is the unit owner responsible for?
  • What does the association maintain?
  • Are there pet restrictions?
  • Are there parking restrictions?
  • Are there rental restrictions?
  • What insurance is required?
  • Are there rules affecting how you intend to use the property?

PHASE 11: Don’t Skip Due Diligence on the New Home

Downsizing doesn’t mean lowering your standards for the property you buy.

Massachusetts has specific protections concerning a buyer’s opportunity to obtain a home inspection.

  • Review your inspection rights.
  • Consider having the property professionally inspected.
  • Review septic/Title 5 information when applicable.
  • Review well information when applicable.
  • Review lead-paint disclosures for applicable properties.
  • Review condominium documents when applicable.
  • Discuss legal documents with your Massachusetts real estate attorney.
  • Review property taxes.
  • Obtain insurance information.
  • Review anticipated maintenance expenses.

PHASE 12: Create a Two-Transaction Calendar

If you’re selling and buying, create one master timeline.

Track both transactions together.

CURRENT HOME — SELLING

  • Prepare home
  • Photography
  • Listing date
  • Showings
  • Offer accepted
  • Buyer inspection period
  • Purchase & Sale
  • Buyer’s financing deadline
  • Appraisal if applicable
  • Moving date
  • Final walk-through
  • Closing

NEW HOME — BUYING

  • Mortgage/financial planning
  • Property search
  • Offer accepted
  • Inspection period
  • Purchase & Sale
  • Financing deadline
  • Appraisal if applicable
  • Insurance
  • Final walk-through
  • Closing
  • Move-in

Your real estate agent, attorney, lender, and movers should understand how the transactions connect, when appropriate.

PHASE 13: Prepare for the Actual Move

Don’t underestimate the logistics.

  • Obtain moving estimates.
  • Confirm mover availability.
  • Reserve movers.
  • Arrange storage if needed.
  • Order packing supplies.
  • Begin packing nonessential belongings.
  • Label boxes by room.
  • Pack an “OPEN FIRST” box.
  • Keep medications personally accessible.
  • Keep important documents with you.
  • Arrange pet care for moving day.
  • Transfer utilities.
  • Forward mail.
  • Update important accounts.
  • Notify insurance companies.
  • Update driver’s license/vehicle information as required.
  • Cancel or transfer services.
  • Arrange cleaning if needed.

PHASE 14: Pack a First-Night Box

Do not bury these items in the moving truck.

Include:

  • Medications
  • Toiletries
  • Change of clothing
  • Towels
  • Bedding
  • Toilet paper
  • Paper towels
  • Phone chargers
  • Coffee/tea supplies
  • Basic dishes and utensils
  • Pet food and supplies
  • Important telephone numbers
  • Basic tools
  • Flashlight
  • Cleaning supplies

10 DOWNSIZING PITFALLS TO AVOID

1. Selling Before Knowing Where You’re Going

Have a housing strategy and backup plan first.

2. Buying Before Understanding Your Net Proceeds

Know approximately what you’ll walk away with—not simply what your house may sell for.

3. Waiting Too Long to Declutter

Sorting decades of belongings can take considerably longer than expected.

4. Renovating Too Much Before Selling

Not every improvement produces an adequate return.

5. Assuming “Smaller” Automatically Means “Cheaper”

Condo fees, taxes, insurance, utilities, assessments, and financing all affect the true monthly cost.

6. Choosing a Home Only for Today

Consider stairs, maintenance, accessibility, transportation, and lifestyle needs over the coming years.

7. Trying to Coordinate Two Closings Without a Backup Plan

Delays happen. Know what you will do if the dates don’t line up.

8. Giving Away Sentimental Belongings Too Quickly

Take your time with meaningful items. Downsizing doesn’t need to mean discarding your memories.

9. Trying to Do Everything Yourself

Professional movers, organizers, estate-sale professionals, attorneys, lenders, tax advisers, contractors, and other specialists can make certain parts of the transition considerably easier.

10. Waiting Until You’re Forced to Move

When possible, planning while you have choices gives you more control over where you live, what you keep, how you sell, and when you move.

THE MOST IMPORTANT DOWNSIZING ADVICE

Don’t begin with the question, “When should I list my house?”

Begin with:

“Where do I want to go, what will that cost, and how can we create the safest path from here to there?”

Only after answering those questions should the selling strategy begin.

Downsizing should not feel like being pushed out of a home you’ve loved.

Done thoughtfully, it can be about reducing responsibilities, simplifying your surroundings, protecting your financial goals, and choosing a home that better fits the life you want now.

I’d call out two Massachusetts-specific points. First, Massachusetts’ current inspection rules prohibit sellers from conditioning acceptance of an offer on a buyer waiving or limiting the buyer’s inspection rights; a required disclosure is part of the process for covered residential transactions. Second, Massachusetts has dedicated housing resources for older adults, including help finding housing with accessibility features.